Triterpenoids

Abstract

Covering: 2013. Previous review: Nat. Prod. Rep., 2015, 29, 1028–1065

This review covers the isolation and structure determination of triterpenoids reported during 2013 including squalene derivatives, lanostanes, holostanes, cycloartanes, cucurbitanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, serratanes, isomalabaricanes and saponins; 350 references are cited.

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1. Introduction

The anticancer activities of triterpenoids and their saponins have been extensively reviewed.^1–8 Other activities such as the antidiabetic properties^9,10 and neuropharmacological effects¹¹ of triterpenoids have also been covered. Surveys of triterpenoids from Albizia,¹²Aphanamixis,¹³Boswellia,¹⁴Calendula,¹⁵Clinopodium,¹⁶Lonicera,¹⁷Schefflera,¹⁸ and Toona¹⁹ species and Argania spinosa,²⁰Olea europea,²¹ and Platycodon grandiflorum,²² have appeared. There is interest in the production of triterpenoids with cell and tissue cultures²³ and enhancing saponin production by cell and gene engineering.²⁴ The biological roles of triterpenoid saponins in plants have been reviewed.²⁵

2. The squalene group

The synthesis of armatol A, from the red alga Chondria armata, has led to the revision of the relative and absolute configuration to 1.²⁶ The configurations of the other compounds in this series, armatols B–F have also been revised and a biosynthetic pathway to the armatols from squalene has been proposed.

3. The lanostane group

Streptoseolactone 2, a protostane derivative from the marine-derived actinomycete Streptomyces seoulensis, shows neuraminidase inhibition activity.²⁷ The structures and biological activities of natural protostane and fusidane triterpenoids have been reviewed.²⁸

The following lanostane derivatives have been reported from Ganoderma species: 16α,26-dihydroxylanosta-8,24E-dien-3-one 3 from the fruiting bodies of Ganoderma hainanense,²⁹ ethyl lucidenate A 4 (ref. 30) and the ganoderic acid 5 (ref. 31) from Ganoderma lucidum, ganorbiformins A 6–G 12 from cultures of Ganoderma orbiforme,³² lucidones D 13–G 16, ganoderesins A 17 and B 18 and 7-oxoganoderic acids Z₂19 and Z₃20 from Ganoderma resinaceum,³³ the related compounds 21–23 from the fruiting bodies of Ganoderma tropicum³⁴ and tsugaric acids D 24 and E 25 from Ganoderma tsugae.³⁵ Three new lanostanes 26–28 have been isolated from the fungus Ceriporia lacerata (associated with Acanthaster planci).³⁶ The lanostane 26 has also been isolated from another strain of Ceriporia lacerata (an endophytic fungus of Huperzia serrata) together with compound 29.³⁷ Other lanostane derivatives include the two pentanorlanostanes curvalarols A 30 and B 31 from the soil fungus Curvularia borreriae,³⁸ the oxalate esters 32 and 33 from the fungus Perenniporia maackiae,³⁹ fasciculols J 34–M 37 from the mushroom Naematoloma fasciculare⁴⁰ and terresterol 38 from the oomycete Saprolegnia terrestris.⁴¹ 15-O-Acetylganolucidate A 39 and the tetraketo-acid 40 have been isolated from Antrodia camphorata together with the ethyl esters of the known lucidenic acids A and F.⁴²

The structure 41, originally proposed for a lanostane from Wyethia mollis, has been revised to 42 on the basis of an X-ray crystallographic analysis.⁴³ Other simple lanostanes include klainedoxalanostenone 43 from the stem bark of Klainedoxa gabonensis,⁴⁴ moruslanosteryl acetate 44 from the stem bark of Morus alba,⁴⁵ conyzagenins A 45 and B 46 from Conyza canadensis,⁴⁶ the spiroacetals yunnanterpenes D 47 and E 48 from Cimicifuga yunnanensis⁴⁷ and the unusual 3β-hydroxylanosta-8,17(20)-diene-22-carboxylic acid 49 from a crown gall induced on Eucalyptus tereticornis.⁴⁸ Structure 50 has been proposed for turpetholanostenol from the roots of Operculina turpethum.⁴⁹ Two other compounds, 51 and 52, from this source, have been assigned unlikely structures with a Δ⁵-7α,3α-hemiacetal. Further rearranged lanostane derivatives have been isolated from Abies species. These include compounds 53–58 from Abies sibirica and the unrearranged lanostanes 59,⁵⁰ the methyl ester 60 of the known abiesonic acid and the E-isomer 61 of sibiric acid, together with the ring-A cleaved derivative 62, from the oleoresin of Abies balsamea.⁵¹ The friedolanostane (mariesane) derivatives garcihombronanes K 63 and L 64 have been found in the twigs of Garcinia hombroniana.⁵² Omphalocarpoidone 65 is a constituent of the wood of Tridesmostemon omphalocarpoides.⁵³ Scillanostasides H–L are new glycosides from the bulbs of Scilla scilloides.⁵⁴ Scillanostasides I and J have the new genin 66.

The 29-norlanostane derivatives 29-norpenasterone 67 and 68 have been isolated from a marine sponge of the genus Penares together with the lanostanes 69–72.⁵⁵ The structure of the 29-nor compound 68 was confirmed by X-ray crystallographic analysis. Urabosides A and B and ulososide F are new glycosides from the marine sponge Ectyoplasia ferox.⁵⁶ Urabosides A and B have the new 30-norlanostane genins 73 and 74, respectively. The genin 75 of ulososide F is known but its side chain stereochemistry has been revised. A glycosyl ester from Artemisia absinthium has the new genin 76.⁵⁷

Several new sea cucumber holostane glycosides have been isolated. Typicosides A₁, A₂, B₁, C₁ and C₂ are from Actinocucumis typica.⁵⁸ Typicoside A₁ has a known genin while the others have the new genins 77 (C₁) and 78 (A₂, B and C₂). Cladolosides B₁, B₂, C, C₁, C₂ and D from Cladolabes schmeltzii have the new genins 79 (B₂, C and D) and 80 (B₁ and C₁) while C₂ has a known genin.⁵⁹ Cucumariosides I₁, I₃ and I₄ (ref. 60) and I₂ (ref. 61) are from Eupentacta fraudatrix. Only cucumarioside I₄ has a new genin 81 with a pentanor side chain. Turquetoside A from Staurocucumis turqueti⁶² and eleganoside A from Gelsemium elegans⁶³ have known genins.

Several new skeletal types have been reported from Schisandra and related species. Lancolides A 82–D 85, from Schisandra lancifolia, are accompanied by preschisanartanin O 86.⁶⁴ The structures of 82, 83, 85 and 86 were all confirmed by X-ray crystallographic analyses. The related schilancidilactones V 87 and W 88 are from the fruit of Schisandra wilsoniana.⁶⁵ Schinchinenins A 89–H 96 and schinchinenlactones A 97–C 99 have been reported from the leaves and stems of Schisandra chinensis.⁶⁶ The structure of schinchinenin A 89 was confirmed by X-ray crystallographic analysis. Further constituents from the stems of Schisandra chinensis include schisdilactones H 100 and I 101.⁶⁷ Pseudolarenone 102, from Pseudolarix amabilis, has an unusual bicyclo[8.2.1]tridecane core.⁶⁸ Other new Schisandra compounds include schisarisanlactones A 103 and B 104 from the fruit of Schisandra arisanensis⁶⁹ and schicagenins D 105–F 107 and negleschidilactones A 108 and B 109 from the stems of Schisandra neglecta.⁷⁰

Kleinhospitines A 110–D 113, cycloartanes with spiro-nitrogen containing side chains, have been isolated from Kleinhovia hospita.⁷¹ The Chinese medicine Shengma (Cimicifuga dahurica) is a rich source of cimigenol derivatives and related cycloartanes 114–122.⁷² Only three of the new saponins, heracleifolinosides A–F, from Cimicifuga heracleifolia, have new genins 123 (A and C) and 124. (B).⁷³ The aerial parts of Cimicifuga yunnanensis produce an interesting range of metabolites which include cycloartanes yunnanterpenes A 125–C 127 and F 128, the cleaved cycloartanes 15,16-secocimiterpenes A 129 and B 130 and the tetranor-derivative cimilactone C 131.⁴⁷ The structures of yunnanterpene A 125 and 15,16-secocimiterpene A 129 were confirmed by X-ray crystallographic analyses. Carinatins A 132–H 139 are new compounds from the leaves and twigs of Gardenia carinata.⁷⁴Aphanamixis grandifolia is the source of aphagrandinoids A 140–D 143.⁷⁵

New 9,10-cleaved cycloartanes include cattienoids A 144–C 146 from the mushroom Tomophagus cattienensis,⁷⁶ balansinone 147 from the leaves and twigs of Casearia balansae⁷⁷ and compound 148 from the goat willow Salix caprea.⁷⁸ Seven new cycloartane derivatives are reported from Gardenia gummifera resin with the trivial names gummiferartanes 1 149–5 153, 8 154 and 9 155.⁷⁹

Other new cycloartanes reported this year include 3α-hydroxy-23-oxocycloart-25(27)-en-26-oic acid 156 from the oleoresin of Abies balsamea,⁵¹ perviridisinols A 157–C 159 from Aglaia perviridis,⁸⁰ compounds 160 and 161 from Dasymaschalon dasymaschalum,⁸¹ 12α,16β-dihydroxycycloartane-3,24-dione 162 from Curculigo orchioides whose structure was confirmed by X-ray crystallographic analysis,⁸² odoratanone A 163 from Aglaia odorata,⁶³ the Z-coumaroyl ester of dihydrocycloeucalenol 164 from Nervilia fordii,⁸³ the acetate 165 from the stems and leaves of Quercus variabilis,⁸⁴ the 28,29-dinorcycloartane 166 and its 24,25-dihydro-derivative 167 from Marcetia latifolia,⁸⁵ annonaretin A 168 from the leaves of Annona reticulata⁸⁶ and esters 169 and 170 from Trichilia connaroides.⁸⁷

Tareciliosides N–S are cycloartane saponins from Tarenna gracilipes.⁸⁸ Tareciliosides N and S have the new genins 171 and 172, respectively. The others have known genins. Further saponins from Nervilia fordii include nervisides D–H, of which only G and H have a new genin 173.⁸⁹ Agroastragaloside V is a saponin with a new genin 174 from Astragalus membranaceous.⁹⁰ Cyclopassiflosides XII 175 and XIII 176, from Passiflora edulis, also have new genins.⁹¹ Cycloartane saponins with known genins include cycloasgenin C 3-O-β-D-xylopyranoside from Astragalus mucidus⁹² and cyclolehmanoside C from Astragalus lehmannianus⁹³ and saponins from Astragalus halicacabus,⁹⁴Beesia calthaefolia⁹⁵ and Thalictrum fortunei.⁹⁶

A review of the pharmacological activities of cucurbitane triterpenoids, particularly the anticancer activities of kuguacin J, from Momordica charantia, has been published.⁹⁷ New cucurbitane derivatives include compounds 177–182 from Momordica charantia,⁹⁸ the 27-nor-derivatives 183 and 184 from the fruit of Momordica charantia var. abbreviata⁹⁹ and compounds 185 and 186 from the fruit pulp of Momordica charantia.¹⁰⁰ The hydroperoxides 187 and 188 have been reported from the seeds of watermelon Citrullus lanatus.¹⁰¹ The stereochemistry at C-9 reported for 3,10-epoxides 189 and 190, from the dried fruit of Vitex negundo, seems unusual.¹⁰² Datiscosides I–O are cucurbitane glycosides with known genins from Datisca glomerata.¹⁰³

4. The dammarane group

An interesting group of nordammaranes 191–197 has been isolated from Viburnum mongolicum.¹⁰⁴ Three nordammaranes 198–200 have also been obtained from Dysoxylum hainanense.¹⁰⁵ Other dammaranes include ixorene 201 from the leaves of Ixora coccinea,¹⁰⁶ the ring A-cleaved derivative 202 from the leaves of Dysoxylum grande,¹⁰⁷ 3-acetylaglinin C 203 from the leaves of Aglaia odorata,¹⁰⁸ mauritic acid 204 from the roots of Mauritia flexuosa,¹⁰⁹ altissimanin C 205 from Ailanthus altissima¹¹⁰ and the 25,26,27-trinordammarane 206 from the dried fruit of Forsythia koreana.¹¹¹

Hodulosides XI and XII are new saponins from the seeds of Hovenia trichocarpa.¹¹² They both have the new genin 20,26-epoxypseudojujubogenin 207. Several new saponins, combretasides A–G, have been found in Combretum inflatum.¹¹³ There are four new genins 208 (A and B), 209 (C and D), 210 (E and F) and 211 (G). Two new saponins from Gymnostemma pentaphyllum have the new genins 212 and 213.¹¹⁴ Hydrolysis of the total Gymnostemma pentaphyllum saponins afforded three new compounds, gypensapogenins E 214–G 216.¹¹⁵ The structure of gypensapogenin E 214 was confirmed by X-ray crystallographic analysis.

The saponins of Panax species continue to attract attention. Sanchirhinoside D, with the new genin 217, was obtained from Panax notoginseng.¹¹⁶ Hydrolysis of the saponin from the leaves and stem of Panax notoginseng afforded notoginsengaglycone MPD 218.¹¹⁷ Hydrolysis of the total ginsenosides of Panax ginseng gave the new compound 219 whose structure was confirmed by X-ray crystallographic analysis.¹¹⁸ Three ginsenosides Rh₁₀, Rg₁₁ and 12-O-glucoginsenoside Rh₄ have been isolated from the heat-processed roots of Panax ginseng.¹¹⁹ Only ginsenoside Rg₁₁ has a new genin 220. The arabinoside 221 was also isolated from the heat-processed roots of Panax ginseng.¹²⁰ The leaves and stems of Panax quinquefolium afforded pseudoginsenoside RT₆222 and its genin pseudoginsengenin R₁223.¹²¹ Heptdamoside A is a dammarane saponin from Schefflera heptaphylla with the new genin 3β,6α,20S,26-tetrahydroxy-24E-dammaren-12-one 224.¹²²

Dammarane saponins with known genins include chikusetsusaponins LM₃–LM₆ (ref. 123) and VIII¹²⁴ from Panax japonicas, ginsenjilinol¹²⁵ and 20R-ginsenoside Rf¹²⁶ from Panax ginseng, jujubosides I–IV from Ziziphus jujuba,¹²⁷ a different jujuboside I¹²⁸ and jujuboside A₂ (ref. 129) from Zizyphus jujuba var. spinosa, sanchirhinosides A₁–A₆ and B from Panax notoginseng,¹³⁰ quinquefolosides Ld and Le from Panax quinquefolium,¹³¹ and unnamed saponins from Panax notoginseng.^116,132

The unusual structure 225 of aphanamgrandiol A, a rearranged tirucallane derivative from Aphanamixis grandifolia, has been confirmed by X-ray crystallographic analysis.¹³³ Two 19(10→9)-abeo derivatives, tiliacols A 226 and B 227, have been reported from the semi-mangrove plant Hibiscus tiliaceus.¹³⁴ Aquilacallanes A 228 and B 229 are tirucallane derivatives from the leaves of Aquilaria sinensis.¹³⁵ Aquilacallane B 229 has an extra methyl group at C-25. Other new tirucallanes include 230 from resin of Pistacia lentiscus,¹³⁶ brumollisols A 231–C 233 from the stems of Brucea mollis,¹³⁷ the trinor-derivative sikkimenoid F 234 from the aerial parts of Euphorbia sikkimensis¹³⁸ and compound 235 from the roots of Salacia hainanensis.¹³⁹ The bark of Ailanthus altissima (the “Tree of Heaven”) is the source of the tirucallane derivatives altissimanins A 236, B 237, D 238 and E 239.¹¹⁰ Altissimanins D 238 and E 239 are 24- and 23-esters of the known tirucallane piscidinol A with the secodammarane shoreic acid. Hirtinone 240, from Trichilia hirta is described as a cycloartane but is actually a 9,19-cycloeuphane derivative.¹⁴⁰ Further compounds from the stem of Melia toosendan include the euphanes meliasenins S 241–W 245 and the tirucallane meliasenin X 246.¹⁴¹ The names meliasenins S and T have already been used. The 3,24-diepimer of meliasenin X, cochinchinoid K 247, together with 3-epimesendanin S 248 have been reported from Walsura cochinchinensis.¹⁴² The structure of cochinchinoid K 247 was confirmed by X-ray analysis. The related mesendanin M 249 has been found in Melia azedarach.¹⁴³ The euphane 250 is a metabolite of the endophytic fungus Phomopsis chimonanthi isolated from Tamarix chinensis.¹⁴⁴

Dichapetalins N 251, O 252–R 255 and S 256 have been obtained from Dichapetalum mombuttense, Dichapetalum zenkeri and Dichapetalum leucosia, respectively.¹⁴⁵ Dysoxylumglabretols A 257 and B 258 were isolated from Dysoxylum mollissimum as mixtures of 21-epimers.¹⁴⁶ Dictamins A 259–C 261 are trinorapotirucallanes from Dictamnus dasycarpus.¹⁴⁷ The structure of dictamin A 259 was confirmed by X-ray crystallographic analysis. The fruit of Aphanamixis polystachya is the source of the apotirucallanes polystanins A 262 and B 263 and the tirucallanes polystanins C 264 and D 265.¹⁴⁸ 3-Tigloylsapelin D 266 is a further apotirucallane constituent of the fruit of Melia azedarach.¹⁴⁹

The twigs of Brucea javanica proved to be a rich source of apotirucallanes, yielding fourteen new compounds, brujavanones A 267–N 280.¹⁵⁰ During this work the structure of bruceajavanin C was revised to its C-21 epimer 281. Other new compounds in this series include feroniellides C 282–E 284 from Feroniella lucida,¹⁵¹ lepidotrichilins A 285 and B 286 from Trichilia lepidota,¹⁵² polystanin E 287 from the fruit of Aphanamixis grandifolia,¹⁵³288, 289 and dihydrosapelin E acetate 290 from Turraea pubescens¹⁵⁴ and azadirahemiacetal 291 from Azadirachta indica.¹⁵⁵

4.1 Tetranortriterpenoids

Interesting new tetranortriterpenoid skeletal types continue to appear. Thaixylomolin A 292 has a 6,7-cleaved skeleton while thaixylomolins B 293 and C 294 both incorporate a pyridine ring.¹⁵⁶ They are constituents of Xylocarpus moluccensis. The structure of harperforatin 295, from Harrisonia perforata, was confirmed by X-ray crystallographic analysis.¹⁵⁷ It was accompanied by harperfolide 296. New trijugin-related derivatives include cipatrijugins G 297 and H 298 from Cipadessa cinerascens,¹⁵⁸ compound 299, also named cipatrijugin G, and also from Cipadessa cinerascens,¹⁵⁹ and trijugins I 300 and J 301 from Trichilia connaroides.¹⁶⁰

Cipaferens A 302–D 305 are constituents of the leaves of Cipadessa baccifera.¹⁶¹ Phyllanthoids A 306 and B 307 are two C,D-rearranged derivatives from Phyllanthus cochinchinensis.¹⁶² The structure of phyllanthoid A 306 was confirmed by X-ray crystallographic analysis.

Ten limonoids, cochinchinoids A 308–J 317 have been reported from Walsura cochinchinensis.¹⁴² The structure of cochinchinoid A 308 was confirmed by X-ray analysis. Rubescins A 318–C 320 are constituents of Trichilia rubescens.¹⁶³ The limonoids mesendanins K 321 and L 322 have been isolated from Melia azedarach.¹⁴³ Extraction of the kernels of Azadirachta indica afforded the new compounds 323, 324 and azadiralactone 325.¹⁵⁵

X-Ray crystallographic analysis established the 21S-configuration of evorubodinin 326 (21-O-methyllimonexic acid) from Euodia rutaecarpa var. bodinieri.¹⁶⁴ The ring A cleaved limonoids aphanalides I 327–M 331 have been isolated from the fruit of Aphanamixis grandifolia.¹⁵³ The structure of aphanalide I 327 was confirmed by X-ray crystallographic analysis. Other compounds from this source include the rearranged aphagranols A 332 and B 333 (ref. 165) and aphanamolides C 334 and D 335.¹⁶⁶ Toonins A 336 and B 337 are new constituents of the roots of Toona sinensis.¹⁶⁷Sandoricum koetjape is the source the cleaved limonoids sanjecumins A 338 and B 339.¹⁶⁸ Andirolide S 340 is a related ring-cleaved limonoid from the flowers of Carapa guianensis together with the intact limonoid andirolide Q 341 and the defuro-derivative andirlide R 342.¹⁶⁹

Various limonoids, turrapubins A 343–K 353 have been obtained from Turraea pubescens.¹⁵⁴ More ring C-cleaved derivatives 354–365, accompanied by the intact limonoids 366 and 367, have been reported from the fruit of Melia azedarach.¹⁷⁰ The name ohchininolide has been assigned to 358. Compound 355 has also been isolated from kernals of Azadirachta indica.¹⁵⁵ Other ring C-cleaved constituents include walsogynes B 368–G 373 from Walsura chrysogyne¹⁷¹ and toosendalinin 374,¹⁷² isolated as an epimeric mixture, and the nimbolinin derivatives 375–377,¹⁷³ together with compound 378, from the fruit of Melia toosendan. Dysoxylum mollissimum is the source of the AB-cleaved limonoids dysoxylumasins A 379–F 384.¹⁷⁴

The phragmalin derivatives chukfuransins A 385–D 388 from Chukrasia tabularis,¹⁷⁵ and guianolides A 389 and B 390, from Carapa guianensis,¹⁷⁶ all have novel features involving cyclisations of the furan ring. The structures of chukfuranisins A 385 and C 387 and of guianolide A 389 were all confirmed by X-ray crystallographic analyses. Andirolides T 391–V 393 are further constituents of the flowers of Carapa guianensis.¹⁶⁹ Twenty new mexicanolide derivatives, trichinenlides A 394–T 413, have been isolated from Trichilia sinensis.¹⁷⁷ Secotrichagmalin A 414 and trichanolides A, B, C 415, D 416 and E 417 have been reported from Trichilia connaroides.¹⁶⁰ Trichanolides A and B are identical to trichinenlides I 402 and D 397, respectively. The structure of trichanolide A was confirmed by X-ray crystallographic analysis.

1,2-Cleaved derivatives include trichilitons G 418 and H 419 from Trichilia connaroides⁸⁷ and deacetyl-2α-methoxykhayanolide E 420 and kigelianolide 421 from Kigelia africana.¹⁷⁸ The structure of deacetyl-2α-methoxykhayanolide E 420 was confirmed by X-ray analysis.

New derivatives from Xylocarpus granatum include xylomexicanins C 422 and D 423,¹⁷⁹ xylogranins A 424 and B 425.¹⁸⁰ and granatumins I 426, J 427 and K 428 (accompanied by granatumin H which is a known compound).¹⁸¹ Other related derivatives include 11α-hydroxyswietephragmin B 429 from Swietenia mahogani (accompanied by swietephragmins H and I which are known compounds),¹⁸² chukvelutilide G 430 and chukrasin F 431 from Chukrasia tabularis var. velutina,¹⁸³ thaixylomolins D 432–F 434 from Xylocarpus moluccensis¹⁸⁴ Khayaseneganins A 435–H 442 are further constituents of Khaya senegalensis.¹⁸⁵

4.2 Quassinoids

There is little activity in the quassinoid field. Bruceine M 443 has been isolated from the fruit of Brucea javanica¹⁸⁶ and altissinols A 444 and B 445 from Ailanthus altissima.¹⁸⁷ Altissinol B 445 is not a new compound and was identified as 13,18-didehydroexcelsin in 1980.¹⁸⁸

5. The lupane group

A review presenting spectral data of natural lupane triterpenoids has been published with a view to helping analysis of new structures.¹⁸⁹ The anti-HIV activity of betulinic acid and its derivatives have been covered in a short review.¹⁹⁰ Officinatrione 446, with an unusual 17,18-secolupane skeleton, was isolated from Taraxacum officinale where it occurs with four intact lupanes 447–450.¹⁹¹ The structure of officinatrione 446 was confirmed by X-ray analysis. The structures of three compounds from Saprosma merrillii were originally assigned as ursane derivatives.¹⁹² However it was later established that they were the lupane derivatives 451–453 by the X-ray analysis of 453.¹⁹³ Moruslupenoic acid B 454, from the stem bark of Morus alba, is 3β-hydroxy-12,20(29)-lupadien-26-oic acid where it co-occurs with the well-known 3β-hydroxy-20(29)-lupen-28-oic acid which has been named as moruslupenoic acid A.⁴⁵ Actinidin A 455, from Actinidia deliciosa, has been identified as 12,20(29)-lupadiene-2β,3β,28-triol.¹⁹⁴ Other simple lupane derivatives include lupane-3β,16β,20,23,28-pentol 456 (ref. 195) and 20(29)-lupene-3β,16β,23,28-tetrol 457 (ref. 196) from Gymnema sylvestre, 24-hydroxy-20(29)-lupen-3-one 458 and 3β-hydroxy-20(29)-lupen-24-al 459 from Ilex cornuta, 11α,23-dihydroxy-3-oxo-20(29)-lupen-28-oic acid 460 from Acanthopanax trifoliatus,¹⁹⁷ 20(29)-lupene-2β,3β,22α-triol 461 and 3β-hydroxy-2-oxo-29-lupanoic acid 462 from the roots of Salacia hainanensis,¹³⁹ the acetal 463 from Siphonodon celastrineus,¹⁹⁸ the 19,21-epoxide 464 from Abelmoschus esculentus¹⁹⁹ and the decanoyl ester of lupeol from Cadaba farinosa.²⁰⁰

Betulinic amide 465 and its 3-O-β-D-glucopyranoside 466 have been isolated from Rhododendron lepidotum.²⁰¹ New lupane saponins with known genins include the 28-O-β-D-glucopyranosyl ester of platanic acid from Tetracera scandens,²⁰² lonimacranthoside A₁ from Lonicera macranthoides²⁰³ and ryobusaponins E–G from Clethra barbinervis²⁰⁴ and unnamed saponins from Lonicera macranthoides²⁰⁵ and Pulsatilla chinensis.²⁰⁶

6. The oleanane group

Teydealdehyde 467, from Nepeta teydea,²⁰⁷ has a contracted ring A and lacks ring E and the related laevigatone A 468 has been found in Uncaria laevigata where it occurs with the 24-noroleananes 469 and 470 and the intact oleanane derivatives 471–473.²⁰⁸ The oleanane 471 has also been isolated from Uncaria sessilifructus and named as uncarilic acid together with the 5,6-seco derivative secouncarilic acid 474.²⁰⁹ The 19(18→17)-abeo-28-noroleanane derivatives stewartiisins A 475–C 477 have been isolated from Phlomis stewartii.²¹⁰ Sambucasan A 478 is a 28-nor-12,16-oleanadiene from Sambucus williamsii.²¹¹ Alstoprenyol 479, from Alstonia scholaris, has been reported to have the unusual 18α-configuration.²¹² Xyloketal 480 is a hemiacetal derivative from Cassine xylocarpa²¹³ and a related hemiacetal 481 has been found in Lantana montevidensis.²¹⁴ 3β,21β-Dihydroxy-12-oleanen-29-oic acid 482, from Maytenus royleanus, has been named ficusonic acid.²¹⁵ Japanese fermented tea (Camellia sinensis leaves) is the source of two oleanan-12-one derivatives 483 and 484.²¹⁶ Other new simple oleanane derivatives include 13(18)-oleanene-3β,16β,23,28-tetrol 485 and four related 12-oleanene derivatives 486–489 from Gymnema sylvestre,¹⁹⁶ 3β,12-dihydroxy-12-oleanen-11-one 490 from Siphonodon celastrineus,¹⁹⁸ 1β,2α,3β,19β-tetrahydroxy-12-oleanen-28-oic acid 491 and the related compounds 492–494 from Euphorbia sieboldiana,²¹⁷ 12-oleanene-1α,3β,6β-triol 495 from Vernicia fordii,²¹⁸ 3-oxo-12,18-oleanadien-29-oic acid 496 from Limnophila indica,²¹⁹ the 13,28-epoxides 497 and 498 from Lysimachia parvifolia,²²⁰ the 12-oleanen-27-oic acids 499 and 500 from Chrysosplenium carnosum²²¹ and 2α,3β-dihydroxy-11,13(18)-oleanadien-28,19β-olide 501 from Rhaphiolepis indica var. tashiroi.²²²

Celosins I and II, from Celosia argentea, are saponins with the new genin 3β-hydroxy-12-oleanene-23,25,28-trioic acid 502.²²³ Other oleanane saponins with new genins include clematangoside B from Clematis tangutica with 3β,21α,23-trihydroxy-12-oleanen-28-oic acid 503,²²⁴ clinoposapanins A–C from Clinopodium chinense with the genins 504–506, respectively,²²⁵ gordonsaponins B and E from Gordonia kwangensis with the genin 12-oleanene-3β,15α,16α,28-tetrol 507,²²⁶ heptoleosides A and B from Schefflera heptaphylla with the genins 508 and 509 respectively,¹²² ilexpublesnins L and M from Ilex pubescens with 3β,19α-hydroxy-12-oleanene-24,28-dioic acid 510,²²⁷ pittangretoside I from Pittosporum angustifolium with the 17,22-seco genin 511,²²⁸ psychotrianoside B from a Psychotria sp. with 13β,28-epoxy-3β,16β-dihydroxy-12-oleanen-29-al 512,²²⁹ ryobunin C from Clethra barbinervis with 3α,19α,21α,24-tetrahydroxy-12-oleanen-28-oic acid 513,²³⁰ saikosaponin W and 21β-hydroxysaikosaponin b₂ from Bupleurum chinense with the genins 514 and 515 respectively,²³¹ sarosiensins I–IV, VI and VII from Trifolium medium with the genins 516–520,²³² saponins from Genista ulicina with the genins 521–525,²³³ and saponins from Xanthoceras sorbifolia with the genin 12,15-oleanadiene-3β,21β,22α,28-tetrol 526.²³⁴

New oleanane saponins with known genins that have been assigned trivial names are listed in Table 1

Table 1 Trivial names and sources of new oleanane saponins with known genins

Trivial name	Plant species	Reference
2′′- and 6′′-O-acetylrandianins	Nematostylis anthophylla	235
6′′-Acetylsaikosaponins b1, b3 and e	Bupleurum chinense	231
Achyranthosides B and D	Achyranthes bidentata	236
Aesculiosides C1–C15	Aesculus californica	237
Assamicoside A	Glochidion assamicum	238
Caraganins A and B	Caragana microphylla	239
Chiococcasaponins III–V	Chiococca alba	240
Clematangosides A, C, D	Clematis tangutica	224
Clematochinenosides H–J	Clematis chinensis	241
Congmuyenosides C–E	Aralia elata	242
Cowpeasaponins I and II	Vigna sinensis	243
Cylindroside A	Cylindrokelupha dalatensis	244
Eryngiosides M and N	Eryngium yuccifolium	245
Gordonsaponins A, C, D, F–K	Gordonia kwangsiensis	226
Heptoleosides C and D	Schefflera heptaphylla	122
Kakkasaponins II and III	Pueraria thomsonii	246
Longicarposides A–I	Gordonia longicarpa	247
Mandshunosides C–E	Clematis mandshurica	248
Magnosides A and B	Cybianthus magnus	249
Neanoside A	Neanotis wightiana	250
Nebulosides A and B	Gypsophila arrostii var. nebulosa	251
Nummularoside	Lysimchia nummularia	252
Paritrisides A–F	Paris polyphylla var. yunnanensis	253
Patrinovilosides A and B	Petrinia villosa	254
Phaseoloidesides A–D	Entada phaseoloides	255
Piptadeniaoside	Piptadeniastrum africanum	256
Pittangretosides A–H	Pittosporum angustifolium	228
Platycodons A and B	Platycodon grandiflorum	257
Psychotrianosides A, C–G	Psychotria sp.	229
Pulsatilloside F	Pulsatilla koreana	258
Ryobusaponins A–D	Clethra barbinervis	204
Sarosiensin V	Trifolium medium	232
Sibiricasaponin E	Polygala sibirica	259
Soysaponins M1–M3	Glycine max	260
Thyrsiloside A	Lysimachia thyrsiflora	252
Tomentosides A–C	Anemone tomentosa	261
Virgaureasaponins 4–6	Solidago virgaurea	262
Xanthohuskisides A and B	Xanthoceras sorbifolia	263

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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

Sources of new oleanane saponins with known genins not assigned trivial names

Plant species	Reference
Anabasis setifera	264
Anemone raddeana	265
Anemone taipaiensis	266 and 267
Aralia elata	268
Ardisia gigantifolia	269
Astragalus tauricolus	270
Benincasa hispida	271
Calliandra pulcherrima	272
Clematis lasiandra	273
Clematis tangutica	274
Gypsophila trichotoma	275 and 276
Ilex cornuta	277
Lonicera macranthoides	205
Lysimachia parvifolia	220
Pittospermum verticillatum ssp. verticillatum	278
Pulsatilla chinensis	279
Ricinus communis	280
Sapindus mukorossi	281 and 282
Saponaria officinalis	283
Sesbania vesicaria	284
Swartzia apetala var. glabra	285
Swertia yunnanensis	286
Trifolium hybridum	287
Xanthoceras sorbifolia	234 and 288

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New oleanane esters include the tetraacetate of 12-oleanene-3β,16β,23,28-tetrol and three esters of 12-oleanene-3β,16β,21β,22α,23,28-hexol from Gymnema sylvestre,¹⁹⁵ and the 3-acetate of 12-oleanene-3β,9α,17β-triol 527 from Abelmoschus exculentus.¹⁹⁹ An acetaldehyde acetal 528 has been identified as a constituent of Terminalia brownii.²⁸⁹ Several oleanane esters 529–533 have been isolated from Dorstenia arifolia.²⁹⁰ Further new oleanane esters include the angeloyl esters 534–536 from Camellia oleifera,²⁹¹ the dipalmitoyl ester 537 from Chrysanthemum macrocarpum,²⁹² the cis-coumaroyl ester 538 and the trans-feruloyl ester 539 from Rhodomyrtus tomentosa²⁹³ and the 3-sulfate of 540 3β,16β-dihydroxy-12-oleanen-28-oic acid from Schefflera elegantissima.²⁹⁴

Zenkeric acid 541, a constituent of Hypodaphnis zenkeri, has been identified as 2α,3α-dihydroxy-14-taraxeren-28-oic acid.²⁹⁵ 3-Oxo14-taraxeren-30-al 542 has been found in Vitex trifolia var. simplicifolia.²⁹⁶ Microcisin 543, the vanilloyl ester of taraxerol, has been isolated from the roots of Microcos tomentosa.²⁹⁷ The dicinnamoyl ester 544 of karounidiol is a constituent of fruits of Benicasa hispida.²⁷¹ Three multiflorane esters 545–547, including the p-nitrobenzoyl ester 547, have been found in seeds of zucchini (Cucurbita pepo).²⁹⁸ Related esters 548–550 have been isolated from pumpkin seeds (Cucurbita maxima).²⁹⁹ Two related 3,4-secoglutinane derivatives torreyanoxane 551 and euphorbiane 552 have been isolated from Torreya nucifera³⁰⁰ and Euphorbia tirucalli,³⁰⁰ respectively. The structure of euphorbiane 552 was confirmed by X-ray analysis. Simple glutinane derivatives include 5-glutinene-3β,21α-diol 553 from Celastrus vulcanicola,²¹³ 5-glutinene-1α,3β-diol 554 from Vernicia fordii²¹⁸ and glutinane-3β,5β-diol 555 from Rhaphiolepis indica var. tashiroi.²²²

A review of naturally occurring friedelanes, isolated between 1977 and March 2011 has been published.³⁰¹ Ovalifolones A 556 and B 557, from Garcinia ovalifolia,³⁰² and maytensifolone 558, from Maytenus distichophylla,³⁰³ are new friedelane derivatives. Phyllaembicone A 559, isolated from the roots of Phyllanthus emblica, is 29,30-dinorfriedelane-3,20-dione.³⁰⁴ 16β-Hydroxypristimerin 560 is a 24-norfriedlane quinine methide from Maytenus salicifolia.³⁰⁵ Three ring-A cleaved norfriedelane derivatives named as norfriedelins A 561–C 563 have been identified in Malpighia emarginata.³⁰⁶ The structure of norfriedelin A 561, containing an interesting α-keto-β-lactone, was confirmed by X-ray analysis. The 3-benzoyl ester 564 of pluricostatic acid has been found in Trigonostemon xyphophylloides³⁰⁷ and 25-hydroxyfriedelane-3,21-dione 565 and its 25-benzoate 566 have been isolated from Siphonodon celastrineus.¹⁹⁸ The dodecyl ester 567 of 7β-hydroxy-3-oxofriedelan-28-oic acid has been found in Pouzolzia indica.³⁰⁸

7. The ursane group

The sources and pharmacological properties of ursolic acid have been reviewed.^309–311 The 30-nor ursane derivatives rubrajaleelol 568 and rubrajeelic acid 569 have been identified in Plumeria rubra.³¹² A further 30-nor derivative 3β-hydroxy-30-nor-21-ursen-20-one 570 has been found in Eupatorium fortunei.³¹³ A 24-nor ursane derivative 571 together with 3β,19α-dihydroxy-12-ursene-24,28-dioic acid 572 have been isolated from Emmenopterys henryi.³¹⁴ Urmiensolide 573, from Salvia urmiensis, is the first example of an E-ring ε-lactone.³¹⁵ The structure of urmiensolide 573 was confirmed by X-ray analysis. Gluinosalactones A 574, B 575 and C 576 are 28,20-ursanolides isolated from the leaves of Rehmannia glutinosa.³¹⁶ Three 28,13-ursanolides 577–579 have been identified in Isodon excisoides.³¹⁷

Seventeen ursane derivatives 580–596 have been isolated from Siphonodon celastrineus including the 2,3-seco aldehyde derivative 594 and two phenylpropanoid adducts 595 and 596.¹⁹⁸ Fulgic acids A 597 and B 598, from Potentilla fulgens, have been identified as 2α,3α,20β-trihydroxy-12-ursen-28-oic acid and the 3β-epimer, respectively.³¹⁸ 6β-Hydroxy-12-ursen-3-one 599 a constituent of Boswellia sacra, has been named nizwanone and it is accompanied by 11α-ethoxy-β-boswellic acid 600 that is likely to be an isolation artefact.³¹⁹ Other new simple ursane derivatives include 2α,3β,23,27-tetrahydroxy-12-ursen-28-oic acid 601 from Actinidia deliciosa,¹⁹⁴ four derivatives 602–605 from Uncaria laevigata,²⁰⁸ 12,15-ursadien-3α-ol 606 from Croton bonplandianum,³²⁰ 4-epi-barbinervic acid 607 from Verbena officinalis,³²¹ 2α,3β,6β,19α,24-pentahydroxy-12-ursen-28-oic acid 608 from Ludwigia hyssopifolia³²² and 2α,3α,19α,23-tetrahydroxy-12,20(30)-ursadien-28-oic acid 609 from Callicarpa nudiflora.³²³

New ursane saponins with new genins include hepturosides A–C from Schefflera heptaphylla with the genins 610–612 respectively,¹²² ilexpublesnins C and D from Ilex pubescens with 3β,19α-dihydroxy-24-oxo-12-ursen-28-oic acid 613,²²⁷ ryobunins A and B from Clethra barbinervis with 3α,16α,19α,24-tetrahydroxy-12-ursen-28-oic acid 614 and the 18,19-seco derivative 615 respectively,²³⁰ a saponin from Potentilla multicaulis with the new genin 2α,3β,19α,23,30-pentahydroxy-12-ursen-28-oic acid 616³²⁴ and a saponin from Asparagus racemosus with 3β-hydroxy-1,12,19-ursatrien-28-oic acid 617.³²⁵

Ursane saponins with known genins include actinidicoside from Premna fulva,³²⁶ asprellanosides C–E from Ilex asprella,³²⁷ heptursoside D from Schefflera heptaphylla,¹²² ilexgenin A2 (ref. 328) and ilexoside P³²⁹ from Ilex pubescens, monepalosides M and N from Morina nepalensis var. alba,³³⁰ sibiricasaponins A–D from Polygala sibirica²⁵⁹ and ilexpuplesnins E and G–K from Ilex pubescens.²²⁷ Unnamed saponins with known genins have been isolated from Callicarpa nudiflora,³²³Ilex asprella³³¹ and Ilex cornuta.²⁷⁷

Prunol 618, from Prunus cerasoides, has been identified as an ester of ursolic acid with 2,3,6-trihydroxybenzoic acid.³³² Other new ursane esters include the 28-formate of 12-ursene-3β,28-diol and its 3-acetate derivative from Ilex cornuta,³³³ the 6-acetate of ursane-3β,6β,19α-triol from Astilbe chinensis,³³⁴ the 30-cis-p-coumaroyl ester of 3β,30-dihydroxy-12-ursen-28-oic acid from Teucrium viscidum,³³⁵ the 2-cis-p-coumaroyl ester and the 2-trans-p-coumaroyl ester of 2α,3β,19α-trihydroxy-12-ursen-28-oic acid from Prinsepia utilis,³³⁶ and four long-chain ursane esters 619–622 from Dorstenia arifolia. Alstoprenylene 623, from Alstonia scholaris, has been reported to be a 24-norursane with the unusual 18α-stereochemistry.²¹² Clerodendrumic acid 624, from Clerodendrum glabrum, has also be reported with this stereochemistry.³³⁷ The acetonide 625 is likely to be an artefact from chromatography of the extract of Rhododendron hainanense.³³⁸

Ilexpublesnin F is a taraxastane saponin with a known genin from Ilex pubescens.²²⁷ The 3-acetate of 12,20(30)-taraxastadiene-3β,11α,21α-triol has been isolated from Echinops galalensis.³³⁹

8. The hopane group

The structure of sonhafouonic acid 626, from Zehneria scabra camerunensis, was confirmed by X-ray analysis as 3β,6β,25-trihydroxy-20(29)-hopen-23-oic acid.³⁴⁰ Hopane-3β,21α-diol 627 has been isolated from the leaves of Carissa carandas and has been named carandinol.³⁴¹Humata tyermanni is the source of 20(29)-hopen-24-ol 628.³⁴² The new hopane saponin glinuside C 629, from Glinus oppositifolius, has a new genin.³⁴³ Dryocrassol xylopyranoside, with a known hopane genin, has been isolated from Alsophila spinulosa.³⁴⁴ The migrated hopane derivatives capillirol B 630 (neophopane-3β-ol) and capillirone 631 (30-norfernan-22-one) have been identified in Adiantum capillus-veneris.³⁴⁵

9. Miscellaneous compounds

Two chiratane triterpenoids, kouitchenoids A 632 and B 633 have been isolated from Swertia kouitchensis.³⁴⁶Aster tataricus is the source of the five shionane triterpenoids astataticusol A 634 and astataticusones A 635–D 638.³⁴⁷ Stellettin N 639, from a sponge of the genus Stelletta, is an isomalabaricane triterpenoid that shows potent protein-tyrosine phosphatase 1B inhibition.³⁴⁸

Three tricyclic triterpenoids with unusual skeletons, kadcotriones A 640–C 642, have been isolated from Kadsura coccinea.³⁴⁹ Biosynthetic pathways to the kadcotriones, from a common lanostane precursor, have been proposed. The biosynthesis of volvalerenol A 643, from the roots of Valeriana hardwickii, is thought to involve head-to-tail linkages of two units of farnesyl diphosphate.³⁵⁰

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