Triterpenoids

Joseph D. Connolly and Robert A. Hill

Department of Chemistry, Glasgow University, Glasgow, UK G12 8QQ

Received (in Cambridge, UK) 21st August 2003First published as an Advance Article on the web 23rd October 2003

Covering: 2001. Previous review: Nat. Prod. Rep., 2002, 19, 494

This review covers the isolation and structure determination of triterpenoids including squalene derivatives,lanostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes,friedelanes, ursanes, hopanes, fernanes, sipholanes, isomalabaricanes, serratanes and saponins. The literature fromJanuary to December 2001 is reviewed and 242 references are cited.

1 Introduction2 The squalene group3 The lanostane group4 The dammarane group4.1 Tetranortriterpenoids4.2 Quassinoids5 The lupane group6 The oleanane group7 The ursane group8 The hopane group9 Miscellaneous compounds

10 References

1 Introduction

The biological activities of triterpenoids continue to be ofinterest. Reviews have appeared on the aphrodisiac propertiesof the triterpenoids from Panax ginseng,1 the biological activ-ities of triterpenoids from liquorice root 2 and antimyco-bacterial plant terpenoids.3 The anti-tumourogenic propertiesof ursolic acid 4 and the possible use of celastrol for the treat-ment of Alzheimer’s disease 5 further emphasise the biologicalimportance of triterpenoids. The use of terpenoids, includingtriterpenoids, as chemosystematic markers in conifers has beendiscussed.6

2 The squalene group

Armatols A–F 1–6 are brominated squalene derivatives fromthe Indian Ocean alga Chondria armata.7 The complete stereo-chemistry of the epoxysqualene tritetrahydrofurandiol 7 fromSpathelia glabrescens 8 has been confirmed by synthesis.9 Con-centricol 8 is a squalene hexol from Daldinea concentrica.10 Thebis-epoxide auriculol 9 has been isolated from Dolabella auricu-

640 Nat. Prod. Rep., 2003, 20, 640–659 DOI: 10.1039/b204068a

This journal is © The Royal Society of Chemistry 2003

laria.11 Four new squalene ethers have been found in Laurenciaviridis.12 These include martiriol 10, pseudodehydrothyrsiferol11, dioxepandehydrothyrsiferol 12 and 16-epihydroxydehydro-thyrsiferol 13. Four irregular triterpenoids 14–17 have beenisolated from the marine diatom Rhizosolenia setigera.13

Testudinariols A 18 and B 19 from Pleurobrancus testudin-arius have been synthesised.14 The absolute configuration oflongilene peroxide 20, isolated from the wood of Eurycomalongifolia, has been established by synthesis.15 Molecular model-ling studies have revealed that the original structure proposedfor glabrescol 21 is not the most thermodynamically stable andtherefore synthetic evidence was very important in the structureelucidation.16

The squalene cyclase from the bacterium Zymomonas mobilisdemonstrates its lack of specificity by producing a range ofpolycyclic metabolites including α- and γ-polypodatetraenes 22and 23, dammara-20,24-diene 24, 17-isodammara-12,24-diene25, eupha-7,24-diene 26, hop-17(21)-ene 27, neohop-13(18)-ene28, 17-isodammara-20,24-diene 29, neohop-12-ene 30, fern-8-ene 31, diploptene 32, and hop-21-ene 33.17

3 The lanostane group

Alisol F 24-acetate 34 is a new protostane from Alisma orien-talis.18 New metabolites of Ganoderma lucidum includelucidenic acid N 35 (lucidenic acid LM1) and methyl lucidenateF 36.19 Three new pentanorlanostane derivatives, cladosporidesB 37, C 38 and D 39, have been isolated from a Cladosporiumsp.20 Cladosporides A and B show antifungal activity againstAspergillus fumigatus. A new 21,24-cyclolanostane derivative 40has been reported from the wood rotting fungus Inonotusobliquus.21 Fuscoporianol A, which is the 25-O-methyl ether of40, occurs in Fuscoporia obliqua together with B 41 and C 42.22

The structure of fuscoporianol A was confirmed by X-rayanalysis. The structure of ananosic acid A 43, an unusualrearranged lanostane from the stem bark of Kadsura ananosa,has been confirmed by X-ray analysis.23 Other new lanostanesinclude the trienes 44 and 45 from Guarea rhophalocarpa,24 sub-lateriols A 46, B 47 and C 48 from the edible mushroomNaematoloma sublateritium 25 and 3β,24-dihydroxy-24-methyl-lanost-8-en-30-oic acid 49, together with the lanostane saponinformoside B, from the Caribbean sponge Erylus formosus.26

Feroxosides A 50 and B 51 are nor-lanostane saponins fromEctyoplasia ferox.27 Erylosides G–J, lanostane saponins fromthe sponge Erylus nobilis, have new genins 52 and 53.28 Colos-solactones A–G 54–60 form an interesting series of lanostanesand modified cycloartanes from the mushroom Ganodermacolossum.29 It should be noted that colossolactone A 54 is notactually a lactone. Schiprolactone A 61, from Schisandrapropinqua, has a novel side chain.30

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Two unusual cleaved cycloartanes, pseudolarolides E 62 andF 63, have been reported from Pseudolarix kaempferi.31 Theirstructures were established by X-ray crystallographic analysis.Five 29-nor-3,4-seco-cycloartanes 64–68 have been isolatedfrom Antirhea acutata.32 The aerial roots of Ficus microcarpacontain the 27-nor-derivative 69 and the 25,26,27-trinor-derivative 70.33 Compound 71 and cycloabyssinone 72 arenor-cycloartanes from Artemisia caruifolia 34 and Harrisoniaabyssinica,35 respectively. Other new cycloartanes includetillandsinone 73 and cyclolaudenyl formate 74 from Tillandsiafasciculata,36 the acetate 75 from Dysoxylum malabaricum,37

and compounds 76 and 77, together with many triterpenoid

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esters, from the flowers of Chrysanthemum morifolium.38

Thalictoside F is a new saponin from Thalictrum thunbergiiwith the new genin 78, the 21,24-diepimer of thalictoside E.39

The full details of the structure elucidation of thalictosides Dand E are included in this paper.

The constituents of Cimifuga species have been reviewed.40

Four new saponins, bugbanosides C 79, D 80, E 81 and F 82have been isolated from Cimifuga simplex.41 A new cimigenolglycoside 83 and two trinor-derivatives 84 and 85, with newgenins, have been reported from Cimifuga dahurica.38,42 Actaea-epoxide 3-β--xylopyranoside 86 is a new glycoside fromActaea racemosa (Cimifuga racemosa).43 Other new compoundsfrom Cimifuga racemosa include 87–97 44 and 25-O-methyl-cimigenol 3-O-α--arabinopyranoside (cimiracemoside B).45

2�-O-acetylactein 92 and 2�-O-acetyl-27-deoxyactein 93 areconstituents of Cimifuga foetida 46 while 22R-hydroxycimifugol94 and the shengmanol derivative 95 are found in Cimifugaacerina.47

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Askendosides G and A and cycloglobiceposide B are knowncycloartane saponins from Tragacantha stipulosa.48 Astragalusprusianus contains two new saponins prusianosides A 96 andB 97.49 New cycloartane saponins have also been reportedfrom Astragalus trojanus (trojanosides I–K) 50 and Astragaluscaprinus.51

Liouvillosides A and B are sulfated holostane glycosidesfrom Staurocamis liouvillei.52 Patagonicoside A, a holostaneglycoside with a new aglycone 98, has been isolated from Psoluspatagonicus.53 The aglycone 99 of frondoside F, a minorsaponin constituent of the sea cucumber Cucumaria frondosa,contains an unusual 18 22 lactone.54

Neocucurbitacins A 100 and B 101, from the Brazilian folkmedicine “Buchinha” (Luffa operculata), have an inhibitoryeffect on some gene expression in a human osteoblast-like cellline.55 Momordica charantia is a rich source of triterpenoidsaponins. The new cucurbitacin derivatives, goyaglycosidesA–H 102–109, were accompanied by known cucurbitane

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saponins and oleanane saponins (goyasaponins I–III).56 Thealdehyde 110 has been obtained from an extract of the wholeplant of Momordica charantia.57 Two seco-cucurbitane deriv-atives 111 and 112 have been isolated from Russula lepida.58

4 The dammarane group

The structures of 15α-acetoxycleomblynol A 113, from Cleomeamblyocarpa,59 and cabraleadiol 3-acetate 114, from Aglaialawii,60 have been established by X-ray analysis. The 20S,24Sstereochemistry of cabraleadiol is thus established. Other newdammaranes include 115 and 116 from the fruits of Forsythiasuspensa 61 and semialactone 117, isofouquierone peroxide 118and fouquierone 119 from Rhus javanica.62

New dammarane saponins continue to appear. The hexanor-derivative notoginsenoside R10 120 has been found in the rootsof Panax notoginseng.63 Ginsenosides Rh5 121, Rh6 122, Rh7

123, Rh8 124 and Rh9 125, from the leaves of Panax ginseng, allapart from Rh7 123 have new genins.64 Polysciasoside A 126,from Polyscias fulva, is a saponin of 3β,16β,20S-trihydroxy-dammar-24-en-12-one.65 Two new glycosides, notoginsenosidesT1 127 and T2 128, have been isolated following mild acidichydrolysis of the crude root saponins of Panax notoginseng.66 Amethod for regioselective enzymatic galactosylation and gluco-sylation of protopanaxatriol ginsenosides has been published.67

Papers on new dammarane saponins include bacopasides I andII from Bacopa monniera,68 quinquenosides L1, L2 and L9 fromthe leaves and stems of Panax quinquefolium,69 notoginseno-sides L, M and N from Panax notoginseng,70 ginsenosides I andII from the flower buds of Panax ginseng 71 and ginsenoside Rh5

and vina-ginsenoside R25 from Panax vietnamensis.72

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A new homocyclotirucallane, sinetirucallol 129, has beenisolated from Spiranthes sinensis.73 Its structure was establishedby X-ray analysis. Eight new tirucallanes, dyvariabilins A–H130–137, have been reported from Dysoxylum variabile 74 while

another, 138, was found in Dysoxylum malabaricum.37 Othercompounds in this series include the apotirucallane 139 fromAzadirachta indica,75 the 14,18-cycloapotirucallanes 140 and141 from Guarea jamaicensis 76 and the nor-derivatives mala-banones A 142 and B 143 from Ailanthus malabarica.77

4.1 Tetranortriterpenoids

Many new limonoids have appeared this year. The three hirtinderivatives 144–146, from Trichilia pallida, show antifeedantactivity.78 Meliacinolactol 147, limocin C 148 and limocin D149 are further constituents of Azadirachta indica.79 Furtherrearranged limonoids from Harrisonia perforata includehaperforins C2 150, F 151 and G 152.80 Their structures were

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determined by X-ray analysis, as were those of 7-isovaleryl-cycloseverinolide 153 and 7-isovalerylcycloepiatalantin 154from the root bark of Severinia buxifolia.81 Pterorhachis zenkericontains 9β-amoorstatin 155 and 3-deacetylamoorstatin 156.82

The ring D unsaturated δ-lactone, deoxyobacunone 157, fromthe root bark of Harrisonia abyssinica, shows stimulatory activ-ity against Striga hermonthica seeds.83 Other new limonoidsinclude cedrellin 158 from Cedrela sinensis,84 shihulimonin A159 (previously isolated in 1965 and named limonexic acid)

from Evodia rutaecarpa,85 21-O-methyllimonexic acid 160 and8,14-epoxyfraxinellone 161 from Raulinoa achinata 86 and 1-O-methylichangensin 162 and sudachinoids A 163, B 164 and C165 from Citrus sudachi.87 Polygonumins A 166 and B 167are the E- and Z-feruloyl esters of desacetylnomilin fromPolygonum orientale.88 1,2-Dihydroamoorinin 168 is a newlimonoid from Aphanamixis polystacha.89 Three new ring Ccleaved derivatives, melianol 169, desfuranodesacetylnimbin-17-one 170 and meliatetraone 171, have been reported from theleaves of Azadirachta indica.90

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The full details for the structures of khayanolides A and B,from Khaya senegalensis, have appeared and a new compound,khayanolide C 172, has also been obtained.91 In a separatepaper, three further derivatives, 1-O-acetylkhayanolide 173,khayanone 174, and 2-hydroxyseneganolide 175, are describedfrom Khaya senegalensis.92 The structures of two limonoids,febrifugin 176 and cipadesin 177, from Cipadessa baccifera,have been confirmed by X-ray analysis.93

4.2 Quassinoids

New quassinoids include cedronolactone 178 from Simabacedron,94 12-epi-11-dehydroklaineanone 179 from Eurycomalongifolia,95 iandonoside A 180, B 181 and iandonone 182 fromEurycoma harmandiana 96 and 16β-O-methylneoquassin 183and 16β-O-ethylneoquassin 184 from the wood of Picrasmacrenata.97

5 The lupane group

Sachunoside is a seco-abeo-lupane saponin from Acanthopanazdivaricatus var. sachunensis.98 The aglycone is sachunogenin185. The acid 186 and hydroperoxide 187 occur in Ficus micro-carpa.99 Other new lupanes include 6α-hydroxybetulinic acid188 from Eugenia moraviana,100 lup-20(29)-ene-1β,2α,3β-triol189 from Cephalomappa sinensis,101 21-hydroxylupa-1,12-dien-3-one 190 from the roots of Hemidesmus indicus,102 and 2α,6β-dihydroxybetulinic acid 191 (isolated in 1999 as divergioic acid)and 6β-hydroxyhovenic acid 192, which is the aglycone ofquadranoside II, from Combretum quadrangulare.103 The 3,7-dibenzoate 193 and the 7-benzoate 194 of 3α,7β-dihydroxylup-20(29)-en-28-oic acid have been isolated from the stem barkof Picramnia teapensis.104 Ulmicins A–E 195–199 are lupaneesters from Ulmus davidiana var. japonica.105 Other estersinclude 200 from Mimusops elengi,106 lawsonic acid 201 from

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Lawsonia alba,107 and 202, 203 and a range of 3-O-acyl esters oflupeol from Parahancornia amapa. 108 The twig bark of Pyrusserotina contains a further five fatty esters of lupeol.109 Four

lupane saponins, isolated from Pulsatilla chinensis, include onenew genin 3β,20,23-trihydroxylupan-28-oic acid 204.110 Coccin-ioside K is a betulinic acid saponin from Coccinia indica 111 and alupane saponin has been isolated from Arenaria filicaulis.112

6 The oleanane group

Trypterygium wilfordii is a rich source of oleanane, friedelaneand ursane triterpenoids.113 In addition to the nor-oleanane 205and the seco-oleanane 206, it produces the lactone 207, thecarboxylic acids 208–211, the friedelanes 212 and 213 and thenor-friedelane 214. Interestingly, compounds 212 and 213 have

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an additional two carbon fragment attached to C-6. The lac-tones melliferone 215, 216 and patrinolide A 217 have beenreported from Brazilian propolis (Myrceugenia euosma),114

Nigella sativa 115 and Patrinia scabiosaefolia,116 respectively. Therange of polyhydroxyoleanenoic acids includes the triol 218from the fruit of Rosa davidii,117 the tetrol buergericic acid 219from Rubus buergeri,118 6β-hydroxyarjunic acid 220 fromCombretum quadrangulare,103 the triol 221 from Eriobotryadeflexa 119 and cucubalugenin A 222 from Cucubalus baccifer.120

Hemidesmusyl acetate 223, from Hemidesmus indicus,apparently lacks a C-3 oxygen substituent 102 as does the 27-nor-aldehyde 224 from the roots of Lavandula stoechas ssp.stoechas.121 It is accompanied by the aldehyde 225. 3,21-

Dioxoolean-18-en-28-oic acid 226 is a constituent of Acaciaaulacocarpa.122 The 3,4-seco-derivative 227 has been isolatedfrom Phoradendron reichenbachianum.123 The 3β,22α-diol,α-sophoradiol 228, has been reported from the stem ofErythrina sigmoidea.124 The hydroperoxide 229 has been foundin the aerial roots of Ficus microcarpa.99

Papers have appeared on the triterpenoids of the stem barkof Albizzia versicolor and A. schimperana,125 pyrotechnoic acid230, an ether of oleanolic acid from Leptadenia pyrotechnica,126

and tetra-, penta- and hexadecanoyl esters of oleanolic acid.127

Four new esters 231–234 have been reported from Lippiaturbinata 128 and one 235 from Eugenia sandwicensis.129 The

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Table 1 New oleanane saponins

Compound(s) Source Ref.

Albiziatrioside A Albizia subdimidiata 142Anhuienosides A–F Anemone anhuiensis 143Araliasaponins V–IX Aralia elata 144Arjunetoside Terminalia arjuna 145Basellasaponins A–D Basella rubra 146Beesioside Q Beesia calthaefolia 147Bidentatoside I Achyranthes bidentata 148Bidentatoside II Achyranthes bidentata 149Calendsaponins A–D Calendula officinalis 150Centellasaponin D Centella asiatica 151Chikusetsusaponin V methyl ester Achyranthes bidentata 149Clematibetosides A–C Clematis tibetana 152Colchisides A and B Hedera colchica 153Conyzasaponins A–G Conyza blinii 154Congmunosides V, VII, XV, XVI Aralia elata 155Crataegioside Rubus crataegifolius 156Eclalbasaponins XI and XII Eclipta prostrata 157Eclabatin Eclipta alba 158Escins Ivg, Ivh and Vib Aesculus chinensis 159Eupteleasaponin VI–XII Euptelea polyandra 160Glycoside D2 Fatsia japonica 161Glycosides L–C2 and L–I2 Scheffleropsis angkae 162Glycosides St–C2, St–D1, St–D2 Tetrapanax papyriferum 163Glycosides St–E2, St–F2, St–J2, St–K2 Tetrapanax papyriferum 164Glycosides St–H2, St–I2 Tetrapanax papyriferum 165Junceosides A–C Arenaria juncea 166Latifolosides I–Q Ilex latifolia 167Maetenosides A and B Maesa tenera 168Pisumsaponins I and II Pisum sativum 169Prostratosides D and E Polycarpon prostratum 170Prostratosides F–H Polycarpon prostratum 171Protoprimuloside B Primula elatior 172Saikosaponin q-1 Bupleurum chinense 173Saikosaponins V-1 and V-2 Bupleurum chinense 174Securiosides A and B Securidaca inappendiculata 175Sinofoside A Sinofranchetia chinesis 176Subcapitatosides B and C Aralia subcapitata 177Tanguticosides A and B Clematis tangutica 178Vitaboliside A 2�-methylglucuronate Albizia gummifera 179Zygoeichwaloside I Zygophyllum eichwaldii 180

complete proton and carbon NMR assignments of severaloleanane and ursane triterpenoids from Mentha villosa havebeen published. 130 Crystal structures have been publishedfor wilforlide A 130 from Trypterygium wilfordii 131 and 3β-methoxyolean-18-ene (meliacin) from the marine fungusChaetomium olivaceum. 132

The 24,30-dinor-oleanane derivative 236 has been found inPaeonia delavayi 133 while the 24,28-dinor-compound reman-gilone D 237 occurs in Physena madagascariensis.134 A 27-nor-

oleanane 238 has been reported from the stem bark of Vitisvinifera.135

Camelliosides A–D are oleanane saponins, from Camelliajaponic, with known genins.136 An X-ray crystal structure analy-sis of camellenodiol, the genin of camelliosides A and B,revealed that it is 239 with a 28β- and not an 18β-hydroxylgroup. The structure of the corresponding ketone, camel-lendionol, should be revised to 240. Three saponins, one ofwhich has the new genin gymnemagenol 241, have been isolatedfrom Gymnema sylvestre.137 A new saponin anemoside Btogether with a new oleanane anemonolide 242 have beenreported from Anemone rivularis.138 Fargosides A–E are newsaponins from Holboellia fargesii.139 Fargoside B has a newgenin, the 29-nor-oleanane derivative 243. The new saponin244, from Terminalia arjunis, also has a new genin.140 Centel-lasaponin A, from Centella asiatica, has the new genin 245.141

New oleanane saponins that have been assigned trivial namesare listed in Table 1.

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New oleanane saponins, that have not been assigned trivialnames, have been isolated from: Acanthophyllum squarrosum,181

Astragalus trigonus,182 Bellis perennis,183 Chenopodium quinoa,184

Elattostachys apetala,185 Fagonia cretica,186 Fatsia japonica,187

Glycyrrhiza sp.,188 Isertia pittieri,189 Ixeris sonchifolia,190a Koel-reueria paniculata,190b Phytolacca americana,191 Sanguisorbaofficinalis,192 Sapindus emarginatus,193 Schefflera arboricola 194

and Terminalia alata.195

The structure of the multiflorane derivative 246 fromMomordica cochinchinensis has been confirmed by X-ray analy-sis.196 Sandorinic acids A 247, B 248 and C 249 are threemultifloranes from Sandoricum indicum.197

Two seco-friedelanes 250 and 251 have been isolated from theleaves of Austroplenckia populnea.198 The nor-seco-derivative252 is accompanied in Tripterygium wilfordii by the known

acetal 3,24-epoxy-24-ethoxy-2-hydroxyfriedelan-29-oic acid,whose structure was confirmed by X-ray analysis.199 A dinor-friedelane, 6α-hydroxytriptocalline A 253, has also been iso-lated from Tripterygium wilfordii.200 Other new friedelanesinclude calotropfriedelenyl acetate 254 from Calotropisprocera,201 3-methoxyfriedel-2-en-1-one 255 from Salaciapetenensis 202 and three 27,16α-lactones 256–258 from Mallotusrepandas.203 The structure of lactone 257 was confirmed byX-ray analysis. The bis-friedelane derivative scutionin αB 259has been reported from Maytenus blepharodes and M. magel-lanica together with the corresponding 6�,7�-dihydro- and6β-methoxy-6�,7�-dihydro-derivatives.204

7 The ursane group

Two ursane hydroperoxides 260 and 261 and a cyclic peroxide262 have been isolated from Ficus microcarpa.99 The structureof 262 was confirmed by X–ray analysis. The aerial roots ofFicus macrocarpa contain two 13,27-cycloursanes 263 and264.33 The structure of the former was confirmed by X-rayanalysis. Swinhoeic acid 265 is an unusual 18,19-seco-ursane

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from Rubus swinhoei.205 The 16,17-seco-derivatives seco-hemidesursenyl acetate 266 and seco-hemideursenol 267, fromHemidesmus indicus,102 and the 14,15-seco-compound 268, fromPluchea lanceolata,206 have also been reported. Six anti-androgenic ursanes: cordiaketals A 269 and B 270, cordianone271 and cordianals A 272, B 273 and C 274, have been isolatedfrom the leaves of the Brazilian plant Cordia multispicata.207

The highly oxygenated 2α,3α,19α,25-tetrahydroxyursene-23,28-dioic acid 275 is a constituent of Rhaponticum uniflorum.208

Two ursane methyl ethers 276 and 277 have been found inSalvia roborowskii.209 Lawsonia alba contains the feruloyl ester278.107 Other ursanes include: the diene 279 from Rubuschroosepalas,210 the lactone 280 from the fruit of Rosa davidii,117

calotropursenyl acetate 281 from Calotropis procera,201 actinidicacid 282, a phytoalexin from unripe Kiwi fruit,211 two 30-

carboxylic acids 283 and 284 from Trypterygium wilfordii,113 theketo-triol-acid 285 from Eriobotrya deflexa,119 and urs-12-ene-3β,6β,19α,23-tetrol 286 from Mimusops elengi.106 30-Nor-urs-12-ene-3β,19α-diol 287 is a constituent of Debregeasia salicifo-lia 212 while 19α,24-dihydroxy-3-oxo-12-ursen-28-oic acid 288occurs in Rhododendron simsii.213 The feruloyl ester 289 is foundin Eriobotrya japonica.214

Five new ursane saponins have been reported fromTupidanthus calyptratus, with two new genins 290 and 291.215

Kudinosides I–P are new ursane saponins from the leaves ofIlex kudincha.216 Kudinolic acid 292 is the aglycone ofkudinosides I–K. Zygophyloside N is another ursane saponinwith a new genin 293, from Zygophyllum gaetulum.217 Urs-12-

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ene-3β,21α,28-triol 294 is the new genin of latifoloside I fromIlex latifolia where it occurs with latifoloside J which has aknown genin.218 The 20S-isomer of the 28-O β--glucopyrano-syl ester of rotundioic acid 295 has been claimed as a constitu-ent of the leaves of Ilex argentina.219 Two new saponins 296 and297, with known genins, have been isolated from Centipeda min-ima.220 Other ursane saponins with known genins include cen-tellasaponins B and C from Centella asiatica,151 latifolosides Kand L from Ilex latifolia bark 221 and constituents of Clemato-clethra scandens 222 and Sanguisorba officinalis.192

The resin of Protium heptaphyllum contains the new ursane298 together with two taraxastanes 299 and 300.223 Three

new taraxastanes 301, 302 and 303 have been reported fromSaussurea petrovii.224 The diol 302 has also been found in Picrisevae.225 22α-Methoxyfaradiol 304 and its 3-palmitate are con-stituents of the flowers of Chrysanthemum morifolium.38

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8 The hopane group

Three isomeric series of hopanoids, 17β,21β, 17β,21α and17α,21β, have been detected in several Frankia species and othersoil bacteria. Their presence raises fundamental questionsconcerning the biosynthesis of the bacteriohopanes.226 32,35-Anhydrobacteriohopanetetrol 305 has been identified inPlakortis simplex.227 Other new hopanes include 306 228 and thenor-epoxide 307 229 from Adiantum lunulatum and the diolacetate 308 from Aschersonia tubulata.230 The neohopanecaffeate 309 has been reported from Filicum decipiens.231 Sper-gulins A and B are hopane saponins with known genins.232

8α-Hydroxyfernan-25,7β-olide 310, 3α-hydroxy-4α-methoxy-filicane 311 and 19α-hydroxyferna-7,9(11)-diene 312 have beenisolated from Adiantum caudatum.233 The complete proton and

carbon NMR assignments of fern-9(11)-en-28-oic acid havebeen published.234

9 Miscellaneous compounds

Hoogianal 313 is a new constituent of Iris hoogiana.235 A rangeof sipholane derivatives has been identified in Siphonochalinasiphonella including sipholenols F 314, G 315 and H 316, sip-holenone D 317, sipholenosides A 318 and B 319, neviotine B320, siphonellinol B 321 and dahabinone A 322.236 New isoma-labaricane derivatives include 323–325 from a Jaspis sponge,237

stelliferin riboside 326 from Geodia globostellifera 238 and the 27-nor-derivatives geoditins A 327 and B 328 from Geodiajaponica.239

Chirat-16-ene-3β,24-diol 329 has been identified in Swertiachirata.240 The serratane epoxides 330, 331 and 332 have beenisolated from Picea jezoensis var., jezoensis.241 The structures of330 and 331 were confirmed by X-ray analysis. Adiantutirucal-lene B 333 and adiantulanostene B 334 are strange triterpenoidsfrom Adiantum venustrum.242

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