evaluation of chemical constituents and important ...reviewarticle evaluation of chemical...
TRANSCRIPT
Review ArticleEvaluation of Chemical Constituents and Important Mechanismof Pharmacological Biology in Dendrobium Plants
Yau Lam1 Tzi Bun Ng2 Ren Ming Yao1 Jun Shi1 Kai Xu1
Stephen Cho Wing Sze1 and Kalin Yanbo Zhang1
1School of Chinese Medicine LKS Faculty of Medicine The University of Hong Kong 10 Sassoon Road Hong Kong2School of Biomedical Sciences Faculty of Medicine The Chinese University of Hong Kong Shatin NT Hong Kong
Correspondence should be addressed to Tzi Bun Ng b021770mailservcuhkeduhk Stephen Cho Wing Sze stephenshkuhkand Kalin Yanbo Zhang ybzhanghkucchkuhk
Received 24 November 2014 Accepted 9 February 2015
Academic Editor Wagner Vilegas
Copyright copy 2015 Yau Lam et alThis is an open access article distributed under the Creative Commons Attribution License whichpermits unrestricted use distribution and reproduction in any medium provided the original work is properly cited
Dendrobium species commonly known as ldquoShihurdquo or ldquoHuangcaordquo represents the second largest genus of Orchidaceae which areused commonly as tonic herbs and healthy food in many Asian countries The aim of this paper is to review the history chemistryand pharmacology of differentDendrobium species on the basis of the latest academic literatures found in Google Scholar PubMedSciencedirect Scopus and SID
1 Introduction
The origin of orchids (Orchidaceae) probably has to bebackdated to 120 million years ago It is the largest familygroup among angiosperms as well as themost highly evolvedfamily of the flowering plants with approximately 25000 to35000 species under 750 to 900 genera [1ndash4] Dendrobiumspecies commonly known as ldquoShihurdquo or ldquoHuangcaordquo isthe second largest genus in Orchidaceae Most Dendrobiumspecies grow best in relatively high and mountainous areasat 1400ndash1600m above sea level at a mild temperature andin a humid and foggy environment Characterized by abroad geographical distribution which allows Dendrobiumspecies to grow into tremendous diversities producing a largenumber of interspecific hybrids with different morphologicalfeatures they are widely distributed in Asia Australia andEurope for instance in India Sri Lanka China JapanKorea New Guinea and New Caledonia [5] In the earlyage using molecular approaches would delimit the subtribe-Dendrobiinae affecting approximately 1100 species (900 inDendrobium Sw) from Indo-Asian and Pacific regions [6 7]and more than 1200 species in Australasia are from variousDendrobium species Today Indo-Asian and Pacific regionshave one of the largest and most diverse and taxonomicallyproblematic orchid groups [8] Interestingly there has been
a long history of the usage of first-rate herbs and folktraditional herbs in India and China [9]
Since the ancient times (600 BC) in India the oldestreferences regarding the use of medicinal herbs are foundin the Sanskrit literature namely ldquoCharaka Samhitardquo Theearliest treatise on ldquoAyurvedardquo describes the property of plantdrugs and their uses In the Ayurvedic system of medicineFlickingeria macraei is used in ldquoAyurvedardquo It is commonlynamed as ldquojeevantirdquo and is used as an astringent to thebowels as an aphrodisiac and in asthma and bronchitis[10] Other commonly used orchid drugs in the Ayurvedicsystem are salem including jewanti (Dendrobium alpestre)Similarly it is the first time for China to regard orchids asherbal medicines [11] The Emperor ldquoShen-Nungrdquo advised onthe medicinal properties of Dendrobium species in ldquomateriamedicardquo in the 28th century BC [12] As early as 200 BC theChinese pharmacopoeia ldquoThe Sang Nung Pen Tsao Chingrdquomentioned Dendrobium as a source of tonic astringentanalgesic and anti-inflammatory substances [13] In SongDynasty (960ndash1279 AD) It mentioned the medicinal uses oforchids namely Dendrobium species according A Diagnosisof Medical Herbs from the ldquoZheng Lei Ben Caordquo In MingDynasty (1368ndash1644) many references on the use of orchidsas medicinal herbs were available [14]
Hindawi Publishing CorporationEvidence-Based Complementary and Alternative MedicineVolume 2015 Article ID 841752 25 pageshttpdxdoiorg1011552015841752
2 Evidence-Based Complementary and Alternative Medicine
2 The Chemical Compounds ofDendrobium Species
The stem of Dendrobium species has been used in traditionalChinesemedicine as a tonic and antipyretic since ancient daysfor treating human disorders However misidentificationand adulteration led to a loss of therapeutic potency andpotential intoxication For decades fast developingmoleculartechniques using DNA fingerprinting DNA sequencing andDNA microarray have been applied extensively to authen-ticate Chinese medicinal materials including various Den-drobium species [15] namely D aphyllum D candidum Dchrysanthum D densiflorum D huoshanense D gratiosissi-mumD longicornuD nobileD secundumD chrysotoxumD crystallinum D fimbriatum and others [16] In the earlyyears Williams and Harborne conducted a major surveyof leaf flavonoids at the Plant Science Laboratories of theUniversity of Reading in UK They conducted research on142 species belonging to 75 genera and found that the mostcommon constituents were flavone C-glycoside and flavonols[17] Since then about 100 compounds from 42 Dendrobiumspecies including 32 alkaloids 6 coumarins 15 bibenzyls 4fluorenones 22 phenanthrenes and 7 sesquiterpenoids con-stituents have been discussed and reviewed [18ndash31] (Table 1)To date various Dendrobium species are known to producea variety of secondary metabolites The biological activitiesand pharmacological actions of all of these compounds wereinvestigated in detail [32ndash39]
3 The Pharmacological Effects ofDendrobium Species
31 Antioxidant Activities Oxidative stress is induced byfree radicals that participate in a variety of chemical reac-tions with biomolecules leading to a pathological conditionReactive oxygen species (ROS) is one of the major freeradicals It mainly comprises superoxide (O
2
minus) and nitricoxide (NO) radicals including (1) catalase (CAT) (2) perox-idase (POD) (3) ascorbate peroxidase (APX) (4) 221015840-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) or ABTS (5)hydroxyl and (6) 11-diphenyl-2-picrylhydrazyl (DPPH) rad-icals During these processes it was found that the content ofmalondialdehyde (MDA) was increased
However cells possess two distinctive antioxidant defensesystems to counteract the damage including enzymatic anti-oxidants and nonenzymatic antioxidants Enzymatic antiox-idants comprise catalase superoxide dismutase (SOD) gluta-thione peroxidase (GPx) and others associated with en-zymesmolecules Nonenzymatic antioxidants include ascor-bic acid (vitamin C) 120572-tocopherol (vitamin E) and 120573-carotene which play a key role in removing reactive oxygenspecies
Oxidative stresses have been classified as exogenousfactors and endogenous factors Factors related to environ-mental stress includewatersoil drought stress chilling injurystress and soundwave stressTherewere studies on the effectsof cold storage on cut Dendrobium inflorescences showingthat chilling injury symptoms for floral buds and open flowers
ofDendrobium could lead to oxidative stress stemming fromthe production of reactive oxygen species In this process thedecrease of cellular functions by peroxidation of membranelipids when lipoxygenase enzymes are degraded in cellsHowever this physiological process in floral buds and openflowers is part of antioxidant defense systems which candecrease the content of oxygen free radicals and other oxygencompounds It indicates the protective cellular functions andantioxidant capacity This is an adaptive nature to ensuresome plants survive in the freezing winter [62]
In addition soundwave stress is one of the environmentalstresses similar to the low temperature stress Studies ofthe effects of sound wave stress on D candidum yieldeddata indicated it as a lipid peroxidation parameter whichcan regulate the levels of MDA Firstly the MDA content indifferent organs is increased and then declines afterwardswhich will then be followed by an increase again That givesa net increase of the level of MDA It was noted that theMDA level appears to be the lowest when the activities ofantioxidant enzymes are the highest However the levelsof MDA are yet to be fully understood We believe theantioxidant enzymes could protect plant cells from oxidativedamage in sound wave stress [63] However the correlationbetween themechanisms of antioxidant action and the soundwave stress and chilling injury stress has yet to be identified
Water deficit caused by soil drought is one of the mostfrequent environmental stresses The effects of exogenousdrought menace prompting further increases in the activityof ROS and decrease in themalondialdehyde (MDA) contentto prevent the breakage of DNA and protein degradationfrom doing damage to plant life [64] It is well knownthat nitric oxide (NO) is a ubiquitous signal moleculeinvolved in many life processes of plants seed germinationhypocotyl elongation leaf expansion root growth lateralroots initiation and apoptosis and so forth It is also involvedin multiple plant responses to environmental stress Datademonstrated that at lower concentrations of exogenous NOwith 50mmol Lminus1 SNP the activation of POD SOD and CATwas significantly increased and the MDA content decreasedwith 50Ml SNPNO could protect D huoshanense against theoxidative insult caused by a drought stress meanwhile a highlevel of RWCcan bemaintained Furthermore it suggests thatthe molecular messenger NO can trigger epigenetic variationand increase the demethylation ratio ofmethylated sites forDhuoshanense by using DNA analysis These results may implythat the expression of some genes is involved in the responseto drought stress triggered by NO [65]
Numerous Dendrobium species such as D nobile D den-neanum D huoshanense D chrysotoxum D moniliforme Dtosaense D linawianum D candidum D loddigesii and Dfimbriatum have polysaccharides as the active compoundsPolysaccharides play important roles in many biologicalprocesses and are used to treat various diseases [66 67]Polysaccharides isolated from D nobile D huoshanense Dchrysotoxum andD fimbriatum species manifest antioxidantand free radical scavenging activities D nobile polysac-charide displayed the highest scavenging activity towardhydroxyl ABTS and DPPH free radicals [40 68 69] How-everD fimbriatum polysaccharide has significant scavenging
Evidence-Based Complementary and Alternative Medicine 3
Table1Th
ecom
poun
dsof
vario
usDendrobium
species
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Da
moenu
mBibenzylsd
erivatives
Amoenylin
R 1=R 3
=MeR 2
=OHR
4=HR
5=OMe
1
23
456
AB
120572
120572998400
1998400
2998400
3998400
4998400
5998400
6998400
OR 1
R 2
OR 3
R 4
R 5[19
]
Isoamoenylin
R 1=R 3
=MeR 2
=OMeR 4
=OHR
5=H
Moscatilin
(analogues)
mdash341015840-D
ihydroxy-5-m
etho
xybibenzyl
mdashmdash
R 1=R 2
=R 4
=HR
3=MeR 5
=OH
mdashR 1
=R 3
=MeR 2
=OHR
4=HR
5=OMe
mdashR 1
=R 3
=MeR 2
=OAc
R4=HR
5=OMe
mdashR 1
=R 3
=MeR 2
=OMeR 4
=OAc
R5=H
mdashR 1
=Ac
R2=R 4
=HR
3=MeR 5
=OAc
mdashR 1
=R 3
=MeR 2
=R 5
=OHR
4=OMe
mdashR 1
=R 3
=MeR 2
=R 4
=OMeR 5
=OH
mdashR 1
=R 3
=MeR 2
=R 5
=OMeR 4
=OAc
mdashR 1
=R 2
=R 5
=HR
3=MeR 4
=OH
mdashR 1
=Ac
R2=R 5
=HR
3=MeR 4
=OAc
mdashR 1
=R 2
=R 3
=R 4
=HR
5=OH
Dc
andidu
mBibenzylsd
erivatives
DendrocandinC
((S)-344-tr
ihydroxy-5120572-dim
etho
xybibenzyl)
DendrocandinD
((S)-344-tr
ihydroxy-5-m
etho
xy-120572-ethoxybibenzyl)
DendrocandinE
(3344-te
trahydroxy-5-m
etho
xybibenzyl)
R 1=R 2
=R 5
=OHR
3=R 6
=OCH
3R 4
=H
R 1=R 2
=R 5
=OHR
3=OCH
3R 6
=OCH
2CH
3R 4
=H
R 1=R 2
=R 4
=R 5
=OHR
3=OCH
3R 6
=H
1
23
4
56
120572
120572998400
1998400
2998400
3998400
4998400
5998400
6998400
R 1
R 2
R 3
R 4
R 5
R 6
[20]
Amotin
(type
1sesquiterpenoids)
mdash
HO
OH
O
O
OO
Me
HH
[19]
4 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Amoenin(ty
pe2sesquiterpenoids)
mdash
HO HO
OH
O Me
H
OO
[19]
Flaccidin(910
-dihydroph
enanthropyran)
mdash
O
HO
OM
e
OH
[19]
Bibenzylsd
erivatives
44-Dihydroxy-35-dim
etho
xybibenzyl
34-Dihydroxy-54dimetho
xybibenzyl
3-O-M
ethylgigantol
Dendrop
heno
lGigantol
New
compo
unds
DendrocandinA
((R)-34-dihydroxy-54120572-tr
imetho
xybibenzyl)
R 2=R 5
=OHR
1=R 3
=OCH
3R 4
=R 6
=OH
R 1=R 2
=OHR
3=R 5
=OCH
3R 4
=R 6
=OH
R 1=OHR
3=R 4
=R 5
=OCH
3R 2
=R 6
=H
R 2=R 4
=R 5
=OHR
1=R 3
=OCH
3R 6
=H
R 1=R 5
=OHR
3=R 4
=OCH
3R 2
=R 6
=H
R 1=R 2
=OHR
3=R 5
=R 6
=OCH
3R 4
=H
1
23
4
56
120572
120572998400
1998400
2998400
3998400
4998400
5998400
6998400
R 1
R 2
R 3
R 4
R 5
R 6
[21]
DendrocandinB
(4-[2-[(2S3S)-3-(4-hydroxy-35-dimetho
xyph
enyl)-2-
hydroxym
ethyl-8
-metho
xy-23-
dihydrob
enzo[14]dioxin-6-yl]ethyl]-1-m
etho
xyl
benzene)
mdashOO
12
345
6
120572120572998400
1998400
2998400
3998400 4998400
5998400
6998400
1998400998400
2998400998400
3998400998400 4998400998400
5998400998400
6998400998400
7998400998400
8998400998400
9998400998400
H3CO
OCH
3
OCH
3
OCH
3
OH
OH
[21]
Evidence-Based Complementary and Alternative Medicine 5
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Da
phyllum
Aromaticcompo
unds
Flavanthrin
mdash
OCH
3
OCH
3
OH
OH
HO
HO
[22]
Coelonin
Iusia
nthridin
R 1=OHR
2=OMe
R 1=OMeR 2
=OH
HO
R 1
R 2
[22]
Moscatin
mdashO
H
OH
OM
e
[22]
Gigantol
Batatasin
III
R 1=R 3
=OMeR 2
=OH
R 1=OHR
2=HR
3=OMe
HO
R 1
R 2
R 3
[22]
6 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dibutylph
thalate
Diisob
utylph
thalate
R=CH
2CH
2CH
2CH
3R=CH
2CH(C
H3)
2
CCO
R
OR
O O
[22]
P-hydroxyphenylpropion
icmethyleste
rmdash
COO
Me
OH
[22]
Dc
ariniferum
Phenanthrenequ
inon
e
Dendron
one(5-hydroxy-7-metho
xy-910
-dihydro-14-
phenanthrenequ
inon
e)mdash
O
MeO
OH
2
34
110
a8a
87
65
4b4a
109
O
[23]
Dc
hrysotoxum
Aromaticorganicc
ompo
unds
(Fluorenon
es)
Dendrofl
orin
DenchrysanA
R 1=HR
2=OH
R 1=OHR
2=H
O
OCH
3
OH
OH
R 1R 2
[24]
145-tr
ihydroxy-7-m
etho
xy-9H-fluo
ren-9-on
emdash
OCH
3
OH
OH 4
56 7
89
123
8a9a4a
4b
OH
O
[24]
Evidence-Based Complementary and Alternative Medicine 7
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(Fluorenol)
(9R)-4metho
xy-9H-fluo
rene-259-tr
iol
R=H
OR
OR
RO
OM
e
[25]
Phenanthrene
27-dihydroxy-8m
etho
xyph
enanthro[45-bcd]pyran-
5(5H
)-on
emdash
O
O
OH
OH
OM
e
[25]
Dd
ensifl
orum
Bibenzyl
Densifl
orolA
mdash
O
MeO
O
OH
1
2
33
a4
5
6
77
a
1998400
2998400
1998400998400
2998400998400
3998400998400
49984009984005998400998400
6998400998400
7998400998400
[26]
Phenanthrenedion
e
Densifl
orolB
R=H
HO
1
2
3
4a 10
a8
a
4b
45
6
910
7
8
OM
e
O
O
R
[26]
8 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dendrofl
orin
R=OH
OH
OH
OR1
234
a
9a
8a
4b
45
6
9
7
8OM
e
[26]
Know
nas
oleano
licacid
andb-sitosterolcom
poun
ds
(A)D
engibsin
R=H
OH
OH
OR1
23
9a
8a
4a
4b
45
6
9
7
8OM
e
[26]
(B)C
yprip
edin
R=OMe
O
RO
HO
OM
e1
2
3
8a
4a
4b
45
6
910
10a
7
8
[26]
(C)G
igantol
(D)M
oscatilin
(E)T
ristin
R=OHR
=HR
=OMe
R=R=OMeR=OH
R=R=OHR
=H
R
OH
OM
e
R998400 R998400998400
[26]
(F)N
aringenin
(G)H
omoerio
dictyol
R=H
R=OMe
OOO
H
OH
HO
R[26]
Evidence-Based Complementary and Alternative Medicine 9
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(H)M
oscatin
mdashO
H
HO
OM
e
[26]
(I)2
6-dihydroxy-157-trim
etho
xyph
enanthrene
mdashO
H
HO
OM
e
OM
e
MeO
[26]
(J)4
7-dihydroxy-2-metho
xy-910
-dihydroph
enanthrene
mdash
OH
HO
OM
e[26]
(K)S
coparone
(L)S
copo
letin
(M)A
yapin
R=R=OMe
R=OMeR=OH
R+R=OCH
2OO
O
R R998400[26]
Dlongicornu
Mon
oaromatic
compo
unds
Bis(2-ethylhexyl)phthalate
Dibutylph
thalate
CH2C
H(C
2H5)(C
H2)
3CH
3(C
H2)
3CH
3
O O
OR
OR
[27]
Ethylh
aematom
mate
C 11H
12O
5
HO
CHO
OH
COO
C 2H5
CH3
[27]
10 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
MethylB
-orcinolcarboxylate
C 10H
12O
4
HO
OH
CH3
H3C
COO
CH3
[27]
N-D
ocosyltra
ns-fe
rulate
Ferulaldehyde
R=CO
OCH
2(CH
2)20CH
3R=CH
O
R
HH
OH
OCH
3
[27]
Dn
obile
Sesquiterpenes
(Dendron
obilins
A)
Cop
acam
phane-type
(1R2R
4S5S6S8S9R)-28-
Dihydroxycopacamph
an-15-on
eH H
H
H
H
O
HO
OH
(R)
11 109
7
15
1214
13
16 5
(R) (R)
(S)
(S)
(S)
(S)
[28]
Picrotoxane-type
(2b3b4b5b)-2411-Trihydroxy-picrotoxano
-3(15)-lacton
e
H
H H
H
H
O O
HO
OH
OH
1214
15
133
11
110
9
6[28]
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
2 Evidence-Based Complementary and Alternative Medicine
2 The Chemical Compounds ofDendrobium Species
The stem of Dendrobium species has been used in traditionalChinesemedicine as a tonic and antipyretic since ancient daysfor treating human disorders However misidentificationand adulteration led to a loss of therapeutic potency andpotential intoxication For decades fast developingmoleculartechniques using DNA fingerprinting DNA sequencing andDNA microarray have been applied extensively to authen-ticate Chinese medicinal materials including various Den-drobium species [15] namely D aphyllum D candidum Dchrysanthum D densiflorum D huoshanense D gratiosissi-mumD longicornuD nobileD secundumD chrysotoxumD crystallinum D fimbriatum and others [16] In the earlyyears Williams and Harborne conducted a major surveyof leaf flavonoids at the Plant Science Laboratories of theUniversity of Reading in UK They conducted research on142 species belonging to 75 genera and found that the mostcommon constituents were flavone C-glycoside and flavonols[17] Since then about 100 compounds from 42 Dendrobiumspecies including 32 alkaloids 6 coumarins 15 bibenzyls 4fluorenones 22 phenanthrenes and 7 sesquiterpenoids con-stituents have been discussed and reviewed [18ndash31] (Table 1)To date various Dendrobium species are known to producea variety of secondary metabolites The biological activitiesand pharmacological actions of all of these compounds wereinvestigated in detail [32ndash39]
3 The Pharmacological Effects ofDendrobium Species
31 Antioxidant Activities Oxidative stress is induced byfree radicals that participate in a variety of chemical reac-tions with biomolecules leading to a pathological conditionReactive oxygen species (ROS) is one of the major freeradicals It mainly comprises superoxide (O
2
minus) and nitricoxide (NO) radicals including (1) catalase (CAT) (2) perox-idase (POD) (3) ascorbate peroxidase (APX) (4) 221015840-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) or ABTS (5)hydroxyl and (6) 11-diphenyl-2-picrylhydrazyl (DPPH) rad-icals During these processes it was found that the content ofmalondialdehyde (MDA) was increased
However cells possess two distinctive antioxidant defensesystems to counteract the damage including enzymatic anti-oxidants and nonenzymatic antioxidants Enzymatic antiox-idants comprise catalase superoxide dismutase (SOD) gluta-thione peroxidase (GPx) and others associated with en-zymesmolecules Nonenzymatic antioxidants include ascor-bic acid (vitamin C) 120572-tocopherol (vitamin E) and 120573-carotene which play a key role in removing reactive oxygenspecies
Oxidative stresses have been classified as exogenousfactors and endogenous factors Factors related to environ-mental stress includewatersoil drought stress chilling injurystress and soundwave stressTherewere studies on the effectsof cold storage on cut Dendrobium inflorescences showingthat chilling injury symptoms for floral buds and open flowers
ofDendrobium could lead to oxidative stress stemming fromthe production of reactive oxygen species In this process thedecrease of cellular functions by peroxidation of membranelipids when lipoxygenase enzymes are degraded in cellsHowever this physiological process in floral buds and openflowers is part of antioxidant defense systems which candecrease the content of oxygen free radicals and other oxygencompounds It indicates the protective cellular functions andantioxidant capacity This is an adaptive nature to ensuresome plants survive in the freezing winter [62]
In addition soundwave stress is one of the environmentalstresses similar to the low temperature stress Studies ofthe effects of sound wave stress on D candidum yieldeddata indicated it as a lipid peroxidation parameter whichcan regulate the levels of MDA Firstly the MDA content indifferent organs is increased and then declines afterwardswhich will then be followed by an increase again That givesa net increase of the level of MDA It was noted that theMDA level appears to be the lowest when the activities ofantioxidant enzymes are the highest However the levelsof MDA are yet to be fully understood We believe theantioxidant enzymes could protect plant cells from oxidativedamage in sound wave stress [63] However the correlationbetween themechanisms of antioxidant action and the soundwave stress and chilling injury stress has yet to be identified
Water deficit caused by soil drought is one of the mostfrequent environmental stresses The effects of exogenousdrought menace prompting further increases in the activityof ROS and decrease in themalondialdehyde (MDA) contentto prevent the breakage of DNA and protein degradationfrom doing damage to plant life [64] It is well knownthat nitric oxide (NO) is a ubiquitous signal moleculeinvolved in many life processes of plants seed germinationhypocotyl elongation leaf expansion root growth lateralroots initiation and apoptosis and so forth It is also involvedin multiple plant responses to environmental stress Datademonstrated that at lower concentrations of exogenous NOwith 50mmol Lminus1 SNP the activation of POD SOD and CATwas significantly increased and the MDA content decreasedwith 50Ml SNPNO could protect D huoshanense against theoxidative insult caused by a drought stress meanwhile a highlevel of RWCcan bemaintained Furthermore it suggests thatthe molecular messenger NO can trigger epigenetic variationand increase the demethylation ratio ofmethylated sites forDhuoshanense by using DNA analysis These results may implythat the expression of some genes is involved in the responseto drought stress triggered by NO [65]
Numerous Dendrobium species such as D nobile D den-neanum D huoshanense D chrysotoxum D moniliforme Dtosaense D linawianum D candidum D loddigesii and Dfimbriatum have polysaccharides as the active compoundsPolysaccharides play important roles in many biologicalprocesses and are used to treat various diseases [66 67]Polysaccharides isolated from D nobile D huoshanense Dchrysotoxum andD fimbriatum species manifest antioxidantand free radical scavenging activities D nobile polysac-charide displayed the highest scavenging activity towardhydroxyl ABTS and DPPH free radicals [40 68 69] How-everD fimbriatum polysaccharide has significant scavenging
Evidence-Based Complementary and Alternative Medicine 3
Table1Th
ecom
poun
dsof
vario
usDendrobium
species
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Da
moenu
mBibenzylsd
erivatives
Amoenylin
R 1=R 3
=MeR 2
=OHR
4=HR
5=OMe
1
23
456
AB
120572
120572998400
1998400
2998400
3998400
4998400
5998400
6998400
OR 1
R 2
OR 3
R 4
R 5[19
]
Isoamoenylin
R 1=R 3
=MeR 2
=OMeR 4
=OHR
5=H
Moscatilin
(analogues)
mdash341015840-D
ihydroxy-5-m
etho
xybibenzyl
mdashmdash
R 1=R 2
=R 4
=HR
3=MeR 5
=OH
mdashR 1
=R 3
=MeR 2
=OHR
4=HR
5=OMe
mdashR 1
=R 3
=MeR 2
=OAc
R4=HR
5=OMe
mdashR 1
=R 3
=MeR 2
=OMeR 4
=OAc
R5=H
mdashR 1
=Ac
R2=R 4
=HR
3=MeR 5
=OAc
mdashR 1
=R 3
=MeR 2
=R 5
=OHR
4=OMe
mdashR 1
=R 3
=MeR 2
=R 4
=OMeR 5
=OH
mdashR 1
=R 3
=MeR 2
=R 5
=OMeR 4
=OAc
mdashR 1
=R 2
=R 5
=HR
3=MeR 4
=OH
mdashR 1
=Ac
R2=R 5
=HR
3=MeR 4
=OAc
mdashR 1
=R 2
=R 3
=R 4
=HR
5=OH
Dc
andidu
mBibenzylsd
erivatives
DendrocandinC
((S)-344-tr
ihydroxy-5120572-dim
etho
xybibenzyl)
DendrocandinD
((S)-344-tr
ihydroxy-5-m
etho
xy-120572-ethoxybibenzyl)
DendrocandinE
(3344-te
trahydroxy-5-m
etho
xybibenzyl)
R 1=R 2
=R 5
=OHR
3=R 6
=OCH
3R 4
=H
R 1=R 2
=R 5
=OHR
3=OCH
3R 6
=OCH
2CH
3R 4
=H
R 1=R 2
=R 4
=R 5
=OHR
3=OCH
3R 6
=H
1
23
4
56
120572
120572998400
1998400
2998400
3998400
4998400
5998400
6998400
R 1
R 2
R 3
R 4
R 5
R 6
[20]
Amotin
(type
1sesquiterpenoids)
mdash
HO
OH
O
O
OO
Me
HH
[19]
4 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Amoenin(ty
pe2sesquiterpenoids)
mdash
HO HO
OH
O Me
H
OO
[19]
Flaccidin(910
-dihydroph
enanthropyran)
mdash
O
HO
OM
e
OH
[19]
Bibenzylsd
erivatives
44-Dihydroxy-35-dim
etho
xybibenzyl
34-Dihydroxy-54dimetho
xybibenzyl
3-O-M
ethylgigantol
Dendrop
heno
lGigantol
New
compo
unds
DendrocandinA
((R)-34-dihydroxy-54120572-tr
imetho
xybibenzyl)
R 2=R 5
=OHR
1=R 3
=OCH
3R 4
=R 6
=OH
R 1=R 2
=OHR
3=R 5
=OCH
3R 4
=R 6
=OH
R 1=OHR
3=R 4
=R 5
=OCH
3R 2
=R 6
=H
R 2=R 4
=R 5
=OHR
1=R 3
=OCH
3R 6
=H
R 1=R 5
=OHR
3=R 4
=OCH
3R 2
=R 6
=H
R 1=R 2
=OHR
3=R 5
=R 6
=OCH
3R 4
=H
1
23
4
56
120572
120572998400
1998400
2998400
3998400
4998400
5998400
6998400
R 1
R 2
R 3
R 4
R 5
R 6
[21]
DendrocandinB
(4-[2-[(2S3S)-3-(4-hydroxy-35-dimetho
xyph
enyl)-2-
hydroxym
ethyl-8
-metho
xy-23-
dihydrob
enzo[14]dioxin-6-yl]ethyl]-1-m
etho
xyl
benzene)
mdashOO
12
345
6
120572120572998400
1998400
2998400
3998400 4998400
5998400
6998400
1998400998400
2998400998400
3998400998400 4998400998400
5998400998400
6998400998400
7998400998400
8998400998400
9998400998400
H3CO
OCH
3
OCH
3
OCH
3
OH
OH
[21]
Evidence-Based Complementary and Alternative Medicine 5
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Da
phyllum
Aromaticcompo
unds
Flavanthrin
mdash
OCH
3
OCH
3
OH
OH
HO
HO
[22]
Coelonin
Iusia
nthridin
R 1=OHR
2=OMe
R 1=OMeR 2
=OH
HO
R 1
R 2
[22]
Moscatin
mdashO
H
OH
OM
e
[22]
Gigantol
Batatasin
III
R 1=R 3
=OMeR 2
=OH
R 1=OHR
2=HR
3=OMe
HO
R 1
R 2
R 3
[22]
6 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dibutylph
thalate
Diisob
utylph
thalate
R=CH
2CH
2CH
2CH
3R=CH
2CH(C
H3)
2
CCO
R
OR
O O
[22]
P-hydroxyphenylpropion
icmethyleste
rmdash
COO
Me
OH
[22]
Dc
ariniferum
Phenanthrenequ
inon
e
Dendron
one(5-hydroxy-7-metho
xy-910
-dihydro-14-
phenanthrenequ
inon
e)mdash
O
MeO
OH
2
34
110
a8a
87
65
4b4a
109
O
[23]
Dc
hrysotoxum
Aromaticorganicc
ompo
unds
(Fluorenon
es)
Dendrofl
orin
DenchrysanA
R 1=HR
2=OH
R 1=OHR
2=H
O
OCH
3
OH
OH
R 1R 2
[24]
145-tr
ihydroxy-7-m
etho
xy-9H-fluo
ren-9-on
emdash
OCH
3
OH
OH 4
56 7
89
123
8a9a4a
4b
OH
O
[24]
Evidence-Based Complementary and Alternative Medicine 7
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(Fluorenol)
(9R)-4metho
xy-9H-fluo
rene-259-tr
iol
R=H
OR
OR
RO
OM
e
[25]
Phenanthrene
27-dihydroxy-8m
etho
xyph
enanthro[45-bcd]pyran-
5(5H
)-on
emdash
O
O
OH
OH
OM
e
[25]
Dd
ensifl
orum
Bibenzyl
Densifl
orolA
mdash
O
MeO
O
OH
1
2
33
a4
5
6
77
a
1998400
2998400
1998400998400
2998400998400
3998400998400
49984009984005998400998400
6998400998400
7998400998400
[26]
Phenanthrenedion
e
Densifl
orolB
R=H
HO
1
2
3
4a 10
a8
a
4b
45
6
910
7
8
OM
e
O
O
R
[26]
8 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dendrofl
orin
R=OH
OH
OH
OR1
234
a
9a
8a
4b
45
6
9
7
8OM
e
[26]
Know
nas
oleano
licacid
andb-sitosterolcom
poun
ds
(A)D
engibsin
R=H
OH
OH
OR1
23
9a
8a
4a
4b
45
6
9
7
8OM
e
[26]
(B)C
yprip
edin
R=OMe
O
RO
HO
OM
e1
2
3
8a
4a
4b
45
6
910
10a
7
8
[26]
(C)G
igantol
(D)M
oscatilin
(E)T
ristin
R=OHR
=HR
=OMe
R=R=OMeR=OH
R=R=OHR
=H
R
OH
OM
e
R998400 R998400998400
[26]
(F)N
aringenin
(G)H
omoerio
dictyol
R=H
R=OMe
OOO
H
OH
HO
R[26]
Evidence-Based Complementary and Alternative Medicine 9
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(H)M
oscatin
mdashO
H
HO
OM
e
[26]
(I)2
6-dihydroxy-157-trim
etho
xyph
enanthrene
mdashO
H
HO
OM
e
OM
e
MeO
[26]
(J)4
7-dihydroxy-2-metho
xy-910
-dihydroph
enanthrene
mdash
OH
HO
OM
e[26]
(K)S
coparone
(L)S
copo
letin
(M)A
yapin
R=R=OMe
R=OMeR=OH
R+R=OCH
2OO
O
R R998400[26]
Dlongicornu
Mon
oaromatic
compo
unds
Bis(2-ethylhexyl)phthalate
Dibutylph
thalate
CH2C
H(C
2H5)(C
H2)
3CH
3(C
H2)
3CH
3
O O
OR
OR
[27]
Ethylh
aematom
mate
C 11H
12O
5
HO
CHO
OH
COO
C 2H5
CH3
[27]
10 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
MethylB
-orcinolcarboxylate
C 10H
12O
4
HO
OH
CH3
H3C
COO
CH3
[27]
N-D
ocosyltra
ns-fe
rulate
Ferulaldehyde
R=CO
OCH
2(CH
2)20CH
3R=CH
O
R
HH
OH
OCH
3
[27]
Dn
obile
Sesquiterpenes
(Dendron
obilins
A)
Cop
acam
phane-type
(1R2R
4S5S6S8S9R)-28-
Dihydroxycopacamph
an-15-on
eH H
H
H
H
O
HO
OH
(R)
11 109
7
15
1214
13
16 5
(R) (R)
(S)
(S)
(S)
(S)
[28]
Picrotoxane-type
(2b3b4b5b)-2411-Trihydroxy-picrotoxano
-3(15)-lacton
e
H
H H
H
H
O O
HO
OH
OH
1214
15
133
11
110
9
6[28]
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
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[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 3
Table1Th
ecom
poun
dsof
vario
usDendrobium
species
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Da
moenu
mBibenzylsd
erivatives
Amoenylin
R 1=R 3
=MeR 2
=OHR
4=HR
5=OMe
1
23
456
AB
120572
120572998400
1998400
2998400
3998400
4998400
5998400
6998400
OR 1
R 2
OR 3
R 4
R 5[19
]
Isoamoenylin
R 1=R 3
=MeR 2
=OMeR 4
=OHR
5=H
Moscatilin
(analogues)
mdash341015840-D
ihydroxy-5-m
etho
xybibenzyl
mdashmdash
R 1=R 2
=R 4
=HR
3=MeR 5
=OH
mdashR 1
=R 3
=MeR 2
=OHR
4=HR
5=OMe
mdashR 1
=R 3
=MeR 2
=OAc
R4=HR
5=OMe
mdashR 1
=R 3
=MeR 2
=OMeR 4
=OAc
R5=H
mdashR 1
=Ac
R2=R 4
=HR
3=MeR 5
=OAc
mdashR 1
=R 3
=MeR 2
=R 5
=OHR
4=OMe
mdashR 1
=R 3
=MeR 2
=R 4
=OMeR 5
=OH
mdashR 1
=R 3
=MeR 2
=R 5
=OMeR 4
=OAc
mdashR 1
=R 2
=R 5
=HR
3=MeR 4
=OH
mdashR 1
=Ac
R2=R 5
=HR
3=MeR 4
=OAc
mdashR 1
=R 2
=R 3
=R 4
=HR
5=OH
Dc
andidu
mBibenzylsd
erivatives
DendrocandinC
((S)-344-tr
ihydroxy-5120572-dim
etho
xybibenzyl)
DendrocandinD
((S)-344-tr
ihydroxy-5-m
etho
xy-120572-ethoxybibenzyl)
DendrocandinE
(3344-te
trahydroxy-5-m
etho
xybibenzyl)
R 1=R 2
=R 5
=OHR
3=R 6
=OCH
3R 4
=H
R 1=R 2
=R 5
=OHR
3=OCH
3R 6
=OCH
2CH
3R 4
=H
R 1=R 2
=R 4
=R 5
=OHR
3=OCH
3R 6
=H
1
23
4
56
120572
120572998400
1998400
2998400
3998400
4998400
5998400
6998400
R 1
R 2
R 3
R 4
R 5
R 6
[20]
Amotin
(type
1sesquiterpenoids)
mdash
HO
OH
O
O
OO
Me
HH
[19]
4 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Amoenin(ty
pe2sesquiterpenoids)
mdash
HO HO
OH
O Me
H
OO
[19]
Flaccidin(910
-dihydroph
enanthropyran)
mdash
O
HO
OM
e
OH
[19]
Bibenzylsd
erivatives
44-Dihydroxy-35-dim
etho
xybibenzyl
34-Dihydroxy-54dimetho
xybibenzyl
3-O-M
ethylgigantol
Dendrop
heno
lGigantol
New
compo
unds
DendrocandinA
((R)-34-dihydroxy-54120572-tr
imetho
xybibenzyl)
R 2=R 5
=OHR
1=R 3
=OCH
3R 4
=R 6
=OH
R 1=R 2
=OHR
3=R 5
=OCH
3R 4
=R 6
=OH
R 1=OHR
3=R 4
=R 5
=OCH
3R 2
=R 6
=H
R 2=R 4
=R 5
=OHR
1=R 3
=OCH
3R 6
=H
R 1=R 5
=OHR
3=R 4
=OCH
3R 2
=R 6
=H
R 1=R 2
=OHR
3=R 5
=R 6
=OCH
3R 4
=H
1
23
4
56
120572
120572998400
1998400
2998400
3998400
4998400
5998400
6998400
R 1
R 2
R 3
R 4
R 5
R 6
[21]
DendrocandinB
(4-[2-[(2S3S)-3-(4-hydroxy-35-dimetho
xyph
enyl)-2-
hydroxym
ethyl-8
-metho
xy-23-
dihydrob
enzo[14]dioxin-6-yl]ethyl]-1-m
etho
xyl
benzene)
mdashOO
12
345
6
120572120572998400
1998400
2998400
3998400 4998400
5998400
6998400
1998400998400
2998400998400
3998400998400 4998400998400
5998400998400
6998400998400
7998400998400
8998400998400
9998400998400
H3CO
OCH
3
OCH
3
OCH
3
OH
OH
[21]
Evidence-Based Complementary and Alternative Medicine 5
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Da
phyllum
Aromaticcompo
unds
Flavanthrin
mdash
OCH
3
OCH
3
OH
OH
HO
HO
[22]
Coelonin
Iusia
nthridin
R 1=OHR
2=OMe
R 1=OMeR 2
=OH
HO
R 1
R 2
[22]
Moscatin
mdashO
H
OH
OM
e
[22]
Gigantol
Batatasin
III
R 1=R 3
=OMeR 2
=OH
R 1=OHR
2=HR
3=OMe
HO
R 1
R 2
R 3
[22]
6 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dibutylph
thalate
Diisob
utylph
thalate
R=CH
2CH
2CH
2CH
3R=CH
2CH(C
H3)
2
CCO
R
OR
O O
[22]
P-hydroxyphenylpropion
icmethyleste
rmdash
COO
Me
OH
[22]
Dc
ariniferum
Phenanthrenequ
inon
e
Dendron
one(5-hydroxy-7-metho
xy-910
-dihydro-14-
phenanthrenequ
inon
e)mdash
O
MeO
OH
2
34
110
a8a
87
65
4b4a
109
O
[23]
Dc
hrysotoxum
Aromaticorganicc
ompo
unds
(Fluorenon
es)
Dendrofl
orin
DenchrysanA
R 1=HR
2=OH
R 1=OHR
2=H
O
OCH
3
OH
OH
R 1R 2
[24]
145-tr
ihydroxy-7-m
etho
xy-9H-fluo
ren-9-on
emdash
OCH
3
OH
OH 4
56 7
89
123
8a9a4a
4b
OH
O
[24]
Evidence-Based Complementary and Alternative Medicine 7
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(Fluorenol)
(9R)-4metho
xy-9H-fluo
rene-259-tr
iol
R=H
OR
OR
RO
OM
e
[25]
Phenanthrene
27-dihydroxy-8m
etho
xyph
enanthro[45-bcd]pyran-
5(5H
)-on
emdash
O
O
OH
OH
OM
e
[25]
Dd
ensifl
orum
Bibenzyl
Densifl
orolA
mdash
O
MeO
O
OH
1
2
33
a4
5
6
77
a
1998400
2998400
1998400998400
2998400998400
3998400998400
49984009984005998400998400
6998400998400
7998400998400
[26]
Phenanthrenedion
e
Densifl
orolB
R=H
HO
1
2
3
4a 10
a8
a
4b
45
6
910
7
8
OM
e
O
O
R
[26]
8 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dendrofl
orin
R=OH
OH
OH
OR1
234
a
9a
8a
4b
45
6
9
7
8OM
e
[26]
Know
nas
oleano
licacid
andb-sitosterolcom
poun
ds
(A)D
engibsin
R=H
OH
OH
OR1
23
9a
8a
4a
4b
45
6
9
7
8OM
e
[26]
(B)C
yprip
edin
R=OMe
O
RO
HO
OM
e1
2
3
8a
4a
4b
45
6
910
10a
7
8
[26]
(C)G
igantol
(D)M
oscatilin
(E)T
ristin
R=OHR
=HR
=OMe
R=R=OMeR=OH
R=R=OHR
=H
R
OH
OM
e
R998400 R998400998400
[26]
(F)N
aringenin
(G)H
omoerio
dictyol
R=H
R=OMe
OOO
H
OH
HO
R[26]
Evidence-Based Complementary and Alternative Medicine 9
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(H)M
oscatin
mdashO
H
HO
OM
e
[26]
(I)2
6-dihydroxy-157-trim
etho
xyph
enanthrene
mdashO
H
HO
OM
e
OM
e
MeO
[26]
(J)4
7-dihydroxy-2-metho
xy-910
-dihydroph
enanthrene
mdash
OH
HO
OM
e[26]
(K)S
coparone
(L)S
copo
letin
(M)A
yapin
R=R=OMe
R=OMeR=OH
R+R=OCH
2OO
O
R R998400[26]
Dlongicornu
Mon
oaromatic
compo
unds
Bis(2-ethylhexyl)phthalate
Dibutylph
thalate
CH2C
H(C
2H5)(C
H2)
3CH
3(C
H2)
3CH
3
O O
OR
OR
[27]
Ethylh
aematom
mate
C 11H
12O
5
HO
CHO
OH
COO
C 2H5
CH3
[27]
10 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
MethylB
-orcinolcarboxylate
C 10H
12O
4
HO
OH
CH3
H3C
COO
CH3
[27]
N-D
ocosyltra
ns-fe
rulate
Ferulaldehyde
R=CO
OCH
2(CH
2)20CH
3R=CH
O
R
HH
OH
OCH
3
[27]
Dn
obile
Sesquiterpenes
(Dendron
obilins
A)
Cop
acam
phane-type
(1R2R
4S5S6S8S9R)-28-
Dihydroxycopacamph
an-15-on
eH H
H
H
H
O
HO
OH
(R)
11 109
7
15
1214
13
16 5
(R) (R)
(S)
(S)
(S)
(S)
[28]
Picrotoxane-type
(2b3b4b5b)-2411-Trihydroxy-picrotoxano
-3(15)-lacton
e
H
H H
H
H
O O
HO
OH
OH
1214
15
133
11
110
9
6[28]
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
[1] R L Dressler Phylogeny and Classification of the Orchid FamilyCambridge University Press New York NY USA 1993
[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Disease Markers
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OncologyJournal of
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Oxidative Medicine and Cellular Longevity
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Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
4 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Amoenin(ty
pe2sesquiterpenoids)
mdash
HO HO
OH
O Me
H
OO
[19]
Flaccidin(910
-dihydroph
enanthropyran)
mdash
O
HO
OM
e
OH
[19]
Bibenzylsd
erivatives
44-Dihydroxy-35-dim
etho
xybibenzyl
34-Dihydroxy-54dimetho
xybibenzyl
3-O-M
ethylgigantol
Dendrop
heno
lGigantol
New
compo
unds
DendrocandinA
((R)-34-dihydroxy-54120572-tr
imetho
xybibenzyl)
R 2=R 5
=OHR
1=R 3
=OCH
3R 4
=R 6
=OH
R 1=R 2
=OHR
3=R 5
=OCH
3R 4
=R 6
=OH
R 1=OHR
3=R 4
=R 5
=OCH
3R 2
=R 6
=H
R 2=R 4
=R 5
=OHR
1=R 3
=OCH
3R 6
=H
R 1=R 5
=OHR
3=R 4
=OCH
3R 2
=R 6
=H
R 1=R 2
=OHR
3=R 5
=R 6
=OCH
3R 4
=H
1
23
4
56
120572
120572998400
1998400
2998400
3998400
4998400
5998400
6998400
R 1
R 2
R 3
R 4
R 5
R 6
[21]
DendrocandinB
(4-[2-[(2S3S)-3-(4-hydroxy-35-dimetho
xyph
enyl)-2-
hydroxym
ethyl-8
-metho
xy-23-
dihydrob
enzo[14]dioxin-6-yl]ethyl]-1-m
etho
xyl
benzene)
mdashOO
12
345
6
120572120572998400
1998400
2998400
3998400 4998400
5998400
6998400
1998400998400
2998400998400
3998400998400 4998400998400
5998400998400
6998400998400
7998400998400
8998400998400
9998400998400
H3CO
OCH
3
OCH
3
OCH
3
OH
OH
[21]
Evidence-Based Complementary and Alternative Medicine 5
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Da
phyllum
Aromaticcompo
unds
Flavanthrin
mdash
OCH
3
OCH
3
OH
OH
HO
HO
[22]
Coelonin
Iusia
nthridin
R 1=OHR
2=OMe
R 1=OMeR 2
=OH
HO
R 1
R 2
[22]
Moscatin
mdashO
H
OH
OM
e
[22]
Gigantol
Batatasin
III
R 1=R 3
=OMeR 2
=OH
R 1=OHR
2=HR
3=OMe
HO
R 1
R 2
R 3
[22]
6 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dibutylph
thalate
Diisob
utylph
thalate
R=CH
2CH
2CH
2CH
3R=CH
2CH(C
H3)
2
CCO
R
OR
O O
[22]
P-hydroxyphenylpropion
icmethyleste
rmdash
COO
Me
OH
[22]
Dc
ariniferum
Phenanthrenequ
inon
e
Dendron
one(5-hydroxy-7-metho
xy-910
-dihydro-14-
phenanthrenequ
inon
e)mdash
O
MeO
OH
2
34
110
a8a
87
65
4b4a
109
O
[23]
Dc
hrysotoxum
Aromaticorganicc
ompo
unds
(Fluorenon
es)
Dendrofl
orin
DenchrysanA
R 1=HR
2=OH
R 1=OHR
2=H
O
OCH
3
OH
OH
R 1R 2
[24]
145-tr
ihydroxy-7-m
etho
xy-9H-fluo
ren-9-on
emdash
OCH
3
OH
OH 4
56 7
89
123
8a9a4a
4b
OH
O
[24]
Evidence-Based Complementary and Alternative Medicine 7
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(Fluorenol)
(9R)-4metho
xy-9H-fluo
rene-259-tr
iol
R=H
OR
OR
RO
OM
e
[25]
Phenanthrene
27-dihydroxy-8m
etho
xyph
enanthro[45-bcd]pyran-
5(5H
)-on
emdash
O
O
OH
OH
OM
e
[25]
Dd
ensifl
orum
Bibenzyl
Densifl
orolA
mdash
O
MeO
O
OH
1
2
33
a4
5
6
77
a
1998400
2998400
1998400998400
2998400998400
3998400998400
49984009984005998400998400
6998400998400
7998400998400
[26]
Phenanthrenedion
e
Densifl
orolB
R=H
HO
1
2
3
4a 10
a8
a
4b
45
6
910
7
8
OM
e
O
O
R
[26]
8 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dendrofl
orin
R=OH
OH
OH
OR1
234
a
9a
8a
4b
45
6
9
7
8OM
e
[26]
Know
nas
oleano
licacid
andb-sitosterolcom
poun
ds
(A)D
engibsin
R=H
OH
OH
OR1
23
9a
8a
4a
4b
45
6
9
7
8OM
e
[26]
(B)C
yprip
edin
R=OMe
O
RO
HO
OM
e1
2
3
8a
4a
4b
45
6
910
10a
7
8
[26]
(C)G
igantol
(D)M
oscatilin
(E)T
ristin
R=OHR
=HR
=OMe
R=R=OMeR=OH
R=R=OHR
=H
R
OH
OM
e
R998400 R998400998400
[26]
(F)N
aringenin
(G)H
omoerio
dictyol
R=H
R=OMe
OOO
H
OH
HO
R[26]
Evidence-Based Complementary and Alternative Medicine 9
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(H)M
oscatin
mdashO
H
HO
OM
e
[26]
(I)2
6-dihydroxy-157-trim
etho
xyph
enanthrene
mdashO
H
HO
OM
e
OM
e
MeO
[26]
(J)4
7-dihydroxy-2-metho
xy-910
-dihydroph
enanthrene
mdash
OH
HO
OM
e[26]
(K)S
coparone
(L)S
copo
letin
(M)A
yapin
R=R=OMe
R=OMeR=OH
R+R=OCH
2OO
O
R R998400[26]
Dlongicornu
Mon
oaromatic
compo
unds
Bis(2-ethylhexyl)phthalate
Dibutylph
thalate
CH2C
H(C
2H5)(C
H2)
3CH
3(C
H2)
3CH
3
O O
OR
OR
[27]
Ethylh
aematom
mate
C 11H
12O
5
HO
CHO
OH
COO
C 2H5
CH3
[27]
10 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
MethylB
-orcinolcarboxylate
C 10H
12O
4
HO
OH
CH3
H3C
COO
CH3
[27]
N-D
ocosyltra
ns-fe
rulate
Ferulaldehyde
R=CO
OCH
2(CH
2)20CH
3R=CH
O
R
HH
OH
OCH
3
[27]
Dn
obile
Sesquiterpenes
(Dendron
obilins
A)
Cop
acam
phane-type
(1R2R
4S5S6S8S9R)-28-
Dihydroxycopacamph
an-15-on
eH H
H
H
H
O
HO
OH
(R)
11 109
7
15
1214
13
16 5
(R) (R)
(S)
(S)
(S)
(S)
[28]
Picrotoxane-type
(2b3b4b5b)-2411-Trihydroxy-picrotoxano
-3(15)-lacton
e
H
H H
H
H
O O
HO
OH
OH
1214
15
133
11
110
9
6[28]
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
[1] R L Dressler Phylogeny and Classification of the Orchid FamilyCambridge University Press New York NY USA 1993
[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 5
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Da
phyllum
Aromaticcompo
unds
Flavanthrin
mdash
OCH
3
OCH
3
OH
OH
HO
HO
[22]
Coelonin
Iusia
nthridin
R 1=OHR
2=OMe
R 1=OMeR 2
=OH
HO
R 1
R 2
[22]
Moscatin
mdashO
H
OH
OM
e
[22]
Gigantol
Batatasin
III
R 1=R 3
=OMeR 2
=OH
R 1=OHR
2=HR
3=OMe
HO
R 1
R 2
R 3
[22]
6 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dibutylph
thalate
Diisob
utylph
thalate
R=CH
2CH
2CH
2CH
3R=CH
2CH(C
H3)
2
CCO
R
OR
O O
[22]
P-hydroxyphenylpropion
icmethyleste
rmdash
COO
Me
OH
[22]
Dc
ariniferum
Phenanthrenequ
inon
e
Dendron
one(5-hydroxy-7-metho
xy-910
-dihydro-14-
phenanthrenequ
inon
e)mdash
O
MeO
OH
2
34
110
a8a
87
65
4b4a
109
O
[23]
Dc
hrysotoxum
Aromaticorganicc
ompo
unds
(Fluorenon
es)
Dendrofl
orin
DenchrysanA
R 1=HR
2=OH
R 1=OHR
2=H
O
OCH
3
OH
OH
R 1R 2
[24]
145-tr
ihydroxy-7-m
etho
xy-9H-fluo
ren-9-on
emdash
OCH
3
OH
OH 4
56 7
89
123
8a9a4a
4b
OH
O
[24]
Evidence-Based Complementary and Alternative Medicine 7
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(Fluorenol)
(9R)-4metho
xy-9H-fluo
rene-259-tr
iol
R=H
OR
OR
RO
OM
e
[25]
Phenanthrene
27-dihydroxy-8m
etho
xyph
enanthro[45-bcd]pyran-
5(5H
)-on
emdash
O
O
OH
OH
OM
e
[25]
Dd
ensifl
orum
Bibenzyl
Densifl
orolA
mdash
O
MeO
O
OH
1
2
33
a4
5
6
77
a
1998400
2998400
1998400998400
2998400998400
3998400998400
49984009984005998400998400
6998400998400
7998400998400
[26]
Phenanthrenedion
e
Densifl
orolB
R=H
HO
1
2
3
4a 10
a8
a
4b
45
6
910
7
8
OM
e
O
O
R
[26]
8 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dendrofl
orin
R=OH
OH
OH
OR1
234
a
9a
8a
4b
45
6
9
7
8OM
e
[26]
Know
nas
oleano
licacid
andb-sitosterolcom
poun
ds
(A)D
engibsin
R=H
OH
OH
OR1
23
9a
8a
4a
4b
45
6
9
7
8OM
e
[26]
(B)C
yprip
edin
R=OMe
O
RO
HO
OM
e1
2
3
8a
4a
4b
45
6
910
10a
7
8
[26]
(C)G
igantol
(D)M
oscatilin
(E)T
ristin
R=OHR
=HR
=OMe
R=R=OMeR=OH
R=R=OHR
=H
R
OH
OM
e
R998400 R998400998400
[26]
(F)N
aringenin
(G)H
omoerio
dictyol
R=H
R=OMe
OOO
H
OH
HO
R[26]
Evidence-Based Complementary and Alternative Medicine 9
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(H)M
oscatin
mdashO
H
HO
OM
e
[26]
(I)2
6-dihydroxy-157-trim
etho
xyph
enanthrene
mdashO
H
HO
OM
e
OM
e
MeO
[26]
(J)4
7-dihydroxy-2-metho
xy-910
-dihydroph
enanthrene
mdash
OH
HO
OM
e[26]
(K)S
coparone
(L)S
copo
letin
(M)A
yapin
R=R=OMe
R=OMeR=OH
R+R=OCH
2OO
O
R R998400[26]
Dlongicornu
Mon
oaromatic
compo
unds
Bis(2-ethylhexyl)phthalate
Dibutylph
thalate
CH2C
H(C
2H5)(C
H2)
3CH
3(C
H2)
3CH
3
O O
OR
OR
[27]
Ethylh
aematom
mate
C 11H
12O
5
HO
CHO
OH
COO
C 2H5
CH3
[27]
10 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
MethylB
-orcinolcarboxylate
C 10H
12O
4
HO
OH
CH3
H3C
COO
CH3
[27]
N-D
ocosyltra
ns-fe
rulate
Ferulaldehyde
R=CO
OCH
2(CH
2)20CH
3R=CH
O
R
HH
OH
OCH
3
[27]
Dn
obile
Sesquiterpenes
(Dendron
obilins
A)
Cop
acam
phane-type
(1R2R
4S5S6S8S9R)-28-
Dihydroxycopacamph
an-15-on
eH H
H
H
H
O
HO
OH
(R)
11 109
7
15
1214
13
16 5
(R) (R)
(S)
(S)
(S)
(S)
[28]
Picrotoxane-type
(2b3b4b5b)-2411-Trihydroxy-picrotoxano
-3(15)-lacton
e
H
H H
H
H
O O
HO
OH
OH
1214
15
133
11
110
9
6[28]
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Disease Markers
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OncologyJournal of
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Oxidative Medicine and Cellular Longevity
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PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
6 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dibutylph
thalate
Diisob
utylph
thalate
R=CH
2CH
2CH
2CH
3R=CH
2CH(C
H3)
2
CCO
R
OR
O O
[22]
P-hydroxyphenylpropion
icmethyleste
rmdash
COO
Me
OH
[22]
Dc
ariniferum
Phenanthrenequ
inon
e
Dendron
one(5-hydroxy-7-metho
xy-910
-dihydro-14-
phenanthrenequ
inon
e)mdash
O
MeO
OH
2
34
110
a8a
87
65
4b4a
109
O
[23]
Dc
hrysotoxum
Aromaticorganicc
ompo
unds
(Fluorenon
es)
Dendrofl
orin
DenchrysanA
R 1=HR
2=OH
R 1=OHR
2=H
O
OCH
3
OH
OH
R 1R 2
[24]
145-tr
ihydroxy-7-m
etho
xy-9H-fluo
ren-9-on
emdash
OCH
3
OH
OH 4
56 7
89
123
8a9a4a
4b
OH
O
[24]
Evidence-Based Complementary and Alternative Medicine 7
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(Fluorenol)
(9R)-4metho
xy-9H-fluo
rene-259-tr
iol
R=H
OR
OR
RO
OM
e
[25]
Phenanthrene
27-dihydroxy-8m
etho
xyph
enanthro[45-bcd]pyran-
5(5H
)-on
emdash
O
O
OH
OH
OM
e
[25]
Dd
ensifl
orum
Bibenzyl
Densifl
orolA
mdash
O
MeO
O
OH
1
2
33
a4
5
6
77
a
1998400
2998400
1998400998400
2998400998400
3998400998400
49984009984005998400998400
6998400998400
7998400998400
[26]
Phenanthrenedion
e
Densifl
orolB
R=H
HO
1
2
3
4a 10
a8
a
4b
45
6
910
7
8
OM
e
O
O
R
[26]
8 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dendrofl
orin
R=OH
OH
OH
OR1
234
a
9a
8a
4b
45
6
9
7
8OM
e
[26]
Know
nas
oleano
licacid
andb-sitosterolcom
poun
ds
(A)D
engibsin
R=H
OH
OH
OR1
23
9a
8a
4a
4b
45
6
9
7
8OM
e
[26]
(B)C
yprip
edin
R=OMe
O
RO
HO
OM
e1
2
3
8a
4a
4b
45
6
910
10a
7
8
[26]
(C)G
igantol
(D)M
oscatilin
(E)T
ristin
R=OHR
=HR
=OMe
R=R=OMeR=OH
R=R=OHR
=H
R
OH
OM
e
R998400 R998400998400
[26]
(F)N
aringenin
(G)H
omoerio
dictyol
R=H
R=OMe
OOO
H
OH
HO
R[26]
Evidence-Based Complementary and Alternative Medicine 9
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(H)M
oscatin
mdashO
H
HO
OM
e
[26]
(I)2
6-dihydroxy-157-trim
etho
xyph
enanthrene
mdashO
H
HO
OM
e
OM
e
MeO
[26]
(J)4
7-dihydroxy-2-metho
xy-910
-dihydroph
enanthrene
mdash
OH
HO
OM
e[26]
(K)S
coparone
(L)S
copo
letin
(M)A
yapin
R=R=OMe
R=OMeR=OH
R+R=OCH
2OO
O
R R998400[26]
Dlongicornu
Mon
oaromatic
compo
unds
Bis(2-ethylhexyl)phthalate
Dibutylph
thalate
CH2C
H(C
2H5)(C
H2)
3CH
3(C
H2)
3CH
3
O O
OR
OR
[27]
Ethylh
aematom
mate
C 11H
12O
5
HO
CHO
OH
COO
C 2H5
CH3
[27]
10 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
MethylB
-orcinolcarboxylate
C 10H
12O
4
HO
OH
CH3
H3C
COO
CH3
[27]
N-D
ocosyltra
ns-fe
rulate
Ferulaldehyde
R=CO
OCH
2(CH
2)20CH
3R=CH
O
R
HH
OH
OCH
3
[27]
Dn
obile
Sesquiterpenes
(Dendron
obilins
A)
Cop
acam
phane-type
(1R2R
4S5S6S8S9R)-28-
Dihydroxycopacamph
an-15-on
eH H
H
H
H
O
HO
OH
(R)
11 109
7
15
1214
13
16 5
(R) (R)
(S)
(S)
(S)
(S)
[28]
Picrotoxane-type
(2b3b4b5b)-2411-Trihydroxy-picrotoxano
-3(15)-lacton
e
H
H H
H
H
O O
HO
OH
OH
1214
15
133
11
110
9
6[28]
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
[1] R L Dressler Phylogeny and Classification of the Orchid FamilyCambridge University Press New York NY USA 1993
[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Diabetes ResearchJournal of
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 7
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(Fluorenol)
(9R)-4metho
xy-9H-fluo
rene-259-tr
iol
R=H
OR
OR
RO
OM
e
[25]
Phenanthrene
27-dihydroxy-8m
etho
xyph
enanthro[45-bcd]pyran-
5(5H
)-on
emdash
O
O
OH
OH
OM
e
[25]
Dd
ensifl
orum
Bibenzyl
Densifl
orolA
mdash
O
MeO
O
OH
1
2
33
a4
5
6
77
a
1998400
2998400
1998400998400
2998400998400
3998400998400
49984009984005998400998400
6998400998400
7998400998400
[26]
Phenanthrenedion
e
Densifl
orolB
R=H
HO
1
2
3
4a 10
a8
a
4b
45
6
910
7
8
OM
e
O
O
R
[26]
8 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dendrofl
orin
R=OH
OH
OH
OR1
234
a
9a
8a
4b
45
6
9
7
8OM
e
[26]
Know
nas
oleano
licacid
andb-sitosterolcom
poun
ds
(A)D
engibsin
R=H
OH
OH
OR1
23
9a
8a
4a
4b
45
6
9
7
8OM
e
[26]
(B)C
yprip
edin
R=OMe
O
RO
HO
OM
e1
2
3
8a
4a
4b
45
6
910
10a
7
8
[26]
(C)G
igantol
(D)M
oscatilin
(E)T
ristin
R=OHR
=HR
=OMe
R=R=OMeR=OH
R=R=OHR
=H
R
OH
OM
e
R998400 R998400998400
[26]
(F)N
aringenin
(G)H
omoerio
dictyol
R=H
R=OMe
OOO
H
OH
HO
R[26]
Evidence-Based Complementary and Alternative Medicine 9
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(H)M
oscatin
mdashO
H
HO
OM
e
[26]
(I)2
6-dihydroxy-157-trim
etho
xyph
enanthrene
mdashO
H
HO
OM
e
OM
e
MeO
[26]
(J)4
7-dihydroxy-2-metho
xy-910
-dihydroph
enanthrene
mdash
OH
HO
OM
e[26]
(K)S
coparone
(L)S
copo
letin
(M)A
yapin
R=R=OMe
R=OMeR=OH
R+R=OCH
2OO
O
R R998400[26]
Dlongicornu
Mon
oaromatic
compo
unds
Bis(2-ethylhexyl)phthalate
Dibutylph
thalate
CH2C
H(C
2H5)(C
H2)
3CH
3(C
H2)
3CH
3
O O
OR
OR
[27]
Ethylh
aematom
mate
C 11H
12O
5
HO
CHO
OH
COO
C 2H5
CH3
[27]
10 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
MethylB
-orcinolcarboxylate
C 10H
12O
4
HO
OH
CH3
H3C
COO
CH3
[27]
N-D
ocosyltra
ns-fe
rulate
Ferulaldehyde
R=CO
OCH
2(CH
2)20CH
3R=CH
O
R
HH
OH
OCH
3
[27]
Dn
obile
Sesquiterpenes
(Dendron
obilins
A)
Cop
acam
phane-type
(1R2R
4S5S6S8S9R)-28-
Dihydroxycopacamph
an-15-on
eH H
H
H
H
O
HO
OH
(R)
11 109
7
15
1214
13
16 5
(R) (R)
(S)
(S)
(S)
(S)
[28]
Picrotoxane-type
(2b3b4b5b)-2411-Trihydroxy-picrotoxano
-3(15)-lacton
e
H
H H
H
H
O O
HO
OH
OH
1214
15
133
11
110
9
6[28]
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
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Computational and Mathematical Methods in Medicine
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
8 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Dendrofl
orin
R=OH
OH
OH
OR1
234
a
9a
8a
4b
45
6
9
7
8OM
e
[26]
Know
nas
oleano
licacid
andb-sitosterolcom
poun
ds
(A)D
engibsin
R=H
OH
OH
OR1
23
9a
8a
4a
4b
45
6
9
7
8OM
e
[26]
(B)C
yprip
edin
R=OMe
O
RO
HO
OM
e1
2
3
8a
4a
4b
45
6
910
10a
7
8
[26]
(C)G
igantol
(D)M
oscatilin
(E)T
ristin
R=OHR
=HR
=OMe
R=R=OMeR=OH
R=R=OHR
=H
R
OH
OM
e
R998400 R998400998400
[26]
(F)N
aringenin
(G)H
omoerio
dictyol
R=H
R=OMe
OOO
H
OH
HO
R[26]
Evidence-Based Complementary and Alternative Medicine 9
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(H)M
oscatin
mdashO
H
HO
OM
e
[26]
(I)2
6-dihydroxy-157-trim
etho
xyph
enanthrene
mdashO
H
HO
OM
e
OM
e
MeO
[26]
(J)4
7-dihydroxy-2-metho
xy-910
-dihydroph
enanthrene
mdash
OH
HO
OM
e[26]
(K)S
coparone
(L)S
copo
letin
(M)A
yapin
R=R=OMe
R=OMeR=OH
R+R=OCH
2OO
O
R R998400[26]
Dlongicornu
Mon
oaromatic
compo
unds
Bis(2-ethylhexyl)phthalate
Dibutylph
thalate
CH2C
H(C
2H5)(C
H2)
3CH
3(C
H2)
3CH
3
O O
OR
OR
[27]
Ethylh
aematom
mate
C 11H
12O
5
HO
CHO
OH
COO
C 2H5
CH3
[27]
10 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
MethylB
-orcinolcarboxylate
C 10H
12O
4
HO
OH
CH3
H3C
COO
CH3
[27]
N-D
ocosyltra
ns-fe
rulate
Ferulaldehyde
R=CO
OCH
2(CH
2)20CH
3R=CH
O
R
HH
OH
OCH
3
[27]
Dn
obile
Sesquiterpenes
(Dendron
obilins
A)
Cop
acam
phane-type
(1R2R
4S5S6S8S9R)-28-
Dihydroxycopacamph
an-15-on
eH H
H
H
H
O
HO
OH
(R)
11 109
7
15
1214
13
16 5
(R) (R)
(S)
(S)
(S)
(S)
[28]
Picrotoxane-type
(2b3b4b5b)-2411-Trihydroxy-picrotoxano
-3(15)-lacton
e
H
H H
H
H
O O
HO
OH
OH
1214
15
133
11
110
9
6[28]
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
[1] R L Dressler Phylogeny and Classification of the Orchid FamilyCambridge University Press New York NY USA 1993
[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 9
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
(H)M
oscatin
mdashO
H
HO
OM
e
[26]
(I)2
6-dihydroxy-157-trim
etho
xyph
enanthrene
mdashO
H
HO
OM
e
OM
e
MeO
[26]
(J)4
7-dihydroxy-2-metho
xy-910
-dihydroph
enanthrene
mdash
OH
HO
OM
e[26]
(K)S
coparone
(L)S
copo
letin
(M)A
yapin
R=R=OMe
R=OMeR=OH
R+R=OCH
2OO
O
R R998400[26]
Dlongicornu
Mon
oaromatic
compo
unds
Bis(2-ethylhexyl)phthalate
Dibutylph
thalate
CH2C
H(C
2H5)(C
H2)
3CH
3(C
H2)
3CH
3
O O
OR
OR
[27]
Ethylh
aematom
mate
C 11H
12O
5
HO
CHO
OH
COO
C 2H5
CH3
[27]
10 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
MethylB
-orcinolcarboxylate
C 10H
12O
4
HO
OH
CH3
H3C
COO
CH3
[27]
N-D
ocosyltra
ns-fe
rulate
Ferulaldehyde
R=CO
OCH
2(CH
2)20CH
3R=CH
O
R
HH
OH
OCH
3
[27]
Dn
obile
Sesquiterpenes
(Dendron
obilins
A)
Cop
acam
phane-type
(1R2R
4S5S6S8S9R)-28-
Dihydroxycopacamph
an-15-on
eH H
H
H
H
O
HO
OH
(R)
11 109
7
15
1214
13
16 5
(R) (R)
(S)
(S)
(S)
(S)
[28]
Picrotoxane-type
(2b3b4b5b)-2411-Trihydroxy-picrotoxano
-3(15)-lacton
e
H
H H
H
H
O O
HO
OH
OH
1214
15
133
11
110
9
6[28]
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
10 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
MethylB
-orcinolcarboxylate
C 10H
12O
4
HO
OH
CH3
H3C
COO
CH3
[27]
N-D
ocosyltra
ns-fe
rulate
Ferulaldehyde
R=CO
OCH
2(CH
2)20CH
3R=CH
O
R
HH
OH
OCH
3
[27]
Dn
obile
Sesquiterpenes
(Dendron
obilins
A)
Cop
acam
phane-type
(1R2R
4S5S6S8S9R)-28-
Dihydroxycopacamph
an-15-on
eH H
H
H
H
O
HO
OH
(R)
11 109
7
15
1214
13
16 5
(R) (R)
(S)
(S)
(S)
(S)
[28]
Picrotoxane-type
(2b3b4b5b)-2411-Trihydroxy-picrotoxano
-3(15)-lacton
e
H
H H
H
H
O O
HO
OH
OH
1214
15
133
11
110
9
6[28]
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Diabetes ResearchJournal of
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 11
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a11b)-211-Epo
xy-91113
-trihydroxypicrotoxano3(15)-la
cton
e
H
HHH
H H
OO O
HO H
O
OH
123
14
15
56
9 1
11 10 13
[28]
Picrotoxane-type
(2b3b5b12Rlowast
)-21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
e
H
HHH
H H
O O
HO H
O
OH
1214
15
567
91
11
10 13(R
lowast)
[28]
Picrotoxane-type
(2b3b5b12Slowast)21113
-Trih
ydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
HH
H
HO H
O
OH
1215569
110
11
7
1314
(Slowast
)
[28]
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
[1] R L Dressler Phylogeny and Classification of the Orchid FamilyCambridge University Press New York NY USA 1993
[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
12 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Picrotoxane-type
(2b3b5b9a)-10
-Cyclo-21113
-trihydroxy-
picrotoxano-3(15)-lacton
eO O
H HH
H H HO
HO
OH
121556
9 110
11
7
1314
[28]
Muu
rolene-ty
pe(9b10a)-M
uurol-4
-ene-910
11-tr
iol
H
HHH
HO
OH
OH
12
15 69
110
11
4
2
1314
[28]
Allo
arom
adendrene-type
(10a)-A
lloarom
adendrene-1012
14-tr
iol
H
H
HH
H
HO
OH
OH 12
15
6
91
10
1142
1314
5[28]
Cyclo
copacamph
ane-type
(5b)-C
yclocopacamph
ane-51215
-triol
H
1
14
10
7 24
35
6
1512
1311 H
HH
H
H
HO
OH
OH
[28]
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
[1] R L Dressler Phylogeny and Classification of the Orchid FamilyCambridge University Press New York NY USA 1993
[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Disease Markers
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OncologyJournal of
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Oxidative Medicine and Cellular Longevity
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The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
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Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 13Ta
ble1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Bibenzylderiv
atives
Dendron
opheno
lA221015840991015840-Tetrametho
xy131015840141015840-peroxy-111015840-
bis(bibenzyl)-661015840-diol)
OO
MeO
MeO
OM
e
OM
eHO
OH
12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400
9998400
10998400
11998400
12998400
13998400
14998400
15998400
16998400
[29]
Dendron
opheno
lB1-(2101584061015840-D
imetho
xy7101584081015840-peroxyphenyl-
prop
yl)-29-dimetho
xybibenzyl-691015840-diol)
O
OH
OH
OM
eO
MeO
OM
e
OM
e 12
3 4
56
7
8
9
10
1112
13
14
15
161998400
2998400
3998400
4998400
5998400
6998400
7998400
8998400 9998400
10998400
11998400
[29]
Dthyrsiflorum
Bi-bicyclic
andbi-tr
icyclic
compo
unds
Denthyrsin
[3-(5101584061015840-D
imetho
xybenzofuran-21015840-yl)-67-
dimetho
xy-2H-chrom
en-2-one
O
OO 1
23
45
678
9 10
1998400
2998400
3998400
4998400
59984006998400
7998400
8998400
9998400
H3CO
H3CO
OCH
3
OCH
3
[30]
Denthyrsin
ol(451015840-D
imetho
xy-[111015840]biphenanthrenyl-
25410158407-tetraol
OCH
3
OCH
3
OH
OH
OH
OH
1
2
34
4a
4b
56
7
88
a
910
10a
1998400 3998400
2998400
49984004
a9984004
b998400
5998400
6998400
7998400
8998400
8a998400
9998400
10998400
10a998400
[30]
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
14 Evidence-Based Complementary and Alternative Medicine
Table1Con
tinued
Species
Con
stituent
Chem
icalform
ula
Structures
ofcompo
und
Reference
Denthyrsin
one
(74101584071015840-Trih
ydroxy-22101584081015840-tr
imetho
xy-
[511015840]biphenanthrenyl-14-dione)
OCH
3
O
O
OH
OH
OH
12
34
4a
4b
56
7
88
a910 10
a
1998400
2998400 3998400
49984004
a9984004
b998400
5998400
69984007998400
8998400
8a9984009998400
10998400
10a998400
H3CO
H3CO
[30]
Denthyrsin
in15
7-Trim
etho
xyph
enanthrene-26-diol
OCH
3
OH
H3CO
H3CO
HO
[30]
Scop
aron
emdash
OO
H3CO
H3CO
[30]
b-Sitoste
rol
mdash
OCH
3
OH
OH
[30]
Daucoste
rol
mdash
OCH
3
OH
OH
[30]
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 15
Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile
ABTSradicals
Hydroxylradicals
DPPHradicals
D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)
D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)
lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future
action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]
311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC
50
values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study
Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP
DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()
1mg for DPPHscavenging ()
Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5
05mg for ABTSscavenging ()
1mg for ABTSscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30
05mg for hydroxylscavenging ()
1mg for hydroxylscavenging ()
Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1
scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1
gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1
gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt
DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt
DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1
gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds
indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
16 Evidence-Based Complementary and Alternative Medicine
Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species
Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50
Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75
Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3
D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals
is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]
32 Anti-Inflammatory Activity
321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production
322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R
1= R2=
OCH3R3= OH R
4= H (4) R
1= R2= R3= OCH
3R4= H
(5) R1= R2= OH R
3= R4= H (6) R
1= R3= OCH
3R2
= OH R4= H (7) R
1= OCH
3R2= R3= OH R
4= H (8)
R1= R3= OH R
2= R4= H (9) and R
1= R3= OH R
2=
HR4= OCH
3(10) have been identified Compounds 1ndash3
5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except
compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R
1= R3= OH R
2= R5= OCH
3 R4= H(A)
R1= R4= R5= OH R
2= H R
3= OCH
3(B) R
1= R5=
OH R2= R3= OCH
3 R4= H(C) R
1= R2= OCH
3 R3=
R5= OH R
4= H(D) R
1= H R
2= R3= OH(E) R
1= H
R2= OH R
3= OCH
3(F) R
1= OCH
3 R2= R4= OH R
3
= R5= H(G) R
1= R3= OH R
2= OCH
3(H) R
1= R5=
OH R2= R4= H R
3= OCH
3(I) R1= R3= OCH
3 R2=
R5= OH R
4= H(J) R
1= R2= R4= OH R
3= OCH
3 R5=
H(K) R1= OCH
3 R2= R4= H R
3= R5= OH(L) and
R1= R2= R3= OH R
4= R5= H(M) were elucidated by
analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production
323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-
Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
[1] R L Dressler Phylogeny and Classification of the Orchid FamilyCambridge University Press New York NY USA 1993
[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
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Evidence-Based Complementary and Alternative Medicine 17
Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation
Species Chemical constituent NO DPPH
Dloddigesii
Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash
Dnobile
Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash
lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)
sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]
33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found
that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]
Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile
A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)
Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)
34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC
50values
of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]
In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
[1] R L Dressler Phylogeny and Classification of the Orchid FamilyCambridge University Press New York NY USA 1993
[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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OncologyJournal of
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Oxidative Medicine and Cellular Longevity
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Research and TreatmentAIDS
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Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
18 Evidence-Based Complementary and Alternative Medicine
Polysaccharide
HPS-IB23
OAc3 OAc2 OAc2 OAc3 OAc2
Cytokines factorsHematopoietic growth factors
OAc3 120572-D-Gal 120572-D-Gal
[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n
TNF-120572uarrGC-SFuarr
GM-CSFuarr
rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n
lowastNotes inducementdarr activationuarr
Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation
and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]
35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]
Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related
sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)
In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific
Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
[1] R L Dressler Phylogeny and Classification of the Orchid FamilyCambridge University Press New York NY USA 1993
[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
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Evidence-Based Complementary and Alternative Medicine 19
Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells
Dendrobiumspecies Compoundstructure Lymphocytes
T cell B cell
D nobile
Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)
D moniliforme
Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)
lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme
evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]
In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]
36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]
37 Antitumor Activity
371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human
hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-
7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively
On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar
The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]
372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]
373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]
38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
20 Evidence-Based Complementary and Alternative Medicine
Table 7 The pharmacological effects of Dendrobium species
Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]
(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]
(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]
(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]
(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]
(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]
(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]
(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]
(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]
(SR) Moscatilin moscatin moscatilindiacetate
Inhibited both AA and collagen-induced plateletaggregations [50 51]
(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]
D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]
(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]
(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]
D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Disease Markers
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BioMed Research International
OncologyJournal of
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Oxidative Medicine and Cellular Longevity
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PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 21
Table 7 Continued
Species Chemical compoundsstructures Pharmacological activities References
D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]
D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma
A375 and HL-60 cells [57]
D chrysanthum Dhuoshanense Dendrochrysanene
TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS
[58]
D devonianum Dthyrsiflorum
Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]
D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and
Microbotryum violaceum [61]lowastNotes mdash no tests SR similar
[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]
39 Antimalarial and Antiherpetic Activities
391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]
310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor
(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]
311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)
4 Conclusion
In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Diabetes ResearchJournal of
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
22 Evidence-Based Complementary and Alternative Medicine
antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgments
This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043
References
[1] R L Dressler Phylogeny and Classification of the Orchid FamilyCambridge University Press New York NY USA 1993
[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001
[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008
[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009
[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006
[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999
[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981
[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003
[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011
[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975
[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005
[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959
[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006
[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003
[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011
[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012
[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979
[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003
[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999
[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009
[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008
[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008
[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008
[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004
[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001
[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009
[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007
[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 23
[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005
[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009
[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987
[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989
[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992
[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000
[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001
[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007
[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008
[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009
[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011
[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005
[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011
[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010
[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002
[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane
sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003
[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007
[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010
[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009
[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012
[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012
[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011
[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009
[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011
[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001
[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011
[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010
[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014
[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014
[61] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
24 Evidence-Based Complementary and Alternative Medicine
[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012
[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008
[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006
[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012
[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004
[67] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004
[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010
[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007
[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013
[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010
[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006
[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005
[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998
[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010
[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013
[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012
[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014
[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998
[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001
[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008
[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015
[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014
[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995
[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014
[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014
[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012
[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011
[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008
[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978
[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007
[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 25
[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009
[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999
[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014
[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000
[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995
[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom