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: 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.

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1 Introduction

Interest in the pharmaceutical activities of triterpenoids continues to increase.¹ Reviews have appeared on the triterpenoid constituents of Boswellia serrata,²Lantana camara,³Lysimachia 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 Ekeberins D₁–D₅2–6 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, from the red alga Laurencia mariannensis¹⁵ and omaezakianol 11 and 15,16-anhydrothyrsiferol 12 from Laurencia omaezakiana.¹⁶

The condensation of C₃₂ and C₃₄ macrocyclic aldehydes with the methylated squalene diols 13 and 14 gives rise to the 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 β-amyrin (0.2%) being formed.¹⁹ This enzyme appears to have evolved from the enzymes which lead to pentacyclic products. A lanosterol synthase-deficient yeast strain At1g78500 afforded the two 8,14-seco-derivatives 19 and 20 of α-amyrin and β-amyrin.²⁰ The C-14 configuration of arabidiol 21, produced by At4g15340, has been established as R.²¹ The stereochemistry of the addition of water to triterpenoid cationic intermediates is also discussed. Replacement of Phe699 by threonine in the oxidosqualene-lanosterol cyclase ERG7 from Saccharomyces cerevisiae resulted in the formation of protosta-13(17),24-dien-3β-ol 22 instead of lanosterol.²² Calculations suggest that the biosynthesis of friedelin is a non-stop process which involves pentacyclisation of squalene oxide to the lupanyl cation followed by ten suprafacial 1,2-shifts of methyls and hydrogens.²³ Several reviews have appeared covering aspects of oxidosqualene-lanosterol cyclase,²⁴ engineering squalene cyclising enzymes²⁵ and the properties of oxidosqualene cyclases.^26,27

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

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 derivatives 42–44 from the mangrove plant Hibiscus tiliaceus,⁴⁰45–48 from Euphorbia humifusa,⁴¹49–52 from Diospyros discolor,⁴²53 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,⁴⁹66 and 67 from Ganoderma lucidum⁵⁰ and ganolactone B 68 and ganoderiol A triacetate 69 from Ganoderma sinense.⁵¹ Three unusual Δ¹⁶-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

More lanostane derivatives have been reported from Poria cocus. These include 29-hydroxypolyporenic acid C 74 and 25-hydroxypachymic acid 75,^59,60 poriacosones A 76 and B 77⁶¹ and 15α-hydroxydehydrotumulosic acid 78, 16α,25-dihydroxydehydroeburicoic acid 79, 16-deoxyporicoic acid B 80, poricoic acid CM 81, the endoperoxide 82 and 25-hydroxyporicoic acid H 83.⁶²

Aeruginosols A 84, B 85 and C 86 are constituents of the fruiting bodies of Stropharia aeruginosa.⁶³ Astrapteridiol 87, astrapteridone 88 and 3-epi-astrapteridiol 89 are from the mushroom Astraeus pteridis.⁶⁴ 3-epi-Astrapterdiol 89 shows anti-tuberculosis activity. The structure of astrapteridone 88 was confirmed by X-ray crystallographic analysis. Inonotsulides A 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 and kadcoccilactone R 108 from the stems.⁷¹ The structure of kadsuracoccinic acid A 99 was confirmed by X-ray analysis. Kadsuracoccinic acid C and secococcinic acid F have the same structure 101. Schisanlactone E 109 is a constituent of Kadsura longipedunculata.⁷² The name schisanlactone E has been previously used for a seco-cycloartane derivative.

Oligoporins A 110, B 111 and C 112 are new lanostane saponins from Oligoporus tephroleucus.⁷³ Three new saponins, sativalanosteryl glucoside 113⁷⁴ and orizalanosterolides A 114 and 115⁷⁵ have been reported from rice hulls of Oryza sativa. The unusual compound 116 is a proposed metabolite of Catharanthus roseus hairy root cultures.⁷⁶ Eylosides 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 Holothuria axiloga.⁸³ Arguside A, a cytotoxic glycoside from Bohadschia argus, has the new genin 129⁸⁴ and synaptoside A₁, from Synapta maculata, has the new genin 130 while the co-occurring synaptoside A has a known genin.⁸⁵ Five new oligoglycosides, frondosides A₇-1 – A₇-4 and isofrondoside C, have been reported from Cucumaria frondosa, all with known genins.⁸⁶ Other new holostane saponins with known genins include argusides 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 A^92,93 and C⁹⁴ from Holothuria leucospilota, liouvillosides A₁–A₃, B₁ and B₂ from Staurocumis liouvillei,⁹⁵ marmoroside C from Bohadschia marmorata,⁹⁶ okhotosides A₁-1, A₂-1,⁹⁷ and B₁–B₃⁹⁸ from Cucumaria okhotensis and saponins without trivial names from Actinopyga lecanora⁹⁹ and Pseudocolochirus violaceus.¹⁰⁰ The biological activities of the holostane saponins have been surveyed.^101,102

The amazing skeletal diversity of complex cycloartane-derived products from Schisandra and Kadsura species continues to 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 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 equilibrium with its 20-epimer, schintrilactone B 150.¹⁰⁷ Extraction of the leaves and stems of Schisandra lancifolia afforded lancifodilactones 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 micrandilactones 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 propindilactones 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 of rubrifloradilactone 183, from Schisandra rubriflora, has been confirmed by X-ray analysis.¹¹⁵Schisandra sphenanthera is the source of sphenalactones A–D 184–187¹¹⁶ and sphlenadilactone C 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 lancifodilactone 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 heteroclitalactones 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 kadcoccilactone Q) from Kadsura renchangiana.¹²⁵

Two groups have reported a new cycloartane alkaloid 225 from the rhizomes of Cimicifuga foetida,^126,127 which has two names, cimicifine A and cimicifugadine. Three new ring-D cleaved glycosides 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-β-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 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,¹³⁶247 from Aglaia forbesii,¹³⁷248 from Gnetum pendulum,¹³⁸249 from Derris laxiflora,¹³⁹250 from Skimmia laureola,¹⁴⁰251 from the marine green alga Cladophora fascicularis,¹⁴¹252 from Euphorbia guyoniana,¹⁴²253 from Euphorbia humifusa,¹⁴³ artocapuates A 254 and B 255 from Artocarpus nobilis,¹⁴⁴256–258 from Cocos nucifera,¹⁴⁵259 and 260 from Nigella sativa,¹⁴⁶261 from Fritillaria hupehensis,¹⁴⁷ and the chloro-derivative 262 from Ligularia stenocephala.¹⁴⁸ Reference NMR data from synthetic 23E- and 23Z-cycloart-23-ene-3β,25-diols indicate that structural revision is required for several related triterpenoids.¹⁴⁹

The cycloartane-3β,7β,24R,25-tetraol 263 is a new genin of the cycloartane glycosides from Camptosorus sibiricus.¹⁵⁰ Aquilegiosides K and L, from Aquilegia vulgaris, also have new genins 264 and 265.¹⁵¹ Sutherlandiosides A–D 266–269 are new glucosides from Sutherlandia frutescens.¹⁵² The structure of 266 was confirmed by X-ray analysis. Tareciliosides A–G have been reported from the leaves of Tarenna gracilipes and include the new genins 270–272.¹⁵³ Podocarpasides A–J 273–282 are constituents of the roots of Actea podocarpa.^154,155 The structure of podocarpaside E 277 was revised on the basis of an X-ray analysis.¹⁵⁶ Two new cycloartane xylosides 283 and 284 have been reported from the roots of Actea pachypoda, together with the known 12β-acetoxycimigenol.¹⁵⁷ Cyclomacrogenin B 285 is cycloartane-1α,3β,7β,24R,25-pentaol, which was obtained from Astragalus macropus.¹⁵⁸ A variety of saponins with new genins has been reported from Astragalus species, including bicusposides A 286, B 287 and C 288 from Astragalus bicuspis,¹⁵⁹ mongholicosides A 289 and B 290 from Astragalus membranaceus 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 astramembranosides 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 Camptosorus sibiricus^172,173,174 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 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.

Desacetylfevicordin A 351, from the Indonesian medicinal plant Phaleria macrocarpa, is the same as fevicordin C and has been identified as a natural product for the first time.¹⁹¹ Endecaphyllacins A 352 and B 353 are octanor-cucurbitane constituents of the tubers of Hemsleya endecaphylla.¹⁹² The structure of 352 was confirmed by X-ray analysis. Other new cucurbitacins include 354 and 355 from Cayaponia racemosa,¹⁹³356 and 357 from Physocarpus capitatus,¹⁹⁴ a saponin with a new hexanorcucurbitane genin 358¹⁹⁵ from the fruit of Cucurbita pepo cv. dayangua and colocynthosides A 359 and B 360 from Citrullus colocynthis.¹⁹⁶ Bacobitacins 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 isofoveolate B 370, isoeichlerianic acid 371 and its methyl ester 372, methyl foveolate B 373, isosilvaglins A 374 and B 375, deoxysilvaglin 376 and aglasilvinic acid 377.^202,203 Also the stereochemistry of the known foveolin B (free acid of 373) has been revised. Six new dammaranes, cylindrictones 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 dammaranes include santolins A–C 386–388 from Salvia santolinifolia,²⁰⁶ oliganthas A 389 from Saussurea oligantha,²⁰⁷ gentirigenic acid 390 and gentirigeosides A–E 391–395 from the roots of Gentiana rigescens,²⁰⁸396–398 from Cabralea canjerana,²⁰⁹ the hydroperoxides 399 and 400 from Ligustrum lucidum,²¹⁰401 and the octanor-derivative 402 from Maytenus macrocarpa,²¹¹403 from radix Ranunculus ternati,²¹² foliasalacins A₁–A₄404–407 from the leaves of Salacia chinensis,²¹³408 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 and galls of Sapindus mukurossi.²¹⁷ Sapimnusaponin P has the new genin 413. Bacopasaponin G and bacoside A₆, from Bacopa monniera, are glycosides of 17,20-anhydro-derivatives 414 and 415 of jujubogenin and pseudojujubogenin, respectively.²¹⁸ The aglycone 416 of notoginsenside R₁₀ has been obtained from the leaves of Panax ginseng.²¹⁹ The new glucoside 417 has been isolated from the roots of Panax notoginseng.²²⁰ Notoginsenosides ST-1, ST-2, ST-3 and ST-5 are constituents of steamed Panax notoginseng.²²¹ The first three have the new genins 418–420 respectively. New dammarane saponins from Gymnostemma pentaphyllum include six new genins 421–426²²² while those from Gymnostemma pubescens have two new genins 427 and 428.²²³ New dammarane saponins with known genins include bacopaside 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 L_a and L_b from Panax quinquefolium²³¹ and saponins without trivial names from Panax ginseng²³² and Panax quinquefolium.²³³ A review covering the biosynthesis of the ginsenosides has been produced.²³⁴

Dichapetalins I–J 429–432 are constituents of the stem bark of Dichapetalum gelonoides.²³⁵ Five new dichapetalins, 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, 21α-O-methylmelianodiol 442, 21β-O-methylmelianodiol 443, hispidiol A 25-methyl ether 444 and hispidiol B 25-methyl ether 445,²³⁹ while the fruit of Phellodendron chinense var. glabriusculum gave the pentanor-derivative phellogin 446²⁴⁰ and compound 447.²⁴¹Cedrela sinensis contains the tirucallanes 448 and 449 and the apotirucallanes 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 delavayi²⁴⁵ with two new genins 465 and 466, and sapinmusaponins Q and R, with known genins, from the galls of Sapindus mukorossi.²⁴⁶

4.1 Tetranortriterpenoids

Walsuronoid A 467 is a peroxide derivative from Walsura robusta.²⁴⁷ It is accompanied by walsuronoids B 468 and C 469, which apparently are rare tetranor-dammarane derivatives. The authors suggest that they are formed by methyl migration following acid-catalysed 14,15-epoxide ring opening of a limonoid. The structure of walsuronoid A 467 was confirmed by X-ray analysis. A Malleastrum species from the Madagascar rainforest afforded malleastrones A–C 470–472.²⁴⁸ The structures of malleastrones A and B were confirmed by X-ray analyses. Munronin G 473 is a new compound from Munronia delavayi.²⁴⁹ Other new compounds include the azadirone derivatives 474 and 475 from Turraea cornucopia,²⁵⁰ dysoxylins A–D 476–479 from Dysoxylum gaudichaudianum²⁵¹ and chisosiamensin 480 from the seeds of Chisocheton siamensis.²⁵² X-ray structure analyses of the known epoxyazadiradione²⁵³ and 6α-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 8β,14α-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 as natural products. Turraea pubescens²⁶¹ and Amoora tsangii²⁶² are also rich sources of limonoids. The former produced turrapubesic 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 Melia toosendan.²⁶⁶ Two unusual limonoids, ceramicine A 521, which lacks methyl groups at C-4, and the ring-C-seco walsogyne A 522, have been reported from Chisocheton ceramicus and Walsura chrysogyne respectively.²⁶⁷ 12-O-Methylnimbolinin A 523 and the meliacarpin derivative 524 have been identified in fruits of Melia azedarach.²⁶⁸ The gedunin derivative ekeberin C₁525 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 cyclopropylphragmalin 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 Chukrasia tabularis,^38,275 the cyclic carbonate chuktabrin A 557 and the unusual chuktabrin B 558 also from the twigs and leaves of Chukrasia tabularis,²⁷⁶ the acetals chuktabularins 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 C₂568 and C₃569 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 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 limonoids include dysodensiols A–C 607–609 from Dysoxylum densiflorum,²⁸⁷ 9α-hydroxyfraxinellone 9-O-β-D-glucopyranoside 610, dictamnusine 611, dictamdiol 612 and dictamdiol B 613 from the root bark of Dictamnus dasycarpus,²⁸⁸ and isodictamdiol 614 and the known dictamdiol 615 from the root of Dictamnus radicis.^289,290 The structures of both 614 and 615 were confirmed by X-ray analyses. The authors suggest that these compounds have opposite absolute configurations to other limonoids, but this would be very unusual and requires confirmation.

Plants of the Cipadessa genus contain a varied range of limonoids. Cipadessalide 616 and rubralin D 617 are constituents of Cipadessa baccifera,²⁹¹ while Cipadessa cinerascens contains cipadesins D 618 and E 619.²⁹² Another group has published 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 mexicanolide derivatives 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 xyloccensin Y from the same source.²⁹⁷ A review covering the 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-3β,6α-diol 647,²⁹⁹ which has previously been claimed from Perilpoca aphylla.³⁰⁰ Due to differences in NMR data the authors suggest that the Perilpoca aphylla constituent should be reassigned as the corresponding 6β-isomer. Sorbinal B 648, from Sorbus cashmariana, has been assigned the structure lupa-12,22(29)-diene-2α,3β,23,28-tetrol.³⁰¹ The structure of sorbinol B 648 is incorrectly drawn in the reference with a 5,6-double bond. Other new lupane alcohol derivatives include lup-20(29)-ene-3β,22β-diol 649 from Moldenhawera nutans,³⁰² lup-20(30)-ene-1β,3β,29-triol 650 from Salvia sclareoides³⁰³ and the acetates 651 and 652 from Salvia macrochlamys.³⁰⁴ Foliasalacins B₁–B₃653–655 are new lupane derivatives from the leaves of Salacia chinensis.²¹³ The lupan-29-al derivatives 656–658 from Acacia mellifera show cytotoxic activity,³⁰⁵ and the lupan-28-oic acid derivatives 659 and 660 from Fagara tessmannii have α-glucosidase inhibitory properties.³⁰⁶Gypsophila repens is the source of the unusual lupane sulfate gypsophilin 661 and its glucosyl ester gypsophilinoside 662.³⁰⁷ The methyl ester 663 and the 3-acetate 664 of alphitolic acid have been isolated from seeds of Ziziphus jujuba var. spinosa³⁰⁸and the resin of Garcinia hanburyi³⁰⁹ respectively, and the related 20,29-dihydro derivative 665 has been found in Eugenia grandis stem bark.³¹⁰ Other simple lupane derivatives include the 27-carboxylic acids 666 and 667 from Potentilla discolor³¹¹and the hemiacetal lantabetulal 668 from roots of Rhus javanica var. roxburghiana.³¹² Ocimol 669 from Ocimum basilicum is the ester of betulinic acid with methyl vanillate.³¹³ Other lupane aromatic esters include the cinnamate 670 and the 4-hydroxybenzoate 671 from Helicteres angustifolia,³¹⁴ 3-ferruloyllupeol 672 from Ceriops tagal³¹⁵ and the caffeoyl esters 673 from Xanthoceras sorbifolia³¹⁶ and 674–676 from Peganum nigellastrum.³¹⁷ 3α-Hydroxylup-20(29)-en-28,19β-olide 677 is a constituent of Perrottetia arisanensis, where it occurs with the esters 678–680.³¹⁸

20,29,30-Trinorlup-18-en-3β-ol 681 from Arabidopsis thaliana has been given the misleading name trinorlupeol.³¹⁹ The 17-hydroperoxy-28-norlup-20(29)-en-3β-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 humifusa.¹⁴³ The related 3,4-secolupane derivative 686 is a constituent of Viburnum awabuki together with the 30-norlupane 687.³²¹ 16β-Hydroxylupa-1,20(29)-dien-3-one 688 and 16β-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-secolupane 690 has been isolated from Microtropis fokiensis together with the 7-oxygenated derivatives 691 and 692.²⁹⁴ The lupane saponin 693 from fruits of Polygonum orientale has a new genin.³²³ Acankoreosides F–H, from Acanthopanax koreanum, also have new lupane genins 694–696, respectively.³²⁴ Lupane saponins with known genins include stallatoside B and erucasaponin A from the cactus Stenocereus eruca³²⁵ and a saponin from roots of Carthamus tinctorius.³²⁶

Gouanic acids A 697 and B 698 from aerial parts of Gouania ulmifolia³²⁷ and 1-epi-ceanothic acid 699 from Gleditsia sinensis³²⁸ are 3(2→1)-abeo-lupane derivatives. Elephanmollen 700 is a D:C-friedolupane derivative from Elephantopus mollis that shows cytotoxic properties.³²⁹

6 The oleanane group

Two rearranged oleanane derivatives, dysoxyhainanins A 701 and B 702, have been identified from Dysoxylum hainanense.³³⁰ 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, phlomishexaols 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 secooleananes 718 and 719 are shown in the reference with the 18α-configuration but there is no evidence for this stereochemistry. The ring-A cleaved oleanane 720 has been obtained from the floral spikes of Betula platyphylla var. japonica.²¹⁶ 24-Noroleana-3,9(11),12-triene 721 has been identified in olibanum from Boswellia serrata.³³⁶ It is possible that this nortriterpene is a pyrolysis product. 24-Nor-3-oxoolean-12-en-28-oic acid 722 has been named hederagonic acid, a name used previously for the 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 2α,3α,16α-trihydroxy-24-noroleana-4(23),12-dien-28-oic acid 725 from Salvia palaestina,³³⁸ the 30-nor-derivative 726 from Stauntonia obovatifoliola ssp. intermedia,³²² and the 3,25-epoxy-28-noroleananes lantadienone 727 and camaradienone 728 from Lantana camara. The 3,25-epoxy derivative lantanoic acid 729 has also been found in Lantana camara,³³⁹whereas the related lantanolal 730 and lantanalol 731 are constituents of Rhus javanica var. roxburghiana.³¹² Dryobalanolide 732 has been isolated from Eucalyptus camaldulensis.³⁴⁰ Dryobalanolide 732 had previously been isolated as the 3,23-acetonide. The 3,23-acetonide of aceriphyllic acid 733 has been found in Aceriphyllum rossii together with the 3-ketone 734.³⁴¹ The triacetate 735 has been isolated from the roots of Ligularia sagitta after acetylation.³⁴² It is not clear whether the natural product is the corresponding triol or an acetylated compound. Foliasalacin C 736 is olean-12-ene-3β,15α-diol from the leaves of Salacia chinensis.²¹³

The 21β-hydroxyoleanane derivatives 737–741³⁴³ and 21β-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-2α,3β,21β,23,28-pentol 744 from Laportea crenulata,³⁴⁶ olean-12-ene-3β,6β,21β-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 30-noroleanane esters 769–771.³⁶² Other new oleanane esters include the maslinic esters 772 and 773 from Hippophae rhamnoides,³⁶³ the 27-(4-hydroxybenzoyl) derivative 774 from Heliceres angustifolia,³¹⁴ lippiacin 775 from Lippia nodiflora,³⁶⁴ patrirupin A 776 from Patrinia rupestris,³⁶⁵ basilol 777 from Ocimum basilicum,³¹³ camarolic acid 778 and lantrigloylic acid 779 from Lantana camara,³⁶⁶ the ferruloyl esters 780 and 781 from Ludwigia octovalvis,³⁶⁷ the p-coumaroyl esters 782 and 783 from Barringtonia racemosa³⁶⁸ and 784 from Rhizophora stylosa,³⁶⁹ the 27-caffeoyl ester 785 from Peganum nigellastrum,³⁷⁰ the 3,5-dihydroxycinnamoyl ester 786 from Drypetes tessmanniana²⁹⁹ and the angeloyl ester 787 from Lantana hispida.³⁷¹ The disulfate esters 788 and 789 are constituents of Melissa officinalis.³⁷²

Psidiumoic acid 790, from Psidium guajava, is an unusual 2-hydroxyethyl ether.³⁷³ β-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 from Eryngium yuccifolium including the genin 801,³⁸¹ saponins from Fagonia arabica including the disulfate 802,³⁸² saponins from Glycyrrhiza uralensis including 22β-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 brauhica with 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 trachelosperoside F 834 from Trachelospermum jasminoides with a new 30-nor genin.³⁹⁹ New oleanane saponins with known genins that have been assigned trivial names are listed in Table 1.

Table 1

Trivial name	Plant species	Reference
Acanthopanaxoside E	Acanthopanax senticosus	400
Achyranthosides G and H	Achyranthes fauriei	401
Aesculiosides IIe–IIk and IIIa–IIIf	Aesculus pavia	402
Akebosides La and Lb	Akebia quinata	403
Ardisiacrenoside I	Ardisia crenata	404
Arganins L and O–R	Argania spinosa	405
Assamicins VI–VIII	Aesculus assamica	406
Asteratoidesoside A	Aster souliei	407
Bodinierin C	Elsholtzia bodinieri	408
Brevifoliasaponin	Calliandra brevifolia	409
Cauloside H	Caulophyllum thalictroides	410
Cernuasides A–D	Pulsatilla cernua	411,412
Chakasaponins V and VI	Camellia sinensis	413
Chionaeosides A–D	Paronychia chionaea	414
Clematiganoside A	Clematis ganpiniana	415
Codonolasides I–III	Codonopsis lanceolata	416,417
Congmuyanoside I	Aralia elata	418
Dexylosyltubeimoside III	Bolbostemma paniculatum	419
Dipterosides A–E	Dipteronia dyeriana	420
Floratheasaponins D–I	Camellia sinensis	421
Foliatheasaponins I–V	Camellia sinensis	422
Giganteasaponins 5 and 6	Solidago gigantea	423
Giganteosides L–N	Cephalaria gigantea	424
Gleditzsioside Z	Gleditisia sinensis	425
Gummiferaosides A–C	Albizia gummifera	426
Gymnemosides W1 and W2	Gymnema sylvestre	427
Gypsosaponins A (Gypoldoside A) –C	Gypsophila oldhamiana	428,429
Hehuanoside A	Albizia julibrissin	430
Helianthosides 4 and 5	Helianthus annuus	431
Hydrocosisaponins A–F	Hydrocotyle sibthorpioides	432
Ilexpernoside F	Ilex pernyi	433
Ilexsaponin C	Ilex pubescens	434
Impatiprins A–C	Impatiens pritzellii var. hupehensis	435
Isoescins VIa–VIIa	Aesculus turbinata	436
Lancemasides B–G	Codonopsis lanceolata	437,438
Lonicerosides D and E	Lonicera japonica	439
Lysichrisides A and B	Lysimachia christinae	440
Montanosides 1 and 2	Clematis montana	441
Nigellosides A–D	Nigella damascena	442
Oblonganosides L–M	Ilex oblonga	443
Onjisaponins	Polygala tenuifolia	444,445
Perennisaponins A–F	Bellis perennis	446
Perennisosides I–VII	Bellis perennis	447
Pharbitosides A and B	Pharbitis nil	448
Pithelucosides A–C	Pithecellobium lucidum	449
Puberosides A and B	Glochidion puberum	450
Raddeanoside R19	Anemone raddeana	451
Repensosides A–F	Gypsophila repens	452
Sapinmusaponins K–N	Sapindus mukorossi	217
Serrulatins A–E	Photinia serrulata	453
Sigmoiside E	Erythrina sigmoidea	454
Stauntoside A	Suantonia chinensis	455
Stryphnosides A–F	Stryphnodendron fissuratum	456
Theasaponins A6, A7 and B5	Camellia sinensis	457
Tenuifoside A	Polygala tenuifolia	458
Vaccaroside I	Vaccaria segetalis	459
Xanifolias Y0, Y2, Y3 and Y7	Xanthoceras sorbifolia	460
Yemuosides YM21–YM25	Stauntonia chinensis	461

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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
Achras sapota	462
Akebia quinata	463,464
Albizia lebbeck	465
Albizia procera	466
Androsace umbellata	467
Anemone flaccida	468
Ardisia gigantifolia	469
Arenaria juncea	470
Aronia melanocarpa	471
Artemisia sphaerocephala	472
Aster novi	473
Carthamus tinctorius	474
Chenopodium quinoa	475
Combretum laxum	476
Combretum molle	477
Cordia piauhiensis	478
Garcinia hanburyi	309
Gueldenstaedtia multiflora	479
Lactuca scariola	480
Lactuca scariola	481
Lonicera japonica	482,483
Lonicera macranthoides	484
Lysimchia davurica	485
Meryta denhamii	486
Myrsine africana	487
Nylandtia spinosa	488
Paronychia argentea	489
Phaseolus vulgaris	490
Polygala tenuifolia	491
Polyscias guilfoylei	492
Pulsatilla chinensis	493
Schima noronhae	494
Xanthium strumarium	495
Xanthoceras sorbifolia	316,496,497
Zygophyllum fabago	498

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A survey of the occurrence and biological activities of 13,28-epoxyoleanane saponins has been published.⁴⁹⁹

Two 2,3-secotaraxerane esters 835 and 836 have been found in Elateriospermum tapos.⁵⁰⁰ Crassifoate 837 is an epoxytaraxerane ester from Nepeta crassifolia.⁵⁰¹ Other taraxerane esters include the formyl ester of taraxerol 838 from Rhizophora stylosa,³⁶⁹ fibrarecisin 839 from Fibraurea recisa⁵⁰² and the p-coumaroyl ester 840 from Craibiodendron henryi.⁵⁰³ Four multiflorane esters 841–844 have been identified from Lagenaria siceraria.⁵⁰⁴ Spirowallichiione 845 is a rearranged multiflorane from Euphorbia wallichii.⁵⁰⁵Derris laxiflora contains trans-cinnamoylglutinol 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 2α,3β-dihydroxyfriedelan-28-oic acid.⁵⁰⁷ 12α-Hydroxyfriedelan-3-one 853 is a constituent of Maytenus gonoclada,⁵⁰⁸ and 2β-hydroxy-3-oxofriedelan-30-oic acid 854 is found in Dichapetalum barteri.⁵⁰⁹ 28-Hydroxyzeylanol 855 is 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 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-3β,20β-diol 874 and the corresponding 3-acetate 875 are constituents of the stem bark of Ficus cordata.⁵¹⁵ The unusual 3,25-epidioxy derivatives 876 and 877 have been claimed from Gentiana aristata.⁵¹⁶ The 1,5-epidioxy derivative 878 is found in Vladimiria muliensis together with ursane-3β,13α,18β-triol 879.⁵¹⁷ Other simple ursane alcohol derivatives include urs-12-ene-1β,3β,11α-triol 880 from Plumbago zeylanica,⁵¹⁸ sorbinol A 881 from Sorbus cashmariana,³⁰¹ and 11α-methoxyurs-12-ene-3α,21β-diol 882 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 3β-urs-12-en-29-oic acid.⁵¹⁹ 3β-Hydroxy-12-oxoursan-28,13β-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 3β,6β-dihydroxyurs-12-en-27-oic acid from Astilbe chinensis.⁵²² The structure of 3β,24- dihydroxyurs-12-en-27-oic acid 889, also from Astilbe chinensis, has been confirmed by X-ray analysis.⁵²³ The urs-12-ene-27,28-dioic acids metatrichosins A 890 and B 891 have been found in Metadina trichotoma.⁵²⁴ Speciosaperoxide 892 is a hydroperoxide from Chaenomeles speciosa.⁵²⁵ 2β,3α,6α,20β,23,30-Hexahydroxyurs-12-en-28-oic acid 893, together with the related 28-glucosyl ester 894, have been identified in Actinidia valvata.⁵²⁶ Further new urs-12-en-28-oic acid derivatives include camaranoic acid 895 from Lantana camara,³³⁹ cheiranthic acid 896 from Oenothera cheiranthifolia,⁵²⁷ silymin A 897 from Silybum marianum,³⁴⁵ madhunolic acid 898 from Madhuca latifolia,⁵²⁸ diospyric acids A 899 and B 900 from Diospyros kaki,⁵²⁹ santolinic acid 901 from Salvia santolinifolia,⁵³⁰ eleganenes A 902 and B 903 from Myricaria elegans,⁵³¹ the 19α-alcohols 904 and 905 from Dischidia esquirolii⁵³² and 906 from Canthium multiflorum.⁵³³ 3α,13β-Dihydroxyurs-11-en-28-oic acid 907 has been claimed from Hedyotis crassifolia.⁵³⁴ The corresponding 28,13-lactone structure may be more likely. The 11α,12α-epoxy-28,13β-lactones 908 and 909 together with the acetate 910 are constituents of Cecropia catharinensis.⁵³⁵ Other ursane esters include 3β-acetoxyurs-18-ene 911 from Asteracantha longifolia,⁵³⁶ 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 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,⁴⁷⁶Cordia piauhiensis,⁴⁷⁸ and Zygophyllum geslini.⁵⁴⁷

The 20,28-epoxytaraxastane 929 derivative is a constituent of Potentilla multicaulis.⁵¹⁴ Punicanolic acid 930 is 3β,20α-dihydroxytaraxastan-28-oic acid from flowers of Punica granatum.⁵⁴⁸ Other new taraxastane triterpenoids include taraxast-20(30)ene-3β,12β-diol 931 from Craibiodendron yunnanense,^549,550 taraxasta-1,20(30)-dien-3-one 932 from Sida acuta,⁵⁵¹ taraxast-20(30)-ene-3β,16β,21α-triol 933 from Centipeda minima,⁵⁵² the corresponding 21-hydroperoxide 934 from Arnica montana⁵⁵³ and 3β,22α-dihydroxytaraxast-20-en-30-al 935 from Polyalthia nemoralis.⁵⁵⁴ Oliganthas B 936 is a new taraxastane derivative from Saussurea oligantha.²⁰⁷ 19β-Taraxast-20(30)-ene-3β,21α-diol 937 was isolated from Ixeris chinensis in 2006 and has now been identified in Cichorium intybus and named cichoridiol.²⁶³ The palmitoyl esters 938 and ussuriensin C 939 have been discovered in Conyza candanesis⁵⁵⁵ and Celastrus rosthornianus, respectively.³⁵⁹ Pubescenosides C and D, from Ilex pubescens, have the new genin 3β-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 3β-Hydroxyhop-21E-en-29-oic acid 945 has been found in Dipentodon sinicus.⁵⁵⁹ The 21αH-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 21βH-arborinane esters 948 and 949 have been identified from Anoectochilus roxburghii 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 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 malbrancheogenin 964.⁵⁶⁸

Five highly oxygenated serratane triterpenoids 965–969 have been isolated from Diphasiastrum complanatum.⁵⁶⁹ Ekeberin A 970 is a baccharane derivative from the stem bark of Ekebergia capensis¹² and the spiro-hemiketal 971 is a constituent of the liverwort Lepidozia chordulifera.⁵⁷⁰ A 3,4-seco-baccharane derivative 972 has been found in the leaves and stem bark of Aglaia foveolata.⁵⁷¹ Foliasalacins D₁–D₃973–975 are D:B-friedobaccharanes from leaves of Salacia chinensis.⁵⁷² Two shionane derivatives 976 and 977 have been identified in Aster ageratoides var. oophyllus.⁵⁷³ The unusual elaeophorbate 978 has been claimed from leaves of Elaeophorbia drupifera.⁵⁷⁴

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