Triterpenoids

Contents

• 1. Introduction

• 2. The squalene group

• 3. The lanostane group

• 4. The dammarane group
  • 4.1 Tetranortriterpenoids
  • 4.2 Quassinoids

• 5. The lupane group

• 6. The oleanane group

• 7. The ursane group

• 8. The hopane group

• 9. Miscellaneous compounds

• 10. Conflicts of interest

• References

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Abstract

Covering 2014. Previous review: Nat. Prod. Rep., 2017, 34, 90–122

This review covers the isolation and structure determination of triterpenoids reported during 2014 including squalene derivatives, lanostanes, holostanes, cycloartanes, cucurbitanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, serratanes, isomalabaricanes and saponins; 374 references are cited.

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1. Introduction

The interest in the pharmacological activities of triterpenoids continues to be very important.¹ Several reviews have covered the anticancer effects of triterpenoids.^2–9 Other activities that have been highlighted include anti-HIV,^10–12 antiinflammatory,¹³ antiviral⁶ and against neurodegenerative disorders.¹⁴ As many of the active compounds are saponins there has been an interest in their synthesis¹⁵ and biosynthesis.¹⁶ Reviews have also appeared covering triterpenoids found in Astragalus species,¹⁷Gymnema sylvestre,¹⁸Panax species,^19,20Sapindus species²¹ and Siraitia grosvenorii²² and plants of the Schisandraceae.^23–25 Triterpenoid biosynthesis in plants²⁶ and the mechanisms of oxidosqualene cyclases²⁷ have also been covered.

2. The squalene group

Two interesting series of polyisoprenoid derivatives, terreolides A 1–F 6 and saponaceolides H 7–P 15, have been reported from the previously unknown poisonous European mushroom Tricholoma terreum.²⁸ The known saponaceolide B 16 was also obtained. The structures of terreolides A 1 and D 4 and saponaceolide B 16 were confirmed by X-ray crystallographic analyses. A complex polyisoprenoid glycoside, from the fruit of Lycium chinense, has been assigned the putative structure 17.²⁹

3. The lanostane group

The flow of Ganoderma lanostanes continues.³⁰Ganoderma boninense is the source of ganoboninketals A 18, B 19 and C 20.³¹ Fornicatins D 21, E 22 and F 23 and ganodercochlearins A 24, B 25 and C 26 are constituents of Ganoderma cochlear.³² The structure of ganodercochlearin B 25 was confirmed by X-ray analysis of the corresponding diacetate. Cultures of Ganoderma sp. KM01 produced ganodermalactones B 27, D 28 and E 29.³³ The structure of ganodermalactone B 27 was confirmed by X-ray analysis and was shown to have the same structure as the previously reported colossolactone C, from Ganoderma colossum,³⁴ however the pmr and cmr spectra for rings A and B are not in agreement.

Other Ganoderma lanostanes include ganoderic acids XL₁30 and XL₂31, 20-hydroxyganoderic acid AM₁32, ganoderenic acid AM₁33 and ganoderesin C 34 from Ganoderma theaecolum,³⁵ methyl lucidenate B 35 (ref. 36) and the butyl esters 36 and 37 (ref. 37) from the fruiting bodies of Ganoderma lucidum and the norlanostane 38 from the fruiting bodies of Ganoderma tropicum.³⁸ The biological and pharmacological activities of ganoderic acid and lucidenic acid have been covered in a review.³⁹

The mushroom Inonotus obliquus is a rich source of the 21,24-cyclolanostanes inonotusols A 39–E 43.⁴⁰ They are accompanied by inonotusols F 44 and G 45. Inonotusols B 40, D 42 and E 43 have unusual configurations at C17 and inonotusol F 44 has an unusual configuration at C20 and methylation at C24. Further C24-methylated metabolites of Inonotus obliquus include inotolactones A 46 and B 47.⁴¹ Hexatenuins A 48, B 49 and C 50, from the fruiting body of Hexagonia tenuis, also have an extra carbon at C-24.⁴²

The protostane 51, from the bark of Garcinia ferrea, is accompanied by the lanostanes garciferolides A 52 and B 53.⁴³ Two rearranged lanostanes 54 and 55 have been isolated from Abies nukiangensis together with compounds 56–59.⁴⁴ The structures of 54 and the known 60 were confirmed by X-ray analyses. 3-O-Methylabiesatrine A 61 is a rearranged lanostane from Abies delavayi.⁴⁵

Two naphthalene esters, lanostenyl naphthoates A 62 and B 63 have been reported from the rhizomes of Acorus calamus.⁴⁶ The related compounds 64–66 are found in the bark of Ficus religiosa.⁴⁷ The mariesane derivative opaciniol B 67 and the lanostane opaciniol C 68 are constituents of Garcinia opaca.⁴⁸ Opaciniol B 67 is the same as garcihombronane K isolated from Garcinia hombroniana in 2013.⁴⁹ The rearranged lanostane 69 has been isolated from Garcinia hombroniana.⁵⁰

Other lanostanes include manglanostenoic acids A 70–D 73 from Mangifera indica var. Fazli,⁵¹ myrrhalanostenyl acetate 74, myrrhalanostenol 75, and myrrhalanostenoic acid 76 from the oleoresin of Commiphora myrrha,⁵² 3β-hydroxylanosta-9(11),24-dien-21-oic acid 77 and its methyl ester 78 from Protorhus longifolia,^53,54 the norlanostane 79 from Euphorbia bupleuroides,⁵⁵ the ester 80 from the fruit of Cuminum cyminum,⁵⁶ kiusianin A 81 from Tilia kiusiana⁵⁷ and methyl ether 82 from Cymbopogon citratus.⁵⁸ Compounds 83 and 84, from the branches and leaves of Polyalthia obliquei, were originally thought to be tirucallane derivatives but are now considered to be lanostanes.^59,60 Lanostane saponins with known genins have been isolated from Cuminum cyminum⁵⁶ and Panax ginseng.^61,62

Investigations of several sea cucumbers have resulted in the identification of more holostane saponins, some with interesting pharmacological activities.^63,64 Cladolosides A₁–A₆, from Vietnamese Cladolabes schmeltzii, have the new genins 85–89.⁶⁵ Coustesides A–J are new saponins from Bohadschia cousteaui.⁶⁶ Coustesides B and G have the new genin 90 and C and D the new genins 91 and 92, respectively. All the others have known genins.

Variegatusides C–F have been isolated from Stichopus variegates.⁶⁷ Only variegatuside C has a new genin 93. Holothurins D and E, with the new genin 94 and holothurinoside X, with the new genin 95, are constituents of Holothuria lessoni together with holothurinosides Y and Z with known genins.⁶⁸ The new genin 96 has been reported for pseudocnoside A from Pseudocnus dubiosus leoninus.⁶⁹ Holostane saponins with known genins include cucumariosides F₁ and F₂ from Eupentacta fraudatrix,⁷⁰ kolgaosides A and B from Kolga hyalina,⁷¹ stichloroside F from Stichopus chloronotus⁷² and violaceusosides C, D, E and G from Pseudocolochirus violaceus.⁷³

Cucurbitane triterpenoids of mushroom origin have been covered in a review.⁷⁴ Three interesting furanoid cucurbitane derivatives, roseic acid 97 and roseolactones A 98 and B 99, have been isolated from Russula aurora and Russula minutula.⁷⁵Empetrun nigrum var. japonicum is the source of the migrated cucurbitane nigrum-24-en-3β-ol 100.⁷⁶

New cucurbitane derivatives isolated from Hemsleya species include 101 and 102 from Hemsleya amabilis⁷⁷ and hemslepenside A 103, 16,25-di-O-acetylcucurbitacin F 2-O-β-D-glucopyranoside 104 and 16-O-acetylcucurbitacin F 105 from Hemsleya penxianensis.⁷⁸ New cucurbitanes are still being found in the various parts of Momordica charantia.⁷⁹ The fruit is the source of kuguacins T 106–W 109 (ref. 80) and charantosides D 110–G 113.⁸¹ The structure of kuguacin W 109 was confirmed by X-ray analysis.

The leaves and stem yielded karavilagenin F 114, karavilosides XII 115 and XIII 116 and momordicines VI 117, VII 118 and VIII 119.⁸² A separate investigation of the leaves led to the isolation of compounds 120 and 121.⁸³ Two new glycosides were reported from the seeds, one with the new genin 122.⁸⁴

Kinoin D 123 is an octanorcucurbitane derivative from the roots of Ibervillea sonorae.⁸⁵ Minor cucurbitane glycosides from Siraitia grosvenorii include 11-deoxymogrosides V and VI and 11-deoxyisomogroside V, all with known genins.⁸⁶ 23,24-Dihydrocucurbitacin C 124 is a new compound from Cucumus sativus.⁸⁷ The unlikely stereochemistry of 125 has been proposed for a compound from the leaves and twigs of Euonymus alatus.⁸⁸

An impressive list of new compounds from Schisandra chinensis includes wuweizidilactones J 126–P 132, schindilactones I 133, J 134 and K 135, preschisanartanin N 136 and schisdilactone J 137.⁸⁹ Lancifonins A 138–F 143 are new compounds from Schisandra lancifolia.⁹⁰Schisandra sphenanthera is the source of schisphendilactones A 144 and B 145.⁹¹ The structures of lancifonin A 138 and schisphendilactone A 144 were confirmed by X-ray analyses.

Other new compounds include heteroclitalactone N 146 from the stems of Kadsura heteroclitus⁹² and micrandiactone H 147 from Kadsura coccinea.⁹³ The reported stereochemistry for micrandiactone H 147 is unusual and probably requires revision. The name of 147 should be changed to micrandilactone H in line with other compounds in the series.

Cochlates A 148 and B 149 are cleaved cycloartane derivatives from Ganoderma cochlear.³² The structure of cochlate B 149 was confirmed by X-ray analysis. Cultures of Ganoderma sp. KM01 produce further cleaved derivatives ganodermalactones A 150, C 151, F 152 and G 153.³³ The structures of ganodermalactones F 152 and G 153 were confirmed by X-ray analyses. The revised structure 154 has been assigned to colossolactone G, a further metabolite of these cultures.

An impressive number of side-chain variations is to be found in the 3,4-secocycloartanes lithocarpic acids A 155–N 168 from Lithocarpus polystachyus.⁹⁴ Lithocarpic acids O 169–S 173 are further examples from the same source.⁹⁵ The structure of lithocarpic acid A 155 was confirmed by X-ray analysis.

The three cycloartane xylosides 174–176, from Beesia calthaefolia, all have new genins.⁹⁶ New compounds from Cimicifuga species include the rearranged cycloartanes yunnanterpene G 177 and 12,18-didehydro-26-methoxyacetol 178, isodahurinol 24-acetate 25-methyl ether 179, 15,16-secoshengmanol C 180 and the glycosides 181 and 182 from the aerial parts of Cimicifuga yunnanensis,⁹⁷ cimifoetidanols A 183–H 190 and cimifoetidanosides A 191 and B 192 from the rhizomes of Cimicifuga foetida⁹⁸ and glycosides 193 and 194 from the roots of Cimicifuga simplex.⁹⁹ The structure of cimifoetidanol A 183 was confirmed by X-ray analysis.

Two new cycloartanes 195 and 196 have been found in Kleinhovia hospita.¹⁰⁰ The arabinoside 196 has a new genin. Two new glycosides, one with the new genin 197, have been reported from Landoltia punctata.¹⁰¹ Neomacrotriol 198 and the 29-norcycloartanes neomacroin 199, neomacrolactone 200 and related compounds 201–206 have been isolated from Neoboutonia macrocalyx.¹⁰² The related 29-nor-derivative 207 has been found in Cinnamosma fragrans.¹⁰³

Other new cycloartanes include caloncobic acid C 208 and caloncobalactone C 209 from the leaves of Caloncoba glauca,¹⁰⁴ the glucoside rhizostyloside 210, with a new genin, from Rhizophora stylosa,¹⁰⁵ compound 211 from Cassia italica,¹⁰⁶ and the tetrol 212 from the leaves and twigs of Walsura yunnanensis.¹⁰⁷ The unusual 23-methylene structure 213 has been proposed for a constituent of Piper thomsonii.¹⁰⁸

Compounds 214 and 215 have been isolated as mixtures of 24-epimers from Euphorbia fischeriana.¹⁰⁹ Two glycosides 216 and 217 from the roots of Cimicifuga simplex are described as galactopyranosides but drawn as furanosides.⁹⁹ Cycloarta-12,25-dien-3β-ol has been claimed as a constituent of Cameroonian brown propolis but the structure drawn is actually the 9(19)-cyclodammarane 218.¹¹⁰ 25-Hydroperoxycycloartanol 219 is a constituent of Euphorbia bupleuroides.⁵⁵

Cycloartane saponins with known genins include krugianoside A from Astragalus plumosus var. krugianus¹¹¹ and riparsaponin from Homonoia riparia¹¹² and saponins from Beesia calthaefolia,¹¹³Cimicifuga foetida¹¹⁴ and Euphorbia boissierana.¹¹⁵

4. The dammarane group

An interesting group of new dammaranes 220–233 has been reported from the stems of Dysoxylum binecteriferum.¹¹⁶ Several 13,17-secodammaranes are among the 20-epi-derivatives dysotriflorins A 234–M 246 from Dysoxylum densiflorum.¹¹⁷ The structure of dysotriflorin I 242 was confirmed by X-ray analysis.

Dysomollisol 247 and dysomollisone 248 are constituents of the fruit of Dysoxylum mollissimum.¹¹⁸ Dysomollisone 248 has been assigned an unusual rearranged side-chain. The octanor-derivative rosanol A 249 has been found in the roots of Rosa rugosa.¹¹⁹ Horipenoids A 250–H 257, from Homonoia riparia, include several other octanor-derivatives.¹²⁰ The structure of horipenoid E 254 was confirmed by X-ray analysis. Thirteen new dammarane saponins have been isolated from Gentianella azurea including the glucosides 258–260 whose structures were confirmed by X-ray analyses.¹²¹ Glucosides 258–260 have new genins. Further new genins 261–265 are found in the new dammarane saponins. The known gentirigenic acid and gentirigeoside A were also obtained from Gentianella azurea and their structures have been revised to 266 and 267, respectively, on the basis of X-ray analyses. The genins of the known gentirigeosides B and E were also revised to 268 and 269, respectively.

Phlomisumbrosides A and B are new glycosides from Phlomis umbrosa with the new genins 270 and 271.¹²² The 27-nordammarane 272 and the glucoside 273, with a known genin, are further constituents of the leaves of Panax ginseng.¹²³ The three 3,12-diketones 274–276 were obtained from the same source.¹²⁴ The epoxydammaranetetrol 277 has been isolated from the stems and leaves of American ginseng and given the erroneous name 3α-ocotillol (ocotillol is an epoxydammaranediol).¹²⁵

New compounds from Gynostemma pentaphyllum include two saponins with new genins 278 and 279,¹²⁶ the saponins damulins C and D with the new genins 280 and 281 (ref. 127) and the keto-lactone 282.¹²⁸ Cyclocarioside K, from Cyclocarya paliurus,¹²⁹ and tubeimoside C, from Bolbostemma paniculatum,¹³⁰ also have new genins, 283 and 284, respectively. Other new dammaranes include the ring A-cleaved derivative 285 from Aglaia abbreviata,¹³¹ deacetybrachycarpon-22-ene 286 from Cleome arabica,¹³² the 30-nor-24-methyl derivative floccosic acid 287 from Nepeta floccosa,¹³³ the keto-triol 288 from the root bark of Ailanthus altissima¹³⁴ and farmanol 289 from Nepeta suavis.¹³⁵

New dammarane saponins with known genins include cyclocarioside J from Cyclocarya paliurus,¹³⁶ jujubosides D and E (duplicate names) from Ziziphus jujuba,¹³⁷ notoginsenosides FZ, LX and LY from Panax notoginseng¹³⁸ and saponins from Aralia elata¹³⁹ and Panax notoginseng.¹⁴⁰ The pharmacological activities and production of saponins from Centella asiatica have been reviewed.

Fourteen new dichapetalin derivatives have been obtained from Dichapetalum gelonioides including 22-deoxydichapetalin P 290, 25-deacetyldichapetalins M 291 and P 292, dichapetalins T 293, U 294, V 295 and W 296, 6α-hydroxydichapetalin V 297, 22-deoxy-4′′-methoxydichapetalin V 298, 4′′-demethoxy-7-dihydrodichapetalin W 299, 7-dehydrodichapetalins E 300, G 301 and Q 302 and 29α-hydroxy-21-dehydrodichapetalin Q 303.¹⁴¹ The structure of 22-deoxydichapetalin P 290 was confirmed by X-ray analysis. The unusual 16,25-cyclised tirucallane structures 304 and 305 have been proposed for asperols A and B from Canarium asperum.¹⁴²

Other new tirucallane derivatives include the acetals 306–309 from Dysoxylum binectariferum,¹⁴³ trichostemonol 310 and the corresponding 3-acetate 311, trichostemonate, from the stem bark of Walsura trichostemon,^144,145 indicalilacols A 312–D 315 from the fruits of Azadirachta indica,¹⁴⁶ toosendansin D 316 from Melia toosendan,¹⁴⁷ compounds 317 and 318 from Celastrus stylosus,¹⁴⁸ the 21-epimers paramignyols A 319 and B 320 from Paramignya scandens¹⁴⁹ and dysoxylumin A 321 (duplicate name) from Dysoxylum densiflorum.¹⁵⁰ The unusual structure 322 has been ascribed to a constituent of Melia azedarach.¹⁵¹

Xylogranatumines A 323–G 328 are new apotirucallenes from the Chinese mangrove Xylocarpus granatum.¹⁵² Other members of this class are represented by compounds 330–332 from the leaves of Walsura trichostemon,¹⁵³ dictamnins A 333 and B 334, 21-epimers from the bark of Dictamnus dasycarpus,¹⁵⁴ cedrodorols A 335 and B 336 from Cedrela odorata¹⁵⁵ and compound 337 from Melia azedarach.¹⁵⁶

4.1 Tetranortriterpenoids

There is a strong interest in the biological activities of limonoids.^157–160 Anticancer^161,162 and pesticidal¹⁶³ activities of limonoids have also been highlighted. The publication of new members of this class continues unabated. Walsucochinoids C 338–R 353, from Walsura cochinchinensis, form an interesting group of rearranged derivatives.¹⁶⁴ The structures of walsuchinoids C 338 and L 347 were confirmed by X-ray analyses.

Xylogranatopyridines A 354, B 355 and prexylogranatopyridine 356, from the Chinese mangrove Xylocarpus granatum, are closely related to the known xylogranatin F 357 and hainangranatumin D 358.¹⁶⁵ The unusual 9,11-seco-derivative toonasecone A 359 has been isolated from Toona ciliata.¹⁶⁶

A series of amides, amooramides A 360–L 371, has been reported from the twigs and leaves of Amoora tsangii.¹⁶⁷ The highly oxygenated tetranortriterpenoids 372–376, from the fruits of Melia toosendan, are accompanied by the ring-C cleaved derivatives 377–379.¹⁶⁸ Compound 378 has also be isolated from Melia azedarach together with 380.¹⁶⁹

Nine new cedrelone derivatives, walsuranolide B 381, 11β-hydroxy-23-O-methylwalsuranolide 382, yunnanolides A 383 and B 384, yunnanol A 385, the isowalsuranolide derivatives 386–389, have been isolated from the leaves and twigs of Walsura yunnanensis.¹⁰⁷ Dysoxylamins B 390, C 391 (duplicate names) and compounds 392 and 393 are constituents of Dysoxylum densiflorum.¹⁵⁰ Other derivatives with intact skeletons include flexuosoids A 394 and B 395 from Phyllanthus flexuosus¹⁷⁰ and compound 396 from the flowers of Azadirachta indica var. siamensis.¹⁷¹

The A,D-seco derivatives clauemargines A 397–L 408 have been isolated from the stems of Clausena emarginata.¹⁷² The structure of clauemargine A 397 was confirmed by X-ray analysis. Other A,D-seco derivatives include euodirutaecins A 409 and B 410, as an inseparable mixture, evodirutaenin A 411 and shihulimonin A1 412 from the rhizomes of Coptis chinensis and Euodia rutaecarpa¹⁷³ and kihadanin C 413 from the root bark of Dictamnus dasycarpus.¹⁷⁴ 23-O-Methyldasylactone B 414 is a further constituent of Dictamnus dasycarpus.¹⁷⁴

Ring B-cleaved derivatives are represented by aphagranols D 415–H 419 from the fruits of Aphanamixis grandifolia¹⁷⁵ and the methyl angolensate derivatives cipaferens E 420–J 425 from the seeds of Cipadessa baccifera.¹⁷⁶ The mexicanolide derivatives, cipaferens K 426, L 427 and M 428, were also isolated together with the known compounds cipadesin A and 2R-methylbutanoylproceranolide whose structures were confirmed by X-ray analyses.

The seemingly endless investigations of the constituents of Azadirachta indica have, unsurprisingly, produced more unremarkable ring C-cleaved derivatives. These include the 28-deoxynimbolide derivative 429,¹⁷⁷ compounds 430–432,¹⁷⁸ nimbolide B 433 and nimbic acid B 434 (ref. 179) and compounds 435–437 from Azadirachta indica¹⁸⁰ and compounds 438–441 from Azadirachta indica var. siamensis.¹⁸¹ The uncleaved derivatives 442–446 (ref. 180) and 447 and 448 (ref. 181) were also obtained.

Three new ring C-cleaved derivatives 449–451, along with a host of known compounds, have been reported from the fruits of Melia azedarach.¹⁸² The leaves and bark are the source of the new derivatives 452–454 (ref. 183) while the meliacarpin derivative 455 was found in the leaves.¹⁵⁶ Toosendansins A 456, B 457 and C 458 are constituents of Melia toosendan.¹⁴⁷ The ichangin derivative 459, 9α-hydroxyhortolide A 460 and 11β-hydroxyhortolide C 461 were isolated from Hortia orcadia.¹⁸⁴

New skeletal variations of rearranged limonoids continue to appear. The structures of trichiconins A 462 and B 463, from Trichilia connaroides, were confirmed by X-ray analyses.¹⁸⁵ They were accompanied by trichiconin C 464. Zaphaprinins A 465–Y 489 are modified prieurianin derivatives from the fruits of Aphanamixis grandifolia.¹⁸⁶ The structures of zaphaprinins B 466, E 469 and P 480 were confirmed by X-ray analyses. Eight members of this group are ethyl esters and are presumably artefacts of the extraction process.

A similar group of compounds, aphanamixoids C 490a–P 502, has been reported from Aphanamixis polystachya.¹⁸⁷ Cineracipadesin G 503 (ref. 188) and the swietenine derivative 504 (ref. 189) are constituents of Cipadessa cinerascens.

Compounds from an Indian Xylocarpus granatum include granatumins L 505–U 514 (ref. 190) and granatumins V 515–Y 518.¹⁹¹ The structures of granatumins L 505 and Y 518 were confirmed by X-ray analyses. Granatumins M 506 and V 515 have also been isolated from Xylocarpus granatum by another group and named xylomexicanins H and G, respectively.¹⁹² They occur with xylomexicanins E 519 and F 520 that were drawn with the wrong absolute configuration in the reference.

Other constituents of Xylocarpus granatum include the phragmalin derivatives 521–524 (ref. 193) and xylocartin C 525.¹⁹⁴ Xylorumphins E 526–J 531 and 2-hydroxyxylorumphin F 532 are constituents of the seeds of Xylocarpus rumphii.¹⁹⁵ The structure of xylorumphin G 528 was confirmed by X-ray analysis.

Carapanolides C 533–I 539 (ref. 196) and carapanolides J 540, K 541 and L 542 (ref. 197) have been reported from the seeds of Carapa guianensis. The structure of carapanolide F 536 was confirmed by X-ray analysis.

Further investigations of Khaya ivorensis have resulted in the isolation of 14,15-didehydroruageanin A 543 and 3-O-(3-methylbutanoyl)seneganolide A 544 (ref. 198) and ivorenoids A 545–F 550.¹⁹⁹ Velutinasins A 551–H 558 are phragmalin derivatives from Chukrasia tabularis var. velutina.²⁰⁰ Velutinalide C 559 is another new compound from this source.²⁰¹

Neobeguea mahafalensis is the source of the phragmalin derivatives libiguin A 560 and libiguin B 561 (in equilibrium with its keto tautomer).²⁰² These compounds are reported to have aphrodisiac properties. 2-Acetylsoymidin B 562 and soymidins D 563 and E 564 are constituents of Soymida febrifuga.²⁰³ Swielimonoids A 565–F 570 are additional constituents of Swietenia macrophylla seeds.²⁰⁴ Chukvelutilides I 571–O 577 are further new phragmalin derivatives from the seeds of Chukrasia tabularis.²⁰⁵ Synthetic studies have indicated that the biosynthesis of the 1,8,9-orthoester moiety in phragmalins involves intermediates with an ester at C-1.²⁰⁶

4.2 Quassinoids

Eurylactones E 578, F 579 and G 580, eurycomalides D 581, and E 582 and 13α,18-dihydroeurycomanone 583 are new constituents of the roots of Eurycoma longifolia.²⁰⁷ Other constituents of Eurycoma longifolia include Δ⁴-14-hydroxyglaucarbol 584, 5-isoeurycomadilactone 585, eurycomadilactone 586 and 13-epieurycomadilactone 587 (ref. 208) and eurycomalide C 588.²⁰⁹ The structures of Δ⁴-14-hydroxyglaucarabol 584 and 5-isoeurycomadilactone 585 were confirmed by X-ray analyses. Shinjulactone O 589 has been isolated from the root bark of Ailanthus altissima.²¹⁰

5. The lupane group

Betulinic acid has been reported to have a variety of pharmacological activities including antitumour activity.^211,212 The first example of a 23-norlupane, 3-hydroxy-23-nor-5,20(29)-lupadien-7-one 590, has been reported from Lagerstroemia indica.²¹³Euonymus carnosus is a prolific source of lupane triterpenoids. Fifteen new compounds 591–605, including the 30-nor-derivatives 601–605, have been isolated.²¹⁴ The structure of 591 was confirmed by X-ray analysis. 19-Epibetulin 606 and 19-epi-20,28-epoxy-3-lupanol 607 have been reported from Hibiscus syriacus.²¹⁵

Other simple lupane derivatives include salacinins A 608 and B 609 from Salacia hainanensis,²¹⁶ the acetates 610 from Boswellia sacra²¹⁷ and 611 and 612 from Salvia viridis,²¹⁸ 20(29)-lupene-3β,11α-diol 613 together with its 3-palmitate and the 30-norlupane palmitate 614 from Saussurea phyllocephala,²¹⁹ sorbanolic acid 615 from Sorbus lanata²²⁰ and the 2-hydroxyhexanoyl ester of 3-epibetulinic acid 616 from Dillenia indica.²²¹ 3β,6β,29-Trihydroxy-20(30)-lupen-28-oic acid 617 and its β-D-glucopyranosyl ester 618 are constituents of Licania cruegeriana.²²² Lupane saponins with known genins include schekwangsiensides F and G from Schefflera kwangsiensis²²³ and saponins from Eryngium agavifolium.²²⁴

6. The oleanane group

Oleanane triterpenoids and their saponins have a wide range of pharmacological activities.^225–227 Oleanolic acid^228–231 and maslinic acid²³² have been well studied, particularly for their antitumour effects.

Cyclocaric acid A, from Cyclocarya paliurus, was claimed to have the structure 619 with an oxetane ring.²³³ Synthesis of the oxetane 619 and re-examination of the original literature report indicates that cyclocaric acid A is identical with hederagenin 620.²³⁴ The 2,3-seco-derivative 621 has been found in Ligularia przewalskii,²³⁵ and the 2,3-seco anhydride 622 is a constituent of Microtropis fokiensis where it is accompanied by the intact oleananes 623, 624 and the 18-oleanene derivative 625.²³⁶ Further 18-oleanene derivatives include 2α,3β-dihydroxy-18-oleanen-28-oic acid 626 from Lawsonia inermis²³⁷ and the corresponding 29-oic acid 627 from Mentha suaveolens.²³⁸

The 3,4-seco-derivatives camelliaoleans A 628 and B 629, together with the 28-noroleanane derivatives 630 and 631, have been isolated from Camellia japonica.²³⁹ Liquidaformone 632 is another 28-noroleanane from fruits of Liquidambar formosana.²⁴⁰ Asprellol C 633 is a 24-noroleanane from Ilex asprella,²⁴¹ whereas the noroleananes 634 and 635 have been found in Akebia trifoliata²⁴² and glyyunnansapogenin I 636 is from Glycyrrhiza yunnanensis.²⁴³

Two unusual 9(11)-oleanene derivatives 637 and 638, lacking a ketone at C-12, have been isolated from Boswellia ovalifiolata.²⁴⁴ Cannabifolin A 639, from Vitex negundo var. cannabifolia, has unusual cis-fused C/D rings.²⁴⁵ It is accompanied by cannabifolins E 640 and F 641. Rusaic acid B 642, from the roots of Rosa rugosa, has a contracted ring A.¹¹⁹

Other simple oleanane derivatives include 12-oleanene-1β,3β,11α,28-tetrol 643 and its 3-palmitate 644 from Saussurea phyllocephala,²¹⁹ uncarinic acids F 645, G 646 and H 647 from Uncaria rhynchophylla,²⁴⁶ schekwangsiensin 648 from Schefflera kwangsiensis,²²³ glaucescic acid 649 from Terminalia glaucescens,²⁴⁷ the 28,13-olide 650 from Ekebergia capensis,²⁴⁸ 3α-hydroxy-12-oleanene-23,28,29-trioic acid 651 from Acanthopanax gracilistylus²⁴⁹ and 12-oleanene-3β,7β,15α,28-tetrol 652 from Salvia argentea var. aurasiaca.²⁵⁰

3β-Hydroxy-11,13(18)-oleanadiene-23,28-dioic acid 653, previously identified as the genin of saponarioside J, has been isolated from Anoectochilus elwesii.²⁵¹ Yunganosides L, M, N₁, N₂, O and P are saponins from Glycyrrhiza yunnanensis with the new genins yunganogenins L 654–P 658.²⁴³ Licorice-saponins M3 and N4, from Glycyrrhiza glabra, have the new genin 659.²⁵² Licorice-saponin M3 is the same as uralsaponin T that has been isolated from Glycyrrhiza uralensis together with uralsaponins P–S and W that have the new genins 660 and 661, respectively.²⁵³

Other oleanane saponins with new genins include centellasaponins E and I, from Centela asiatica, with the genins 662 and 663,²⁵⁴ hippophosides A–D, from Hippophae rhamnoides ssp. sinensis, with the genins 664 and 665,²⁵⁵ oleiferasaponin B₂, from Camellia oleifera, with the genin 666,²⁵⁶ tubeimosides A and B, from Bolbostemma paniculatum, with the genins 667 and 668,¹³⁰ saponins from Akebia trifoliata with the noroleanane genins 669 and 670,²⁵⁷Entada phaseoloides with the genins 671–673,²⁵⁸Eclipata prostrata with the genin 12-oleanene-3β,16β,29-triol 674 (ref. 259) and Silphium asteriscus also with the genin 674 together with eleven related genins 675–685.²⁶⁰

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
Angulasaponins A–D	Vigna angularis	261
Aristatosides A–C	Cephalaria aristata	262
Bafouoside C	Cussonia bancoensis	263
Caspicaosides E–K	Gliditsia caspica	264
Celosins H–J (celosin I is a duplicate name)	Celosia argentea	265
Clematiunicinosides A–H	Clematis uncinata	266
Comastomasaponins A–H	Comastoma pedunculatum	267
Conyzasaponins R, S	Conyza japonica	268
Conyzasaponins T, U	Conyza japonica	269
Davisianosides A, B	Cephalaria davisiana	270
Flaccidosides V–VII	Anemone flaccida	271
Grindeliosides A–C	Grindelia argentina	272
Ilexasprellanosides D–F	Ilex asprella	273
Ilexpublesnin R	Ilex pubescens	274
Leptocarposide	Ludwigia leptocarpa	275
Licorice-saponin O4	Glycyrrhiza glabra	252
Lobeliodosides A–D	Lysimachia lobelioides	276
Lonicerosides F–J	Lonicera japonica	277
Officinoterpenoside D	Rosmarinus officinalis	278
Oleiferosides A–H	Camellia oleifera	279
Oleiferoside B1	Camellia oleifera	256
Paradoxosides A–E	Vitellaria paradoxa	280
Pittangretosides N, O, P	Pittosporum angustifolium	281
Pittangretosides A1, B1, J, K, M, Q–Z	Pittosporum angustifolium	282
Potentillanoside F	Potentilla anserina	283
Salbiges A, B	Salicornia herbacea	284
Sarconepaside C	Sarcopyramis nepalensis	285
Schefflesides A–H	Schefflera kwangsiensis	286
Schefflesides I–L	Schefflera kwangsiensis	287
Sieboldiisaponin B	Stachys sieboldii	288
Simenoside A	Gypsophila simonii	289
Schekwangsiensides A–E	Schefflera kwangsiensis	223
Uralsaponins M, N, O, U, V, Y	Glycyrrhiza uralensis	253
Yemuosides YM36, YM37	Stauntonia chinensis	290
Yunganoside E3	Glycyrrhiza yunnanensis	243

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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
Acacia auriculiformis	291
Anemone rivularis var. flore-minore	292
Callicarpa nudiflora	293
Centratherum anthelminticum	294
Clematis argentilucida	295
Croton lachnocarpus	296
Eclipta prostrata	259 and 297
Entada phaseoloides	258
Eryngium planum	298
Ganophyllum giganteum	299
Garcinia hanburyi	300
Gymnema sylvestre	301
Gypsophila arrostii var. nebulosi, Gypsophila bicolor	302
Manilkara hexandra	303
Melissa officinalis	304
Momordica charantia	305
Paonychia anatolica ssp. balansae	306
Patrinia scabra	307
Polycarpaea corymbosa var. eriantha	308
Polygala tenuifolia	309
Pycnanthemum flexuosum	310
Sapindus mukorossi	311
Silene rubicunda	312
Silphium asteriscus	260
Tremastelma palaestinum	313
Xanthoceras sorbifolia	314

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The unlikely acetone hemiacetal 686 has been reported as a constituent of Isodon adenantha.³¹⁵ 11,21-Dihydroxy-1-oleananone 687 and four esters 688–691 are claimed to be substituents of Coriandrum sativum.³¹⁶ Other new oleanane esters include the 3-palmitoyl ester of 3β,28-dihydroxy-12-oleanen-11-one (procerenone) from Omphalocarpum procerum,³¹⁷ and the oleoyl ester 12,18-oleanadien-3β-ol.³¹⁸ Leonurusoleanolides E 692–J 697, from Leonurus japonicus, are further esters of the 19(18→17)-abeo-28-noroleanane phlomistetraol B.³¹⁹

Malaytaxerate 698, from Sapium baccatum, is a ring-E contracted nortaraxerane derivative.³²⁰Davidia involucrata is the source of the ring-A contracted nortaraxeranes davinvolunols A 699 and B 700 and davinolunone A 701 together with the intact taraxeranes davinolunones B 702 and C 703.³²¹ The structure of the 2,3-secotaraxerane pycanocarpine 704, from Pleiocarpa pycnantha, was established by X-ray analysis.³²² A taraxerane saponin with a known genin has been isolated from the roots of Clematis argentilucida.³²³ The structures of both the multiflorane derivative turranoic acid 705 and turraenine 706, from a Turraea species, were also established by X-ray analysis.³²⁴ Turraenine 706 is an unusual nitrogen-containing dimeric normultiflorane. Three multiflorane esters 707–709 have been isolated from seeds of Cucurbita maxima.³²⁵ The glutinane derivative klodorol A 710, from Kleinia odora, is 5α-hydroxydebdropanoxide.³²⁶ The authors draw klodorol A 710 with incorrect stereochemistry at C-13 and C-14.

The structures of the friedelane triterpenoids found in Maytenus species have been summarised.³²⁷ Glaucalactone B 711 is a 29-norfriedelane 27,20-lactone from Caloncoba glauca¹⁰⁴ and hainanenone 712 is a 23-norfriedelane derivative from Drypetes hainanensis.³²⁸ The 23,24-dinorfriedelane pristimerol 713, from Celastrus aculeatus, has been given the same name as the reduction product of pristimerin.³²⁹ Galphimines K 714 and L 715 are further 3,4-seco-derivatives from Galphimia glauca.³³⁰ Other friedelane derivatives include salacinin C 716 from Salacia hainanensis,²¹⁶ the 3-ketones 717 and 718 from Maytenus robusta³³¹ and the esters 718 and 720 from Drypetes hoanensis.³³² The structure of 717 was confirmed by X-ray analysis. The known norfriedelane celastrol from Triperygium wilfordii has shown interesting antitumour activity.³³³

7. The ursane group

The antitumour activity of ursolic acid has been highlighted.^334,335 The unusual 9,25-cyclo-12-ursen-3β-ol 721 has been reported from Cameroonian brown propolis.¹¹⁰ The ring-A modified ursanes davinvolunic acids A 722, B 723 and C 724 have been isolated from Davidia involucrata.³³⁶ Davinvolunic acid C 724 contains an unusual methyl hemiacetal. The leaves of Vitex negundo var. cannabifolia are the source of cannabifolins A 725, C 726 and D 727.²⁴⁵ The structure of cannabifolin A 725 was confirmed by X-ray analysis to have cis-fused rings C and D. Two ursane derivatives 728 and 729, with the unusual 20αH-configuration, have been identified in Ilex cornuta.³³⁷ Asprellols A 730 and B 731, from Ilex asprella, are 24-norursane derivatives.²⁴¹ Urs-12-ene-2α,3β,19α-triol 732, from Terminalia arjuna, has been named torment.³³⁸

Other simple ursane derivatives include cymosic acid 733 from Rosa cymosa,³³⁹ elatumic acid 734 from Omphalocarpum elatum,³⁴⁰ erandione 735 from Ricinus communis,³⁴¹ klodorone A 736 from Kleinia odora,³²⁶ meyanthic acid 737 and urs-12-ene-2α,3α,19α,24,28-pentol 738 from Meyna (Vangueria) spinosa,³⁴² uncarinic acids H 739 and I 740 from Uncaria rhynchophylla,²⁴⁶ 3α,6β,19α-trihydroxyurs-12-en-28-oic acid 741 from Mitragyna diversifolia,³⁴³ 3β,20β-dihydroxyursan-28-oic acid 742 from Malus domestica,³⁴⁴ 3α,11β-dihydroxyurs-12-en-28-oic acid 743 from Gentiana veitchiorum,³⁴⁵ three compounds 744–746 from Zizyphus jujuba,³⁴⁶ three compounds 747–749 from Microtropis fokienensis²³⁶ and nine ursanes 750–758 from Salvia argentea var. aurasiaca.²⁵⁰

Centrellasaponin J, from Cenrella asiatica, has the new ursane genin 759.²⁵⁴ Further new ursane genins include 760 from Callicarpa nudiflora,²⁹³761 from Clematis argentilucida,³²³762 and 763 from Panax ginseng⁶¹ and 764–766 from Schefflera heptaphylla.³⁴⁷

Named ursane saponins with known genins include fagonoside A from Fagonia cretica,³⁴⁸ grandoside from Syzygium grande,³⁴⁹ ilexsaponins G and H from Ilex pubescens,³⁵⁰ ilexasprellanosides A–C from Ilex asprella,²⁷³ ilexpublesnins N–Q (Q is the same as zygoeichwaloside H isolated in 2007(ref. 351)) from Ilex pubescens,²⁷⁴ officinoterpenoside C from Rosmarinus officinalis,²⁷⁸ potentillanosides A–E²⁸³ and G³⁵² from Potentilla anserina, sieboldiisaponins A³⁵³ and C²⁸⁸ from Stachys sieboldii, and zygofaboside C from Zygophyllum fabago.³⁵⁴ Unnamed saponins with known genins have been isolated from Eucommia ulmoides,³⁵⁵Ilex cornuta,^356,357Melissa officinalis,³⁰⁴Schefflera heptaphylla³⁴⁷ and Vitex negundo.³⁵⁸

Further ursane esters include the acetate 767 from Boswellia sacra,²¹⁷ the acetate 768 from Mentha suaveolens,²³⁸ ferulates 769 and 770 from Ampelopsis japonica.³⁵⁹ and the palmitate 771 from Inula cappa.³⁶⁰ Flaccidoside IV is a taraxastane saponin with a known genin from Anemone flaccida.²⁷¹ The unusual 3β-acetoxy-22,28-cyclobauer-7-ene 772 has been identified in Ixeris chinensis.³⁶¹

8. The hopane group

The 2,3-seco-21αH-hopane derivatives 773 and 774 have been isolated from Megacodon stylophorus.³⁶² The structure of 773 was confirmed by X-ray analysis. Ribosylhopane 775, which has been postulated as a precursor of C₃₅ bacteriohopanepolyols in Streptomyces coelicolor, has now been found in blocked mutants.³⁶³ Two fernane derivatives 776 and 777 have been reported from Lonicera quinquelocularis however the structures are drawn lacking C-28 in the reference.³⁶⁴ A fernane saponin, from Spergula fallax, has the new genin 778.³⁶⁵

9. Miscellaneous compounds

The unlikely structure 779 has been assigned to a triterpene rhamnoside from Sesbania aculeata.³⁶⁶ Three gammacerane saponins, from Spergula fallax, have the new genin 780.³⁶⁵Lycopodium japonicum is the source of the serratane derivatives lycojaponicuminols A 781–F 786 (ref. 367) and the formate esters 787 and 788.³⁶⁸

Fatsioside A, from fruit of Fatsia japonica, has the new bacchane genin 789.³⁶⁹ The structure of the norshionane derivative astershionone A 790, from Aster tataricus, was established by X-ray analysis.³⁷⁰ The related astershionones B 791–F 795 were also isolated. Opaciniol A 796, from Garcinia opaca, is a hexnormalabaracane derivative.⁴⁸ Further isomalabaricane derivatives, jaspiferins C 797–F 800 have been found in the South China Sea sponge Jaspis stellifera.³⁷¹ Phyteujaposide 801 is an unusual polypodane cyclic saponin from Phyteuma japonicum.³⁷² Further iridal triterpenoids from Iris species include irisgermanone 802 from Iris germanica³⁷³ and spirioiridotectals A 803–F 808 from Iris tectorum.³⁷⁴

10. Conflicts of interest

There are no conflicts of interest.

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