npr review
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Cite this: Nat. Prod. Rep., 2011, 28, 1580
www.rsc.org/npr REVIEW
Natural sesquiterpenoids
Braulio M. Fraga*
Received 2nd June 2011
DOI: 10.1039/c1np00046b
Covering: January 2010 to December 2010. Previous review: Nat. Prod. Rep. 2010, 27, 1681.
This review covers the isolation, structural determination, synthesis and chemical and microbiological
transformations of natural sesquiterpenoids. The literature is reviewed, and 417 references are cited.
1 Introduction
2 Farnesane
3 Monocyclofarnesane
4 Bicyclofarnesane
5 Bisabolane and heliannane group
6 Sesquipinane, sesquicamphane and fumagillane
7 Trichothecane, herbertane, laurane and cuparane
8 Chamigrane
9 Carotane, cedrane, zizaane and prezizaane
10 Cadinane, copaane, oplopane and cubenane
11 Himachalane, longipinane and longifolane
12 Caryophyllane, clovane, caryolane, punctaporonin
group, silphiperfolane, presilphiperfolane, camer-
oonane, silphinane, isocomane and quadrane
13 Humulane, lactarane, hirsutane, marasmane, illudane,
illudalane, tremulane, precapnellane, capnellane, africa-
nane, pentalenane, lippifoliane and asteriscane
14 Germacrane
15 Elemane
16 Eudesmane, lindenane, axane and oppositane
17 Vetisperane
18 Eremophilane, valencane and bakkane
19 Guaiane, xanthane, pseudoguaiane, patchoulane, bour-
bonane and carabrane
20 Aromadendrane, bicyclogermacrane, valerenane, aris-
tolane, nardosinane and zierane
21 Pinguisane
22 Salviolane
23 Miscellaneous sesquiterpenoids
24 References
1 Introduction
A review on the structures, biological activities and phyloge-
netic relationships of terpenoids from marine ciliates of the
Instituto de Productos Naturales y Agrobiolog�ıa, CSIC, 38206 La Laguna,Tenerife, Canary Islands, Spain. E-mail: [email protected]; Fax: +34-922260135; Tel: +34-922251728
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genus Euplotes has appeared.1 The chemistry and biological
activity of species of the Saussurea genus2 and the pharma-
ceutical properties of the Amberboa plants3 have been reviewed.
The biotransformation by fungi and mammals of sesquiter-
penes isolated from liverwort has been published,4 while the
functional and evolutionary relationships between terpene
synthases from species of Australian Myrtaceae have been
investigated.5 A study of the intestinal permeability of eight
sesquiterpenes, constituents of traditional Chinese medicines,
using the Caco-2 cell monolayer model has appeared.6 The
reaction mechanism and the catalytic fidelity of two
This journal is ª The Royal Society of Chemistry 2011
sesquiterpene synthases, Cop4 and Cop6, from Coprinus cinereus
have been studied.7
2 Farnesane
A new sesquiterpene 1 with biological activity has been iso-
lated from hairy root cultures of Artemisia annua.8–10 2,3-
Dihydrohomofarnesal 2 has been identified as a component of
the sex attractant pheromone of the female seed beetle Cal-
losobruchus rhodesianus,11 whilst the norsesquiterpene 3 may
also be a possible component of this pheromone.12 The
sesquiterpene glycosides 4 and 5 have been found in extracts
of Breynia fruticosa13 and Gynostemma yixingense,14 respec-
tively. Several compounds of this type 6 have been obtained
from the pericarps of Sapindus rarak.15 A novel lactone (6R)-
dehydroxysipandinolide 7, probably derived from a germa-
crane sesquiterpene, has been isolated from the rhizomes of
Curcuma wenyujin.16 The essential oil of Melicope obscura
contains the new sesquiterpene 8, which has been named
melicopenol.17
The bacterium Escherichia coli has been metabolically engi-
neered in order to increase its farnesol production by har-
nessing the exogenous mevalonate pathway.18 Neroplomacrol 9
and neroplofurol 10 are two new nerolidol derivatives, which
have been found in the inner stem bark of Oplopanax
horridus.19 Two new irregular sesquiterpenes, tricinonoic acid
11 and tricindiol 12, have been obtained from an extract of
Fusarium tricinctum, which is an endophytic strain in the root
of the Mexican Sonora desert plant Rumex hymenosepalus.20
The sesquilavandulyl aldehyde 13 is a component of Ligusticum
grayi roots. This plant is very rich in other sesquiterpenoids,
which are described in the ‘‘Miscellaneous sesquiterpenoid’’
section of this review.21
Braulio M: Fraga
Braulio M. Fraga was born in
Tenerife (1944) and received his
PhD in Chemistry at the
University of La Laguna
(1970), where he lectured in
Organic Chemistry for several
years. In 1971 he was honoured
with the Young Researcher
Award of the Spanish Royal
Society of Chemistry. He
obtained a permanent position in
the Spanish Council for Scien-
tific Research as Tenured
Scientist in 1972, being later
appointed Research Scientist
(1986) and Research Professor
(1987). He was director of the Institute of Natural Products
(Tenerife) from 1988–1991, and has been the representative of the
Spanish Council for Scientific Research in the Canary Islands since
1991. He had previously been appointed Professor of Organic
Chemistry at the University of Valencia (1981). His research
interests range from the chemistry to the biotransformation of
natural products, especially in the terpenoid field. He has authored
more than two hundred scientific publications.
This journal is ª The Royal Society of Chemistry 2011
Nitropyrrolins A–E22 14–18 and heronapyrroles A–C23 19–21
are cytotoxic farnesyl nitropyrroles, which have been isolated
from saline cultures of marine-derived bacteria of the actinomy-
cete family Streptomycetaceae, while aspernidine A 22 and
aspernidine B 23 are two farnesyl isoindolinone-alkaloids, which
have been found in an extract of the fungusAspergillus nidulans.24
The roots of Ferula ferulaeoides contain two new sesquiterpenes,
ferulactone A 24 and ferulactone B 25.25 The structure of mac-
agigantin, a farnesylated flavonol, has been determined as 6-far-
nesyl-kaempherol. This compound has been isolated from
Macaranga gigantea.26 Another species of this genus,Macaranga
pruinosa, contains macapruinosin A 26 and macapruinosin B 27,
which are a stilbene and a flavonoid derivative, respectively,
containing an irregular sesquiterpenyl side chain with a cyclo-
butane ring.27 Cristatomentin 28 is a green pigment of mixed
biogenetic origin, which has been obtained from Albatrellus
cristatus.28 A chemical study of the soft coral Sinularia capillosa29
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afforded three new sesquiterpenoids, named capillobenzopyranol
29, capillobenzofuranol 30 and capillofuranocarboxylate 31.
A stereospecific total synthesis of (+)-davana acid, (+)-nor-
davanone and (+)-davanone has been reported.30 The (R)- and
(S)-enantiomers of juvenile hormone III acid and (R)-juvenile
hormone III-d3 have been synthesized.31 An efficient synthesis of
the antileukaemic sesquiterpene (+)-caparratriene has been
described.32
3 Monocyclofarnesane
Monaspilosuslin 32 is a new monocyclofarnesane sesquiterpene,
which has been isolated from the extraction of red yeast rice
fermented with the fungus Monascus pilosus.33 Known
compounds of this type have been isolated from Inula
ensifolia.34 Three megastigmane glucosides crotalionosides A–C
33–35 have been found in an extract of Crotalaria zanzibarica,35
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while canangaionoside 36 has been obtained from Cananga
odorata. In this last work, the absolute configuration of brey-
niaionoside A was also determined.36 Elaeocarpionoside 37 is
another glucoside, which has been obtained from the leaves of
Elaeocarpus japonicus.37 The species Gynostemma pentaphyllum
contains five new megastigmane glycosides 38–42, which have
been named gynostemosides A–E.38 Two acetylated compounds
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of this class, matenoside A 43 and matenoside B 44, have been
isolated from Ilex paraguariensis.39 Three conjugates of an
abscisic acid derivative 45 and phenolic glucosides have been
isolated from the roots of Lindera strychnifolia.40 The absolute
stereochemistry of the megastigmane glycoside icariside B5 has
been revised to 46.41
It has been shown that 3-hydroxy-b-ionone, isolated from the
moss Rhynchostegium pallidifolium, inhibits the shoot and root
growth of cress seedlings.42 Monocyclofarnesane sesquiterpenes,
found in the marine macroalga Ulva fasciata, have free-radical
scavenging properties.43
A chemical investigation of the roots of Ferula flabelliloba44
afforded three new sesquiterpene coumarins farnesiferone B 47,
flabellilobin A 48 and flabellilobin B 49. Synthetic studies have
been carried out to construct analogues with the basic skeleton of
galbanic acid, a biologically-active sesquiterpene-coumarin.45 A
racemic total synthesis of elegansidiol, farnesiferol B and farne-
siferol D has been reported.46
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4 Bicyclofarnesane
The drimane sesquiterpene kairatene 50 has been isolated from
Eurotia ceratoides.47 Another two compounds of this type,
changweikangic acid A 51 and changweikangic acid B 52, have
been found in an extract of the Chinese drug ‘‘Compound
Changweikang’’, which is made from the aqueous extracts of two
plants, Daphniphyllum calycinum and Polygonum hydropiper.48 A
chemical study of the leaves of Canella winterana afforded a new
hemiacetal 53, which has been named muzigodiol.49 The poly-
godial derivative 54 has been isolated from Pseudowintera
insperata. This paper included a chemotaxonomic study of the
New Zealand species of this genus.50 Chromatography of an
extract of the liverwort Bazzania novae-zelandiae51 led to the
isolation of the rearranged drimane derivative 55.
The antiprotozoal activity of several drimane and coloratane
sesquiterpenes towards Trypanosoma brucei and Plasmodium
falciparum has been investigated. These compounds were
obtained from the medicinal plant Warburgia ugandensis.52 The
enantioselective synthesis of 3(S)-hydroxy-polygodial derivatives
and the evaluation of their vanilloid activity have been repor-
ted,53 while the preparation of 9a-fluorinated drimanes and the
evaluation of their antifeedant properties have also been
described.54
Craterellins A–C 56–58 are new merosesquiterpenes, which
have been found in cultures of the basidiomycete Craterellus
odoratus,55 whilst epoxyphomalins C–E 59–61 are cytotoxic
metabolites, which have been obtained from a marine-derived
fungus Paraconiothyrium sp.,56 previously classified as a Phoma
species. It should be noted that the structures of craterellin C 58
and epoxyphomalin D 60 are described as epimeric in one oxy-
methine (C-10) in the polyketide moiety. However, the authors of
both works report similar NMR spectra for both compound in
methanol-d4 and acetone-d6, respectively. Indeed, the chemical
shifts and coupling constants of this oxygenated methine are
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similar (dC 76.8, dH 3.49, J ¼ 7.6 Hz for 58; dC 76.8, dH 3.51, J ¼7.7 Hz for 60), which seems to indicate that these two sesqui-
terpenes have the same relative structure, probably 60. The
marine fungus Aspergillus versicolor57 contains the novel mer-
oterpenoid asperdemin 62. Another compound of this type is
epi-cochlioquinone A 63, whose first total synthesis has been
achieved.58 This sesquiterpene had been obtained from the
fermentation broth of the fungus Stachybotrys bisbyi.59 Cultures
of another microorganism, Penicillium cecidicola, afforded the
new meroterpene pentacecilide D 64. In this work, the absolute
configuration of pentacecilides A–D was also determined.60
A review on the cytotoxic terpene quinones from marine
sponges has appeared.61 The synthesis and natural occurrence
of the quinone/hydroquinone sesquiterpenes have been
reviewed.62,63 A chemical study of a red macroalga of the
Peyssonnelia genus64 afforded the hydroquinones peyssonoic acid
A 65 and peyssonoic acid B 66. Four new
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sesquiterpenoid-aminoquinones, 18-aminoarenarone 67,
19-aminoarenarone 68, 18-methylaminoarenarone 69, 19-methyl-
aminoarenarone 70 and popolohuanone F 71, have been isolated
from a marine sponge, Dysidea sp.65 Nakijiquinones J–R 72–80
are sesquiterpenoid quinones with an amine residue, which have
been found in three collections ofOkinawanmarine sponges of the
family Spongiidae.66
Oridamycin A 81 and oridamycin B 82 have been isolated from
the fermentation broth of a Streptomyces sp.67 These two new
indolo-sesquiterpene alkaloids are selective anti-Saprolegnia
parasitica antibiotics. Xiamycin 83 is another sesquiterpene of
this type with anti-HIV activity which has been obtained from
a Streptomyces sp., an endophytic fungus of the mangrove plant
Bruguiera gymnorrhiza.68 Polysin 84 is an inhibitor of phospho-
fructo kinase in Trypanosoma brucei, which has been obtained
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from Polyalthia suaveolens (Annonaceae).69 This plant, also
named as Greenwayodendron suaveolens, contains the novel
sesquiterpene alkaloids 85–87, which possess antibiotic
properties.70
The species Ferula gumosa71 contains the new sesquiterpene-
coumarins gumosin 88, gumoside A 89 and gumoside B 90, while
another compound of this type tunetacoumarin A 91 has been
identified as a component of Ferula tunetana.72 Interesting
cytotoxic properties have been shown by drimartol A, a sesqui-
terpene coumarin ether, which has been obtained from hairy root
cultures of Artemisia annua.73
Peyssonol A, an anti-HIV natural product, has been synthe-
sized and its structure revised to 92. In this work, the synthesis of
peyssonoic acid A was also carried out.74 A total synthesis of
(+)-stachyflin75 and a formal synthesis of (+)-puupuhenone and
other related metabolites,76 have been described, while a rapid
assembly of the tetracyclic core of the puupuhenone group of
marine sesquiterpenes has been published.77
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5 Bisabolane and heliannane group
The rhizomes of Curcuma longa78 contain four new bisabolene
sesquiterpenes, which have been named curculones A–D, 93–96.
Another compound of this type 97 has been isolated from
Leontopodium andersonii.79 Ashitabaol A 98 is a novel anti-
oxidative sesquiterpene, which has been obtained from the seeds
of Angelica keiskei.80 Chromatography of an extract of Ligularia
altaica afforded four bioactive sesquiterpenes, altaicalarins A–D
99–102,81,82 whilst a zingiberene diglucoside 103 has been isolated
from Butea monosperma.83
Seven bisabolane derivatives have been obtained by an
efficient cyclization of (2Z,6E)-farnesyl diphosphate with
5-epi-aristolochene synthase.84 The effects of curcuphenol on cell
proliferation and apoptosis in Caco-2 human colon cancer cells85
and of (�)-a-bisabonol in human endothelian cells86 have been
investigated. The cloning and characterization of a novel gene
that encodes (S)-b-bisabolene synthase from ginger, Zingiber
officinale, has been reported.87
Two nitrogenous bisabolene sesquiterpenes 104 and 105 have
been found in an extract of a Hainan sponge, Axinyssa sp.88 The
marine-derived fungus Verticillium tenerum contains the new
sesquiterpenes verticinols A 106 and B 107,89 while expansol A
108, expansol B 109 and two sydonic acid derivatives 110 and 111
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have been obtained from another microorganism of this type,
Penicillium expansum.90 Three bisabolene derivatives 112–114
have been found in anAspergillus species, which had been isolated
from a gorgonian soft coral, Dichotella gemmacea.91 Chroma-
tography of an extract of the marine red alga Laurencia compo-
sita92 afforded the bisabolane derivative 115. Another species of
this genus, Laurencia catarinensis, contains seven new haloge-
nated metabolites 116–122, which possess cytotoxic properties.93
A concise synthesis of the antifeedant sesquiterpene 123 has
been described,94 while the first enantioselective synthesis of
(�)-gossonorol, and the cyclization of its epoxide to form boi-
vinianin B, have been achieved.95 Curcuphenol, curcudiol, cur-
cuhydroquinone,96 curcuphenol and xanthorrhizol97 have been
synthesized as their racemates. Short syntheses of (S)-turmer-
one98 and meiogynin A99 have been reported. An asymmetrical
total synthesis of ent-heliaspirones A and C has been accom-
plished,100 whilst racemic101 and enantioselective102 preparations
of heliannuol D have been described.
6 Sesquipinane, sesquicamphane and fumagillane
The new bergamotene derivatives brasilamides A–D 124–127
have been isolated from cultures of the plant endophytic fungus
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Paraconiothyrium brasiliense.103 Several exo- and endo-3,8-dihy-
dro-b-santanols104 and campholene105 derivatives, with odorant
properties, have been prepared. A stereoselective total synthesis
of (�)-ovalicin has been described.106
7 Trichothecane, herbertane, laurane and cuparane
A new cytotoxic trichothecene macrolide, roritoxin E 128, has
been obtained from solid cultures of Myrothecium roridum,
which had been isolated from the roots of Artemisia annua.107
The dereplication of macrocyclic trichothecenes from extracts of
filamentous fungi, using UV and NMR profiles, has been
studied.108
Three novel herbertane sesquiterpenes 129–131 have been
found in an extract of Herbertus dicramus,109 whilst known bio-
logically-active sesquiterpenes of this type have been isolated
from the Tahitian liverwort Mastigophora diclados.110 The
sesquiterpene ether 8,10-dibromo-3,7-epoxylaur-13-ol has been
obtained from a red alga of the Laurencia genus.111 Total
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syntheses of enokipodins A, B,112 cuparene-1,4-diol and
enokipodins A–D113 have been reported.
8 Chamigrane
The novel norsesquiterpene peroxides steperoxides A–D 132–135
have been obtained from the fungus Steccherinum
ochraceum,114,115 while another nor-chamigrane merulin A 133,
and the chamigranes merulin B 136 and merulin C 137, have been
found in an extract of the culture broth of an endophytic fungus
XG8D, which was isolated from the mangrove plant Xylocarpus
granatum.116 We have observed that steperoxide B and merulin A
have the same structure 133.
The halogenated sesquiterpene 138 has been found in an
extract of the marine red alga Laurencia composita.92 The
antileishmanial activity of elatol has been studied. This
sesquiterpene is the major constituent of Laurencia
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dendroidea.117 The microbiological transformation of pacifenol
and two semisynthetic derivatives by the fungi Aspergillus
niger, Gibberella fujikuroi and Mucor plumbeus has been
investigated.118 A general enantioselective route to the chami-
grene family of sesquiterpenes has been developed. In this way,
the total synthesis of elatol, laurencenone C and of the
proposed structure of laurencenone B has been accom-
plished.119 Another total synthesis of (�)-laurencenone C has
been reported.120
9 Carotane, cedrane, zizaane and prezizaane
The new sesquiterpene 139 has been isolated from the stem
bark of Daphne aurantiaca.121 A phytochemical study of the
aerial part of the Algerian medicinal plant Ferula vesceritensis
afforded the known sesquiterpene lapiferin, which induces
apoptosis in breast cancer cells.122 Another species of this
genus, Ferula tunetana,72 contains the new sesquiterpenic ester
tunetanin A 140. Asperpenoid 141 is a novel seco-carotane
derivative, which has been obtained from the root of Homa-
lomena occulta.123
The biotransformation of a-cedrol by the fungus Neurospora
crassa has been investigated.124 The synthesis of DL-cedrone has
been reported.125 The structure of a recombinant epi-isozizaene
synthase, from Streptomyces coelicolor, has been determined by
X-ray analysis.126
Five new 8,9-seco-prezizaene sesquiterpenoids 142–146 have
been found in an extract of Illicium arborescens,127 whilst hen-
rylactones A–E 147–151 have been isolated from the stems and
roots of Illicium henryi.128 Racemic syntheses of the neurotrophic
sesquiterpenes merrilactone A and anislactone A have been
reported.129
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10 Cadinane, copaane, oplopane and cubenane
Chromatography of an extract of a fungus of the Stereum
genus130 afforded the novel sesquiterpene stereumin G 152.
Four cadinane derivatives 153–156 have been isolated from the
rhizomes of Acorus calamus.131,132 Another species of this
genus, Acorus tatarinowii, contains the new sesquiterpenes
tatarinowin A 157 and tatarinowin B 158,133,134 while chlo-
multin C 159 and chlomultin D 160 are two cadinane deriv-
atives, which have been obtained from Chloranthus
multistachys.135 The glycoside 161 has been isolated from the
roots and rhizomes of Celastrus orbiculatus.136 It has been
shown that 10a-hydroxyartemisinic acid 162 is a constituent of
Saussurea lappa root.137 The cadinane sesquiterpene 163 has
been found in an extract of the aerial parts of Senecio argu-
nensis,138 whilst the norcadinane derivative anomallenodiol 164
has been isolated from Artemisia anomala.139 Cosmosaldehyde
165 and cosmosoic acid 166 are two novel abeo-muurolane
sesquiterpenes, which have been identified as components of
Cosmos sulphureus.140
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The structure of altheacalamene has been determined as
2b-hydroxy-calamene. This compound has been obtained from
the seeds of Althea officinalis.141 The isolation and several
applications of calamene-3,7,8-triol, isolated from the dried bark
of Alangium salviifolium, have been patented. This sesquiterpene
showed DPPH radical-scavenging effect and tyrosinase-inhibit-
ing activity.142
It has been shown that a multiproduct terpene synthase
(MtTPS5), isolated from Medicago truncatula, produces cada-
lane sesquiterpenes via two different mechanisms.143 Quantum
chemical studies on the formation of amorphadiene and amor-
phene sesquiterpenes have been described.144 The inhibitor and
substrate activities of several sesquiterpene hydrocarbons toward
(+)-d-cadinene-8-hydroxylase have been reported. This cyto-
chrome P450 monooxygenase plays an important role in the
biosynthesis of gossypol in Gossypium arboreum.145
The synthesis of hemigossypol and hemigossylic lactone has
been carried out.146 The enantioselective total synthesis of the
marine sesquiterpene 10-isocyano-4-cadinene147 has permitted
the determination of its absolute configuration as 167.
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A review on the recent developments of artemisinin, and its
derivatives, as antimalarial and anticancer agents has
appeared.148 The recent advances in plant-derived natural
products for treatment of malaria have been reviewed.149 A
comparison of the quantitative analysis of artemisinin by
chromatographic techniques and qNMR has shown that this
last method can be used to quantify this antimalarial
sesquiterpene in Artemisia annua samples in a rapid
manner.150
The biosynthesis of artemisinin in growing plants of Arte-
misia annua using 13CO2 has been studied,151 while the molec-
ular cloning of dihydroartemisinic aldehyde reductase and its
implication in the biosynthesis of this sesquiterpene in this
species has been reported.152 A review on the biosynthesis of
artemisinin and the phytochemistry of Artemisia annua has
appeared.153 The acetoxylation of artemisinin at C-9 and
hydroxylation at C-3 in a biotransformation by the soil-fungus
Penicillium simplissimum have been described.154 The possibility
of producing artemisinin in genetically modified species, using
the tobacco plant as a model, has been investigated. In this
way, the production of biosynthetic precursors of this sesqui-
terpene was achieved.155
A concise and stereoselective total synthesis of (+)-artemisinin,
starting from (R)-(+)-citronellal, has been devised.156 It has been
shown that a cytotoxic artemisinin derivative conjugated with
a fluorescent dansyl moiety is accumulated in the endoplasmatic
reticulum.157 The synthesis of artemisinin-glycolipid hybrids with
potent antiangiogenic activity has been reported,158 while the
preparation of 10-substituted triazolyl artemisinins and their
growth inhibitory activity against several cancer cell lines have
been described.159
A new ylangene (copaene) sesquiterpene 168 has been isolated
from the soft coral Lemnalia flava.160 The oplopane derivatives
169 and 170 have been obtained from Ambrosia arborescens161
and Aglaia perviridis,162 respectively. Stereocontrolled syntheses
of (�)-cubebol and (�)-10-epicubebol have been
accomplished.163
11 Himachalane, longipinane and longifolane
The rearrangement of two himachalene epoxides by treatment
with Lewis acids has been described.164 Studies on the anti-
feedant and cytotoxic activity of several longipinane deriva-
tives have been carried out.165 The microbiological
transformations of (+)-a-longipinene166 by the fungus Asper-
gillus niger, and of (�)-isolongifolol167 and (�)-iso-
longifolone168 by the plant pathogenic fungus Glomerella
cingulata have been investigated.
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12 Caryophyllane, clovane, caryolane,punctaporonin group, silphiperfolane,presilphiperfolane, cameroonane, silphinane,isocomane and quadrane
Five new caryophyllane derivatives 171–175 have been isolated
from Buddleja davidii.169Two unusual meroterpenoids, psidial A170
176 and psiguadial B171 177, have been found in extracts from the
leaves of guava (Psidium guajava). A short biomimetic synthesis of
psidial A and guajadial has been accomplished.172 The gorgonian
coral Rumphella antipathies contains the 4,5-seco-caryophyllane
sesquiterpene, rumphellaone A173 178 and the clovane derivative
2b-hydroxyclovan-9-one 179.174Three novel sesquiterpenoids 180–
182, with a rearranged caryophyllane skeleton, have been obtained
from a tropical rainforest basidiomycete,Marasmiellus troyanus.175
The microbiological transformations of caryophyllene oxide by
the fungi Aspergillus niger176 and Neurospora crassa124 have been
investigated. In another studyof this type, the biotransformation of
5a-hydroxycaryophylla-4(12),8(13)-diene by the fungus Macro-
phomina phaseolina has been studied.177 A synthesis of optically
active tetrahydrozerumbone, a powerful balmy fragrance, has been
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described,178while biomimetic syntheses of caryolanemagnolol and
clovanemagnolol havebeenachieved.179Several clovanederivatives
have been prepared and evaluated for their in vitro antifungal
activity against the phytopathogenic fungus Botrytis cinerea.180
The total synthesis of punctaporonin C has been carried out.181
The structure of (�)-epi-presilphiperforlan-1-ol, a sesquiterpene
isolated from Anemia tomentosa, has been reassigned as 9-epi-pre-
silphiperforlan-1-ol 183. In this work, the absolute configuration of
this compoundwas also determined.182Othermajor components of
the essential oil from this plant are silphiperfol-6-ene, pre-
silphiperfol-7-ene andcameroonan-7a-ol.183Thepresilphiperfolane
derivatives184and185havebeen isolated fromaXylaria species,an
endophytic fungus associated with Piper aduncum.184
A biomimetic synthesis of penifulvins B and C has been
accomplished.185 Isocomene and b-isocomene has been synthe-
sized as their racemates.186 The natural source, biology and
synthesis of the quadrane sesquiterpene group have been
reviewed.187
13 Humulane, lactarane, hirsutane, marasmane,illudane, illudalane, tremulane, precapnellane,capnellane, africanane, pentalenane, lippifoliane andasteriscane
The new sesquiterpene 186 has been obtained from Buddleja
davidii,169 whilst five juniferol esters 187–191 have been isolated
from Ferula lycia.188 Known humulane sesquiterpenes have been
isolated from Curcuma ochrorhiza and Curcuma heyneana.189 The
anti-inflammatory effect of zerumbone, obtained from Zingiber
zerumbet, has been studied.190 Three new lactarane sesquiter-
penes, subvellerolactones B, D and E 192–194, with cytotoxic
activity have been found in an extract of the fruiting bodies of
Lactarius subvellereus.191 A total synthesis of furanether B has
been achieved.192
The fungi Xeromphalina sp., Stereum sp. and Pleurocybella
porrigens contain the new hirsutane derivatives xeromphalinones
A–F 195–200, chlorostereone 201 and pleurocybellone A 202,
respectively.193 A chemoenzymatic total synthesis of the hirsu-
tane sesquiterpene (+)-connatusin B has been achieved,194 while
a racemic synthesis of hirsutic acid C has been devised.195 Rus-
sulfoen 203 is a newmarasmane derivative, which has been found
in an extract of Russula foetens.196 The isolation and structural
elucidation of coprinastatin 1 204, coprinol 205 and the triol 206
have been described. These sesquiterpenes, together with
7,7a-diepicoprisnastatin 1 207, the illudosin derivative 208 and
the armillol derivative 209, have been obtained from Coprinus
cinereus.197,198 Ptesculentoside 210 is a novel norsesquiterpene
glucoside, which has been found in an extract of the Australian
bracken fern Pteridium esculentum.199 Chromatography of an
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extract of the basidiomycete Agrocybe salicacola led to the
isolation of a novel unsymmetrical bis-illudane sesquiterpene
211, which has been named agrocybone.200
Three new illudalane sesquiterpenes, (2R)-norpterosin B 212,
its glucoside 213 and semipterosin A 214, have been found in an
extract of Pteris semipinnata.201 Another species of this genus,
Pteris multifida, contains (2R)-pterosin P 215 and dehydropter-
osin B 216.202 The total syntheses of alcyopterosins C, I and L–N
have been accomplished.203 The bioactive sesquiterpene 217 has
been obtained from a culture of the fungus Ganoderma
applanatum.204 A synthesis of cybrodol 218 has been achieved.205
This seco-illudalane sesquiterpene had been obtained from the
bird’s nest fungus Cyathus bulleri.206
Nine tremulane derivatives 219–227 have been isolated from
Phellinus igniarius.207 A short synthesis of dactylol and poitediol
has been accomplished.208 Racemic total syntheses of capnell-9
(12)-ene209 and pentalenene125 have been described, while the
tricyclic core of the lippifoliane group of sesquiterpenes has been
synthesized.210 It has been shown that asteriscunolide A induces
apoptosis and activation of the mitogen-activated protein kinase
pathway in human tumor cell lines.211
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14 Germacrane
The new sesquiterpenes 228 and 229 have been obtained from the
aerial parts of Cleome droserifolia.212 Another nine compounds
of this type, trijugins A–I 230–238, have been found in an extract
of Salvia trijuga,213 while two novel germacrane derivatives
bearing a methylthiopropenoate moiety, 239 and 240, have been
isolated from Thapsia villosa.214 The rhizomes of Curcuma zeo-
daria contain the new sesquiterpenoid 241, which has been
named curcuzederone.215 Known germacrane sesquiterpenes
have been identified as components of Ferula lycia188 and Cur-
cuma malabarica.216 The diketogermacradiene 242 is a precursor
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of the new sesquiterpene 6a-hydroxy-curcumanolide A 243,
which has been obtained from the rhizomes of Curcuma longa.78
The structure of the sesquiterpene 244 has been determined by
X-ray analysis.217 A new germacrane A synthase (HaGAS3) has
been found in glandular trichomes of Helianthus annuus.218
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The new germacrane lactones, which have been isolated from
natural sources during 2010, are shown in Table 1. The structures
245–254 represent the new germacranolides, while the structures
255–257 and 258, 259 have been assigned to the new
heliangolides and melampolides, respectively. No new
cis,cis-germacranolides were obtained this year.
Known germacrane lactones have been identified as compo-
nents of Brachanthemum gobicum,229 Centaurea arenaria,230
Centaurea lippii231 Carpesium rosulatum,232 Lactuca aculeata,233
Smallanthus sonchifolius234 and Vernonia scorpioides.235 The
conformational properties of 6-epi-desacetyllaurenobiolide have
been investigated.236 Studies on acid rearrangement of epoxy-
germacranolides have permitted the determination of the abso-
lute configuration of 1b,10a-epoxy-salonitenolide237 and other
sesquiterpene lactones.238 A second-generation total synthesis of
(�)-diversifolin has been achieved.239
The effects of parthenolide in the oxaliplatinum treatment of
human lung cancer A549 cells, via the inhibition of NF-kB
Table 1 Sources of germacrane lactones
Source Compounds Ref.
GermacranolidesAnthemis melanolepis 245, 246 219Artemisia anomala 247, 248 139Magnolia kobus 249 220Rolanda fruticosa 250 221Schkuhria pinnata 251 222Scorzonera austriaca 252 223Taraxacum udum 253, 254 224HeliangolidesCentaurea sulphurea 255 225Eremanthus argenteus 256, 257 226MelampolidesArtemisia anomala 258 227Gonospermumfruticosum
259 228
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activation and induction of apoptosis, have been studied.240 It
has been shown that water-soluble analogues of this sesquiter-
pene lactone suppress in vivo prostate cancer growth.241
Protective effects of isoatriplicolide tiglate against glutamate-
induced neurotoxicity in primary cultured rat cortical cells have
been observed. This known germacranolide was obtained from
Paulownia coreana and Paulownia tomentosa.242,243
15 Elemane
Kachiraterpenol 260 is a new sesquiterpene, which has been
isolated from Magnolia kachirachirai.244 Two novel elemanolide
dimers with a tricyclic ortho ester moiety, vernodalidimer A 261
and vernodalidimer B 262, have been found in an extract of the
seeds of Vernonia anthelmintica.245 Both compounds can be
formed by Diels–Alder reactions, the first between two verno-
ladin molecules and the second between vernoladin246 263 and
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vernoladol247 264, which are also components of this plant. The
synthesis of occidenol 265 has permitted the correction of its
stereochemistry.248 The structures of two lactones, previously
isolated from Schkhuria anthemoides,249 have been revised222 as
266 and 267.
16 Eudesmane, lindenane, axane and oppositane
The sesquiterpene 268 has been isolated from an unidentified
liverwort of the Gackstroemia genus.250 The eudesmane deriva-
tives 269, 270 and 271 have been obtained from Ambrosia
arborescens,161 Cleome droserifolia,212 and Ecdysanthera rosea,251
respectively. The aerial parts of Gonospermum fruticosum228
contain four new sesquiterpenes related to costol 272–275. Other
compounds of this type 276, 277 and 278, 279 have been found in
extracts from Gymnaster koraiensis252 and Verbesina virginica,253
respectively. The furanoeudesmane chlomultin B 280 is another
new sesquiterpene, which has been obtained from Chloranthus
multistachys,135 whilst the methyl esters 281, 282 and 283 have
been identified as components of Dimerostemma arnottii254 and
Echinops ritro,255 respectively. The species Chrysanthemum indi-
cum,256 Curcuma wenyujin16 and Sarcanda glabra257 contain the
new eudesmane sesquiterpenes chrysanthemdiol A 284, curco-
dione 285 and glabranol B 286, respectively. A chemical study of
a Tibetan folk medicinal species, Pulicaria insignis, afforded the
trinorsesquiterpene 287.258 Another compound of this type 288
has been obtained from the aerial parts of Senecio argunensis.138
The meroterpene psidial C 289 has been found in an extract of
the leaves of Psidium guajava.170 The glucosides litchioside A 290
and litchioside B 291 have been identified as components of
lychee seed (Litchi chinensis).259 The methyl esters 292 and 293
have been obtained from Inula japonica,260 whilst the glucoside
294 has been isolated from Chloranthus anhuiensis.261 Known
eudesmane derivatives have been isolated from Aeschynanthus
mengxinggensis,262 Inula falconeri,263 Nectandra cissifiora264 and
Shorea javanica.265
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Table 2 Sources of eudesmanolides
Source Eudesmanolides Ref.
Ajania przewalskii 295 281Anthemis melanolepis 296 219Anthemis ruthenica 297 282Aster himalaicus 298 283Chloranthus anhuiensis 299, 300 284Chloranthus spicatus 301–304 285Curcuma wenyujin 305 16Daucus glaber 306 286Dimerostemma arnottii 307 254Inula helenium 308, 309 287Inula japonica 310–335 260,288Inula racemosa 336, 337 289Lactuca sativa 338, 339 290Lactuca tatarica 340 291Pulicaria insignis 341 258Salvia castanea 342, 343 292Sarcandra glabra 344 293Saussurea involucrata 345 294Sonchus arvensis 346, 347 295Trattinickia rhoifolia 348–350 296
Enantioselective total syntheses of dihydrojuneol266 and
(+)-carainterol A267 have been accomplished, while depsilairdin
has been synthesized by esterification of lairdinol A with a tetra-
depsipeptide.268 A preparation of ar-occidol has been reported.269
The sesquiterpene 1a-hydroxy-b-dihydroagarofuran has been
obtained from the fruits ofCryptomeria fortunei.270 Other dihydro-
b-agarofuran derivatives have been isolated this year from Celas-
trus angulatus,271,272 Celastrus paniculatus,273 Maytenus jelskii,274
Maytenus spinosa, Maytenus vitisidaea,275 Osyris lanceolata276 and
Tripterygium wilfordii.277,278 The synthesis and insecticidal activity
of new celangulin-V derivatives have been reported.279 A racemic
synthesis of a-agarofuran has been achieved.280
The new eudesmanolides, which have been obtained from
different species, are listed in Table 2. Their structures have been
shown to be 295–350.
There are several points to note in relation to these eudesma-
nolides. A norsesquiterpene lactone 295 with a rare carbon
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skeleton has been isolated from Ajania przewalskii,281 whilst the
novel lactam cespilactam A 351 has been found in an extract of
the Formosan soft coral Cespitularia hypotentaculata.297 Known
eudesmanolides have been obtained from Atractyloides chi-
nensis.298 Structural modifications have been carried out on
alantolactone and isoalantolactone, with the aim to understand
the larvicidal activity of these eudesmanolides against Aedes
aegypti. In this work, the absolute configurations of these
lactones were determined by X-ray analysis.299 Syntheses of novel
a-santonin derivatives as potential cytotoxic agents have been
carried out.300
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The lindelane sesquiterpenes oxyonoseriolide 352 and
hedyosmone 353 have been obtained from the bark of Hedyos-
mum angustifolium.301 The structure of glabranol A, isolated
from Sarcandra glabra,257 has been determined as 354. This plant
also contains the linderanolide sarcandralactone A 355 and the
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dimers sarcandrolides A–E 356–360.293 Other lindelane dimers,
chloramultiols A–F 361–366, have been found in extracts from
Chloranthus multistachys,302,303 whilst another research group has
described the isolation of the dimers multistalide A 367 and
multistalide B 368 from this same species.304
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A formal and racemic synthesis of axamide-1 and axisonitrile-
1 has been achieved.305 The new oppositane sesquiterpenes lep-
tocladolin A 369 and leptocladolin B 370 have been identified as
components of the Formosan soft coral Sinularia leptoclados.306
Another sesquiterpene 371 with this skeleton has been isolated
from Senecio argunensis.307
17 Vetisperane
The new solavetivone derivative argutosine D 372 has been iso-
lated from Incarvillea arguta,308 whilst 3-hydroxysolavetivone-b-
D-glucoside A and 3-hydroxysolavetivone-b-D-glucoside B have
been obtained from the leaves of Nicotiana tabacum.309 Studies
on the production of phytoalexins, with a vetispirane skeleton,
by hairy root cultures of Hyoscyamus albus have been
described.310
18 Eremophilane, valencane and bakkane
A study of the fermentation of the fungus Xylaria sp. BCC 21097
afforded seven new eremophilane derivatives 373–379.311
Another sesquiterpene of this type, xylaranic acid 380, has been
found in an extract of a second species of this genus, Xylaria sp.
101,312 whilst 1-(xylarenone A)xylariate 381 has been obtained
from a third species, Xylaria sp NCY2, which is an endophyte of
the plant Torreya jackii.313 Two new eremophilane derivatives,
cupressolide A 382 and cupressolide B 383, have been isolated
from another Xylariaceous microorganism, which is endophytic
in the tissues of Cupressus lusitanica leaves.314 Another endo-
phytic fungus, Microdiplodia sp. KS 75–1, contains two new
sesquiterpenoids 384 and 385. In this work, the stereochemistry
at C-8 of phomadecalin C and phomadecalin D have been cor-
rected to 386 and 387, respectively.315 Cryptosphaerolide 388 is
a cytotoxic Mcl-1 inhibitor, which has been obtained from saline
cultures of a marine-derived species of the Cryptosphaeria
genus.316
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The sesquiterpene glucoside 389 has been isolated from the
roots of Lindera strychnifolia,40 whilst argutosines A–C 390–392
and delavayol 393 have been obtained from Incarvillea arguta308
and Incarvillea delavayi,317 respectively. Other new compounds of
this type 394–411 and lineariifolianone 412 have been found in
extracts from the rhizomes of Farfugium japonicum318 and from
the aerial parts of Inula lineariifolia,319 respectively. A chemical
study of Parasenecio deltophylla320 led to the isolation of five
eremophilane derivatives 413–417, whilst an investigation of
Senecio santelisis321 afforded the sesquiterpenes 418 and 419.
Other species of this genus, Senecio ambraceus322 and Senecio
nemorensis,323 contain the new eremophilenelactones 420 and
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Table 3 New eremophilane sesquiterpenes from Ligularia species
Source Eremophilanes Ref.
Ligularia anoleuca 426 325Ligularia fischeri 427–433 326,327,328,329Ligularia muliensis 434, 435 330Ligularia oligonema 436 331Ligularia veitchiana 437 332
421, respectively. The eremophilane sesquiterpenes 422–424 are
stress metabolites, which have been isolated from Chloranthus
anhuiensis261 after treatment with CuCl2. The new eremophila-
nolide 425 has been obtained from Carpesium cernuum.324 The
studies on components of the Ligularia genus have continued
with intensity during this year (see Table 3).
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Mass spectrometry of crude extracts of fourteen samples of
Ligularia virgaurea, collected in two provinces of China, has
permitted the classification of this species into two phyto-
chemical groups.333 The absolute configuration of ten known
eremophilane sesquiterpenes, isolated from Petasitis hybridus,
has been assigned by comparison of their simulated and
experimental circular dichroism spectra.334 The intermediacy of
a eudesmane cation in the cyclization of farnesyl diphosphate
to (+)-aristolochene, catalyzed by aristolochene synthase, has
been reported.335 An enantioselective total synthesis336 of
(�)-platyphyllide has permitted the revision of its absolute
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configuration as the (6S,7S)-enantiomer 438. This sesquiterpe-
noid had been isolated from Senecio platyphylloides.337,338 The
structural requirements for repellency of several nootkatone
derivatives against the Formosan subterranean termite,
Coptermes formosanus, have been investigated.339 Different
methodologies have been employed in a study on the selective
hydrogenation of the ring system of nootkatone and other
valencane derivatives.340
Ligulactone A 439 and ligulactone B 440 are two bakkeno-
lides, which have been isolated from Ligularia fischeri.341 The
cytotoxic activity of a new lactone of this type 441, isolated from
Petasites tatewakianus, has been evaluated.342 Diastereoselective
total syntheses of bakkenolides A,343 I, J and S344 have been
accomplished.
19 Guaiane, xanthane, pseudoguaiane, patchoulane,bourbonane and carabrane
The sesquiterpene 10,11,12-guaianetriol 442 and 1,10,11,12-
guaianetetrol 443 have been isolated from an endophytic fungus
S49 of Cephalotaxus hainanensis,345 while xylaranol A 444 and
xylaranol B 445 have been found in an extract of Xylaria sp.
101.312 The fruiting bodies of Lactarius hatsudake contain lac-
tarioline A 446 and lactarioline B 447, two guaiane derivatives
with biological properties.346 Oreolactone 448 is another azulene-
type pigment, which has been obtained from the rhizomes of
Oreocnide frutescens.347 The guaiane derivatives 449, 450, 451–
455 and 456 have been isolated from Acorus calamus,131 Cleome
droserifolia,212 Daucus carota,348,349,350,351 and Daphne
aurantiaca,121 respectively. Another two new compounds of this
type 457 and 458 have been obtained from the fruits of Torilis
japonica.352 The sesquiterpenoids 459, 460 and 461 have been
found in extracts from Curcuma longa,78 Croton regelianus353 and
Saussurea laniceps,354 respectively. The structure of chlomultin A
has been determined as 462. This furanoguaiane is a component
of Chloranthus multistachys.135 Blumeaenes A–J 463–472 are
guaiane esters with NO inhibitory activity, which have been
obtained from Blumea balsamifera.355 A phytochemical study of
the flowers of Artemisia rupestris356 afforded four novel guai-
pyridine alkaloids, which have been named rupestines A–D 473–
476. Another species of this genus, Artemisia anomala,227
contains the seco-acid 477.
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The structures of leptocladol A, leptocladol B and 1-epi-
chabrolidione A have been determined as 478–480, respectively.
These guaiane derivatives have been isolated from a Formosan
soft coral, Sinularia leptoclados.357 Known guaiane sesquiter-
penes have been identified as components of Curcuma malabar-
ica.216 The structure of curcumenol, a known sesquiterpene from
Curcuma zeodaria, has been confirmed by X-ray analysis.358
The characterization of a d-guaiane synthase from cultured
cells of Aquilaria plants has been reported. This enzyme is
responsible for the formation of the sesquiterpenes in agar-
wood.359 Enantiospecific total syntheses of aciphyllene360 and
isocalamusenone361 have been achieved. (R)-Limonene has been
used as starting material in the synthesis of two epimeric 11-
hydroxy-guaiadienes 481 and 482.362 A racemic synthesis of
clavukerin K 483 has been described,363 while an enantioselective
synthesis of this last sesquiterpene and isoclavukerin A has been
accomplished.364 Four research groups have carried out
racemic365 and enantiospecific366–368 syntheses of the guaiane
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Table 4 Sources of guaianolides
Source Guaianolides Ref.
Ajania przewalskii 485 281Amberboa ramosa 487, 488 369Artemisia anomala 499, 508, 517, 518, 529 139,227,370Artemisia dubia 484, 486, 490, 495–498, 509 371Carpesium cernuum 519 324Chloranthus anhuiensis 528 284Chrysanthemum indicum 503, 504 256Cichorium glandulosum 489, 492 372Daphne aurantiaca 520–523 121Daucus glaber 511–516 286Echinops ritro 502, 505 255Inula japonica 310–317 288Inula linearifolia 524–527 319Lactuca sativa 507 290Lactuca tatarica 491 291Schkuhria pinnata 251 222Scorzonera austriaca 493, 494, 500, 501, 506 223Thapsia villosa 510 214
sesquiterpene (�)-englerin A, a potent and selective inhibitor of
renal cancer cell growth, which had been isolated from
a Tanzanian plant. A short synthesis of teucladiol and iso-
teucladiol has been accomplished.208
New guaianolides have been isolated during the period
covered by this review (see Table 4). The novel guaian-6a,12-
olides, i.e. 484–509, are listed in Table 5 and other new guaia-
nolides are represented by the 6b,12-lactones 510–516, the dimers
251, 310–317 and 517, the guaian-8,12-olides 518–525 and the
seco-guaianolides 526–529.
Known guaianolides have been isolated from Anthemis sege-
talis,373 Lactuca aculeata233,374 and Lactuca altaica.375 A biomi-
metic total synthesis of (+)-ainsliadimer A has been
accomplished,376 whilst a synthesis of the guaianolide ring system
has been achieved, starting from (R)-(�)-carvone.377 The cata-
lytic hydrogenation and the addition of methanol to a-methy-
lene-g-lactones in eremanthine derivatives have been studied.378
The design and synthesis of novel guaianolide-endoperoxides as
potential antimalarial agents have been reported.379 It has been
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shown that the lactone trilobide activates the production of
interferon-g and nitric oxide,380 whilst diversolides A, D, F and
G were active against Epstein-Barr virus early antigen activation,
induced by a phorbol derivative.381
The xanthane sesquiterpene curcumadionol 530 has been
obtained from Curcuma wenyujin.16 The total synthesis and the
determination of the absolute configuration of (+)- and
(�)-sundiversifolide have been achieved. In this work, another
three xanthanolides, 8-epi-xanthatin, dihydroxanthatin and
xanthatin, were also prepared.382 The semisynthesis of xanthinin
and 4-epi-isoxanthanol, and their protein farnesyltransferase
inhibitory activity, have been reported.383
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Table 5 Novel guaian-6a,12-olidesa
Name StructurePosition ofdouble bond(s) Substituents and configurations Ref.
Artemdubolide F 484 1–2, 9–10, 11–13 3a-OH, 4a-OH, 8a-OH 371Artemdubolide F derivative 485 1–2, 9–10, 11–13 3a-OH, 4a-OH, 8a-OAng 281Artemdubolide G 486 2–3, 11–13 1a-OH, 4b-OH, 8a-OAc, 10a-OH 371Amberbin A 487 3–4 8a-OAc, 10a-OH, 11a 369Amberbin B 488 3–4 8a-OAc, 10a-OGlc, 11a 369Cichoralexin derivative 489 3–4 2-oxo, 8a-OAng, 10b, 11a 372Artemdubolide D 490 3–4, 9–10, 11–13 1a-OH, 8a-OSen 371Involucratin derivative 491 3–4, 10–1 2-oxo, 8a-OH, 11b-OH, 15-OH 291Austricin derivative 492 3–4, 10–1 2-oxo, 8a-OMesen, 11a 372Scorzoaustriacin derivative 493 3–4, 10–1 2-oxo, 8a-OH, 11a, 14-OVali 223Scorzoaustriacin derivative 494 3–4, 10–1 2-oxo, 8a-OSO3H, 11a, 14-OVali 223Artemdubolide A 495 3–4, 10–14, 11–13 1a-OH, 8a-OSen 371Artemdubolide B 496 3–4, 10–14, 11–13 1a-OH, 8a-OMebu 371Artemdubolide C 497 3–4, 10–1, 11–13 8a-OMebu 371Artemdubolide E 498 3–4, 11–13 2-oxo, 8a-OH, 10b,1b-epoxy 371Leucodin derivative 499 3–4, 11–13 2-oxo, 5a-OH, 10b-OH 227Scorzoaustriacin 500 4–15, 10–14 3b-OH, 11a, 13-R 223Scorzoaustriacin glucoside 501 4–15, 10–14 3b-OGlc, 11a, 13-R 223A D7(11)-guaianolide 502 7–11, 10–14 3a-OH, 4a, 13-OH 255Chysanthguaianolactone A 503 9–10 1a-OH, 3a,4a-epoxy, 8a-OAng, 11a 256Chysanthguaianolactone B 504 10–1 3a,4a-epoxy, 8a-OAng, 11a 256Deoxoleucodin derivative 505 10–1 3a-OH, 4a, 11b, 14-OH 255Estafiatol derivative 506 10–14 3b-OH, 4b, 11a 223Amphoricarpolide derivative 507 10–14, 11–13 4a-OGlc, 15-OH 290Bibsanin derivative 508 11–13 1a,2a-epoxy, 3b-Cl, 4b-OH, 10b-OH 227Artemdubolide H 509 11–13 1b-Cl, 2b-OH, 3b,4b-epoxy, 8a-OMebu, 10b-OH 371
a R ¼ aminomethyl-g-butyrolactone.
Thenewpseudoguaiane sesquiterpene531hasbeen isolated from
Trichiliaquadrijuga,384while the lactones 532,533and534,535have
been obtained from Ambrosia arborescens161 and Inula japonica,260
respectively. Another novel pseudoguaianolide 536 have been
found in an extract of Inula linearifolia.319 Known compounds of
this type, with cytotoxic activity, have been obtained from
Ambrosia peruviana.385 The quantitative variation of the sesquiter-
pene lactones helanin and dihydrohelanin in different German
Arnica montana populations has been investigated.386 The anti-
proliferative effect and ultra structural alteration induced by psi-
lostachyn on Trypanosoma cruzi has been described.387
The cyclization of singly labelled [2-2H1]farnesyl diphosphate
catalyzed by recombinant patchoulol synthase from Pogostemon
cablin has been studied. In this work, a new semisystematic
nomenclature has been proposed with the aim of distinguishing
the three different skeleta of the patchoulane sesquiterpenes.388
1602 | Nat. Prod. Rep., 2011, 28, 1580–1610
The new bourbonenolide 537 has been isolated from the leaves
and twigs of Rolanda fruticosa.221 Pubescenone 538 is an 11(7/
6)abeo-14-nor-carabrane sesquiterpene, which has been found in
an extract of the aerial parts of Siegesbeckia pubescens.389 The
synthesis and antifungal activity of several carabrone derivatives
have been described.390
This journal is ª The Royal Society of Chemistry 2011
20 Aromadendrane, bicyclogermacrane, valerenane,aristolane, nardosinane and zierane
Twonew aromadendrane sesquiterpenoids 539 and 540 have been
isolated from cultures of the fungus Agrocybe salicacola.391 The
liverwort Plagiochila bursata392 contains the 2,3-seco-aromaden-
drane 541, while an alloaromadendrane derivative 542 has been
obtained from the rhizomes of Ligusticum chuanxiong.393 A
chemical study of theVietnamese nudibranchmolluskPhyllidiella
pustulosa394 afforded another compound of this type 543. The
meroterpenes psidial B 544 and psiguadial A 545 have been found
in extracts from the leaves of Psidium guajava.170,171 It has been
shown that a SAV_76 synthase from Streptomyces avermitilis
catalyzes the cyclization of farnesyl diphosphate to a new tricyclic
sesquiterpene alcohol 546, which has been named avermitilol.395
The new bicyclogermacranes 547 and 548 have been isolated
from the aerial parts of Calamintha ashei,396 whilst other
sesquiterpenes volvalerenals A–E 549–553 and volvalerenic acids
This journal is ª The Royal Society of Chemistry 2011
A–C 554–556 have been obtained from the roots of Valeriana
officinalis.397 This last plant also contains the novel sesquiterpe-
noid volvalerenone A 557.398 Another compound of this type
valerena-4,7(11)-diene, a highly active sedative, has been
synthesized starting from valerenic acid.399
The sesquiterpenoid 558 has been isolated from an unidentified
liverwort of the Gackstroemia genus.250 A new aristolane sesqui-
terpene 559 has been found in the marine red alga Laurencia sim-
ilis.400Chromatography of an extract of the soft coralParalemnalia
thyrsoides afforded seven novel nardisonane derivatives 560–566,
which have been named paralemnolins J–P.401 Later, another three
sesquiterpenes 560, 567 and 568were obtained from the same coral
species, and named paralemnolins J, K and L, respectively.160
Consequently, to avoid confusion the last two compounds 567 and
568 should be renamed as paralemnolins R and S, respectively. The
novel zierane lactone chandiolide 569 has been found in an extract
of the Tahitian liverwort Chandonanthus hirtellus.402
Nat. Prod. Rep., 2011, 28, 1580–1610 | 1603
21 Pinguisane
Two chemical constituents of the Vietnamese liverwort Porella
densiflora403 have been identified as the novel sesquiterpenoids
norpinguisone 570 and its methyl ester 571.
22 Salviolane
Two new salvionane derivatives 572 and 573 have been isolated
from the aerial parts of Senecio argunensis.307
23 Miscellaneous sesquiterpenoids
The structure of stereumin F has been determined as 574. This
new sesquiterpene has been obtained from a fungus of the
Stereum genus.130 Abiespiroside A 575 is a novel sesquiterpene
spirolactone, which has been found in Abies delavayi,404 whilst
the dilactone gaultheriadiolide 576 has been isolated from
Gaultheria yunnanensis.405 The bark and root of Thottea
hainanensis contain the sesquiterpene thotteodiol 577, which
possesses a new carbon skeleton.406 The meroterpenoid globi-
ferane 578 has been identified as a component of Cordia globifera
root.407 The structures of terebanene, teredenene and ter-
ebinthene, have been determined as 579–581, respectively. These
compounds, isolated from the fruits of Schinus terebinthifolius,
have a new carbon framework named terebanane, which prob-
ably derives from an illudane sesquiterpene.408 Cryptotrione 582
is a C35 terpenoid, formed by the coupling of a unique bicyclic
sesquiterpene and an abietane diterpene. This substance is
a component of Cryptomeria japonica.409
The root of Ligusticum grayi contains the new thapsane
derivatives thapsadiene 583, a-thapsenol 584 and b-epithapsenol
585, and another fourteen sesquiterpenes representing eight
novel carbon skeleta, named as pretapsane (a-pretapsenol 586
and b-pretapsenol 587), isothapsane (isothapsadiene 588, a-iso-
thapsenol 589 and b-isothapsenol 590), ligustigrane
1604 | Nat. Prod. Rep., 2011, 28, 1580–1610 This journal is ª The Royal Society of Chemistry 2011
(a-ligustigrenol 591 and b-ligustigrenol 592), isoligustigrane
(a-isoligustigrenol 593 and b-isoligustigrenol 594),
preisothapsane (a-preisothapsenol 595 and b-preisothapsenol
596), allothapsane (allothapsenol 597), isoprethapsane (iso-
prethapsenol 598) and oshalagrane (oshalagrenol 599).21
The gorgonian coral Rumphella antipathies contains rum-
phellclovane A 600, which possesses a novel carbon framework,
which probably arises from a clovane sesquiterpene.174 The
structures 601 and 602 have been assigned to two sesquiterpenes
with antibacterial properties, obtained from the marine macro-
alga Ulva fasciata.410
Total syntheses of (�)-crassifolone, (�)-dihydrocrassifolone411
and (+)-frondosin B412 have been carried out. Echinopines A and
B have been synthesized in both enantiomeric and racemic
forms.413 A stereoselective synthesis of (�)-urechitol A has been
achieved.414 (R)-Carvone has been used as starting material in the
synthesis of the optical antipode of the sesquiterpene 5-sen-
ecioyloxy-10,11-epoxy-thapsan-10-ol.415 The first total synthesis
of (+)-chabranol has been accomplished in six steps.416 This
compound had been recently isolated fromNephthea chabrolii.417
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