Triterpenoids

Contents

• 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

• References

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Abstract

Covering: 2011. Previous review: Nat. Prod. Rep., 2012, 29, 780–818.

This review covers the isolation and structure determination of triterpenoids including squalene derivatives, lanostanes, holostanes, cycloartanes, cucurbitanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, onoceranes and saponins; 308 references are cited.

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1 Introduction

Interest in the biological activities of triterpenoids continues with reviews on their anti-inflamatory,^1,2 antiviral,³ antitumour,^4–6 anti-HIV⁷ and insecticidal⁸ activities and for treatment of metabolic and vascular diseases.⁹ Surveys have appeared describing the triterpenoids isolated from Anemone raddeana,¹⁰Poria cocos,¹¹Lantana¹² and Simaba¹³ species and Pinaceae¹⁴ and Meliaceae¹⁵ families. Triterpenoid saponins show a range of biological activities¹⁶ and this has generated interest in their biosynthesis¹⁷ and improvement of yields from natural sources.¹⁸ Reviews covering triterpenoid saponins from Camellia¹⁹ and Polygala²⁰ species and the Theaceae²¹ and Caryophyllaceae and Illecebraceae²² families have appeared.

2 The squalene group

15-Dehydroxythyrsenol A 1, prethyrsenol A 2 and 13-hydroxyprethyrsenol A 3 are new cytotoxic squalene derivatives from Laurencia viridis.²³ The related compounds 22-hydroxy-15(28)-dehydrovenustatriol 4, secodehydrothyrsiferol 5, iubol 6 and 1,2-dehydropseudodehydrothysiferol 7 have also been isolated from Laurencia viridis by the same group.²⁴ Squalene-1,10,24,25,30-pentol 8, which shows moderate antimycobacterial activity, has been reported from the leaves and twigs of Rhus taitensis.²⁵ The biochemistry and molecular biology of squalene has been reviewed.²⁶

3 The lanostane group

Schiglauzic acid 9 and schiglaucyclozic acid 10 are new lanostanes from the stems of Schisandra glaucescens.²⁷ The structures of both compounds were confirmed by X-ray analyses. The three lanostanes 11, 12 and 13, from the leaves of Abies spectabilis, are accompanied by the mariesane derivative 14 and the 18(13→17)-abeo-lanostane 15.²⁸ The rearranged lanostane 16 and 24,25,26-trihydroxylanost-7-en-3-one 17 have been isolated from Abies nephrolepis.²⁹ The tetradecanoyl ester 18 is a constituent of Euphorbia sapinii.³⁰

Bioactive lanostane derivatives from fungi include 19 and 20 from Poria cocos³¹ and 24,25,26-trinor-3-oxolanosta-7,9(11)-dien-24-oic acid 21³² and methyl ganoderate A acetonide 22 and butyl ganoderate H 23³³ from Ganoderma lucidum. The epoxyganoderic acid 24 is also a constituent of Ganoderma lucidum.³⁴ The biological properties of triterpenoids from Poria cocos³⁵ and Ganoderma lucidum³⁶ have been reviewed.

Fasciculols H 25 and I 26 are constituents of the Chinese mushroom Naematoloma fasciculare.³⁷ The entomopathogenic fungus Hypocrella sp. BCC 14524 is the source of the lanostanes hypocrellols A–G 27–33.³⁸ Xylariacins A 34, B 35 and C 36 have been isolated from Xylarialeum sp. A45, an endophytic fungus isolated from Annona squamosa.³⁹ Inonotsutriols D 37 and E 38 have been reported from the white rot fungus Inonotus obliquus.⁴⁰

Erylosides R₁, T₁, T₂, T₃, T₄, T₅ and T₆ are lanostanesaponins with known genins from the Caribbean sponge Erylus formosus.⁴¹ Of the five new saponins, scillanostasides A–E, isolated from the bulbs of Scilla scilloides, only A and B have new genins 39 and 40.⁴² Lanostan-3β-ol 41 is a new genin of a diglucuronoside from the flowers of Punica granatum.⁴³

Cucumariosides H₅, H₆, H₇ and H₈ are new holostane glycosides from the sea cucumber Eupentacta fraudatrix.⁴⁴ Cucumarioside H₈ has a new genin 42 with an unusual 16,22-epoxide. Patagonicosides B and C, sulphated glycosides from the sea cucumber Psolus patagonicus, display antifungal activity.⁴⁵ Patagonicoside B has the new genin 43. Two new glycosides with known genins, liouvillosides A₄ and A₅, have been isolated from the sea cucumber Staurocucumis liouvillei.⁴⁶

Interesting new compounds from Schisandra species include henrischinins A–C 44–46 from Schisandra henryi with an oxabicyclo[3.2.1]octane moiety in the side chain,⁴⁷ the bisnor-derivative schinarisanlactone A 47 from Schisandra arisanensis⁴⁸ and the tricyclic derivative schiglautone A 48 from the stems of Schisandra glaucescens.⁴⁹ The structure of henrischinin B 45 was confirmed by X-ray analysis. 2β-Hydroxymicrandilactone C 49,⁵⁰ schintrilactone C 50⁵¹ and wilsoniadilactones D–F 51–53⁵² are new constituents of Schisandra chinensis, Schisandra sphenanthera and Schisandra wilsoniana, respectively. Four new peroxy-lactones, pseudodarolides Q₂54, T₁55 and T₂56⁵³ and 25-epipseudolarolide Q 57,⁵⁴ have been isolated from Pseudolarix kaempferi. Huangqiyenins G–J 58–61 are new saponins from Astragalus membranaceus.⁵⁵ The xyloside cimipodocarpaside 62 has been reported from Cimifuga racemosa.⁵⁶ The myxomycete Tubulifera arachnoidea afforded the new 9,10-secocycloartane tubiferic acid 63.⁵⁷

Sinocalycanchinensins A–H 64–71 are 29-norcycloartanes from the leaves of Sinocalycanthus chinensis.⁵⁸ Sinocalycanchinensins A–E 64–68 are 3,4-seco-derivatives while sinocalycanchinensin F 69 has a 2,3-cleaved ring A. Other 3,4-cleaved cycloartanes include gardenoins I 72 and J 73 from the exudates of Gardenia thailandica⁵⁹ and coccinetanes B–G 74–79 from Kadsura coccinea.⁶⁰ Secopisonic acid from Pisonia umbellifera⁶¹ and gardenoin H from the apical buds of Gardenia obtusifolia⁶² are identical with coccinetane E 77. Gardenoins E–G 80–82 are other constituents of Gardenia obtusifolia.⁶² Angustific acid A 83, from Kadsura angustifolia, has an unusual bridged lactone.⁶³ It is accompanied by angustific acid B 84 and angustifodilactones A 85 and B 86. The compounds are reported to have anti-HIV activity.

In separate studies ten new cycloartanes and glycosides87–96⁶⁴ and three new glycosides, two (97 and 98) with new genins,⁶⁵ have been reported from Cimifuga foetida. Six new glycosides99–104 have been isolated from the rhizome of Cimifuga heracleifolia⁶⁶ and two, tareciliosides L and M with new genins 105 and 106, from the leaves of Tarenna gracilipes.⁶⁷ Tareciliosides H–K have known genins.

The 18(13→17)-abeocycloartane 107 is a constituent of the bark and leaves of Garcinia benthami, where it occurs along with the 14,17-friedolanostanes 108–110.⁶⁸ Other new cycloartanes include combretanones A–G 111–117 and combretic acids A 118 and B 119 from Combretum quadlangulare,⁶⁹ bicusposides D–F 120–122 from Astragalus bicuspis,⁷⁰ macrostachyosides A 123 and B 124 from Mallotus macrostachyus,⁷¹ cycloart-24-ene-2α,3β-diol 125 from the stigma of Zea mays⁷² and boniatic acids A 126 and B 127 from Radermachera boniana.⁷³ Bonianic acids A 126 and B 127 showed some antitubercular activity. Codonopilates A–C 128–130 are cycloartane esters from Codonopsis pilosula.⁷⁴

Novel cycloartanesaponins with known genins include askendoside K from Astragalus taschkendicus,⁷⁵ cicerosides A and B from Astragalus cicer,⁷⁶ shengmaxinsides A–C from Cimicifuga simplex,⁷⁷ and unnamed saponins from Astragalus mucidus.⁷⁸ The biological activities of cycloartanetriterpenoids have been reviewed.⁷⁹

Machilusides A 131 and B 132, from the stem bark of Machilus yaoshansis, are cucurbitane glycosides with an unusual C-glycoside moiety.⁸⁰ The roots of Machilus yaoshansis afforded seven new glycosides133–139.⁸¹ These authors also revised the C-24 configurations of several known compounds, including cucurbitacins S and T and colocyhthins A, B and C, from 24S to 24R. Compounds 140 and 141, from the roots of Wilbrandia ebracteata, are reported to have cytotoxic activity.⁸² New cucurbitanes from Momordica charantia include the antioxidants taiwacins A 142 and B 143 from the stems and fruit,⁸³144–148⁸⁴ and 149 and 150.⁸⁵ Compound 148 is a 19-nor-derivative with an aromatic ring B. The biological activities of compounds from Momordica charantia have been reviewed.⁸⁶

4 The dammarane group

Gypensapogenins A 151 and B 152 are modified dammaranes, with an unusual ring A, from Gynostemma pentaphyllum, where they are found with gypensapogenins C 153, D 154 and the glucoside155⁸⁷ and the 21,24-cyclo derivative 156 and the nonanordammarane 157.⁸⁸ The structure of gypensaponin A 151 was confirmed by X-ray analysis. Other new dammaranes include gardaubryones A–C 158–160 from Gardenia aubryi,⁸⁹161–163 from the berries of Panax ginseng,⁹⁰164–170 from the floral spikes of Betula platyphylla var. japonica,⁹¹ the 24-epimers 171 and 172 from the apical buds of Gardenia collinsae,⁹² dammara-20(22),24-diene-3β,26,27-triol 173 from the leaves and twigs of Rhus taitensis²⁵ and the α-ketol 174 from the exudate of the leaves of Cerasus yedoensis.⁹³ The structure recently proposed for ailexcelone, from Ailanthus excelsa, is similar to that of gardaubryone B 159 but its spectroscopic data are inconsistent with this structure, The revised structure, 24,25-dihydroxytirucall-7-en-3-one, has been proposed and the structure of the corresponding 3β-hydroxy-derivative should also be revised.⁸⁹

Four new saponins, operculinosides A–D 175–178, have been reported from the aerial parts of Operculina turpethum.⁹⁴ The structure of operculinoside A175 was confirmed by X-ray analysis. Of the six saponinsginsenosides Re₁- Re₆ have been reported from the root of Panax ginseng, only ginsenoside Re₅179 has a new genin.⁹⁵ Panajaponol, from the roots of Panax japonicus var. major, is identical to ginsenoside Re₅179 but was drawn with the wrong double bond geometry.⁹⁶ Reviews on the pharmacological activities of the ginsenosides have appeared.^97,98

Novel dammaranesaponins with known genins include betalnosides B and C from Betula alnoides,⁹⁹ centellosides A and B and ginsenosides Mc and Y from Centella asiatica,¹⁰⁰ginsenosides Ra₄–Ra₉¹⁰¹ and 20R-ginsenoside ST₂¹⁰² from Panax ginseng, gypenosides GC1–GC7 from Gynostemma pentaphyllum,¹⁰³ notoginsenosides SFt₁–SFt₄ from Panax notoginseng,¹⁰⁴ pseudoginsenosides G₁ and G₂ from Panax quinquefolium,¹⁰⁵ yesanchinosides R₁ and R₂ from Panax japonicus¹⁰⁶ and unnamed saponins from Gynostemma pentaphyllum.¹⁰⁷

Toona ciliata var. pubescens is the source of the tirucallane derivatives toonapubesins A–G 180–186.¹⁰⁸ Toonapubesin G 186 has a rearranged side chain. The tirucallanes 187–192, together with dysoxylumstatins A–C 193–195, have been reported from Dysoxylum lukii.¹⁰⁹ Dysoxylumstatin C 195 is an apotirucallane γ-lactone. Several nor-tirucallane derivatives 196–199 have been isolated from Aphanamixis grandifolia.¹¹⁰ Compound 199 was also isolated as dysolenticin G from the twigs and leaves of Dysoxylum lenticellatum, a rich source of interesting tirucallane derivatives including dysolenticin A200, with its rearranged side chain, and dysolenticins B–F 201–205 and H–J 206–208.¹¹¹ The structures of 200, 202, 203, 205 and 207 were confirmed by X-ray analyses. Other new tirucallane derivatives from Aphanamixis grandifolia include aphagranins A–G 209–215¹¹² and compounds 216–220.¹¹³ Several of these compounds look suspiciously like artefacts of the extraction process. Cornus walteri is also a good source of new tirucallane derivatives.¹¹⁴ The constituents of this plant include cornusalterins A–L 221–232. Ailanthusaltenin A, from the stem bark of Ailanthus altissima,¹¹⁵ is the same as cornusalterin D224. Other new tirucallanes include 233 from Euphorbia sapinii,³⁰234 from the resin of Boswellia carterii,¹¹⁶ the dihydroxy acid 235 from Jordanian propolis¹¹⁷ and 236 and 237 from Azadirachta indica.¹¹⁸

Only seven euphane triterpenoids have been reported. They are compounds 238–241 from the bark of Broussonetia papyrifera,¹¹⁹ nepetadiol 242 from Nepeta suavis¹²⁰ and the 21,24-cycloeuphane 243 and cinamodiol acetate 244 from the bark of Melia azedarach.¹²¹

Cumingianols A–C 245–247 are cycloapotirucallane derivatives from Dysoxylum cumingianum.¹²² Other constituents include cumingianoside R 248, a rare glycoside in this series, the apotirucallane derivatives, cumingianols D 249 and E 250, and the tirucallane, cumingianol F 251.

4.1 Tetranortriterpenoids

Reviews have appeared on limonoids from the Meliaceae¹²³ and from Trichilia emetica¹²⁴ and on the synthesis of limonoid natural products.¹²⁵ Kokosanolides A 252 and C 253 are rearranged limonoids from the seeds and bark of Lansium domesticum cv. Kokossan.¹²⁶ Other interesting derivatives include chisomicines A 254, B 255 and C 256 from the bark of Chisocheton ceramicus,¹²⁷ 5,6-didehydrodesepoxyhaperforin C2 257 and harrpernoids B 258 and C 259 from the fruit of Harrisonia perforata,¹²⁸ aphapolynins A 260 and B 261¹²⁹ and aphanamolides A 262 and B 263¹³⁰ from Aphanamixis polystachya. The structures of kokosanolide A 252, chisomicines A–C 254–256 and aphapolyrin A 260 were all confirmed by X-ray analyses.

The lack of a furan ring is the notable feature of the tris-nor derivatives toonapubesic acids A 264 and B 265 from Toona ciliata var. pubescens.¹⁰⁸ The structure of the methyl ester of toonapubesic acid A was confirmed by X-ray analysis. Ceramicines E–I 266–270 constitute a series of 1-oxo derivatives from Chisocheton ceramicus.¹³¹ The structure of the previously published ceramicine B 271 has been confirmed by X-ray analysis. Meliarachins A–K 272–282 are further limonoids from the twigs and leaves of Melia azedarach.¹³²

Dasylactones A 283 and B 284 are degraded derivatives from Dictamnus dasycarpus.¹³³ Raputiolide 285 is a ring-A cleaved limonoid from Raputia heptaphylla.¹³⁴Toona ciliata var. henryi is a rich source of ring-B cleaved derivatives, affording toonacilianins A–L 286–297.¹³⁵ Toonacilianins K 296 and L 297 are 29-nor derivatives. Two further 29-nor derivatives, toonaciliatins N 298 and O 299 have been reported from Toona ciliata var. yunnanensis, where they occur along with toonaciliatin P 300.¹³⁶ Three methyl angolensate derivatives 301–303 have been found in the root bark of Entandrophragma angolense, where they occur with the gedunin derivatives 304 and 305.¹³⁷ Compound 301 is the same as moluccensin O which was published in 2010. Thaimoluccensin A 306 is an andirobin derivative from the seeds of Xylocarpus moluccensis.¹³⁸ Although its structure was confirmed by X-ray analysis the wrong relative configuration was published in the original paper.

Four new ring C cleaved limonoids 307–310 have been isolated from the fruit of Melia toosendan, together with the tirucallane derivatives meliasenins S 311 and T 312.¹³⁹ Meliasenin T 312 was also obtained from Melia azedarach seeds where it occurs with the tirucallane 313, the toosendanin esters314 and 315 and the nimbolinin C derivative 316.¹⁴⁰ The ring-C cleaved hydroperoxide317 has been isolated from Azadirachta indica.¹¹⁸

The flow of new mexicanolide and phragmalin derivatives continues unabated. Chukrasia tabularis var. velutina is a particularly rich source. The new derivatives reported from this source include velutabularins A–J 318–327,¹⁴¹ tabulalides F–N 328–336,¹⁴² tabulalins A–E 337–341,¹⁴³ chukvelutilide H 342 and tabularisin R 343,¹⁴⁴ tabulvelutins A 344 and B 345¹⁴⁵ and tabulalin F 346.¹⁴⁶ Many of these compounds are trivial variants of known systems. Velutabularins A–J 318–327 are cyclopropyl derivatives with a modified ring D and tabulvelutin A 344 is a 19-nor derivative. A similar range of phragmalin derivatives, swietenitins N–X 347–357, has been isolated from the twigs of Swietenia macrophylla.¹⁴⁷ The structure of swietenitin N 347 was confirmed by X-ray analysis. The stereochemistry of the known compound 14,15-dihydroepoxyfebrinin B 358 was also established during this study. The leaves of Trichilia connaroides produced trichagmalins A–F 359–364 and several acetyl derivatives 365–369, together with trichanolide370.¹⁴⁸ The gedunin andirolide A 371, the mexicanolides andirolides B–D 372–374 and the phragmalins andirolides E–G 375–377 have been reported from the flowers of Carapa guianensis.¹⁴⁹ The structure of andirolide E 375 was confirmed by X-ray analysis. Other phragmalin derivatives include thaimoluccensins B 378 and C 379 from the seeds of Thai Xylocarpus moluccensis¹³⁸ and godvarin K 380 from the Godvari mangrove Xylocarpus moluccensis.¹⁵⁰

New quassinoids are few in number. They include 2′-isopicrasin A 381 from the stems of Picrasma quassinoides,¹⁵¹ bruceines K 382 and L 383 from the ripe fruit of Brucea javanica,¹⁵² yadanziolides T–V 384–386 from the stems of Brucea mollis¹⁵³ and nothospondin 387 from Nothospondias staudtii.¹⁵⁴

5 The lupane group

The pharmacological activities of lupeol¹⁵⁵ and lupanesaponins¹⁵⁶ have been reviewed. Lactucenyl acetate 388, from Lactuca indica, has a migrated lupane structure which is identical to the structure originally assigned to tarolupenyl acetate.¹⁵⁷ The structure of tarolupenyl acetate has been revised to lup-19(21)-en-3β-yl acetate 389. Breynceanothanolic acid390 is a 25-nor-ceanothic acid derivative from roots of Breynia fruticosa.¹⁵⁸ The ring A-secolupane dysoxyhainic acid H 391 is from Dysoxylum hainanense.¹⁵⁹Liquidambar formosana is the source of liquidambarone 392 which is 18α,29-epoxy-20R-hydroxy-28-norlupan-3-one.¹⁶⁰ Sorbicins A 393 and B 394 are lupane derivatives from Sorbus cashmiriana.¹⁶¹ Olibanum, the gum resin of Boswellia carterii, is the source of olibanumols F 395 and G 396.¹⁶² Other simple lupane derivatives include lupane-3β,18α,19β-triol 397 from Garcinia tetralata,¹⁶³ lup-12-ene-3β,28-diol 398 from roots of Diospyros virginiana,¹⁶⁴ the 3β,19β-dihydroxy derivatives 399 and 400 from Paragonia pyrimidata,¹⁶⁵ and the 23,27,28-trioic acid 401 from Heteropanax fragrans.¹⁶⁶ Pulsatilla triterpenic acid A 402, from Pulsatilla chinensis, is an acetal of 5-hydroxymethylfurfural and 3β,23-dihydroxylup-20(29)-en-28-oic acid.¹⁶⁷ The caffeate esters403¹⁶⁸ and 404¹⁶⁹ are from Alnus firma and Alangium salviifolium, respectively, while the palmitate ester405 is found in leaves of Rauvolfia vomitoria.¹⁷⁰ The 21-configuration of 405 has not been established. Seven lupanesaponins with known genins have been isolated from Stryphnodendron fissuratum.¹⁷¹

6 The oleanane group

Several ring-A seco-oleananetriterpenoids have been isolated, including the 2,3-seco-oleanenetrioic acid 406 from Dillenia philippinensis,¹⁷² dysoxyhainic acid F 407, G 408, I 409 and J 410 from Dysoxylum hainanense,¹⁵⁹ the 12-ketone 411 and 13(18)-ene 412 from Betula pendula,¹⁷³ the 3-methyl ester 413 from Kalopanax pictus¹⁷⁴ and ivorengenin B 414 from Terminalia ivorensis.¹⁷⁵ The unusual 9,25-cycloolean-12-en-3β-yl β-D-glucofuranoside 415 has been reported to be a constituent of Celestris australis¹⁷⁶ and the same group has identified 9,25-cyclo-3β-(β-D-glucopyranosyloxy)-16α-hydroxyolean-12-en-28-oic acid 416 in Symplocos paniculata.¹⁷⁷ The 24,30-dinoroleanane417, 30-noroleanane418 and 24-noroleanane419 derivatives are present in the roots of Paeonia rockii ssp. rockii.¹⁷⁸ A review covering the structures and pharmacological activity of noroleanane triterpenoids has been published.¹⁷⁹ The antitumour activities of oleananetriterpenoids have been surveyed.¹⁸⁰

Fatsicarpains A–G 420–426 are oleanane derivatives from leaves and twigs of Fatsia polycarpa.¹⁸¹ The structures of fatsicarpain A 420 and the co-occurring known oleananes 427 and 428 were confirmed by X-ray analyses. 15α-Hydroxysoyasapogenol B 429, 7β,15α-hydroxysoyasapogenol B 430 and 7β,29-dihydroxysoyasapogenol 431 are metabolites of the endophytic fungus Pestalotiopsis clavispora, isolated from Bruguiera sexangula.¹⁸² The structure of 15α-hydroxysoyasapogenol B 429 was confirmed by X-ray analysis. The structure of olean-13(18)-ene-3,12,19-trione432, from Sedum linare, was also established by X-ray analysis.¹⁸³

Other new simple oleanane derivatives include ambradiolic acid A 433 from Liquidambar formosana,¹⁶⁰ 16α,23,29-trihydroxy-3-oxoolean-12-en-28-oic acid 434 from Kalopanax pictus,¹⁷⁴ ivorengenin A 435 from Terminalia ivorensis,¹⁷⁵ salacetal 436 from Salacia longipes var. camerunensis,¹⁸⁴ olean-12-ene-3α,23-diol 437 from Salvia miltiorrhiza,¹⁸⁵ camelliagenone 438 from Barringtonia asiatica,¹⁸⁶ the 1,3-diols 439 and 440 from Viburnum chingii,¹⁸⁷ 2α,3α,19α,23-tetrahydroxyolean-12-en-28-oic acid 441 from Rosa laevigata,¹⁸⁸ 3β-hydroxyolean-18-en-1-one 442 from Juglans chinensis,¹⁸⁹443–449 from Nannoglottis carpesioides¹⁹⁰ and olibanumol E 450 from olibanum, the gum resin of Boswellia carterii.¹⁶²

Pulsatilla triterpenic acids B 451 and C 452, from Pulsatilla chinensis, are hederagenin acetal derivatives.¹⁶⁷ The first glycyrrhetic acid amino acid conjugate, dendrophen 453, has been isolated from Dendronephthya hemprichi.¹⁹¹ The aglycone 454 of the known castanopsinin E_a has been found in leaves of Castanopsis fissa.¹⁹² Other new oleanane ester derivatives include the caffeoyl ester of germanicol455 from Barringtonia asiatica,¹⁸⁶esters456–459 from Glochidion assamicum,¹⁹³ uragogin 460 from Crossopetalum uragoga,¹⁹⁴ and the sulfateesters461–463 from Gypsolphila pacifica.¹⁹⁵

Clethroidosides A–G are oleananesaponins from Lysimachia clethroides.¹⁹⁶ Clethroidosides F and G have the new genins 464 and 465, respectively; the others have known genins. Heterogenoside F, from Lysimachia heterogenea, is identical to clethroidoside F and it is found with heterogenoside E that has a known genin.¹⁹⁷ The genins of glaucasides A and B, from Atriplex glauca var. ifiniensis, are the new compounds 466 and 467 whereas glaucaside C has the known genin saikogenin G. Camellia sinensis is a rich source of saponins including rogchaponins R1–R10.¹⁹⁸ Rogchaponins R1, R2 and R4–R7 have the new genins 468–473, respectively. Myrseguinoside D, from Myrsine seguinii, has the new genin 474.¹⁹⁹ It is accompanied by myrseguinoside E which is the same as the known ardisicrenoside J. Dianthosaponins A–F are found in Dianthus japonicus.²⁰⁰ Dianthosaponins E and F have the new genins 475 and 476, respectively. Bridgesides A1, C1, C2, D1, D2, E1 and E2, from Echinopsis macrogona, include the new genins 477 and 478.²⁰¹ Other oleananesaponins with new genins include 3β,12β,30-trihydroxyoleanan-28,13β-olide 479 from Patrinia scabiosaefolia,²⁰² the esters480 and 481 from Maesa lanceolata,²⁰³ oleana-11,13(18)-diene-3β,16α,21β,28-tetrol 482 and the corresponding 21 ketone483 from Bupleurum falcataum and Bupleurum rotundifolium,²⁰⁴ and coryternic acid 484 from Corydalis ternate.²⁰⁵

New oleananesaponins with known genins that have been assigned trivial names are listed in Table 1.

Table 1

Trivial name	Plant species	Reference
Androsacin	Androsace integra	206
Apodytines A–F	Apodytes dimidiata	207
Ardisicrenosides I, J, M	Ardisia crenata	208
Ardisicrenoside N	Ardisia crenata	209
Azafrines 1, 2	Crocus sativus	210
Bifinosides A–C	Panax bipinnatifidus	211
Blighosides A–C	Blighia sapida	212
Caraganosides C, D	Caragana microphylla	213
Caryophyllacosides A, B	Gypsophila paniculata	214
Catunarosides A–D	Catunaregam spinosa	215
Catunarosides E–H	Catunaregam spinosa	216
Celosins A, B	Celosia argentea	217
Celosins E, G	Celosia argentea	218
Dexyloprimulanin	Labisia pumila	219
Dialiumoside	Dialium excelsum	220
Dipsacus saponins J, K	Dipsacus asper	221
Elatoside L	Aralia elata	222
Esculentoside T	Phytolacca acinosa	223
Gordonosides I–P	Gordonia chrysandra	224
Halimodendrin I	Halimodendron halodendron	225
Libericosides A1, A2, B1, B2, C2	Atroxima liberica	226
Lonimacranthoide I	Lonicera macranthoides	227
Mandshunosides A, B	Clematis mandshurica	228
Micranthosides A–C	Polygala micrantha	229
Mollusides A, B	Albizia mollis	230
Onjisaponin Wg	Polygala tenuifolia	231
Parkiosides A–C	Butyrospermum parkii	232
Platycoside O	Platycodon grandiflorum	233
Pseudoginsenoside RT1 butyl ester	Panax japonicus var. major	96
Puberosides C–E	Glochidion puberum	234
Rheedeiosides A–D	Entada rheedei	235
Scoposides F, G	Cephalaria spp.	236
Umbellatosides A, B	Hydrocotyle umbellata	237

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The sources of new oleanane saponins with known genins that have not been assigned trivial names are listed in Table 2.

Table 2

Plant species	Reference
Albizia inundata	238
Anemone rivularis var. flore-minore	239
Anemone taipaiensis	240
Aralia elata	241
Arenaria montana	242
Bellis perennis	243
Catunaregam spinosa	244
Cylicodiscus gabunensis	245
Dianthus superbus	246
Erthrophleum fordii	247
Ganoderma applanatum	248
Gymnocladus chinensis	249
Gypsophila perfoliata	250
Juglans sinensiss	189
Kalopanax pictus	174
Lathyrus rattan	251
Medicago polymorpha	252
Microsechium helleri	253
Nephelium lappaceum	254,255
Panacis majoris	256
Phytolacca americana	257
Salsola imbricata	258
Sanguisorba tenuifolia var. alba	259
Symplocos caudata	260
Symplocos lancifolia	261

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Pachanosides C1, E1, F1 and G1 are pachanane saponins from Echinops macrogona with the genins 485–488, respectively.²⁰¹ The structure of pachanol C 485 has been revised.

The rearranged oleanane derivatives phlomishexaols C 489 and D 490 have been found in the roots of Phlomis umbrosa.^262,263 The biosynthetic origin of the spirotriterpenoid cleistanone 491, from Cleistanthus indochinensis, is not clear from its structure.²⁶³ The rearranged oleanane derivative 492 has been claimed from Rhododendron campanulatum.²⁶⁴ The stereochemistry of the methyl group at C-18 of 492 is unusual. The multiflorane endoperoxide dibenzoate 493 is a constituent of processed seeds of Trichosanthes kirilowii.²⁶⁵ 3β-Acetoxyglutin-5(10)-en-6-one 494 has been found in roots of Scorzonera austriaca.²⁶⁶

New friedelanetriterpenoids include 21α-hydroxyfriedelane-1,3-dione 495 from Salacia verrucosa,²⁶⁷ 12α-hydroxyfriedelane-3,16-dione 496²⁶⁸ and 12α,29-dihydroxyfriedelan-3-one 497²⁶⁹ from Maytenus gonoclada, 3β-hydroxyfriedelane-7,12,22-trione 498 from Drypetes laciniata²⁷⁰ and 11α-friedelan-3-one 499 from Myrica rubra.²⁷¹ The norfriedelane derivative 3-O-methyl-6-oxopristimerol 500 is a constituent of Maytenus chubensis.²⁷² Blepharodin 501, from Maytenus magellanica, is an adduct with a phenylpropanoid derivative.¹⁹⁴

7 The ursane group

The 18,19-secoursane derivatives 502 and 503 have been isolated from Rosa laevigata together with 28-norursa-12,17-diene-2α,3β,23-triol 504 and the arabinoside505 whose genin has an unusual 19α-stereochemistry.¹⁸⁸ The related 18,19-secoursane derivative 506 has been reported from leaves of Diospyros kaki.²⁷³ Atriplicaide A 507 is an unusual N-acetyl lactam from Zygophyllum eurypterum where it is found with atriplicaide B 508 which is 3β,24dihydroxyursan-28,13-olide.²⁷⁴ Related 28,13-olides 509 and 510 have been isolated from Isodon coetsa²⁷⁵ and Schefflera heptaphylla,²⁷⁶ respectively. Proceraursenolide 511, from the roots of Calatropis procera, is claimed to be 18αH-urs-12-en-25,3β-olide.²⁷⁷ Other new simple ursane derivatives include cordinoic acid 512 from Cordia latifolia,²⁷⁸ urs-12-ene-3α,23-diol 513 from Salvia miltiorrhiza,¹⁸⁵ 18αH-ursene-3β,20β-diol 514 from Boswellia carterii,¹¹⁶ 1α,2α,3β,16α,19α,20β-hexahydroxyurs-12-en-28-oic acid 515 from Pedicularis kansuensis,²⁷⁹ glutinolic acid 516 from Rehmannia glutinosa,²⁸⁰ and 3β,7β,24-trihydroxyurs-12-en-28-oic acid 517 from Saurauja roxburghii.²⁸¹ New ursane ester derivatives include conrauidienol 518 from Ficus conraui,²⁸² 3β-acetoxyursa-11,13(18)-dien-28-oic acid 519 from Eucalyptus camaldulensis,²⁸³3-O-acetyluncaric acid520 from Radermachera boniana,⁷³ sambucilate 521 from Sambucus adnata²⁸⁴ and the palmitate esters522 and 523 from Viburnum betulifolium.²⁸⁵

Clethroidoside H, from Lysimchia clethroides, is an ursane saponin with the new genin ursa-9(11),12-diene-2α,3β,21β,30-tetrol 524.¹⁹⁶ The 18,19-secoursane derivative 525 is the genin of dunnianolactones A–C from Ilex dunniana.²⁸⁶ A saponin given the duplicate name ilexsaponin C, from Ilex pubescens, has the new genin 28-norursa-12,17-dien-2β-ol 526.²⁸⁷ Other unnamed ursanesaponins with the new genins include 3β,23-dihydroxyurs-12-en-28-oic acid 527 from Jugalans sinensis,¹⁸⁹ and 2,3β,16α,23-tetrahydroxyurs-12-en-28-oic acid 528 from Lathyrus aphaca.²⁵¹

Ursane saponins with known genins include asiaticoside G from Centella asiatica,²⁸⁸ clethric acid 28-O-β-D-glucopyransyl ester and mussaendoside T from Anthocephalus chinensis,²⁸⁹ ilekudinchosides A–D²⁹⁰ and W²⁹¹ from Ilex kudincha, symplocosins A and B from Symplocos cochinchinensis var. philippensis,²⁹² zygophylloside S from Zygophyllum coccineum²⁹³ and unnamed saponins from Ilex chamaedryfolia,²⁹⁴Juglans sinensis,¹⁸⁹Sanguisorba tenuifolia var. alba²⁵⁹ and Symplocos lancifolia.²⁶¹

19β-Hydroxy-3,4-seco-4(23),20(30)-taraxastadien-3-oic acid 529 has been isolated from buds of Betula pendula.¹⁷³ The tanninester530 of 2α,3β,23,24-tetrahydroxytaraxastan-28,20β-olide is a constituent of leaves of Castanopsis fissa.¹⁹² The taraxastane hemiacetal 531 has been found in Geum japonicum.²⁹⁵ Celosin F 532 appears to be a taraxastane xyloside from Celosia argentea.²¹⁸

8 The hopane group

The current knowledge of squalene-hopene cyclases has been reviewed.²⁹⁶ The unusual 9,25-cyclo-29-propylhopan-31-ol 533 and 3β-hydroxy-29-propylhopan-31-one 534 have been identified in Celestris australis.¹⁷⁶ The same group claim that the cyclohexylhopane derivative 535 is also found in Celestris australis²⁹⁷ and that the 29-ethylhopane derivative 536 and 32,33,34-trimethylbacteriohopan-3β-yl β-D-glucopyranoside 537 are constituents of Symplocos paniculata.¹⁷⁷ Several N-acylated bacteriohopanehexol mannosamine derivatives 538 have been identified in the thermophilic bacterium Alicyclobacillus acidoterrestris.²⁹⁸ The simple hopane derivatives 539–541²⁹⁹ and 542–547³⁸ are metabolites of the entomopathogenic fungi Conoideocrella tenuis and Hypocrella sp. BCC 14524, respectively.

Twelve arborinane triterpenoids have been isolated from Rubia yunnanensis including rubiyunnanols A–C 548–550, rubiarbonone E 19-acetate 551, 2-hydroxyrubiarbonone E 552, 19,28-didehydroxyrubiarbonol A 553, rubiarbonol A 7-acetate 554, the rubiarbonol A glycoside 555, rubiarboside G 28-acetate 556, rubiarboside G 28-aldehyde 557, 2α-acetoxyrubiarboside 28-acetate 558 and the rubianol E glycoside559.³⁰⁰Adiantum capillus-veneris is the source of filicane-3β,4α-diol 560 and the corresponding 3α-methyl ether 561.³⁰¹ Canarene 562 is an unusual rearranged filicane derivative from Canarium schweinfurthii.³⁰² The structure of canarene 562 was confirmed by X-ray analysis and a biosynthetic scheme for its formation has been proposed.

9 Miscellaneous compounds

Phyteumosides A and B, from Phyteuma orbiculare, have as aglycones the partially cyclised onocerane triterpenoid563 and the polypodane derivative 564, respectively.³⁰³ The structures of the aglycones 563 and 564 were established by X-ray analysis. Lansium domesticum is the source of the onocerane derivatives lamesticumin A 565 and the corresponding ethyl ester 566, lamesticumins B–E 567–570, the 3-ethyl ester of lansic acid571 and ethyl lansiolate 572 together the polypodane derivative lamesticumin F 573.³⁰⁴ Other onocerane derivatives include cupacinoxepin574, from Cupania cinerea³⁰⁵ and kokosanolide B 575 and onocera-7,14-diene-3,21-dione576 from Lansium domesticum cv. Kokossan.¹²⁶

The isomalabaricane triterpenoids stelliferins J–N 577–581 are constituents of the sponge Rhabdastrella cf. globostellata.³⁰⁶ Stelliferins L–N 579–581 have a cyclised side-chain similar to rhabdastins D–G. A sponge of the genus Lipastrotethya is the source of pouosides F–I 582–585 and pouogenins A–E 586–590.³⁰⁷ Three iridal triterpenoids591–593 have been isolated from Iris delavayi.³⁰⁸

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