3-Hydroxybutanolide Derivatives and Avonoid Glucosides From Anoectochilus Roxburghii

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REVIEW
www.rsc.org/npr | Natural Product Reports
Triterpenoids
Joseph D. Connolly and Robert A. Hill*
Received 26th August 2009
First published as an Advance Article on the web 26th November 2009
DOI: 10.1039/b808530g
Downloaded on 06 January 2013

Published on 26 November 2009 on http://pubs.rsc.org | doi:10.1039/B808530G
Covering: January 2007 to December 2008. Previous review: Nat. Prod. Rep., 2008, 25, 794
This review covers the isolation and structure determination of triterpenoids including squalene
derivatives, protostanes, lanostanes, holostanes, cycloartanes, dammaranes, euphanes, tirucallanes,
tetranortriterpenoids, lupanes, oleananes, friedelanes, ursanes, hopanes, isomalabaricanes and
saponins; 574 references are cited.
1
2
3
4
4.1
5
6
7
8
9
10
Introduction
The squalene group
The lanostane group
The dammarane group
Tetranortriterpenoids
The lupane group
The oleanane group
The ursane group
The hopane group
Miscellaneous compounds
References
1 Introduction
Interest in the pharmaceutical activities of triterpenoids
continues to increase.1 Reviews have appeared on the triterpenoid constituents of Boswellia serrata,2 Lantana camara,3
Lysimachia species4 and Maytenus species.5 The classification
and occurrence6 and extraction7 of plant triterpenoid saponins
have been surveyed. Further reviews include the pharmaceutical
activities of pentacyclic triterpenoid saponins,8 the biological
activities of triterpenoid saponins containing monoterpenoid
moieties9 and central nervous system activities of triterpenoid
saponins.10
braunicetals (e.g. 15 and 16), an inseparable mixture of

compounds from the green microalga Botryococcus braunii.17 An
enantioselective total synthesis of achilleol B 17 has led to the
revision of its C-18 configuration.18
Oxidosqualene cyclase homologues from Arabidopsis thaliana
continue to attract attention. At1g78955 (CAMS1) converted
oxidosqualene almost entirely (98%) into the monocyclic product
camelliol C 18, with only traces of achilleol A (2%) and b-amyrin
(0.2%) being formed.19 This enzyme appears to have evolved
from the enzymes which lead to pentacyclic products. A lanosterol synthase-deficient yeast strain At1g78500 afforded the two
8,14-seco-derivatives 19 and 20 of a-amyrin and b-amyrin.20 The
C-14 configuration of arabidiol 21, produced by At4g15340, has
been established as R.21 The stereochemistry of the addition of
water to triterpenoid cationic intermediates is also discussed.
Replacement of Phe699 by threonine in the oxidosqualene-lanosterol cyclase ERG7 from Saccharomyces cerevisiae resulted in
the formation of protosta-13(17),24-dien-3b-ol 22 instead of
lanosterol.22 Calculations suggest that the biosynthesis of
friedelin is a non-stop process which involves pentacyclisation
of squalene oxide to the lupanyl cation followed by ten suprafacial 1,2-shifts of methyls and hydrogens.23 Several reviews have
appeared covering aspects of oxidosqualene-lanosterol cyclase,24
engineering squalene cyclising enzymes25 and the properties of
oxidosqualene cyclases.26,27
2 The squalene group

Tetrahydroxysqualene 1, from the leaves and twigs of Rhus
taitensis, is active against Mycobacterium tuberculosis.11 Ekeberins D1D5 26 are antiplasmodial squalene derivatives from the
stem bark of Ekebergia capensis.12 The absolute configuration of
intricatetraol 7, from Laurencia intricata, has been determined by
total synthesis.13 Several squalene-derived polyethers have been
reported from marine organisms. These include aplysiols A 8 and
B 9 from the mantle of the sea hare Aplysia dactylomela,14
laurenmariannol 10, together with compound 8, from the red alga
Laurencia mariannensis15 and omaezakianol 11 and 15,16-anhydrothyrsiferol 12 from Laurencia omaezakiana.16
The condensation of C32 and C34 macrocyclic aldehydes with
the methylated squalene diols 13 and 14 gives rise to the
Department of Chemistry, Glasgow University, Glasgow, G12 8QQ, UK
This journal is The Royal Society of Chemistry 2010
The lanostane group
The marine-derived fungus Aspergillus sydowii produces the new

protostane triterpenoid 23, a hydrate of the known helvolic
acid.28 In the original paper this compound is described as
a nordammarane. 1,2-Dihydrohelvolic acid 24 has been found in
the entomopathogenic fungus Metarhizium anisopliae.29 Alisolide 25, alisol O 26 and alisol P 27 are new compounds from the
rhizome of Alisma orientale, a rich source of protostanes.30
Unfortunately the name alisol O has already been used. The
X-ray crystal structure of the known alisol B 23-acetate is also
reported in this paper. Other new compounds from Alisma orientale include 25-anhydroalisol F 28 and 11-anhydroalisol F 2931
and 11,25-bisanhydroalisol F 30.32 Compound 29 has also been
named 24-deacetylalisol O, referring to the original alisol O
structure.33
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Abiesanolides E 31, F 32, I 33 and J 34 are new lanostane and

mariesane derivatives from Abies sachalinensis.34,35 The free acid
35 and methyl ester 36 analogues of abiesanolide J have also been
isolated from the same source.36 Marianine 37 and marianosides
A 38 and B 39 are chymotrypsin-inhibitory constituents of the
whole plant of Silybum marianum.37 The structure of a lanostane
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disulfate 40, from the green microalga Tydemania expeditionis,

was confirmed by X-ray crystallographic analysis.38 Lanopropic
acid 41 is a 2,3-secolanostane from Schisandra propinqua var.
propinqua.39 Other new lanostanes include the nigrumane derivatives 4244 from the mangrove plant Hibiscus tiliaceus,40 4548
from Euphorbia humifusa,41 4952 from Diospyros discolor,42 53

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from the stems of Artabotrys uncinatus,43 the acetate 54 from

Fomitopsis pinicola44 and nigralanostenone 55 from the leaves of
Solanum nigrum.45
Colossolactones I 56, II 57, III 58, V 59, VI 60 and VII 61 are
new constituents of the Vietnamese mushroom Ganoderma
colossum.46,47 New compounds from other Ganoderma species
include 3-epi-pachymic acid 62 and 63 from Ganoderma
resinaceum,48 ganoderic acids AP2 64 and AP3 65 from
Ganoderma applanatum,49 66 and 67 from Ganoderma lucidum50
and ganolactone B 68 and ganoderiol A triacetate 69 from
Ganoderma sinense.51 Three unusual D16-lanostanes 7072 have
been reported from Ganoderma lucidum.52 Methyl australate 73,
from Ganoderma australe, shows antimicrobial activity.53 The
pharmacological activities of the Ganoderma triterpenoids,
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including the hepatoprotective54 and anti-cancer55 effects have

attracted a lot of interest.56,57,58
More lanostane derivatives have been reported from Poria cocus.
These include 29-hydroxypolyporenic acid C 74 and 25-hydroxypachymic acid 75,59,60 poriacosones A 76 and B 7761 and
15a-hydroxydehydrotumulosic acid 78, 16a,25-dihydroxydehydroeburicoic acid 79, 16-deoxyporicoic acid B 80, poricoic acid
CM 81, the endoperoxide 82 and 25-hydroxyporicoic acid H 83.62
Aeruginosols A 84, B 85 and C 86 are constituents of the
fruiting bodies of Stropharia aeruginosa.63 Astrapteridiol 87,
astrapteridone 88 and 3-epi-astrapteridiol 89 are from the
mushroom Astraeus pteridis.64 3-epi-Astrapterdiol 89 shows antituberculosis activity. The structure of astrapteridone 88 was
confirmed by X-ray crystallographic analysis. Inonotsulides A

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90, B 91 and C 92,65 inonotsuoxides A 93 and B 94,66 the triol 9567

and inonotsutriols A 96, B 97 and C 9868 are all constituents of
Inonotus obliquus. The structure of inonotsuoxide A 95 was
confirmed by X-ray analysis of the corresponding diacetate.
Kadsura coccinea is a rich source of lanostane derivatives. The

new compounds reported include kadsuracoccinic acids A 99, B
100 and C 101 from the rhizomes,69 secococcinic acids AE
102106, F 101 and coccinilactone A 107 from the rhizomes70
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and kadcoccilactone R 108 from the stems.71 The structure of

kadsuracoccinic acid A 99 was confirmed by X-ray analysis.
Kadsuracoccinic acid C and secococcinic acid F have the same
structure 101. Schisanlactone E 109 is a constituent of Kadsura
longipedunculata.72 The name schisanlactone E has been
previously used for a seco-cycloartane derivative.
Oligoporins A 110, B 111 and C 112 are new lanostane
saponins from Oligoporus tephroleucus.73 Three new saponins,
sativalanosteryl glucoside 11374 and orizalanosterolides A 114
and 11575 have been reported from rice hulls of Oryza sativa. The
unusual compound 116 is a proposed metabolite of Catharanthus
roseus hairy root cultures.76 Eylosides F1F7 and MV are
lanostane saponins from the Caribbean sponges Erylus formosus
and Erylus goffrilleri. The saponins from Erylus formosus include
the new genins 11711977 while erylosides T and U from Erylus
goffrilleri have the new genins 120 and 121.78
Leucospilotaside A, a new holostane glycoside from the sea
cucumber Holothuria leucospilota, has the genin 122.79 The same
genin is present in holothurin A3 from the Vietnamese sea
cucumber Holothuria scabra.80 It is accompanied by holothurin
A4, based on genin 123. 17-Hydroxyfuscocineroside B and

25-hydroxyfuscocineroside B, from the sea cucumber Bohadschia
marmorata, have the genins 124 and 125 respectively.81 Another sea
cucumber, Holothuria hilla, contains hillasides A 126 and B 127.82
Axilogoside, the 22-epimer of holothurin B, with the new genin 128,
has been isolated from Holothuria axiloga.83 Arguside A, a cytotoxic
glycoside from Bohadschia argus, has the new genin 12984 and
synaptoside A1, from Synapta maculata, has the new genin 130
while the co-occurring synaptoside A has a known genin.85 Five
new oligoglycosides, frondosides A7-1 A7-4 and isofrondoside C,
have been reported from Cucumaria frondosa, all with known genins.86 Other new holostane saponins with known genins
include argusides BE from Bohadschia argus,87,88 hillaside C
(ananaside D) from Holothuria hilla,89 impatienside A from
Holothuria impatiens,90 lecanorosides A and B from Actinopyga
lecanora,91 leucospilotasides A92,93 and C94 from Holothuria
leucospilota, liouvillosides A1A3, B1 and B2 from Staurocumis
liouvillei,95 marmoroside C from Bohadschia marmorata,96 okhotosides A1-1, A2-1,97 and B1B398 from Cucumaria okhotensis and
saponins without trivial names from Actinopyga lecanora99 and
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Pseudocolochirus violaceus.100 The biological activities of the holostane saponins have been surveyed.101,102
The amazing skeletal diversity of complex cycloartane-derived
products from Schisandra and Kadsura species continues to
86 | Nat. Prod. Rep., 2010, 27, 79132
impress.103 Preschisanartanin 131 and schindilactones A 132, B

133 and C 134 are constituents of Schisandra chinensis.104 The
structures of 131 and 132 were confirmed by X-ray analyses. The
same source afforded wuweizidilactones AF 135140105 and

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wuweizidilactones G 141, H 142, schindilactones DG 143146,

preschisanartanin B 147 and wuweizilactone acid 148.106 The
structure of 135 was confirmed by X-ray analysis. In solution,
schintrilactone A 149, from Schisandra chinensis, is in equilibrium with its 20-epimer, schintrilactone B 150.107 Extraction of
the leaves and stems of Schisandra lancifolia afforded lancifodilactones IN 151156.108 The structures of 151 and 154 were
confirmed by X-ray analysis. Micrandilactones DG 157160
are further constituents of the leaves and stems of Schisandra

micrantha.109 The structures and stereochemistry of micrandilactones B 161 and C 162 have been confirmed by X-ray
analyses.110 New compounds from Schisandra propinqua var.
propinqua include propindilactones AD 163166111 and propindilactones EJ 167172.112 Rubriflorins AJ 173182 are
constituents of Schisandra rubriflora.113,114 Lignans from this
plant have also been named rubriflorins A and B. The structure
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of rubrifloradilactone 183, from Schisandra rubriflora, has been

confirmed by X-ray analysis.115 Schisandra sphenanthera is the
source of sphenalactones AD 184187116 and sphlenadilactone
C 188 and sphenasin A 189.117 Wilsonianadilactones AC
190192 have been reported from Schisandra wilsoniana.118
Calculations show that the naturally-occurring enol lancifodilactone G 193 is more stable than its keto tautomer.119
Kadcoccilactones AQ 194211 have been isolated from
Kadsura coccinea.71,120 The structure of 194 was confirmed by
X-ray analysis. Kadsura heteroclita is the source of heteroclitalactones GM 212218121 and longipedlactone J 219.122
Other compounds in this series include kadlongilactones CF
220223 from Kadsura longipedunculata,123 polysperlactones A
224 and B 212 (same as heteraclitalactone G) from Kadsura
polysperma124 and renchanglactone A 211 (same as kadcoccilactone Q) from Kadsura renchangiana.125

Two groups have reported a new cycloartane alkaloid 225
from the rhizomes of Cimicifuga foetida,126,127 which has two
names, cimicifine A and cimicifugadine. Three new ring-D
cleaved glycosides 226228 have been isolated from Cimicifuga
rhizome.128 Cimicifoetisides A 229 and B 230 are cytotoxic
glycosides from Cimicifuga foetida.129 Chlorodeoxycimigenol
3-O-b-D-xyloside 231 has been identified in extracts of Cimicifuga
racemosa.130 It appears to be an artefact of the extraction process.
Colossolactones IV 23246 and VIII 23347 are rearranged
cycloartane ring-A lactones from the Vietnamese mushroom
Ganoderma colossum. Monocarpinin 234 and the 28,29-dinorderivative 235 are constituents of Monocarpia marginalis131 and
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Chukrasia tabularis var. velutina,132 respectively. Commiphora

opobalsamum contains nine new cycloartanes 236244.133,134
Other simple new cycloartanes include 245 from Senefelderopsis
chiribiquetensis,135 berenjenol 246 from Oxandra cf.
xylopioides,136 247 from Aglaia forbesii,137 248 from Gnetum
pendulum,138 249 from Derris laxiflora,139 250 from Skimmia
laureola,140 251 from the marine green alga Cladophora
fascicularis,141 252 from Euphorbia guyoniana,142 253 from
Euphorbia humifusa,143 artocapuates A 254 and B 255 from
Artocarpus nobilis,144 256258 from Cocos nucifera,145 259 and
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260 from Nigella sativa,146 261 from Fritillaria hupehensis,147 and

the chloro-derivative 262 from Ligularia stenocephala.148
Reference NMR data from synthetic 23E- and 23Z-cycloart-23ene-3b,25-diols indicate that structural revision is required for
several related triterpenoids.149
The cycloartane-3b,7b,24R,25-tetraol 263 is a new genin of the
cycloartane glycosides from Camptosorus sibiricus.150 Aquilegiosides K and L, from Aquilegia vulgaris, also have new genins
264 and 265.151 Sutherlandiosides AD 266269 are new glucosides from Sutherlandia frutescens.152 The structure of 266 was

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confirmed by X-ray analysis. Tareciliosides AG have been

reported from the leaves of Tarenna gracilipes and include the
new genins 270272.153 Podocarpasides AJ 273282 are
constituents of the roots of Actea podocarpa.154,155 The structure
of podocarpaside E 277 was revised on the basis of an X-ray
analysis.156 Two new cycloartane xylosides 283 and 284 have
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been reported from the roots of Actea pachypoda, together with

the known 12b-acetoxycimigenol.157 Cyclomacrogenin B 285 is
cycloartane-1a,3b,7b,24R,25-pentaol, which was obtained from
Astragalus macropus.158 A variety of saponins with new genins
has been reported from Astragalus species, including bicusposides A 286, B 287 and C 288 from Astragalus bicuspis,159

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mongholicosides A 289 and B 290 from Astragalus

membranaceus var. mongholicus,160 eremophilosides AK
from Astragalus eremophilus161 (eremophilosides CK have the
new genins 291299) and three saponins from Astragalus
campylosema ssp. campylosema with the new genins 300302.162
New cycloartane saponins with known genins include astramembranosides A and B from Astragalus membranaceus,163
cimiaceroside C, cimifosides AD164 and cimifoetisides VI and
VII165 from Cimicifuga foetida, cycloascauloside B from
Astragalus caucasicus,166 cyclochivinosides B,167 C168 and D169
from Astragalus chivensis, cyclosophoside A from Cassia
sophera,170 cyclotrisectoside from Astragalus dissectus171 and
saponins without
trivial names from Camptosorus
sibiricus172,173,174 and Thalictrum fortunei.175
Machilaminosides A 303 and B 304 are unusual nitrogencontaining cucurbitacins from the stem bark of Machilus
yaoshansis.176 Cucurbitaglycosides A 305 and B 306, with
unspecified stereochemistry at C-24, have been isolated from the
fruit of Cucurbita pepo cv. dayangua.177 Many new cucurbitacins
and their glycosides have been reported from Momordica
charantia. They include 307310 from the stems,178 the known
momordicin I and its 3-malonyl derivative 311,179 karavilagenins
AE 312316 and karavilosides IIX 317327 from the dried
fruit,180,181 karavilagenins A 312 and B 313 and 328 from the
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dried gourds,182 kuguacins AE 329333 from the roots,183

charantosides IVIII 334341 from the fruit,184 glycosides 342.
and 343 together with their genin 344,185 kuguaglycosides AH,
of which CE have new genins 345347, from the root,186 two
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new glycosides from the fruit, one with the new genin 348,187
momordicosides MO with two new genins 349350188 and
momordicoside P189 and momordicine V,190 both with known
genins.

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Desacetylfevicordin A 351, from the Indonesian medicinal

plant Phaleria macrocarpa, is the same as fevicordin C and has
been identified as a natural product for the first time.191 Endecaphyllacins A 352 and B 353 are octanor-cucurbitane constituents of the tubers of Hemsleya endecaphylla.192 The structure of
352 was confirmed by X-ray analysis. Other new cucurbitacins
include 354 and 355 from Cayaponia racemosa,193 356 and 357
from Physocarpus capitatus,194 a saponin with a new hexanorcucurbitane genin 358195 from the fruit of Cucurbita pepo cv.
dayangua and colocynthosides A 359 and B 360 from Citrullus
colocynthis.196 Bacobitacins AD 361364 have been isolated
from Bacopa monnieri.197 The fruit of Siraitia grosvenorii yielded
several new glycosides,198,199 two of which, 11-deoxymogroside
III and 7-oxomogroside II E, have the new genins 365 and 366,
respectively. Glucoside 367 is a constituent of Hintonia
latiflora.200 Delavanosides AE, all with known genins, have been

reported from the tubers of Hemsleya delavayi.201
The dammarane group
Aglaia sylvestris is a rich source of dammaranes. New

compounds include silvaglins A 368 and B 369, methyl isofoveolate B 370, isoeichlerianic acid 371 and its methyl ester 372,
methyl foveolate B 373, isosilvaglins A 374 and B 375, deoxysilvaglin 376 and aglasilvinic acid 377.202,203 Also the stereochemistry of the known foveolin B (free acid of 373) has been
revised. Six new dammaranes, cylindrictones AF 378383, have
been isolated from the leaves of Viburnum cylindricum.204 The
two dammarane derivatives 384 and 385, from Aglaia perviridis,
have an unusual rearranged side-chain.205 Other reports of new
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dammaranes include santolins AC 386388 from Salvia

santolinifolia,206 oliganthas A 389 from Saussurea oligantha,207
gentirigenic acid 390 and gentirigeosides AE 391395 from the
roots of Gentiana rigescens,208 396398 from Cabralea
canjerana,209 the hydroperoxides 399 and 400 from Ligustrum
lucidum,210 401 and the octanor-derivative 402 from Maytenus
macrocarpa,211 403 from radix Ranunculus ternati,212 foliasalacins
A1A4 404407 from the leaves of Salacia chinensis,213 408 and
409 from Phyllanthus polyanthus,214 ailexcelone 410 and ailexcelol
411 from the heartwood of Ailanthus excelsa215 and the methyl
malonate 412 from the floral spikes of Betula platyphylla var.
japonica.216
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Sapinmusaponins O and P are new saponins from the fruit and

galls of Sapindus mukurossi.217 Sapimnusaponin P has the new
genin 413. Bacopasaponin G and bacoside A6, from Bacopa
monniera, are glycosides of 17,20-anhydro-derivatives 414 and
415 of jujubogenin and pseudojujubogenin, respectively.218 The
aglycone 416 of notoginsenside R10 has been obtained from the
leaves of Panax ginseng.219 The new glucoside 417 has been
isolated from the roots of Panax notoginseng.220 Notoginsenosides ST-1, ST-2, ST-3 and ST-5 are constituents of steamed
Panax notoginseng.221 The first three have the new genins 418
420 respectively. New dammarane saponins from Gymnostemma
pentaphyllum include six new genins 421426222 while those from

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Gymnostemma pubescens have two new genins 427 and 428.223

New dammarane saponins with known genins include bacopaside VI from Bacopa monnieri,224 floralginsenosides AF,225
GK, La, Lb226 and MP227 from Panax ginseng flower buds,
jujuboside G from seeds of Zizyphus jujuba,228 notoginsenosides
Rw1, Rw2,229 FP1 and FP2230 from Panax notoginseng,
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quinquefolosides La and Lb from Panax quinquefolium231 and

saponins without trivial names from Panax ginseng232 and Panax
quinquefolium.233 A review covering the biosynthesis of the
ginsenosides has been produced.234
Dichapetalins IJ 429432 are constituents of the stem
bark of Dichapetalum gelonoides.235 Five new dichapetalins,

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acutissimatriterpenes AE 433437, have been reported from the

aerial parts of Phyllanthus acutissima.236 The structures of 433
and 437 were confirmed by X-ray analyses. Aglaiaglabretols A
438, B 439 and C 440 are cytotoxic constituents of Aglaia
crassinervia.237
The simple euphane 441 derivative has been obtained from
Clusia columnaris.238 The fruit of Poncirus trifoliata yielded
four tirucallane derivatives, 21a-O-methylmelianodiol 442,
21b-O-methylmelianodiol 443, hispidiol A 25-methyl ether 444
and hispidiol B 25-methyl ether 445,239 while the fruit of
Phellodendron chinense var. glabriusculum gave the pentanorderivative phellogin 446240 and compound 447.241 Cedrela
sinensis contains the tirucallanes 448 and 449 and the apotirucallanes 450456.242 The structure of 456 was confirmed by
X-ray analysis. A similar mixture of apotirucallanes, agladupols
AC 457459, and tirucallanes, agladupols D 460 and E 461, was
found in the leaves and stems of Aglaia duperreana.243 Other new
compounds include turrapubesols AC 462464 from Turrea
pubescens,244 munronosides IIV from Munronia delavayi245 with
two new genins 465 and 466, and sapinmusaponins Q and R,

with known genins, from the galls of Sapindus mukorossi.246
4.1 Tetranortriterpenoids
Walsuronoid A 467 is a peroxide derivative from Walsura
robusta.247 It is accompanied by walsuronoids B 468 and C 469,
which apparently are rare tetranor-dammarane derivatives. The
authors suggest that they are formed by methyl migration
following acid-catalysed 14,15-epoxide ring opening of a limonoid. The structure of walsuronoid A 467 was confirmed by
X-ray analysis. A Malleastrum species from the Madagascar
rainforest afforded malleastrones AC 470472.248 The structures of malleastrones A and B were confirmed by X-ray analyses. Munronin G 473 is a new compound from Munronia
delavayi.249 Other new compounds include the azadirone
derivatives 474 and 475 from Turraea cornucopia,250 dysoxylins
AD 476479 from Dysoxylum gaudichaudianum251 and
chisosiamensin 480 from the seeds of Chisocheton siamensis.252
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X-ray structure analyses of the known epoxyazadiradione253 and

6a-acetoxyazadirone254 have been published.
A review covering the biological activities of the citrus
limonoids has been published.255 17-epi-Limonin 481 has been
reported from a Citrus species.256 Evolimorutanin 482 from the
unripe fruit of Evodia rutaecarpa257 and methyl uguenenoate 483
from Vepris uguenensis258 are presumably transformation
products of limonin. The obacunol derivatives 484 and 485,
the nomilin derivatives 486 and 487 (odoralide) and
8b,14a-dihydroswietenolide 488 are constituents of the stem bark
of Cedrela odorata.259
The leaves and stems of Toona ciliata contain a range of
limonoids including the nor-derivatives toonaciliatins A 489, F
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490 and G 491 and toonaciliatins BE 492495,H 496 and I

497.260 Toonaciliatins H and I are reported for the first time as
natural products. Turraea pubescens261 and Amoora tsangii262 are
also rich sources of limonoids. The former produced turrapubesic acids AC 498500 and turrapubescins CG 501505 while
the latter yielded amotsangins AG 506512. The C-17 epimer
513 of methyl 6-hydroxyangolensate (the structure is wrongly
drawn in the paper) has been isolated from Cichorium intybus.263
A review covering the biological effects of toosendanin has
been published.264 New compounds from Melia toosendan
include the 12-ketone toosendone 514 and the ring-C-cleaved
acetals 12-ethoxynimbolinins AD 515518.265 Two other ringC-cleaved derivatives, 519 and 520, have also been isolated from

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Melia toosendan.266 Two unusual limonoids, ceramicine A 521,

which lacks methyl groups at C-4, and the ring-C-seco walsogyne
A 522, have been reported from Chisocheton ceramicus and
Walsura chrysogyne respectively.267 12-O-Methylnimbolinin A
523 and the meliacarpin derivative 524 have been identified in
fruits of Melia azedarach.268 The gedunin derivative ekeberin C1
525 is found in the stem bark of Ekebergia capensis.12
There seems to be no end to the list of new bicyclononanolides
and their variants from the Meliaceae family more than fifty
compounds have been reported in the period of review. These
include deacetylkhayanolide E 526, 6S-hydroxykhayalactone
527 and grandifolide A 528 from the stem bark of Khaya
grandifoliola,269 angolensins AC 529531 from the root bark of
Entandrophragma angolense,270 kotschins AC 532534 from the
roots of Pseudocedrela kotschyi,271 swiemahogins A 535 and B
536 from Swietenia mahogani,272 six phragmalin derivatives
537542 from Swietenia macrophylla,273 the cyclopropylphragmalin derivatives tabularisins AD 543546 from
the seeds of Chukrasia tabularis,274 tabularisins EN 547555 and
tabularisin P 556, which is in equilibrium with its non-enolic
form tabularisin O, from the twigs and leaves of Chukrasia
tabularis,38,275 the cyclic carbonate chuktabrin A 557 and the
unusual chuktabrin B 558 also from the twigs and leaves of
Chukrasia tabularis,276 the acetals chuktabularins AD 559562
from the stem bark of Chukrasia tabularis277 and erythrocarpines
AE 563567 from Chisocheton erythrocarpus.278 Erythrocarpine
A is seneganolide A 3-benzoate. Ekeberins C2 568 and C3 569
have been isolated from the stem bark of Ekebergia capensis.12
The Chinese mangrove Xylocarpus granatum is also a good
source of bicyclononanolides related to phragmalin. There is
some duplication in the published trivial names. Several groups
of compounds have been reported including xyloccensins QV
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570577279 (the structure of xyloccensin Q 570 was confirmed by

X-ray analysis and in the original reference the structures are
drawn with the wrong absolute configuration), xylocarpins AI
578586,280 xyloccensins QU 587591281 (duplicate names),
xylogranatin E 592,282 an equilibrium mixture of the hemiacetal
xylocarpin A 593 and its ketol isomer xylocarpin B283 (duplicate
names) and granaxylocarpins A 594 and CE 595597 from the
seeds of Xylocarpus granatum.284 Granaxylocarpin B, from the

same source, appears to be the same as xylocarpin H 585. The
structure of xylocarpin U 591 was revised in this paper.
seco-Dukunolide F 598 is a new limonoid from Lansium
domesticum.285 Trijugins DH 599603, the methyl angolensate
derivative 604 and the two degraded limonoids 605 and 606
are constituents of Trichilia connaroides.286 Other degraded
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limonoids include dysodensiols AC 607609 from Dysoxylum

densiflorum,287 9a-hydroxyfraxinellone 9-O-b-D-glucopyranoside
610, dictamnusine 611, dictamdiol 612 and dictamdiol B 613
from the root bark of Dictamnus dasycarpus,288 and
isodictamdiol 614 and the known dictamdiol 615 from the root of
Dictamnus radicis.289,290 The structures of both 614 and 615 were
confirmed by X-ray analyses. The authors suggest that these
compounds have opposite absolute configurations to other
limonoids, but this would be very unusual and requires
confirmation.
Plants of the Cipadessa genus contain a varied range of
limonoids. Cipadessalide 616 and rubralin D 617 are constituents
of Cipadessa baccifera,291 while Cipadessa cinerascens contains
cipadesins D 618 and E 619.292 Another group has published
104 | Nat. Prod. Rep., 2010, 27, 79132
cipadesins DF 620622 (duplicate names) from Cipadessa

cinerascens.293 Cipatrijugins AD 623626 are constituents of the
leaves of Cipadessa cinerascens.294 Five simple mexicanolide
derivatives 627631 have been isolated from the seeds of
Cipadessa baccifera.295
Undoubtedly the most interesting limonoids to be reported
during this period are xylogranatins FR 632644 from the
Chinese mangrove Xylocarpus granatum.296 They are based on
a highly-cleaved carbon skeleton 644 which can cyclise to form
a furan ring (635643) or incorporate nitrogen to form the
pyridine derivatives xylogranatins FH 632634. A second group
has published another alkaloid, granatoine 645, apparently the
C-3 epimer of xylogranatin F, and the 12-acetate 646 of xyloccensin Y from the same source.297 A review covering the

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occurrence, biosynthesis and biological activity of ring-D- and

ring-B,D-seco-limonoids from the Meliaceae has been
published.298
5 The lupane group

A constituent of Drypetes tessmanniana has been identified as

lup-20(29)-ene-3b,6a-diol 647,299 which has previously been
claimed from Perilpoca aphylla.300 Due to differences in NMR
data the authors suggest that the Perilpoca aphylla constituent
should be reassigned as the corresponding 6b-isomer. Sorbinal B

648, from Sorbus cashmariana, has been assigned the structure
lupa-12,22(29)-diene-2a,3b,23,28-tetrol.301 The structure of sorbinol B 648 is incorrectly drawn in the reference with
a 5,6-double bond. Other new lupane alcohol derivatives include
lup-20(29)-ene-3b,22b-diol 649 from Moldenhawera nutans,302
lup-20(30)-ene-1b,3b,29-triol 650 from Salvia sclareoides303 and
the acetates 651 and 652 from Salvia macrochlamys.304 Foliasalacins B1B3 653655 are new lupane derivatives from the leaves
of Salacia chinensis.213 The lupan-29-al derivatives 656658 from
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Acacia mellifera show cytotoxic activity,305 and the lupan-28-oic

acid derivatives 659 and 660 from Fagara tessmannii have
a-glucosidase inhibitory properties.306 Gypsophila repens is the
source of the unusual lupane sulfate gypsophilin 661 and its
glucosyl ester gypsophilinoside 662.307 The methyl ester 663 and
the 3-acetate 664 of alphitolic acid have been isolated from seeds
of Ziziphus jujuba var. spinosa308and the resin of Garcinia hanburyi309 respectively, and the related 20,29-dihydro derivative 665
has been found in Eugenia grandis stem bark.310 Other simple
lupane derivatives include the 27-carboxylic acids 666 and 667
from Potentilla discolor311and the hemiacetal lantabetulal 668
from roots of Rhus javanica var. roxburghiana.312 Ocimol
669 from Ocimum basilicum is the ester of betulinic acid with
methyl vanillate.313 Other lupane aromatic esters include the
cinnamate 670 and the 4-hydroxybenzoate 671 from Helicteres
angustifolia,314 3-ferruloyllupeol 672 from Ceriops tagal315 and
the caffeoyl esters 673 from Xanthoceras sorbifolia316
and 674676 from Peganum nigellastrum.317 3a-Hydroxylup20(29)-en-28,19b-olide 677 is a constituent of Perrottetia
arisanensis, where it occurs with the esters 678680.318
20,29,30-Trinorlup-18-en-3b-ol 681 from Arabidopsis thaliana
has been given the misleading name trinorlupeol.319 The
17-hydroperoxy-28-norlup-20(29)-en-3b-ols 682 and 683 have
been isolated from Melaleuca ericifolia together with the 17,29epoxide 684 which has an impossible stereochemistry.320 It is
108 | Nat. Prod. Rep., 2010, 27, 79132
possible that 684 has the opposite stereochemistry at C-17. The

3,4-secolupane 685 has been reported from Euphorbia humifusa.143 The related 3,4-secolupane derivative 686 is a constituent
of Viburnum awabuki together with the 30-norlupane 687.321
16b-Hydroxylupa-1,20(29)-dien-3-one 688 and 16b-hydroxy-2,3secolup-20(29)-ene-2,3-dioic acid 689 have been found in
Stauntonia obovatifolia ssp. intermedia.322 The related 2,3-secolupane 690 has been isolated from Microtropis fokiensis together
with the 7-oxygenated derivatives 691 and 692.294 The lupane
saponin 693 from fruits of Polygonum orientale has a new
genin.323 Acankoreosides FH, from Acanthopanax koreanum,
also have new lupane genins 694696, respectively.324 Lupane
saponins with known genins include stallatoside B and erucasaponin A from the cactus Stenocereus eruca325 and a saponin from
roots of Carthamus tinctorius.326
Gouanic acids A 697 and B 698 from aerial parts of Gouania
ulmifolia327 and 1-epi-ceanothic acid 699 from Gleditsia sinensis328
are 3(2/1)-abeo-lupane derivatives. Elephanmollen 700 is
a D:C-friedolupane derivative from Elephantopus mollis that
shows cytotoxic properties.329
The oleanane group
Two rearranged oleanane derivatives, dysoxyhainanins A 701

and B 702, have been identified from Dysoxylum hainanense.330

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Dysoxyhainanin A 701 has a 3(2/1)-abeo rearranged skeleton

with a formamide at C-2 and shows interesting antibacterial
activity. Several 19(18/17)-abeo-28-noroleanenes have been
isolated from rhizomes of Phlomis umbrosa including phlomisone
703, phlomistetraols AC 704706, phlomispentaol 707, phlomishexaols A 708 and B 709, phlomisin 710 and the related
derivatives 711714.331333 The 3,4-secooleanane derivatives 715
from Christiana africana334 and 716719 from the mangrove
plant Hibiscus tiliaceus335 have been identified. The secooleananes 718 and 719 are shown in the reference with the
18a-configuration but there is no evidence for this stereochemistry. The ring-A cleaved oleanane 720 has been obtained from
the floral spikes of Betula platyphylla var. japonica.216 24-Noroleana-3,9(11),12-triene 721 has been identified in olibanum
from Boswellia serrata.336 It is possible that this nortriterpene is
a pyrolysis product. 24-Nor-3-oxoolean-12-en-28-oic acid 722
has been named hederagonic acid, a name used previously for the
110 | Nat. Prod. Rep., 2010, 27, 79132
3-ketone of hederagenin.337 The 24-noroleanane derivative

722 occurs in Gypsohila oldhamiana, together with 3,4-di-epigypsogenin 723 and hederagenin 3-sulfate 724.
Other noroleananes include 2a,3a,16a-trihydroxy-24-noroleana-4(23),12-dien-28-oic acid 725 from Salvia palaestina,338
the 30-nor-derivative 726 from Stauntonia obovatifoliola ssp.
intermedia,322 and the 3,25-epoxy-28-noroleananes lantadienone
727 and camaradienone 728 from Lantana camara. The
3,25-epoxy derivative lantanoic acid 729 has also been found
in Lantana camara,339whereas the related lantanolal 730
and lantanalol 731 are constituents of Rhus javanica var.
roxburghiana.312 Dryobalanolide 732 has been isolated from
Eucalyptus camaldulensis.340 Dryobalanolide 732 had previously
been isolated as the 3,23-acetonide. The 3,23-acetonide of aceriphyllic acid 733 has been found in Aceriphyllum rossii together
with the 3-ketone 734.341 The triacetate 735 has been isolated
from the roots of Ligularia sagitta after acetylation.342 It is not

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clear whether the natural product is the corresponding triol or

an acetylated compound. Foliasalacin C 736 is olean-12-ene3b,15a-diol from the leaves of Salacia chinensis.213
The 21b-hydroxyoleanane derivatives 737741343 and
21b-hydroxyolean-12-en-3-one 742344 have been isolated from
Hippocratea excelsa. Further 21-oxygenated oleananes include
silymin B 743 from Silybum marianum,345 olean-12-ene2a,3b,21b,23,28-pentol 744 from Laportea crenulata,346 olean-12ene-3b,6b,21b-triol 745 from the trunk bark of Tabebuia
heptaphylla,347 the 28-carboxylic acid 746 from neonauclea
sessilifolia348 and the 11,13(18)-dienes 747750 from Tetrapanax
papyriferus.349 Ilexhainanins B 751 and D 752 are olean-12-ene24,28-dioic acid derivatives from Ilex hainanensis.350 Other simple
oleanane derivatives include wilforone 753 from Triperygium

wilfordii,351 the 28-aldehyde 754 from Ligularia odontomanes,352
aegicornin 755 from Aegiceras corniculatum353 and salsolic acid
756354 and salsolins A 757 and B 758355 from Salsola baryosma.
Kalidiumosides C 759 and D 760 and kalidiunin 761 have been
found in aerial parts of Kalidium foliatum.356
Celastrus rosthornianus is the source of the palmitoyl esters
762357 and 763.358 The ester 763 has also been isolated from
Saussurea ussuriensis and named ussuriensin B.359 The fatty acid
esters 764, from Maytenus salicifolia,360 and 765 and 766, from
Scorzonera mongolica,361 have also been identified. Several esters
have been isolated from Saussurea muliensis including the
p-coumaroyl 767 and caffeoyl 768 oleanane derivatives and the
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30-noroleanane esters 769771.362 Other new oleanane esters

include the maslinic esters 772 and 773 from Hippophae rhamnoides,363 the 27-(4-hydroxybenzoyl) derivative 774 from Heliceres
angustifolia,314 lippiacin 775 from Lippia nodiflora,364 patrirupin A
776 from Patrinia rupestris,365 basilol 777 from Ocimum
basilicum,313 camarolic acid 778 and lantrigloylic acid 779 from
Lantana camara,366 the ferruloyl esters 780 and 781 from Ludwigia
octovalvis,367 the p-coumaroyl esters 782 and 783 from
Barringtonia racemosa368 and 784 from Rhizophora stylosa,369 the
27-caffeoyl ester 785 from Peganum nigellastrum,370 the 3,5-dihydroxycinnamoyl ester 786 from Drypetes tessmanniana299 and the
angeloyl ester 787 from Lantana hispida.371 The disulfate esters 788
and 789 are constituents of Melissa officinalis.372
Psidiumoic acid 790, from Psidium guajava, is an unusual
2-hydroxyethyl ether.373 b-Amyrin propyl ether 791 has been
found in Erythrina sigmoidea together with sigmoiside F 792,

which has a new genin.374 Pteleopsoside is an oleanane saponin
with a known genin from Pteleopsis hylodendron, where it occurs
with the triacetate 793.375 Ardisicrenosides K and L are oleanane
saponins from Ardisia crenata.376 Ardisicrenoside L has a new
noroleanane genin 794. Some of the ardisianosides AK, from
Ardisia japonica, have new genins.377 Ardisianoside G has the
same genin 794 as ardisicrenoside L whereas ardisianosides I, J
and K have the genins 795797, respectively. Other new oleanane
saponins with new genins include the xyloside 798 from
Astragalus corniculatus,378 six saponins from Astragalus
flavescens with the genin 21-epi-kudzusapogenol A 799,379
theasaponins A4, A5, C1, E8, E9, G1 and H1 from Camellia
sinensis including the genin 800,380 eryngiosides AL from
Eryngium yuccifolium including the genin 801,381 saponins from
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Table 1
Trivial name
Plant species
Reference
Acanthopanaxoside E
Achyranthosides G and H
Aesculiosides IIeIIk and IIIaIIIf
Akebosides La and Lb
Ardisiacrenoside I
Arganins L and OR
Assamicins VIVIII
Asteratoidesoside A
Bodinierin C
Brevifoliasaponin
Cauloside H
Cernuasides AD
Chakasaponins V and VI
Chionaeosides AD
Clematiganoside A
Codonolasides IIII
Congmuyanoside I
Dexylosyltubeimoside III
Dipterosides AE
Floratheasaponins DI
Foliatheasaponins IV
Giganteasaponins 5 and 6
Giganteosides LN
Gleditzsioside Z
Gummiferaosides AC
Gymnemosides W1 and W2
Gypsosaponins A (Gypoldoside A) C
Hehuanoside A
Helianthosides 4 and 5
Hydrocosisaponins AF
Ilexpernoside F
Ilexsaponin C
Impatiprins AC
Isoescins VIaVIIa
Lancemasides BG
Lonicerosides D and E
Lysichrisides A and B
Montanosides 1 and 2
Nigellosides AD
Oblonganosides LM
Onjisaponins
Perennisaponins AF
Perennisosides IVII
Pharbitosides A and B
Pithelucosides AC
Puberosides A and B
Raddeanoside R19
Repensosides AF
Sapinmusaponins KN
Serrulatins AE
Sigmoiside E
Stauntoside A
Stryphnosides AF
Theasaponins A6, A7 and B5
Tenuifoside A
Vaccaroside I
Xanifolias Y0, Y2, Y3 and Y7
Yemuosides YM21YM25
Acanthopanax senticosus
Achyranthes fauriei
Aesculus pavia
Akebia quinata
Ardisia crenata
Argania spinosa
Aesculus assamica
Aster souliei
Elsholtzia bodinieri
Calliandra brevifolia
Caulophyllum thalictroides
Pulsatilla cernua
Camellia sinensis
Paronychia chionaea
Clematis ganpiniana
Codonopsis lanceolata
Aralia elata
Bolbostemma paniculatum
Dipteronia dyeriana
Camellia sinensis
Camellia sinensis
Solidago gigantea
Cephalaria gigantea
Gleditisia sinensis
Albizia gummifera
Gymnema sylvestre
Gypsophila oldhamiana
Albizia julibrissin
Helianthus annuus
Hydrocotyle sibthorpioides
Ilex pernyi
Ilex pubescens
Impatiens pritzellii var. hupehensis
Aesculus turbinata
Codonopsis lanceolata
Lonicera japonica
Lysimachia christinae
Clematis montana
Nigella damascena
Ilex oblonga
Polygala tenuifolia
Bellis perennis
Bellis perennis
Pharbitis nil
Pithecellobium lucidum
Glochidion puberum
Anemone raddeana
Gypsophila repens
Sapindus mukorossi
Photinia serrulata
Erythrina sigmoidea
Suantonia chinensis
Stryphnodendron fissuratum
Camellia sinensis
Polygala tenuifolia
Vaccaria segetalis
Xanthoceras sorbifolia
Stauntonia chinensis
400
401
402
403
404
405
406
407
408
409
410
411,412
413
414
415
416,417
418
419
420
421
422
423
424
425
426
427
428,429
430
431
432
433
434
435
436
437,438
439
440
441
442
443
444,445
446
447
448
449
450
451
452
217
453
454
455
456
457
458
459
460
461
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Table 2
Plant species
Reference
Achras sapota
Akebia quinata
Albizia lebbeck
Albizia procera
Androsace umbellata
Anemone flaccida
Ardisia gigantifolia
Arenaria juncea
Aronia melanocarpa
Artemisia sphaerocephala
Aster novi
Carthamus tinctorius
Chenopodium quinoa
Combretum laxum
Combretum molle
Cordia piauhiensis
Garcinia hanburyi
Gueldenstaedtia multiflora
Lactuca scariola
Lactuca scariola
Lonicera japonica
Lonicera macranthoides
Lysimchia davurica
Meryta denhamii
Myrsine africana
Nylandtia spinosa
Paronychia argentea
Phaseolus vulgaris
Polygala tenuifolia
Polyscias guilfoylei
Pulsatilla chinensis
Schima noronhae
Xanthium strumarium
Xanthoceras sorbifolia
Zygophyllum fabago
462
463,464
465
466
467
468
469
470
471
472
473
474
475
476
477
478
309
479
480
481
482,483
484
485
486
487
488
489
490
491
492
493
494
495
316,496,497
498
Fagonia arabica including the disulfate 802,382 saponins from

Glycyrrhiza uralensis including 22b-acetoxyglycyrrhizin 803,383
davuricoside N from Lysimachia davurica with the genin 804,384
phytolaccasaponins N-1N-5 from Phytolacca americana
including the genins 805807,385 three saponins from Pimenta
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dioica with the genin 808,386 saponins from Platycodon

grandiflorum with the genins 16-oxoplatycodigenin 809387and the
lactones 810 and 811,388 polygalasaponins XLVIIXL from
Polygala japonica including the genin 812,389 saponins
from Portulaca oleracea with the genins 813 and 814,390 saponins
from Prunella vulgaris including the 28-noroleanane genin 815,391
seven saponins from Silphium radula with genins 816822,392
stachyssaponins AC from Stachys parviflora with the genins
823825,393,394 brauhenosides A and B from Stocksia brauhica
with genins 826 and 827,395 yemuosides YM17YM20 from
Stauntonia chinensis with genins 828830,396 saponins from
Stylosanthes erecta including genins 831 and 832,397 saponins
from Terminalia arjuna with the genin 833398 and trachelosperoside F 834 from Trachelospermum jasminoides with a new
30-nor genin.399 New oleanane saponins with known genins that
have been assigned trivial names are listed in Table 1.
The sources of new oleanane saponins with known genins that
have not been assigned trivial names are listed in Table 2.
A survey of the occurrence and biological activities of
13,28-epoxyoleanane saponins has been published.499
Two 2,3-secotaraxerane esters 835 and 836 have been found in
Elateriospermum tapos.500 Crassifoate 837 is an epoxytaraxerane
ester from Nepeta crassifolia.501 Other taraxerane esters include
the formyl ester of taraxerol 838 from Rhizophora stylosa,369
fibrarecisin 839 from Fibraurea recisa502 and the p-coumaroyl
ester 840 from Craibiodendron henryi.503 Four multiflorane esters
841844 have been identified from Lagenaria siceraria.504
Spirowallichiione 845 is a rearranged multiflorane from
Euphorbia wallichii.505 Derris laxiflora contains trans-cinnamoylglutinol 846 and the oleanane derivatives 847850.139
The structure of the friedelane triterpenoid endodesmiadiol
851, from Endodesmia calophylloides, was confirmed by
X-ray analysis.506 Pluricostatic acid 852, from leaves of
Marila pluricostata, is 2a,3b-dihydroxyfriedelan-28-oic acid.507
12a-Hydroxyfriedelan-3-one 853 is a constituent of Maytenus
gonoclada,508 and 2b-hydroxy-3-oxofriedelan-30-oic acid 854 is
found in Dichapetalum barteri.509 28-Hydroxyzeylanol 855 is

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a new
friedelane from
Dichapetalum
gelonoides.235
Dzununcanone
856,
from
Hippocratea
excelsa,
is
a 3,24-dinor-2,3-seco-friedelane derivative.344 The structure of
dzununcanone 856 is drawn incorrectly in the reference. The
related 3-nor-2,3-seco derivative 857 has been isolated from
Passiflora wilsonii.510 Other norfriedelane derivatives include

trifloralactone 858 and triptocalline B 859 from Microtropis
triflora511 and milicifolines AD 860863 from Maytenus
ilicifolia.512 Milicifolines B 861 and C 862 are related to the
cheiloclines reported by the same group in 2005 (see
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Nat. Prod. Rep., 2008, 25, 794). Spirocarcolitones GL

864869, from the bark of Ruptiliocarpon caracolito, are
rearranged friedelane derivatives.513
7 The ursane group

24-Norursa-3,9(11),12-triene 870 and 24-norursa-3,12-dien-11one 871 have been identified in olibanum from Boswellia
serrata.336 It is not clear whether these norursanes are natural or
decomposition products. The 3-methyl ester of cecropracic acid
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872 as been isolated together with the related 2-nor-aldehyde 873

from Potentilla multicaulis.514 9,26-Cyclours-21-ene-3b,20b-diol
874 and the corresponding 3-acetate 875 are constituents of the
stem bark of Ficus cordata.515 The unusual 3,25-epidioxy derivatives 876 and 877 have been claimed from Gentiana aristata.516
The 1,5-epidioxy derivative 878 is found in Vladimiria muliensis
together with ursane-3b,13a,18b-triol 879.517 Other simple
ursane alcohol derivatives include urs-12-ene-1b,3b,11a-triol 880
from Plumbago zeylanica,518 sorbinol A 881 from Sorbus
cashmariana,301 and 11a-methoxyurs-12-ene-3a,21b-diol 882

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from Hippocratea excelsa.343 Ilexhainanins A 883 and C 884,

from Ilex hainanensis, are urs-12-ene-24,28-dioic acids350 and
nummularic acid 885, from Evolvulus nummularius, is 3b-urs-12en-29-oic acid.519 3b-Hydroxy-12-oxoursan-28,13b-olide 886 has
been reported as a natural product from Plumeria obtusa.520 This
compound has previously been identified as an oxidation
product of ursolic acid acetate.521 The ring-A-cleaved ursane 887
has been obtained from the floral spikes of Betula platyphylla var.
japonica.216
Astilbotriterpenic acid 888 is 3b,6b-dihydroxyurs-12-en-27-oic
acid from Astilbe chinensis.522 The structure of 3b,24- dihydroxyurs-12-en-27-oic acid 889, also from Astilbe chinensis, has been
confirmed by X-ray analysis.523 The urs-12-ene-27,28-dioic acids
metatrichosins A 890 and B 891 have been found in Metadina
trichotoma.524 Speciosaperoxide 892 is a hydroperoxide from
Chaenomeles speciosa.525 2b,3a,6a,20b,23,30-Hexahydroxyurs-
12-en-28-oic acid 893, together with the related 28-glucosyl ester

894, have been identified in Actinidia valvata.526 Further new
urs-12-en-28-oic acid derivatives include camaranoic acid 895
from Lantana camara,339 cheiranthic acid 896 from Oenothera
cheiranthifolia,527 silymin A 897 from Silybum marianum,345
madhunolic acid 898 from Madhuca latifolia,528 diospyric acids A
899 and B 900 from Diospyros kaki,529 santolinic acid 901 from
Salvia santolinifolia,530 eleganenes A 902 and B 903 from Myricaria elegans,531 the 19a-alcohols 904 and 905 from Dischidia
esquirolii532 and 906 from Canthium multiflorum.533 3a,13b-Dihydroxyurs-11-en-28-oic acid 907 has been claimed from
Hedyotis crassifolia.534 The corresponding 28,13-lactone
structure may be more likely. The 11a,12a-epoxy-28,13blactones 908 and 909 together with the acetate 910 are constituents of Cecropia catharinensis.535 Other ursane esters include
3b-acetoxyurs-18-ene 911 from Asteracantha longifolia,536
Nat. Prod. Rep., 2010, 27, 79132 | 119

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3-p-coumaroyl actinidic acid 912 from Actinidia arguta,537

hyptadienic acid 2-benzoate 913 from Hyptis verticillata538 and
the palmitoyl ester ussuriensin A 914 from Saussurea
ussuriensis.359 The disulfate esters 915917 have been isolated
120 | Nat. Prod. Rep., 2010, 27, 79132
from Melissa officinalis together with the glucoside 918, which

has a new genin.372
A new ursane saponin has been found in Centella asiatica
together with its genin 919.539 Other ursane saponins with new

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genins include callianthaside A 920 from Pyrola calliantha,540

ilexhainosides A 921 and B 922 from Ilex hainanensis,541
ilexpernosides A and B with the 24-nor-genins 923 and 924 from
Ilex pernyi,542 glucosyl esters 925 and 926 from Rosa laevigata543
and two saponins with the genins 927 and 928 from Silphium
radula.392 New ursane saponins with known genins include
ilexpernosides CD and GJ from Ilex pernyi,433 ilexsaponin B4
from Ilex pubescens,434 kakisaponin A from Diospyros kaki,544
oblonganosides AF545 and HJ443 from Ilex oblonga and

zygophylosides O and P from Zygophyllum fabago.546 New
ursane saponins with known genins that have not been assigned
trivial names have been isolated from Combretum laxum,476
Cordia piauhiensis,478 and Zygophyllum geslini.547
The 20,28-epoxytaraxastane 929 derivative is a constituent of
Potentilla multicaulis.514 Punicanolic acid 930 is 3b,20a-dihydroxytaraxastan-28-oic acid from flowers of Punica granatum.548
Nat. Prod. Rep., 2010, 27, 79132 | 121

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Other new taraxastane triterpenoids include taraxast20(30)ene-3b,12b-diol 931 from Craibiodendron yunnanense,549,550
taraxasta-1,20(30)-dien-3-one 932 from Sida acuta,551 taraxast20(30)-ene-3b,16b,21a-triol 933 from Centipeda minima,552 the
corresponding 21-hydroperoxide 934 from Arnica montana553
and 3b,22a-dihydroxytaraxast-20-en-30-al 935 from Polyalthia
nemoralis.554 Oliganthas B 936 is a new taraxastane derivative from
Saussurea oligantha.207 19b-Taraxast-20(30)-ene-3b,21a-diol 937
was isolated from Ixeris chinensis in 2006 and has now been
identified in Cichorium intybus and named cichoridiol.263 The
palmitoyl esters 938 and ussuriensin C 939 have been discovered in
Conyza candanesis555 and Celastrus rosthornianus, respectively.359
Pubescenosides C and D, from Ilex pubescens, have the new genin
3b-hydroxytaraxasta-12,18-dien-28-oic acid 940.556 The structure
of the baurene derivative 941, from Vladimiria muliensis, was
confirmed by X-ray analysis.517 The related dinklagenonoate 942 is
a constituent of Dorstenia dinklagei.557
122 | Nat. Prod. Rep., 2010, 27, 79132
The hopane group
Dryopteric acids A 943 and B 944 are hopane derivatives from

rhizomes of Dryopteris crassirhizoma.558 3b-Hydroxyhop-21Een-29-oic acid 945 has been found in Dipentodon sinicus.559 The
21aH-24-norhopane ester 946 is a constituent of Harpullia
arborea560 and the 29-formyl ester of hopane-22S,29-diol 947 is
from Saxiglossum angustissimum.561 Two 21bH-arborinane
esters 948 and 949 have been identified from Anoectochilus roxburghii as the E- and Z-isomers of p-coumaroyl sorghumol.562
Miscellaneous compounds
Iris tectorum is the source of iritectols A 950 and B 951.563

Stellettins L 952 and M 953 are isomalabaricane metabolites of
the marine sponge Stelletta tenuis.564 The corresponding methyl
esters, rhabdastrellins E 954 and F 955, are found in

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Nat. Prod. Rep., 2010, 27, 79132 | 123

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Rhabdastrella aff. distincta together with rhabdastrellins AD

956959.565 The bisisomalabaricanes jaspolides G 960 and H 961
are DielsAlder-type adducts from a Jaspis species.566 The Red
Sea sponge Siphonochalina siphonella produces siphonellinol C
962 and sipholenol I 963.567 Malbrancheosides AD, metabolites
of the fungus Malbranchea filamentosa, are glycosides of malbrancheogenin 964.568
Five highly oxygenated serratane triterpenoids 965969 have
been isolated from Diphasiastrum complanatum.569 Ekeberin A
970 is a baccharane derivative from the stem bark of Ekebergia
capensis12 and the spiro-hemiketal 971 is a constituent of the
liverwort Lepidozia chordulifera.570 A 3,4-seco-baccharane
derivative 972 has been found in the leaves and stem bark of
Aglaia foveolata.571 Foliasalacins D1D3 973975 are D:B-friedobaccharanes from leaves of Salacia chinensis.572 Two shionane
derivatives 976 and 977 have been identified in Aster ageratoides
var. oophyllus.573 The unusual elaeophorbate 978 has been
claimed from leaves of Elaeophorbia drupifera.574
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3-Hydroxybutanolide Derivatives and Avonoid Glucosides From Anoectochilus Roxburghii

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3-Hydroxybutanolide Derivatives and Avonoid Glucosides From Anoectochilus Roxburghii

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View Article Online / Journal Homepage / Table of Contents for this issue

www.rsc.org/npr | Natural Product Reports

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braunicetals (e.g. 15 and 16), an inseparable mixture of

2 The squalene group

This journal is The Royal Society of Chemistry 2010

The lanostane group

The marine-derived fungus Aspergillus sydowii produces the new

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Abiesanolides E 31, F 32, I 33 and J 34 are new lanostane and

disulfate 40, from the green microalga Tydemania expeditionis,

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This journal is The Royal Society of Chemistry 2010

Nat. Prod. Rep., 2010, 27, 79132 | 81

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from the stems of Artabotrys uncinatus,43 the acetate 54 from

including the hepatoprotective54 and anti-cancer55 effects have

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90, B 91 and C 92,65 inonotsuoxides A 93 and B 94,66 the triol 9567

Kadsura coccinea is a rich source of lanostane derivatives. The

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84 | Nat. Prod. Rep., 2010, 27, 79132

This journal is The Royal Society of Chemistry 2010

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and kadcoccilactone R 108 from the stems.71 The structure of

A4, based on genin 123. 17-Hydroxyfuscocineroside B and

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impress.103 Preschisanartanin 131 and schindilactones A 132, B

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wuweizidilactones G 141, H 142, schindilactones DG 143146,

are further constituents of the leaves and stems of Schisandra

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88 | Nat. Prod. Rep., 2010, 27, 79132

This journal is The Royal Society of Chemistry 2010

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of rubrifloradilactone 183, from Schisandra rubriflora, has been

polysperma124 and renchanglactone A 211 (same as kadcoccilactone Q) from Kadsura renchangiana.125

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Chukrasia tabularis var. velutina,132 respectively. Commiphora

260 from Nigella sativa,146 261 from Fritillaria hupehensis,147 and

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This journal is The Royal Society of Chemistry 2010

Nat. Prod. Rep., 2010, 27, 79132 | 91

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confirmed by X-ray analysis. Tareciliosides AG have been

been reported from the roots of Actea pachypoda, together with

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mongholicosides A 289 and B 290 from Astragalus

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