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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

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 Introduction

2 The squalene group

3 The lanostane group

4 The dammarane group

4.1 Tetranortriterpenoids

5 The lupane group

6 The oleanane group

7 The ursane group

8 The hopane group

9 Miscellaneous compounds

10 References

1 Introduction

Interest in the pharmaceutical activities of triterpenoids

continues to increase.1 Reviews have appeared on the triterpe-

noid 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

2 The squalene group

Tetrahydroxysqualene 1, from the leaves and twigs of Rhus

taitensis, is active against Mycobacterium tuberculosis.11 Ekeber-

ins D1 –D5 2–6 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, fromthe red alga

Laurencia mariannensis15 and omaezakianol 11 and 15,16-anhy-

drothyrsiferol 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

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 lano-

sterol 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-lan-

osterol 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 supra-

facial 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

3 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 asa nordammarane. 1,2-Dihydrohelvolic acid 24 has been found in

the entomopathogenic fungus Metarhizium anisopliae.29 Aliso-

lide 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 ori-

entale 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.33Department of Chemistry, Glasgow University, Glasgow, G12 8QQ, UK

This journal is ª The Royal Society of Chemistry 2010 Nat. Prod. Rep., 2010, 27, 79–132 | 79

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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

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 deriv-

atives 42–44 from the mangrove plant Hibiscus tiliaceus,40 45–48

from Euphorbia humifusa,41 49–52 from Diospyros discolor,42 53

80 | Nat. Prod. Rep., 2010, 27, 79–132 This journal is ª The Royal Society of Chemistry 2010

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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 70–72 have

been reported from Ganoderma lucidum.52 Methyl australate 73,

from Ganoderma australe, shows antimicrobial activity.53 The

pharmacological activities of the Ganoderma triterpenoids,

including the hepatoprotective54 and anti-cancer55 effects have

attracted a lot of interest.56,57,58

Morelanostane derivatives have been reportedfrom Poria cocus.These include 29-hydroxypolyporenic acid C 74 and 25-hydroxy-

pachymic acid 75,59,60 poriacosones A 76 and B 7761 and

15a-hydroxydehydrotumulosic acid 78, 16a,25-dihydroxyde-

hydroeburicoic 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 anti-

tuberculosis 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 A–E

102–106, 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 114and 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 F1 –F7 and M–V are

lanostane saponins from the Caribbean sponges Erylus formosus

and Erylus goffrilleri . The saponins from Erylus formosus include

the new genins 117–11977 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 Holothuriaaxiloga.83 ArgusideA, 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 Fivenew oligoglycosides, frondosides A7-1–A7-4 and isofrondoside C,

have been reported from Cucumaria frondosa, all with known gen-

ins.86 Other new holostane saponins with known genins

include argusides B–E 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 A1 –A3, B1 and B2 from Staurocumis

liouvillei ,95 marmoroside C from Bohadschia marmorata,96 okhoto-

sides A1-1, A2-1,97 and B1 –B398 from Cucumaria okhotensis and

saponins without trivial names from Actinopyga lecanora99 and


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Pseudocolochirus violaceus.100 The biological activities of the holo-

stane saponins have been surveyed.101,102

The amazing skeletal diversity of complex cycloartane-derived

products from Schisandra and Kadsura species continues to

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 A–F 135–140105 and


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wuweizidilactones G 141, H 142, schindilactones D–G 143–146,

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 equilib-

rium with its 20-epimer, schintrilactone B 150.107 Extraction of

the leaves and stems of Schisandra lancifolia afforded lancifodi-

lactones I–N 151–156.108 The structures of 151 and 154 were

confirmed by X-ray analysis. Micrandilactones D–G 157–160

are further constituents of the leaves and stems of Schisandra

micrantha.109 The structures and stereochemistry of micrandi-

lactones B 161 and C 162 have been confirmed by X-ray

analyses.110 New compounds from Schisandra propinqua var.

propinqua include propindilactones A–D 163–166111 and pro-

pindilactones E–J 167–172.112 Rubriflorins A–J 173–182 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 A–D 184–187116 and sphlenadilactoneC 188 and sphenasin A 189.117 Wilsonianadilactones A–C

190–192 have been reported from Schisandra wilsoniana.118

Calculations show that the naturally-occurring enol lancifodi-

lactone G 193 is more stable than its keto tautomer.119

Kadcoccilactones A–Q 194–211 have been isolated from

Kadsura coccinea.71,120 The structure of 194 was confirmed by

X-ray analysis. Kadsura heteroclita is the source of hetero-

clitalactones G–M 212–218121 and longipedlactone J 219.122

Other compounds in this series include kadlongilactones C–F

220–223 from Kadsura longipedunculata,123 polysperlactones A

224 and B 212 (same as heteraclitalactone G) from Kadsura

polysperma124 and renchanglactone A 211 (same as kadcocci-

lactone Q) from Kadsura renchangiana.125

Two groups have reported a new cycloartane alkaloid 225from the rhizomes of Cimicifuga foetida,126,127 which has two

names, cimicifine A and cimicifugadine. Three new ring-D

cleaved glycosides 226–228 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-dinor-

derivative 235 are constituents of Monocarpia marginalis131 and


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Chukrasia tabularis var. velutina,132 respectively. Commiphora

opobalsamum contains nine new cycloartanes 236–244.133,134

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,144 256–258 from Cocos nucifera,145 259 and

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-23-

ene-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 Aquile-

giosides K and L, from Aquilegia vulgaris, also have new genins

264 and 265.151 Sutherlandiosides A–D 266–269 are new gluco-

sides from Sutherlandia frutescens.152 The structure of 266 was


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mongholicosides A 289 and B 290 from Astragalusmembranaceus var. mongholicus,160 eremophilosides A–K

from Astragalus eremophilus161 (eremophilosides C–K have the

new genins 291–299) and three saponins from Astragalus

campylosema ssp. campylosema with the new genins 300–302.162

New cycloartane saponins with known genins include astra-

membranosides A and B from Astragalus membranaceus,163

cimiaceroside C, cimifosides A–D164 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 Camptosorussibiricus172,173,174 and Thalictrum fortunei .175

Machilaminosides A 303 and B 304 are unusual nitrogen-

containing 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 307–310 from the stems,178 the known

momordicin I and its 3-malonyl derivative 311,179 karavilagenins

A–E 312–316 and karavilosides I–IX 317–327 from the dried

fruit,180,181 karavilagenins A 312 and B 313 and 328 from the


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dried gourds,182 kuguacins A–E 329–333 from the roots,183

charantosides I–VIII 334–341 from the fruit,184 glycosides 342.

and 343 together with their genin 344,185 kuguaglycosides A–H,

of which C–E have new genins 345–347, from the root,186 two

new glycosides from the fruit, one with the new genin 348,187

momordicosides M–O with two new genins 349–350188 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 Ende-

caphyllacins A 352 and B 353 are octanor-cucurbitane constit-uents 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 hex-

anorcucurbitane genin 358195 from the fruit of Cucurbita pepo cv.

dayangua and colocynthosides A 359 and B 360 from Citrullus

colocynthis.196 Bacobitacins A–D 361–364 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 A–E, all with known genins, have been

reported from the tubers of Hemsleya delavayi .201

4 The dammarane group

Aglaia sylvestris is a rich source of dammaranes. New

compounds include silvaglins A 368 and B 369, methyl iso-

foveolate B 370, isoeichlerianic acid 371 and its methyl ester 372,

methyl foveolate B 373, isosilvaglins A 374 and B 375, deoxy-

silvaglin 376 and aglasilvinic acid 377.202,203 Also the stereo-

chemistry of the known foveolin B (free acid of 373) has been

revised. Six new dammaranes, cylindrictones A–F 378–383, 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 A–C 386–388 from Salviasantolinifolia,206 oliganthas A 389 from Saussurea oligantha,207

gentirigenic acid 390 and gentirigeosides A–E 391–395 from the

roots of Gentiana rigescens,208 396–398 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

A1 –A4 404–407 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

Sapinmusaponins O and P are new saponins from the fruit andgalls 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 Notoginseno-

sides 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 421–426222 while those from


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Gymnostemma pubescens have two new genins 427 and 428.223

New dammarane saponins with known genins include bacopa-

side VI from Bacopa monnieri ,224 floralginsenosides A–F,225

G–K, La, Lb226 and M–P227 from Panax ginseng flower buds,

jujuboside G from seeds of Zizyphus jujuba,228 notoginsenosides

Rw1, Rw2,229 FP1 and FP2230 from Panax notoginseng ,

quinquefolosides La and Lb from Panax quinquefolium231 and

saponins without trivial names from Panax ginseng 232 and Panax

quinquefolium.233 A review covering the biosynthesis of the

ginsenosides has been produced.234

Dichapetalins I–J 429–432 are constituents of the stem

bark of Dichapetalum gelonoides.235 Five new dichapetalins,


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acutissimatriterpenes A–E 433–437, 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 444and hispidiol B 25-methyl ether 445,239 while the fruit of

Phellodendron chinense var. glabriusculum gave the pentanor-

derivative phellogin 446240 and compound 447.241 Cedrela

sinensis contains the tirucallanes 448 and 449 and the apotir-

ucallanes 450–456.242 The structure of 456 was confirmed by

X-ray analysis. A similar mixture of apotirucallanes, agladupols

A–C 457–459, and tirucallanes, agladupols D 460 and E 461, was

found in the leaves and stems of Aglaia duperreana.243 Other new

compounds include turrapubesols A–C 462–464 from Turrea

pubescens,244 munronosides I–IV from Munronia delavayi 245 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 migrationfollowing acid-catalysed 14,15-epoxide ring opening of a limo-

noid. The structure of walsuronoid A 467 was confirmed by

X-ray analysis. A Malleastrum species from the Madagascar

rainforest afforded malleastrones A–C 470–472.248 The struc-

tures of malleastrones A and B were confirmed by X-ray anal-

yses. 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

A–D 476–479 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

490 and G 491 and toonaciliatins B–E 492–495,H 496 and I

497.260 Toonaciliatins H and I are reported for the first time asnatural products. Turraea pubescens261 and Amoora tsangii 262 are

also rich sources of limonoids. The former produced turrapu-

besic acids A–C 498–500 and turrapubescins C–G 501–505 while

the latter yielded amotsangins A–G 506–512. 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 A–D 515–518.265 Two other ring-

C-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 infruits 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 A–C 529–531 from the root bark of

Entandrophragma angolense,270 kotschins A–C 532–534 from the

roots of Pseudocedrela kotschyi ,271 swiemahogins A 535 and B

536 from Swietenia mahogani ,272 six phragmalin derivatives

537–542 from Swietenia macrophylla,273 the cyclo-

propylphragmalin derivatives tabularisins A–D 543–546 from

the seeds of Chukrasia tabularis,274 tabularisins E–N 547–555 and

tabularisin P 556, which is in equilibrium with its non-enolic

form tabularisin O, from the twigs and leaves of Chukrasiatabularis,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 A–D 559–562

from the stem bark of Chukrasia tabularis277 and erythrocarpines

A–E 563–567 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 Q–V


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570–577279 (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 A–I

578–586,280 xyloccensins Q–U 587–591281 (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 C–E 595–597 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 D–H 599–603, 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 A–C 607–609 from Dysoxylum

densiflorum,287 9a-hydroxyfraxinellone 9-O-b-D-glucopyranoside

610, dictamnusine 611, dictamdiol 612 and dictamdiol B 613from 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

cipadesins D–F 620–622 (duplicate names) from Cipadessa

cinerascens.293 Cipatrijugins A–D 623–626 are constituents of the

leaves of Cipadessa cinerascens.294 Five simple mexicanolidederivatives 627–631 have been isolated from the seeds of

Cipadessa baccifera.295

Undoubtedly the most interesting limonoids to be reported

during this period are xylogranatins F–R 632–644 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 (635–643) or incorporate nitrogen to form the

pyridine derivatives xylogranatins F–H 632–634. A second group

has published another alkaloid, granatoine 645, apparently the

C-3 epimer of xylogranatin F, and the 12-acetate 646 of xyloc-

censin 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 NMRdata 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 sor-

binol 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 Foliasa-

lacins B1 –B3 653–655 are new lupane derivatives from the leavesof Salacia chinensis.213 The lupan-29-al derivatives 656–658 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 han-

buryi 309 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 tagal 315 and

the caffeoyl esters 673 from Xanthoceras sorbifolia316

and 674–676 from Peganum nigellastrum.317 3a-Hydroxylup-

20(29)-en-28,19b-olide 677 is a constituent of Perrottetia

arisanensis, where it occurs with the esters 678–680.318

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 17,29-

epoxide 684 which has an impossible stereochemistry.320 It is

possible that 684 has the opposite stereochemistry at C-17. The

3,4-secolupane 685 has been reported from Euphorbia humi-

fusa.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-2,3-

secolup-20(29)-ene-2,3-dioic acid 689 have been found in

Stauntonia obovatifolia ssp. intermedia.322 The related 2,3-seco-

lupane 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 F–H, from Acanthopanax koreanum,

also have new lupane genins 694–696, respectively.324 Lupane

saponins with known genins include stallatoside B and erucasa-

ponin 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

6 The oleanane groupTwo 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 A–C 704–706, phlomispentaol 707, phlo-

mishexaols A 708 and B 709, phlomisin 710 and the related

derivatives 711–714.331–333 The 3,4-secooleanane derivatives 715

from Christiana africana334 and 716–719 from the mangrove

plant Hibiscus tiliaceus335 have been identified. The secoolea-

nanes 718 and 719 are shown in the reference with the

18a-configuration but there is no evidence for this stereochem-

istry. The ring-A cleaved oleanane 720 has been obtained from

the floral spikes of Betula platyphylla var. japonica.216 24-Nor-

oleana-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

3-ketone of hederagenin.337 The 24-noroleanane derivative

722 occurs in Gypsohila oldhamiana, together with 3,4-di-epi -

gypsogenin 723 and hederagenin 3-sulfate 724.

Other noroleananes include 2a,3a,16a-trihydroxy-24-nor-

oleana-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 acer-

iphyllic 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-ene-

3b,15a-diol from the leaves of Salacia chinensis.213

The 21b-hydroxyoleanane derivatives 737–741343 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-ene-

2a,3b,21b,23,28-pentol 744 from Laportea crenulata,346 olean-12-

ene-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 747–750 from Tetrapanax

papyriferus.349 Ilexhainanins B 751 and D 752 are olean-12-ene-

24,28-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 769–771.362

Other new oleanane estersinclude the maslinic esters 772 and 773 from Hippophae rham-

noides,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-dihy-

droxycinnamoyl 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 unusual2-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 A–K, 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 795–797, 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 A–L fromEryngium yuccifolium including the genin 801,381 saponins from


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Table 1

Trivial name Plant species Reference

Acanthopanaxoside E Acanthopanax senticosus 400Achyranthosides G and H Achyranthes fauriei 401Aesculiosides IIe–IIk and IIIa–IIIf Aesculus pavia 402Akebosides La and Lb Akebia quinata 403Ardisiacrenoside I Ardisia crenata 404Arganins L and O–R Argania spinosa 405Assamicins VI–VIII Aesculus assamica 406Asteratoidesoside A Aster souliei 407Bodinierin C Elsholtzia bodinieri 408Brevifoliasaponin Calliandra brevifolia 409

Cauloside H Caulophyllum thalictroides 410Cernuasides A–D Pulsatilla cernua 411,412Chakasaponins V and VI Camellia sinensis 413Chionaeosides A–D Paronychia chionaea 414Clematiganoside A Clematis ganpiniana 415Codonolasides I–III Codonopsis lanceolata 416,417Congmuyanoside I Aralia elata 418Dexylosyltubeimoside III Bolbostemma paniculatum 419Dipterosides A–E Dipteronia dyeriana 420Floratheasaponins D–I Camellia sinensis 421Foliatheasaponins I–V Camellia sinensis 422Giganteasaponins 5 and 6 Solidago gigantea 423Giganteosides L–N Cephalaria gigantea 424Gleditzsioside Z Gleditisia sinensis 425Gummiferaosides A–C Albizia gummifera 426Gymnemosides W1 and W2 Gymnema sylvestre 427Gypsosaponins A (Gypoldoside A) –C Gypsophila oldhamiana 428,429

Hehuanoside A Albizia julibrissin 430Helianthosides 4 and 5 Helianthus annuus 431Hydrocosisaponins A–F Hydrocotyle sibthorpioides 432Ilexpernoside F Ilex pernyi 433Ilexsaponin C Ilex pubescens 434Impatiprins A–C Impatiens pritzellii var. hupehensis 435Isoescins VIa–VIIa Aesculus turbinata 436Lancemasides B–G Codonopsis lanceolata 437,438Lonicerosides D and E Lonicera japonica 439Lysichrisides A and B Lysimachia christinae 440Montanosides 1 and 2 Clematis montana 441Nigellosides A–D Nigella damascena 442Oblonganosides L–M Ilex oblonga 443Onjisaponins Polygala tenuifolia 444,445Perennisaponins A–F Bellis perennis 446Perennisosides I–VII Bellis perennis 447

Pharbitosides A and B Pharbitis nil 448Pithelucosides A–C Pithecellobium lucidum 449Puberosides A and B Glochidion puberum 450Raddeanoside R19 Anemone raddeana 451Repensosides A–F Gypsophila repens 452Sapinmusaponins K–N Sapindus mukorossi 217Serrulatins A–E Photinia serrulata 453Sigmoiside E Erythrina sigmoidea 454Stauntoside A Suantonia chinensis 455Stryphnosides A–F Stryphnodendron fissuratum 456Theasaponins A6, A7 and B5 Camellia sinensis 457Tenuifoside A Polygala tenuifolia 458Vaccaroside I Vaccaria segetalis 459Xanifolias Y0, Y2, Y3 and Y7 Xanthoceras sorbifolia 460Yemuosides YM21 –YM25 Stauntonia chinensis 461


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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-1–N-5 from Phytolacca americana

including the genins 805–807,385 three saponins from Pimenta

dioica with the genin 808,386 saponins from Platycodon

grandiflorum with the genins 16-oxoplatycodigenin 809387and the

lactones 810 and 811,388 polygalasaponins XLVII–XL 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 816–822,392

stachyssaponins A–C from Stachys parviflora with the genins

823–825,393,394 brauhenosides A and B from Stocksia brauhicawith genins 826 and 827,395 yemuosides YM17 –YM20 from

Stauntonia chinensis with genins 828–830,396 saponins from

Stylosanthes erecta including genins 831 and 832,397 saponins

from Terminalia arjuna with the genin 833398 and trache-

losperoside 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 epoxytaraxeraneester 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

841–844 have been identified from Lagenaria siceraria.504

Spirowallichiione 845 is a rearranged multiflorane from

Euphorbia wallichii .505 Derris laxiflora contains trans-cinna-

moylglutinol 846 and the oleanane derivatives 847–850.139

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

Table 2

Plant species Reference

Achras sapota 462Akebia quinata 463,464Albizia lebbeck 465Albizia procera 466Androsace umbellata 467Anemone flaccida 468

Ardisia gigantifolia 469Arenaria juncea 470Aronia melanocarpa 471Artemisia sphaerocephala 472Aster novi 473Carthamus t inctorius 474Chenopodium quinoa 475Combretum laxum 476Combretum molle 477Cordia piauhiensis 478Garcinia hanburyi 309Gueldenstaedtia multiflora 479Lactuca scariola 480Lactuca scariola 481Lonicera japonica 482,483Lonicera macranthoides 484Lysimchia davurica 485Meryta denhamii 486Myrsine africana 487Nylandtia spinosa 488Paronychia argentea 489Phaseolus vulgaris 490Polygala tenuifolia 491Polyscias guilfoylei 492Pulsatilla chinensis 493Schima noronhae 494Xanthium strumarium 495Xanthoceras sorbifolia 316,496,497Zygophyllum fabago 498


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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 A–D 860–863 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 G–L

864–869, 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-11-

one 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

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 deriv-

atives 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-12-

en-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- dihydroxy-

urs-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 Myr-

icaria elegans,531 the 19a-alcohols 904 and 905 from Dischidia

esquirolii 532 and 906 from Canthium multiflorum.533 3a,13b-Di-

hydroxyurs-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-28,13b-

lactones 908 and 909 together with the acetate 910 are constit-

uents of Cecropia catharinensis.535 Other ursane esters include

3b-acetoxyurs-18-ene 911 from Asteracantha longifolia,536


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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 915–917 have been isolated

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 C–D and G–J from Ilex pernyi ,433 ilexsaponin B4

from Ilex pubescens,434 kakisaponin A from Diospyros kaki ,544

oblonganosides A–F545 and H–J443 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-dihy-

droxytaraxastan-28-oic acid from flowers of Punica granatum.548


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Other new taraxastane triterpenoids include taraxast-

20(30)ene-3b,12b-diol 931 from Craibiodendron yunnanense,549,550

taraxasta-1,20(30)-dien-3-one 932 from Sida acuta,551 taraxast-

20(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 beenidentified 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

8 The hopane group

Dryopteric acids A 943 and B 944 are hopane derivatives from

rhizomes of Dryopteris crassirhizoma.558 3b-Hydroxyhop-21E -

en-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 rox-burghii as the E - and Z -isomers of p-coumaroyl sorghumol.562

9 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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Rhabdastrella aff. distincta together with rhabdastrellins A–D

956–959.565 The bisisomalabaricanes jaspolides G 960 and H 961

are Diels–Alder-type adducts from a Jaspis species.566 The Red

Sea sponge Siphonochalina siphonella produces siphonellinol C

962 and sipholenol I 963.567 Malbrancheosides A–D, metabolites

of the fungus Malbranchea filamentosa, are glycosides of mal-

brancheogenin 964.568

Five highly oxygenated serratane triterpenoids 965–969 have

been isolated from Diphasiastrum complanatum.569 Ekeberin A970 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 D1 –D3 973–975 are D:B-frie-

dobaccharanes 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 ﬂavonoid glucosides from Anoectochilus roxburghii

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