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Triterpenoids

Robert A. Hill* and Joseph D. Connolly
School of Chemistry, Glasgow University, Glasgow, G12 8QQ, UK. E-mail: bob.hill@glasgow.ac.uk

Received 7th November 2019

First published on 14th February 2020


Covering 2015. Previous review: Nat. Prod. Rep., 2018, 35, 1294–1329

This review covers the isolation and structure determination of triterpenoids reported during 2015 including squalene derivatives, lanostanes, holostanes, cycloartanes, cucurbitanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, serratanes, isomalabaricanes and saponins; 320 references are cited.


1. Introduction

Reviews have been published on the biological properties of triterpenoids including hypoglycaemic,1 antiparasitic2 and immunomodulatory3 activities and neutrophil elastase inhibition.4 Triterpenoid saponins have been highlighted for a range of bioactivities5 and for their neuroprotection.6 Reviews have also appeared covering triterpenoids found in Albizia species,7 Alstonia scholaris,8 plants of the Amaranthaceae,9 Codonopsis species,10 Medicago sativa,11 Olea europaea12 and Terminalia species.13 Triterpenoids with a five-membered A-ring have also been covered.14

2. The squalene group

Structure 1 has been proposed for auxarthonoside, a squalene glycoside from the sponge-derived fungus Auxarthron reticulatum.15 Four derivatives, silphasqualols A 2–D 5, have been found in the compass plant Silphium laciniatum.16 A compound from cultures of the basidiomycete Antrodiella albocinnamomea apparently has the non-standard structure 6.17 Saponaceolides Q 7, R 8 and S 9 are further constituents of the European mushroom Tricholoma terreum.18 Laurencia viridis is a rich source of squalene derivatives.19 New compounds include 28-hydroxysaiyacenol B 10, saiyacenol C 11 and epoxythyrsiferol A 12 and its 15R,16S-isomer epoxythyrsiferol B. A new pathway for the synthesis of squalene in bacteria has been discovered and the responsible genes identified.20
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3. The lanostane group

A range of protostane derivatives from the rhizomes of Alisma orientale, that show inhibitory effects on human carboxylesterase 2, includes alismanols A 13–G 19, 20-hydroxyalisol C 20, 25-O-ethylalisol A 21 and compounds 22–24.21 The helvolic acid-related compound 25, from the endophytic fungus Aspergillus fumigatus, has an unusual secofusidane skeleton.22
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The Tibetan medicinal mushroom Ganoderma leucocontextum is full of lanostanes including ganoleucoins A 26–L 37 and the meroterpenoid esters ganoleucoins M 38–P 41.23 Many of these compounds inhibit HMG-CoA reductase and α-glucosidase. Ganoboninones A 42–F 47 are secolanostanes from the medicinal mushroom Ganoderma boninense that show antiplasmodial activity.24 Constituents of Ganoderma tropicum include25 compounds 48, 49, and 50 while Ganoderma hainanense contains26 ganohainanic acids A 51, its acetate 52, B 53, C 54, D 55, its acetate 56 and E 57. The structure of ganohainanic acid A 51 was confirmed by X-ray crystallographic analysis. Other constituents of this mushroom include hainanic acids A 58 and B 59, the keto alcohols 60 and 61, hainanaldehyde A 62 and compounds 63 and 64.

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Reviews have appeared highlighting the importance and variety of lanostanes from Ganoderma lucidum.27,28 Newly isolated compounds include ganoderic acid X1 65,29 ganoderlactones A 66–E 70 and ganodernoids A 71–G 77,30 compounds 78 and 79 from the fruiting bodies31 and the triacetate 80.32 Ganocochlearic acid A 81 is an interesting rearranged hexanorlanostane from the fruiting bodies of Ganoderma cochlear where it occurs with cochlate C 82, cochlearic acids A 83 and B 84 and ganodercochlearins D 85–K 92.33 The structures of 83 and 85 were confirmed by X-ray crystallographic analyses.

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Other fungal products include fomefficinin 93 from Fomes officinalis,34 hexagonins A 94–E 98 from the fruiting bodies of Hexagonia apiaria,35 the 21-oic acid 99, the 3,4-seco 3,21-dioic acid 100 and its 3-methyl ester from the fruiting bodies of Laetiporus sulphureus var. miniatus36 and astrasiate 101 and astrasiaone 102 from the edible mushroom Astraeus asiaticus.37 The metabolites 103–111 of Haddowia longipes ressemble those of Ganoderma species.38 Compound 110 is lucidone H, which is a duplicate name, and 111 is the 3-acetate of ganodermatriol. Diaporthe sp. LG23, an endophytic fungus from Mahonia fortunei, produces the ring B aromatic lanostane 112.39

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Ascosteroside C 113 is a mitochondrial respiration inhibitor isolated from an Aspergillus species.40 Gloeophyllins A 114–J 123 form an interesting group of normal and rearranged cytotoxic lanostanes from the Tibetan fungus Gloeophyllum abietinum.41 The structures of compounds 114, 115 and 122 were confirmed by X-ray analyses. Gloeophyllin B 115 has also been isolated from Gloeophyllum odoratum, together with the related compound 124.42

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The 21,24-cyclised lanostanes inonotusanes A 125 and B 126 and the trinorderivatives inonotusane C 127 and obliquic acid 128 are constituents of Inonotus obliquus.43 Scillascillol 129 and scillascillone 130 have been isolated from Scilla scilloides.44 The aglycone 131 of bellevalioside D has been found in Eucomis vandermerwei.45

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Spirochensilides A 132 and B 133 are rearranged lanostanes from Abies chensiensis.46 The structure of spirochensilide A 132 was confirmed by X-ray analysis. Two groups of compounds, neoabieslactones G 134–K 138 and abiestrines K 139–M 142, have been reported from Abies faxoniana.47 Neoabieslactone I 136 shows interesting topoisomerase II inhibitory activity.

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DFT calculations and ROESY data have been used in the stereochemical assignment of abibalsamins C 143–I 150 from the oleoresin of Abies balsamea.48 The abibalsamins are Diels–Alder adducts of lanostane and rearranged lanostane triterpenoids with the monoterpenoid myrcene. Kadsura coccinea is the source of two interesting groups of lanostane derivatives, kadcoccinic acids A 151–J 160 (ref. 49) and kadcoccinones A 161–F 176.50 The structures of 153, 161, 164, 165 and 166 were all confirmed by X-ray crystallographic analyses. Ethyl manwuweizate 167 and methyl manwuweizate 168 are 3,4-secolanostane derivatives from Kadsura heteroclita.51

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Compounds 169–176 are minor constituents of a Vietnamese Penares species.52 The saponin 177, with a new hexanorlanostane genin, has been reported from the sponge Clathria gombawuiensis.53 Lanostane saponins with known genins include eryloside W from Dictyonella marsilii,54 scillascilloside B1 from Scilla scilloides44 and saponins from Mussaenda luteola.55

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The holostane saponins cladolosides C3, E1, E2, F1, F2, G, H1 and H2, from the sea cucumber Cladolabes schmeltzii, have the new genins 178 (C3), 179 (E2, F2, G, H2) and 180 (E1, F1, H1).56 The saponins lessoniosides A, B and D, with the new genin 181, C and E, with the new genin 182, and F and G, with the new genin 183, have been reported from the viscera of the sea cucumber Holothuria lessoni.57 Among the saponins of the sea cucumber Colochirus robusta, colochirosides B1 and B3 have the new genins 184 and 185 respectively whereas colochirosides B2 and C have known genins.58 The C-22 configuration of the saponins of the sea cucumber Cladolabes schmeltzii has been assigned as R.59 Other holostane saponins with known genins include cercodemasoides A–E from Cercodemas anceps,60 cucumarioside E from Cucumaria japonica61 and moebioside A from Holothuria moebii.62 Reviews covering biological and taxonomic significance of sea cucumber holostane saponins63 and their antitumour, anti-inflammatory and immunostimulatory properties64 have been published.

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Cimyunnins A 186–D 189 are cycloartane derivatives with interesting side-chains, from the fruit of Cimicifuga yunnanensis.65 A mixture of 187 and 188 was used to confirm the structures by X-ray crystallographic analysis. Cimyunnin A 186 is a potent angiogenesis inhibitor. Ananosins A 190–E 194, cycloartanes from Kadsura ananosma, have some unusual structures.66

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Abies faxoniana is the source of an impressive group of pairs of lanostane and cycloartane derivatives A1/A2 195/196–H1/H2 209/210, with epimeric spiro-side chains.67 Fourteen new cycloartane derivatives, 211–216 (ref. 68) and 217–224,69 have been isolated from Beesia calthifolia. Other cycloartanes include 225, 226 and 227 from the leaves and twigs of Dysoxylum gotadhora,70 huangqiyegenins V 228 and VI 229 together with the saponins huangqiyenins K and L with the new genins 230 and 231, respectively, from the leaves of Astragalus membranaceus,71 the 21-epimer 232 of the known argenteanone A from the leaves of Lansium domesticum,72 the 3,4-seco derivative 233 from the leaves of Hopea odorata,73 and mangiferenes A 234 and B 235 from Mangifera foetida.74 The structures of 225 and 232 were confirmed by X-ray crystallographic analyses. The 3,4-seco-cycloartanes macrocoussaric acids D 236, E 237 and F 238 have been isolated from Coussarea macrophylla.75

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Gambosides A–F are cycloartane glycosides from Astragalus gombo.76 Gambosides A, B and F have the new genins 239, 240 and 241, respectively. Interest in the cycloartane saponins from Cimicifuga simplex continues.77 Glycosides from the aerial parts of Cimicifuga simplex include the new genins 242–245.78 The structure of the 3-O-β-D-xylopyranoside of 244 was confirmed by X-ray crystallographic analysis. Compounds reported from Cimicifuga heracleifolia include cimiheracleins A 246–D 249, 12β-hydroxyacerinol 250, 11-dehydroxy-15α-hydroxycimicidanol 251, cimigenol-3,12-dione 252, the related enones 253 and 254, compound 255 and 1β-hydroxycimigenol 256 and its 24-epimer 257.79 Two new 18-norschiartane derivatives, wuwezidilactones A 258 and B 259, have been reported from Schisandra lancifolia.80 Two reviews of triterpenoids from Schizandra species have been published.81,82 Cycloartane saponins with known genins include amphipaniculosides C and D from Amphilophium paniculatum83 and saponins from Cimicifuga foetida84 and Mussaenda luteola.55

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The cucurbitacins have interesting pharmaceutical potential.85,86 Cucurbitacin E has been investigated for a wide range of activities.87 The biosynthesis of the bioactive mogrosides from Siraitia grosvenorii has been studied.88 Three papers describe further cucurbitacin constituents of Momordica charantia, including taikugausins C 260, D 261 and E 262,89 kuguacins II 263–VI 267 (ref. 90) and kaguacin X 268.91 The structure of kuguacin II 263 was confirmed by X-ray crystallographic analysis. Citriodora A 269 has been obtained from Eucalyptus citriodora.92 Hemsleypenside B 270 and the 16,25-diacetate 271 of cucurbitacin F have been isolated from Hemsleya jinfushanensis.93 Hemsleypenside B 270 has a new genin. Other cucurbitacin saponins with the new genins 272 and 273 (ref. 94) and 274 and 275 (ref. 95) have been isolated from the leaves and fruit of Citrullus colocynthis. Genins 274 and 275 have an unusual three carbon unit at C16. Cucurbitacin saponins with known genins include mogroside VA1 from Siraitia grosvenorii,96 kaguaglycoside I91 and taikugausins A and B89 from Momordica charantia and hemsleypensides C, D and E from Hemsleya jinfushanensis.93

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4. The dammarane group

The pharmaceutical use of dammarane triterpenoids has been reviewed.97 Reviews have also appeared on the saponins from Panax ginseng98 and Panax notoginseng.99,100 Four new ginsenosides, with melanogenesis inhibitory activity, have been isolated from Panax ginseng but only one of them, 23-O-methylginsenoside Rg11, has a new genin 276.101 Six new dammaranes 277–282 have been obtained from the acidic hydrolysate of the stems and leaves of Panax ginseng.102 The steamed roots of Panax notoginseng yielded notoginsenosides SP1–SP4 with the new genins 283–286 (ref. 103) and notoginsenosides ST7–ST10, 13 and 14 with the genins 287–292.104
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Other dammarane derivatives include gypensapogenins H 293–L 297 from the hydrolysate of the total saponins of Gynostemma pentaphyllun,105 cyclocariosides I 298 (duplicate name) and J 299 from the leaves of Cyclocarya paliurus,106 glylongiposides I and II, with the new genins 300 and 301, from Gynostemma longipes,107 compound 302 from the green walnut husks of Juglans mandshurica108 and compounds 303–306 from Cissus quadrangularis.109

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Two groups of nordammarannes, compounds 307, 308 and 309 from Sanguisorba officinalis110 and hupehenols A 310–E 314 from Viburnum hupehensis,111 have been reported. Macrocoussaric acids A 315, B 316 and C 317 are 3,4-secodammaranes from the Ecuadorian plant Coussarea macrophylla.75

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Epoxynotoginsenoside A is a saponin from Panax notoginseng that is identical to the previously isolated quinquefoloside Lb.112 Dammarane saponins with known genins include actinostemmosides I and J, from Actinostemma lobatum,113 cyclocarioside K from Cyclocarya paliurus,106 20S-ginsenoside RF2 from Panax ginseng,114 notoginsenosides SP5–SP18 (ref. 103) and notoginsenosides ST6, ST11 and ST12 from Panax notoginseng104 and saponins from Gynostemma pentaphyllum115 and Panax ginseng.116–118 The current knowledge of the key enzymes involved in the biosynthesis of saponins from Panax notoginseng has been surveyed.119

Ricinidols A 318 and B 319 have a new rearranged euphane skeleton.120 They occur in Ricinodendron heudelotii together with the euphane derivatives ricinodols C 320–G 324. The structure of 16-epikulinone 325, from Melia azedarach, was established by X-ray crystallographic analysis.121 Other euphanes include the antibacterial toosendanin A 326 from Melia toosendan122 and 25-methoxy-8,23-euphadien-3β-ol 327 from Euphorbia pekinensis.123

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New tirucallane derivatives include 3β-O-tigloylmelianol 328 from Guarea kunthiana,124 congoensins A 329 and B 330 from the bark of Entandrophragma congoënse,125 compounds 331, 332 and 333 from Anopyxis klaineana,126 ficutirucins A 334–I 342 from the fruit of Ficus carica,127 24,25-dihydrolimocinol 343 from Melia azadirachta128 and secotiaminic acid 344 from Entandrophragma congoense.129 Paramigniosides A–E are tirucallane saponins from Paramignya scandens, all with the same genin 345.130

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Polygonifoliol 346, from the latex of the seaside sandmat Euphorbia polygonifolia, is an apotirucallane with an 18(17→14)-abeo rearrangement.131 Piscidinols H 347–L 351 are apotirucallane derivatives from the leaves of Walsura trifoliata that show moderate insecticidal activities.132 The apotirucallol derivative 352 has been isolated from the seeds of Xylocarpus granatum.133

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The apotirucallane and glabretal derivatives prototiamins A 353–G 359 are constituents of the bark of Entandrophragma congoënse.129 The structure of prototiamin C 355 was confirmed by X-ray analysis. Other glabretal derivatives include dictabretals A 360–D 363 from the root bark of Dictamnus dasycarpus,134 pancastatins A 364 and B 365 from the immature fruit of Poncirus trifoliata,135 compound 366 from Atalantia buxifolia136 and dysomollins A 367 and B 368 from Dysoxylum mollissimum var. glaberrimum.137

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Phainanoids A 369–F 374, from Phyllanthus hainanensis, have an interesting new carbon skeleton.138 The structures of A and B were confirmed by X-ray crystallographic analyses. Phainanoids A 369–F 374 exhibited potent immunosuppressive activities. Songbodichapetalin 375 is a new constituent of Phyllanthus songboiensis with cytotoxic activity.139

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4.1. Tetranortriterpenoids

Many new limonoids have been reported this year. Dysomollides A 376–G 382 are constituents of Dysoxylum mollissimum var. glaberrimum.137 Dysoxylum mollissimum is also the source of dysoxylumosins A 383–M 395.140
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The leaves of Trichilia americana are rich in cedrelone derivatives, including americanolides A 396–D 399 and compounds 400–405.141 The structure of americanolide A 396 was confirmed by X-ray crystallographic analysis.

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Munronins A 406–N 419 (ref. 142) and O 420, P 421 and Q 422 (ref. 143) are constituents of Munronia henryi. Unfortunately, the names munronins A–G have been used before and munronin L 415 is the known 23-O-methylvolkensin. The structure of munronin H 412 was confirmed by X-ray crystallographic analysis. Many of the munronins show strong anti-tobacco mosaic virus activity.

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Several 29-nor and related limonoids, toonaciliatones A 423–H 430, have been found in the stem bark of Toona ciliata var. yunnanensis.144 Toonaciliatones A–F are names that have already been used. New compounds from Azadirachta species include azadiraindins A 431–D 434,145 E 435, F 436 and G 437 (ref. 146) and nimbolicidin 438 and nimbocin 439 (ref. 147) from Azadirachta indica and mehaneemin 440 from Azadirachta excelsa.148

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Ciparasins A 441–P 456 constitute an impressive array of rearranged limonoids from Cipadessa cinerascens.149 Ciparasins A 441 and P 456 show strong anti-HIV activities.

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The Thai mangrove Xylocarpus moluccensis is the source of thaixylomolins G 457–N 464, the xyloccensin U derivatives 465 and 466 and the mexicanolide derivatives 467and 468,150 while the seeds of Indian Xylocarpus moluccensis yielded proceranolide propanoate 469 and deacetylangustidienolide 470.151 2,3-Dideacetylxyloccensin S 471 and 30-deacetylxyloccensin W 472 have been isolated from the seeds of Xylocarpus granatum.133 The seeds of Swietenia macrophylla152 and Swietenia humilis153 are the respective sources of swietemacrophin 473 and humilinolides G 474 and H 475. Swietemacrophin 473 is the same as the previously isolated 2-acetylruageanin B and 2-acetoxyswietemahonolide. The structure of humilinolide G 474 was confirmed by X-ray crystallographic analysis.

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Khaysenelides A 476–F 481 are modified furan derivatives from the stem bark of Khaya senegalensis.154 The structures of khaysenelides A 476 and C 478 were confirmed by X-ray crystallographic analyses. Khaysenelide F 481 shows neuroprotective activity. An impressive group of mexicanolide derivatives, khasenegasins A 482–N 495, has been reported from the seeds of Khaya senegalensis.155

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New compounds from Carapa guianensis (andiroba) include andirolides W 496, X 497 and Y 498 from the flower oil156 and carapanolides T 499–X 503 (ref. 157) and M 504–S 510 (ref. 158) from the seeds. The structures of khasenegasin A 482 and carapanolide N 505 were confirmed by X-ray crystallographic analyses. Carapanolide V 501 is the same as andirolide F, isolated in 2011.

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Tabulalins K 511, L 512 and 513 (ref. 159) and velutabularins K 514, L 515 and M 516 (ref. 160) are new phragmalin derivatives from Chukrasia tabularis var. velutina. The structure of velutabularin K 514 was confirmed by X-ray crystallographic analysis. Further phragmalin derivatives, chukvelutilides I 517–X 532, have been isolated from Chukrasia tabularis.161 This paper adds to the confusion in the literature by using duplicate names (chukvelutilides I–O). In addition, chukvelutilides U and V are the same as the previously published chukvelutilides I and L.

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4.2. Quassinoids

Perforalactones A 533, B 534 and C 535 are interesting new quassinoids from Harrisonia perforata.162 Perforalactones A 533 and B 534 have been shown to have insecticidal activity but no cytotoxic activity. Brucea javanica yielded the new derivative bruceene A 536.163 The structures of perforalactone A 533 and bruceene A 536 were confirmed by X-ray analyses. Several new quassinoids, picrajavanicins A 537–G 543, have been reported from Picrasma javanica, collected in Myanmar.164
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5. The lupane group

24-Norbetulin 544 has been identified in Dracaena cinnabari.165 The highly oxygenated lupane derivatives 545 and 546 are constituents of cashew nuts (Anacardium occidentale).166 The related compounds 547 and 548 have been found in Egyptian apple peel (Malus domestica).167,168 Cassine xylocarpa is the source of four new lupane derivatives 549–552 and a further two, 553 and 554, are from Maytenus cuzcoina.169 Other new lupane derivatives include the antibacterial 3β-hydroxy-9(11),12-lupadien-28-oic acid 555 from Sonneratia alba170 and 3β-hydroxy-7-oxo-20(29)-lupen-28-oic acid 556 from Manilkara zapota.171 Novel lupane esters include the 3-hexadecanoyl ester 557 of 20(29)-lupene-3β,7β-diol from Scurrula parasitica parasitic on Nerium indicum,172 the 4-hydroxy-3-methoxybenzoyl ester 558 from Paullinia pinnata,173 the cafeoyl ester 559 from Celastrus stylosus174 and the 2-benzoyl ester of alphitolic acid from Rubus innominatus175 Hancokinoside, from Allophylus africanus, is the 2-O-β-D-glucopyranoside of the known hancokinol although the diagram in the reference is inaccurate.176 Other lupane saponins with known genins include royleanumioside from Teucrium royleanum177 and a saponin from Cyperus rotundus.178
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6. The oleanane group

Three 24-noroleananes, 560, 561 and 562, have been isolated from biogas slurry.179 The structure of 24-nor-12-oleanene-3,22-dione 562 was confirmed by X-ray crystallographic analysis. The related dione 563 has also been found in biogas slurry.180 The 3,4-seco-oleanane derivative 564, from Hypericum ascyron, contains an unusual enedione.181 Four oleananes 565568 with unusual hydroxylation at C18 have been isolated from hawthorn berries (Crataegus pinnatifida).182 Oleananes 566, 567 and 568 exhibited strong antiproliferative activity. Brachyanthera acid A 569, from Stautonia brachyanthera, is 2α,3β,21β,23-tetrahydroxy-12-oleanene-28,29-dioic acid183 and pashia acid 570, from Pyrus pashia, is 2α,3β,27-trihydroxy-12-oleanen-28-oic acid.184
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Other new oleanane derivatives include cyrillin A 571 from Cyrilla racemiflora,185 lancamarolide 572 from Lantana camara,186 silphanolic acid C 573 from Silphium laciniatum,16 termichebulolide 574 from Terminalia chebula,187 ulubelenolide 575 from Tanacetum chiliophyllum var. monocephalum,188 the 28,19-olides 576 and 577 from Styrax tonkinensis,189 the pentahydroxyoleanenone 578 and the corresponding 3-ketone 579 from Gueldenstaedtia verna,190 the 11-hydroperoxide 580 from Holarrhena curtisii,191 3β,6β,29-trihydroxy-12-oleanen-28-oic acid 581 from Spermacoce latifolia,192 2α,3β,29-trihydroxy-12-oleanen-28-oic acid 582 and related compounds 583 and 584 from Akebia trifoliata,193 the 12(18)-enes 585 and 586 from Schnabelia oligophylla194 and 1-oxosiaresinolic acid 587 and 2α,3α-dihydroxy-11,13(18)-oleanadien-28,19β-olide 588 from Rubus innominatus.175

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Termichebuloside A 589, a dimeric oleanane diglucosyl ester from Terminalia chebula, is the 4,4′-diepimer of the known ivorenoside A.187 The rhamnoside 590, from Gueldenstaedtia verna has a new genin.190 Pachystelanoside B is a saponin from Pachystela msolo with the new genin 7α-hydroxyprotobassic acid 591.195 Silenorubicosides E–I are saponins from Silene rubicunda with the new genins 592 (E, F and G), 593 (H) and 594 (I).196

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Licoricesaponins P2 and Q2 are saponins from Glycyrrhiza inflata with the new genins 595 and 596, respectively.197 Genin 596 has an unusual 18αH. Other oleanane saponins with new genins include 22-acetyluralsaponin C from Glycyrrhiza uralensis with genin 597,198 atrioleanoside from Atriplex lasiantha with genin 598,199 indicacin from Fagonia indica with genin 599 (ref. 200) and schisusaponins G and H from Schima superba with genins 600 and 601, respectively,201 and saponins from Anemone amurensis with genin 602,202 Bupleurum chinense with genin 603 (ref. 203) and Ilex cornuta with genin 604.204

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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
Abyssaponins A, B Erythrina abyssinica 205
Aesculiosides S1, S2 Aesculus sylvatica 206
Akeqintoside E Akebia quinata 207
Amphipaniculosides A Amphilophium paniculatum 83
Aquaticasaponins A, B Gleditsia aquatica 208
Ardinuloside Ardisia insularis 209
Bigelovii C Salicornia bigelovii 210
Bigelovii D Salicornia bigelovii 211
Boromoenosides A–D Albizia boromoensis 212
Brachyantheraosides A1–A5, B6, B9 Stauntonia brachanthera 183
Catunarosides I, J Catunaregam spinosa 213
Centellasaponin H Centella asiatica 214
Clematograveolenoside A Clematis graveolens 215
Comastomasaponin I Comastoma pedunculatum 216
Coriacea saponin A Holboellia coriacea 217
Crotalariosides C, (E/Z)-D, (E/Z)-E, (E/Z)-F Polygala crotalarioides 218
Cyrillin B Cyrilla racemiflora 185
Enterolacaciamine Enterolobium cyclocarpum 219
Floraassamsaponins I–VIII Camellia sinensis var. assamica 220
Ginsenoside Ro sulfate Silphium laciniatum 16
Glomerulosides A–H Glochidion glomerulatum 221
Glomerulosides I, II Glochidion glomerulatum 222
Hemslosides Ma4, Ma5 Hemsleya chinensis 223
Hippophosides E, F Hippophae rhamnoides 224
Lebbeckosides A, B Albizia lebbeck 225
Leptocarposides B, C, D Ludwigia leptocarpa 226
Lobatoside O Actinostemma lobatum 113
Lonicerosides K, L, M Weigela subsessilis 227
Macedonoside E Glycyrrhiza uralensis 198
Meliomosides A–G Meliosma henryi 228
Oleiferasaponins C1, C2, C3 Camellia oleifera 229
Oleiferosides I–M Camellia oleifera 230
Oleiferosides N, O Camellia oleifera 231
Oleiferosides P–T Camellia oleifera 232
Pachystelanoside A Pachystela msolo 195
Perennisosides XIII–XIX Bellis perennis 233
Poliusaposides A, B, C Teucrium polium 234
Rotundinoside A Ilex rotunda 235
Serjanioside D Serjania marginata 236
Schefflerasides A, B Schefflera sessiliflora 237
Schekwangsiensides Ia, Ib, IIa, IIb, III–VI, VIIa, VIIb, VIII Schefflera kwangsiensis 238
Schisusaponins A–F Schima superba 201
Securiosides C, D, E Securidaca inappendiculata 239
Stauntosides G, H Stauntonia obovatifoliola 240
Vulgaside I Prunella vulgaris 241
Zanhasaponins D–H Zanha golungensis 242


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
Acanthophyllum laxiusculum 243
Anemone amurensis 202
Anemone taipaiensis 244
Bupleurum chinense 203
Calendula officinalis 245
Callicarpa kwangtungensis 246
Eclipta prostrata 247
Entada phaseoloides 248
Eryngium kotschyi 249
Gueldenstaedtia verna 190
Lecythis pisonis 250
Phryna ortegioides 251
Phyllanthus myrtifolius 252
Pittosporum tobira 253
Polygala crotalarioides 254
Planchonella obovata 255
Sanguisorba officinalis 256
Saponaria officinalis 257
Trifolium argutum 258


New oleanane esters from Barringtonia racemosa include racemosol B 605 and isoracemosol B 606 (ref. 259) and racemosols C 607 and D 608.260 Other new oleanane esters include the formyl ester of β-amyrin from Dichrocephala benthamii,261 the caffeoyl esters 609 and 610 from Waltheria indica262 and the coumaroyl ester 611 from Astilbe rivularis.263

image file: c9np00067d-u41.tif

There have been many reports of the biological activities of oleanane triterpenoids and their saponins including the antitumour activity264 and stem cell differentiation activity265 of oleanolic acid and the antitumour activity of ardipusilloside,266 boswellic acids,267 β-escin268 and raddeanin A.269 The biological properties of glycyrrhizic acid270 and other triterpenoids271 from Glycyrrhiza glabra have been reviewed.

Genicunolides A 612 and B 613 are taraxerane 11,12-epoxides from Euphorbia geniculata.272 The octacosanoyl ester of taraxerol has been found in Clerodendrum philippinum var. simplex.273 3β-Acetoxy-14-taraxeren-12-one 614 is a constituent of Manilkara zapota.171 The coumaroyl esters maesculentins A 615 and B 616 have been isolated from Manihot esculenta.274 The taraxastane 617 has been reported from Neoboutonia macrocalyx with unusual stereochemistry at C13 and C18.275 The 27(13→18)-abeotaraxerane derivative 618, from Pittosporum illicioides, is related to isoaleuritolic acid.276 Two taraxerane saponins with known genins have been reported from Euphorbia dracunculoides.277 9β,26-Epoxy-7-multiforen-3β-ol 619 has been isolated from Trichosanthes baviensis.278 Hainanenone A 620, from Drypetes hainanensis, is 23-nor-3-friedelanone279 and the 24-norfriedelane 621 has been found in Celastrus stylosus.174 Drypetes congestiflora is the source of 3α,16β-friedelanediol 622.280

image file: c9np00067d-u42.tif

7. The ursane group

The antitumour properties of ursolic acid have been well studied.281–283 Urmiensolide B 623 and urmiensic acid 624, from Salvia urmiensis, are 17,22-secoursane derivatives that showed significant antiproliferative activity.284 Further 17,22-secoursanes include the apoptosis-inducing 625 from Salvia urmiensis285 and 626 and 627 from Salvia syriaca.286 Rubus lambertianus is the source of the 18,19-secoursanes 628 and 629 together with the glucopyranosyl esters 630, 631 and 632.287 The related 18,19-secoursane 633 has been isolated from Rubus innominatus together with the ring-A contracted ursanes rubuminatus A 634 and B 635 and the ursanes 636 and 637.175
image file: c9np00067d-u43.tif

Hookerinoid C 638 from Pterocephalus hookeri288 and gelsenorursanes A 639–E 643 from Gelsemium elegans289 are 24-norursanes. Further 24-norursanes 644 and 645 have been obtained from Mostuea hirsuta.290 The 28-norursane 646 is a constituent of Agrimonia pilosa291 and the 28-norursane 647, with an aromatic ring E, is present in Gardenia jasminoides var. radicans.292 Ixeritriterpenol 648 has been reported from Ixeris chinensis with unusual stereochemistry at C13 and C19.293 The structure of 3β,12β,20β-trihydroxy-13(18)-ursen-28,19β-olide 649, from Ilex latifolia, was confirmed by X-ray crystallographic analysis.294 The related lactone 650 also occurs in Ilex latifolia.

image file: c9np00067d-u44.tif

Further simple ursane derivatives include silphanolic acids A 651, B 652 and D 653 from Silphium laciniatum,16 the 11-hydroperoxide 654 from Holarrhena curtisii,191 3β,6β,23-trihydroxy-12,20(30)-ursadien-28-oic acid 655 from Spermacoce latifolia,192 1α,2β,3β,19α-tetrahydroxy-12-ursen-28-oic acid 656 from Vitellaria paradoxa,295 the enone 657 from Codium dwarkense,296 2β,3β,19α,23-tetrahydroxy-12-ursen-28-oic acid 658 and its glycosyl ester from Nauclea officinalis,297 the related compounds 659, 660 and 661 and the glucosyl ester 662 from Oenothera maritima298 and the 27,28-dioic acids 663 and 664 and their 3-glucosides 665 and 666 from Crossopteryx febrifuga.299

image file: c9np00067d-u45.tif

New ursane saponins with new genins include bodiniosides E, F and G with the genins 667, 668 and 669, respectively, from Elsholtzia bodinieri,300 ilexpublesnin S with genin 670, with an unusual 20β configuration, from Ilex pubescens,301 pittangretosides C1 and L with the genins 671 and 672, respectively, from Pittosporum angustifolium302 and vulgaside II with genin 673 from Prunella vulgaris241 and saponins from Callicarpa kwangtungensis with genin 674,246 Ilex cornuta with genin 675 (ref. 303) and Ilex kudingcha with genin 676.304

image file: c9np00067d-u46.tif

Named ursane saponins with known genins include amphipaniculoside B from Amphilophium paniculatum,83 catunarosides K and L from Catunaregam spinosa,213 centellasaponins F and G from Centella asiatica,214 comastomasaponins J and K from Comastoma pedunculatum216 and rotundinosides B, C and D from Ilex rotunda.235 Unnamed saponins with known genins have been isolated from Cassia siamea,305 Clematoclethra scandens ssp. actinidioides,306 Firmiana simplex,307 Ilex cornuta,204,303,308 Ilex kudingcha,304 Ilex latifolia294 and Sanguisorba officinalis.256

Fagonicin 677, from Fagonia indica, is 3β,20β-dihydroxytaraxastan-28-al with an unusual stereochemistry at C13 (ref. 200) and genicunolide C 678, from Euphorbia geniculata, is 5-taraxastene-3β,9α,20α-triol.272 Ilexpublenin T, from Ilex pubescens is a taraxastane saponin with a known genin301 and a saponin from Clematis uncinata also has a known taraxastane saponin.309 The 13,27-cyclo ursane 679 has been identified in Ochradenus arabicus.310

image file: c9np00067d-u47.tif

8. The hopane group

The 17,21-secohopane derivative, scabanol 680, has been isolated from Gentiana scabra.311 Exotheols A 681 and 682, from Exothea paniculata, are 24-norhopane esters.312 3-Filicen-28-oic acid 683 is a constituent of the Chinese fern Lepidogrammitis drymoglossoides.313
image file: c9np00067d-u48.tif

9. Miscellaneous compounds

The unlikely structure 684 has been proposed for allotaraxerolide from Allophylus africanus.176 21β-Hydroxy-14-serratene-3,16-dione 685 has been isolated from Lycopodiella cernua together with the serratane esters 686 and 687.314 Lansioside D 688, from Lansium domesticum, is a derivative of the 21,22-seco-onocerane lansiolic acid.315 Lansioside D 688 showed potent activity against Gram-positive bacteria.
image file: c9np00067d-u49.tif

Six malabaricane derivatives 689–694 have been obtained from Ailanthus malabarica, including two containing cyclobutane rings.316 Further malabaricanes 695 and 696 have been found in Bursera microphylla.317 The isomalabaricane derivatives stellettins N 697, O 698 and P 699 have been identified in extracts of the marine sponge Stelletta tenuis.318 All three stelletins showed significant cytotoxic activities. Stelletin N is a duplicate name.

image file: c9np00067d-u50.tif

Iris tectorum is the source of several iridal triterpenoids including iritectols C 700–F 703 and the 22-epimers 704, 705 and 706 (ref. 319) and polycycloiridals A 707–D 710.320

image file: c9np00067d-u51.tif

10. Conflicts of interest

There are no conflicts of interest.

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