/

104 7 20 104 7 24
104 8 10

2


1985


Reliance Tech-Service Co.
104 7 23 7 24 7
20 7 23







8
Inflammation
Methanolic extract (900 g)
MeOH reflux (10L x 5 x 8 hrs) Filtered concd.
CHCl3 / H2O
water fraction 11.08 ± 5.19 11.00 ± 3.37* 8
Constituents from Vigna vexillata and Their Anti-inflammatory Activity
In our preliminary bioassay, the chloroform layer of methanol extracts of V. vexillata demonstrated significant anti-inflammatory bioactivity. Therefore, the present research is aimed to purify and identify the anti-inflammatory principles of V. vexillata. One new sterol (1) and two new isoflavones (2-3) were reported from the natural sources for the first time and their chemical structures were determined by the spectroscopic and mass spectrometric analyses. In addition, thirty-seven known compounds were identified by comparison of their physical and spectroscopic data with those reported in the literature.
O
O
HO
superoxide anion generation elastase release
1 (12.58 ± 0.82) *** 8.93 ± 1.64
2 (40.57 ± 4.06) *** (17.27 ± 4.19) *
3 4.05 ± 0.66 (12.62 ± 7.17)
9 (6.13 ± 3.26) (-21.93 ± 1.80) ***
10 (2.27 ± 2.70) (-10.96 ± 5.47)
13 (15.45 ± 1.17) *** (11.59 ± 4.53)
19 1.30 ± 0.27 (42.15 ± 2.88) ***
20 (19.26 ± 5.37) * (11.39 ± 4.98)
22 5.87 ± 0.50 (19.37 ± 4.16) **
23 3.13 ± 0.27 4.29 ± 0.49
25 2.66 ± 0.85 2.71 ± 0.25
27 (-1.35 ± 3.50) (16.39 ± 2.85) **
30 (37.34 ± 3.26) *** (7.68 ± 5.60)
31 (20.28 ± 4.96) * (20.11 ± 2.84) **
34 (26.38 ± 6.94) * (31.49 ± 5.00) **
35 (26.81 ± 6.19) * (24.43 ± 4.42) **
36 (17.15 ± 3.77) * (17.88 ± 1.56) ***
37 (8.97 ± 2.64) * (4.34 ± 0.58) **
38 (-0.88 ± 2.98) (-1.04 ± 7.31)
39 (12.45 ± 5.61) (-1.30 ± 3.61)
40 4.47 ± 0.76 5.51 ± 1.07
LY294002 c 1.38 ± 0.22 1.95 ± 0.35
DPI d 0.93 ± 0.52 −
Inhibitory effects of purified samples from V. vexillata on superoxide anion generation and elastase release by human neutrophils in response to FMLP/CB.
10
Constituents from Senecio scandens and Their Antioxidant Bioactivity
Forty-one compounds including two new constituents senecainin A (1) and 3-methoxy- isonicotinic acid (2) were characterized from the methanol extracts of the whole plant of Senecio scandens. The structures of new compounds were comprehensively established with the aids of 1D and 2D NMR spectroscopic and mass spectrometric analyses.
Published paper: Arch. Pharm. Res., 2010, 34, 377-382.
117*
128**
O
O
OH
O
O
N
O
1 – N. A.
7 – 11.3 % ± 0.7
21 – 10.8 % ± 1.1
28 – N. A.
13
14
O
O
HH
O
O
O
O
O
sesamolin
O
O
HH
O
O
O
O
sesamin
•The methanol extract of sesame (Sesamum indicum) seeds was fractionated and purified with the assistance of conventional column chromatography to afford 29 compounds including seven furofuran lignans.
15
at 500 μM
1 − 40.7 ± 3.0 %
2 − 29.0 ± 3.7 %
3 − 27.2 ± 3.1 %*
4 − 39.5 ± 0.3 %
8 − 43.3 ± 2.2 %*
Vitamin C 38.6 ± 1.8 89.7 ± 0.1 %
DPPH radical scavenging bioactivity
BHT 1 2 3 4 5 6 7 8 9
S up
er ox
id e
an io
n in
hi bi
tio n(
Superoxide anions inhibition activity
Published paper: J. Agric. Food Chem., 2011, 59, 3214-3219. 20
Chemical constituents from the
their antimicrobial activity

22

1.5 ~ 2.5 cm0.5 ~ 1.3 cm
23

• FS FSCFSW E.coli
•
CHCl3/H2O
25

FSC (450 g)
(70)
SiO2 C.C. N:E=50:1
SiO2 C.C. N:E=10:1
SiO2 C.C. C:M =300:1
(8)
(70)
(72)
(80)
27

2. LB37
33 34
•
35

Changes in volatile compounds upon aging and drying in oolong
tea production

Published paper: J. Sci. Food Agric., 2010, 91, 293-301. Food Res. Int., 2013, 53, 732-743.
37









• Depending upon the level of fermentation, tea can be categorized into four types:
1. Unfermented- Green tea
4. Post-fermented- Pu-erh tea
• Fermentation It refers to natural browning reactions induced by oxidative enzymes in the cells of tea leaves. 38
Old oolong tea
• Old oolong tea is converted from fresh oolong tea by long- term storage (aging) for more than five years and refined at least annually by a professional drying process.
• Old oolong tea, tasting superior and empirically considered beneficial for human health, is prepared by long-term storage accompanied with periodic drying for refinement.
• The time-consuming and labor-intensive preparation of old oolong tea considerably raises its production cost and thus limits its commercialization at a large scale.



39
GC/MS chromatograms of the aroma concentrates in fresh and old oolong teas
40
Expanded GC/MS chromatograms of the aroma concentrates in fresh and old oolong teas
gr
a
41
GC/MS chromatograms of the aroma concentrates in five preparations of old oolong tea
The reproducible pattern of aroma compositions may be regarded as a unique fingerprint of volatile compounds in old oolong tea and defined
condition of periodical drying processes.
42
2015/8/7
8
GC/MS chromatograms of the aroma concentrates in oolong tea freshly prepared, stored for 10 years (Lugu-stored) and Lugu-old-1
14
20
18
31
25
32
32
26
43
GC/MS chromatograms of the aroma concentrates in oolong tea freshly prepared, treated with a mild drying process (semi-old) and Lugu-old-1
25 26
45
•
Pyrrole Pyridine
•
Bioactive saponins from tea seed pomace with inhibitory effects against
Rhizoctonia solani
Published paper: J. Agric. Food Chem., 2010, 58, 8618-8622. 52
Camellia oleifera was named trivially as tea-oil camellia
because it is cultivated in its homeland of East Asia
specifically for the seeds, which are extracted for commercial
tea oil.
After the extraction of oil, the seed pomace is discarded as
there are no further uses for it. Moreover, no research work
related to the tea seed pomace had been published until now.
53
Rhizoctonia solani causes serious damping-off diseases of numerous crops in Taiwan; it is a major problem especially for the commercial production of vegetable seedlings grown in cell-plug systems.
In our preliminary screening, the methanol extract of tea seed pomace at 100 ppm markedly inhibited the mycelial growth of R. solani by 64.68%.
Rhizoctonia solani kühn AG-4
For the purpose of discovering new plant-derived fungicides for controlling Rhizoctonia damping-off of cabbage seedlings, the seed pomace of C. oleifera was selected as the target.
54
2015/8/7
10
OR
O
OOH
OH
HO
1 R = Gal(1→2)[Rha(1→6)]Glc 2 R = Xyl(1→2)[Rha(1→6)]Glc
CH2OH
O
OH
Camelliaside A (125 ppm) 8.70 ± 0.12 -14.66
Camelliaside B (125 ppm) 8.69 ± 0.12 -14.50
Saponin (100 ppm) 2.78 ± 0.04 63.43
Saponin (60 ppm) 3.30 ± 0.11 56.51
Saponin (30 ppm) 4.04 ± 0.07 46.79
Saponin (10 ppm) 7.10 ± 0.04 6.43
Pencycuron (250 ppm) 1.38 ± 0.14 81.88
Pencycuron (25 ppm) 1.23 ± 0.12 83.86
Pencycuron (2.5 ppm) 2.00 ± 0.13 73.64
Pencycuron (0.25 ppm) 2.54 ± 0.10 66.56
Check 7.59 ± 0.14 0.00
Antifungal activity of the camelliaside A (1), B (2) and saponin (3) from tea seed pomace on the growth of Rhizoctonia solani AG-4 RST-04 on potato dextrose agar (PDA) plates incubated at 27 ºC for 48 hrs
56
57
The infection cushions of Rhizoctonia solani AG-4 RST-04 formed on stem surface of a cabbage seedling treated with (A) or without (B) 1 % (w/v) methanol extract of tea seed pomace under microscope.
58
59
Comparison of antifungal activity of C. chinensis powder prepared by traditional grinding or ultrafining technology
: samples prepared by ultrafing technology. : samples prepared by traditional grinding.
Published paper: J. Nanomater., 2014, 2014, Article ID 262454, 6 pages. 60
Comparison of antifungal activity of M. officinalis powder prepared by traditional grinding or ultrafining technology
: samples prepared by ultrafing technology. : samples prepared by traditional grinding.
0%
20%
40%
60%
80%
2015/8/7
11
Biotransformation
Small organic molecules purified from natural sources provide an incomparable source of inspiration for advances in organic chemistry and disease treatment due to their significant biological properties.
Although some compounds can be easily synthesized by chemical ways, some issues still remain, including complex operation, safety, pollution, and production cost.
61
Biotransformation
Biopreparation has been considered to be an economical technology by synthetic organic chemists in the development of new production routes for chemical and pharmaceutical compounds.
As compared with chemical synthesis, biotransformation is a useful method to produce bioactive compounds with advantages such as high stereo- and regio-selectivity, as well as milder reaction conditions, simple operation procedures, and environmental safety.
62Published paper: Tetrahedron Lett., 2013, 54, 6955-6958.
Arctium lappa L. is a perennial herb that has been cultivated as a vegetable in many countries for a long time.
The seeds of A. lappa L. are extensively used in traditional medicines as diuretic, anti-inflammatory, and detoxifying agents.
63
Arctii Fructus NO Inhibitory Principles from the seeds of A. lappa
64
arctiin
O
O
H3CO
IC50: 9.5 μM Yield: 0.001167%
65
O
O
H3CO
OCH3
OCH3
HO
2
119
O
O
H3CO
HO
OCH3
EtOAc layer (0.5 g)
SiO2 C.C. C:M=300:1 Step gradient with M
(118) (119)
0.07 g 21.0 %
0.26 g 37.4 %
67
(117)
(118)
(119)
67
68
(117)
68
69
(118)
(119)
(117)
(118)
(119)
(117)
(118)
(119)
(117)
The relative abundances of arctiin, arctigenin, and diarctigenin in the incubation period (n = 3–5).
70 70
O
O
OCH3
OCH3
H3CO
GlcO
117
In the present study RS AG-4 was used as a
biocatalyst and arctiin was converted into
arctigenin and diarctigenin both in satisfied yields.
The current report would be an excellent method
to produce a large scale of diarctigenin for the
further medicinal and bioactivity examinations.
72
72
2015/8/7
13

74
( )
superoxide anion generation elastase release
CSE 26.53 ± 4.31* 15.20 ± 1.82**
CSEH 28.38 ± 7.13** 22.79 ± 5.33*
CSEHH 44.02 ± 10.19** 70.76 ± 5.26***
CSEHM 94.99 ± 2.12*** 97.10 ± 2.11***
CSEE 82.73 ± 6.82*** 97.49 ± 3.96***
CSEW 8.39 ± 2.78* 3.94 ± 2.88
Results are presented as mean ± S.E.M. (n=3-4). a Percentage of inhibition (Inh %) at 10 g/mL concentration. * p < 0.05** p < 0.01*** p < 0.001 compared with the control value.
77
N
NH
O
O
H
HO
N
NN
N
NH2
O
OCH3OH
HH
HH
In order to explore the anti-inflammatory principles of the mycelia of Cordyceps sinensis, the crude extract and partially purified fractions were examined for their inhibition of superoxide anion generation and elastase release. Further chemical investigation of the bioactive fractions has resulted in the identification of fifty compounds, including five constituents, cordysinins A-E (1-5) reported from a natural source for the first time. In addition, compounds were examined for their anti-inflammatory activity. 1-(5-Hydroxymethyl-2-furyl)-β- carboline displayed the most significant inhibition of superoxide anion generation and elastase release with IC50
values of 0.45 ± 0.15 and 1.68 ± 0.32 µM, respectively.
Published paper: J. Nat. Prod., 2011, 74, 1996-2000. 78
2015/8/7
14
superoxide anion generation elastase release
65 NT c NT
312 NT NT
313 (28.25 ± 2.73)*** (41.59 ± 6.25)***
318 (5.59 ± 3.26) (7.03 ± 3.76)
321 (6.59 ± 2.11) (2.79 ± 3.64)
322 (12.83 ± 6.94) (10.37 ± 0.55)
326 (5.65 ± 1.64) (11.72 ± 5.92)
327 (9.61 ± 5.51) (11.06 ± 6.14)
329 (21.62 ± 6.28) (7.13 ± 5.55)
331 0.45 ± 0.15 1.68 ± 0.32
336 (6.43 ± 3.72) (6.83 ± 2.46)
338 (11.34 ± 4.95) (13.02 ± 3.20)
Indomethacin 38.32 ± 5.38 31.98 ± 6.49
LY294002 1.12 ± 0.20 1.92 ± 0.22
a Concentration necessary for 50 % inhibition. b Percentage of hibition (Inh %) at 10 mg/mL concentration. Results are presented as mean ± S.E.M.
(n=3-4). * p < 0.05** p < 0.01*** p < 0.001 compared with the control value. c NT meansNot Test.
OO HO
OH HO
114 (34.5 ± 4.09)
170 (40.9 ± 3.17)
171 (25.7 ± 1.89)
218 (17.6 ± 4.67)
228 (29.3 ± 0.54)
269 (29.6 ± 1.90)
318 (37.0 ± 1.11)
319 (31.3 ± 1.08)
320 (28.4 ± 1.64)
321 (12.2 ± 3.43)
322 (26.8 ± 3.08)
326 (29.5 ± 0.90)
327 (27.3 ± 2.04)
328 (20.6 ± 5.01)
12 DPPH
a Percentage of hibition (Inh %) at 500 M concentration. b Concentration necessary for 50 % inhibition.
OHO
Taiwanofungus camphoratus (Niu-chang-chih) (Polyporaceae, Aphyllophorales)
It is a rare and precious type of medical fungus in Taiwan and it is known as “the national treasure of Taiwan”.
The fruiting bodies of Niu-chang-chih have been used as a Chinese folk medicine for the treatment of liver diseases, food and drug intoxication, diarrhea, abdominal pain, hypertension, itchy skin and tumorigenic diseases in Taiwan.
81
Published paper: Int. J. Mol. Sci., 2012, 13, 10432-10440. 82
Published paper: Tetrahedron Lett., 2012, 53, 6202-6204. 83
Viscum coloratum
HO OCH3
2015/8/7
15
HO
a b
c d
Reagents and conditions: a) NaOH, Cu, reflux; b) (i) (CH3)2SO4, Na2CO3, acetone, reflux; (ii) (CH3)2CBr, K2CO3, DMF, reflux; c) (i) m-CPBA, CH2Cl2, room temp; (ii) NaOH-MeOH, room temp; (iii) CH3I, K2CO3, CH3OH, reflux; d) AcCl, SnCl4, CH2Cl2, room temp; e) (CH3)2CBr, K2CO3, DMF, reflux; f) NaOH, H2O-MeOH, room temp; g) Et3SiH, TFA, room temp; h) BCl3, CH2Cl2, 00C.
Br OCH3
• Isolated from Zingiber officinale Rosc.
• IC50 values for inhibiting lipid peroxidation initiated by Fe2+-ascorbic acid in rat brain homogenate were 28.2±0.8 and 35.7±1.5 M.
CH3
O
OCH3
HO
Zingerone
CH3
O
OCH3
HO
Dehydrozingerone

87
OH
O
OCH3
HO
151 156 166 175 177 178 Vit. C Vit. E
DPPH assay
IC0.200(M)
Rat brain assay IC50(M)
ND 60.2±5.8 58.5±3.2 6.3±0.4 41.8±6.3 12.0±0.8 ND 2.5
Iron chelation assay
Antityrosinase
assay

Magnoliophyta -Magnoliopsida
-Theales -Theaceae

571~3 10~11
92 92
OH
93

Minutes 0.0 2.5 5.0 7.5 10.0 12.5 15.0 17.5 20.0 22.5 25.0 27.5 30.0 32.5 35.0 37.5 40.0 42.5 45.0
V o
lt s
EGCG
EC
94

Minutes 0.0 2.5 5.0 7.5 10.0 12.5 15.0 17.5 20.0 22.5 25.0 27.5 30.0 32.5 35.0 37.5 40.0 42.5 45.0
V o
lt s
Retention Time
gallic acid
IC50
0
20
40
60



-
90
110
130
150
170



6 7
97