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

• References

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Abstract

Covering: 2012. Previous review: Nat. Prod. Rep., 2013, 29, 1028–1065

This review covers the isolation and structure determination of triterpenoids reported during 2012 including squalene derivatives, lanostanes, holostanes, cycloartanes, cucurbitanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, serratanes, isomalabaricanes and saponins; 348 references are cited.

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1. Introduction

There is continued interest in the anticancer activities of triterpenoids^1–3 and their potential for treatment or prevention of diabetes and Alzheimer's disease.⁴ The oral absorption and metabolism of triterpenoid saponins has been reviewed.⁵ Surveys of triterpenoids from Ceriops,⁶ and Ilex⁷ species and Sapindus mukorossi,⁸ have appeared.

2. The squalene group

Sapelenins G 1–J 4 are further anti-inflammatory squalene derivatives from the bark of Cameroonian Entandrophragma cylindricum.⁹ The highly oxidised squalene derivative 5 has been isolated from Peruvian Protium subserratum.¹⁰ The structures of saiyacenols A 6 and B 7, from the red alga Laurencia viridis, support the accepted pathway for the formation of the aplysiols.¹¹ The mechanism of triterpene biosynthesis in Botryococcus braunii has been reviewed.¹²

3. The lanostane group

New protostanes include alisol Q acetate 8 (ref. 13) and alisol X 9 (ref. 14) from Alisma orientale and the epoxy-ketone 10 from the leaves of Aglaia odorata.¹⁵ The tetraterpenes abiestetranes A 11 and B 12, from Abies fabri,¹⁶ and abibalsamins A 13 and B 14, from the oleoresin of Abies balsamea,¹⁷ appear to have arisen by Diels–alder cycloadditions of rearranged lanostanes with the monoterpene β-myrcene. The structure of 13 was confirmed by X-ray analysis. A series of rearranged lanostanes, neoabiestrines A 15–F 20, has been reported from Abies recurvata.¹⁸ The structures of neoabiestrine A 15 were confirmed by X-ray analysis. The compounds showed some cytotoxic activity. The mariesane lactone 21 has been obtained from Abies sibirica.¹⁹ The tetranor derivative 22 and the 3,4-secolanostane 23 have been found in Abies holophylla.²⁰

Pseudoferic acids A 24, B 25 and C 26 are interesting new 16,24-cyclised lanostanes from Pseudolarix kaempferi.²¹ The stems of Schisandra glaucescens contain the ring A-cleaved lanostanes schiglausins A 27-H 34, together with the intact derivatives schiglausins I 35 and J 36.²² The structure of schiglausin A 27 was confirmed by X-ray analysis. Schiglausin H 34 is the methyl ester of micranoic acid A. An impressive array of rearranged, ring A-cleaved and intact lanostanes, kadpolysperins A 37–N 50, has been isolated from Kadsura polysperma.²³ Kadcoccitones A 51 and B 52 are unusual rearranged lanostane derivatives from Kadsura coccinea where they occur with kadcoccitone C 53, whose structure was confirmed by X-ray analysis.²⁴ Secococcinic acids G 54–K 58 are further constituents of Kadsura coccinea.²⁵ Three esters 59–61 of 3-epidehydrotumulosic acid have been obtained from Wolfiporia extensa.²⁶ Other new lanostanes include lanosta-5,15-dien-3α-ol 62 from Arctium lappa²⁷ and inonotsuoxodiols B 63 and C 64, epoxyinonotsudiol 65 and methoxyinonotsutriol 66 from Inonotus obliquus.²⁸

Sarasinosides N–R are 30-norlanostane glycosides from the sponge Lypastrotethya sp. with the new genins 67, 68, 69 and the 30-nor-18(13 → 14)-abeo-derivative 70.²⁹ Scillanostaside F, with the new genin 71, and scillanostaside G, with a known tetranorlanostane genin, have been isolated from the bulbs of Scilla scilloides.³⁰

New compounds from Ganoderma sinense include the pentanor derivative ganosineniol A 72, ganoderic acids J_c73 and J_d74, ganodermatetraol 75, the glucosyl ester ganosinoside A 76 with a known genin, ganolucidic acid γ_a77, ganolucidate F 78, ganoderiol J 79 and methyl lucidenate H_a80.³¹ Ganodermacetal 81 is an acetonide from Ganoderma amboinense³² and lucialdehyde E 82 is a further compound from Ganoderma lucidum.³³ Reviews have appeared on the triterpenoids of Ganoderma lucidum^34,35 and lanostanes from fungi.³⁶

Astraodoric acids A 83–D 86 are metabolites of the mushroom Astraeus odoratus.²⁹ The structure of astraodoric acid B 84 was confirmed by X-ray analysis. The structure of astrakurkurol 87, from the Indian edible mushroom Astaeus hygrometricus, was also confirmed by X-ray analysis.³⁷ The corresponding lactone, astrakurkurone 88, was also obtained. Two highly acetylated lanostanes, coprinacins A 89 and B 90, have been reported from Coprinus cinereus.³⁸ Other fungal metabolites include 91–94 from Antrodia camphorate³⁹ and formitoside K 95, a glucoside with a new genin, from Fomitopsis nigra.⁴⁰

Cucumarioside A8 is a lanostane saponin with the new genin 96 from the sea cucumber Eupentacta fraudatrix.⁴¹ The sea cucumber Apostichopus japonicus is the source of several saponins, 26-nor-25-oxoholotoxin A₁ with the new genin 97 and holototoxins D–G.⁴² Holototoxins F and G have the new genin 98 while the genins of D and E are known. Cucumariosides B₁ and B₂⁴³ and cucumariosides H₂, H₃ and H₄,⁴⁴ from Eupentacta fraudatrix, all have known genins. Holostane saponins and their biological activity have been reviewed.⁴⁵

Interesting new structures continue to appear from Schisandra species. Schilancitrilactones A 99, B 100 and C 101 have been reported from Schisandra lancifolia.⁴⁶ The structures of all the schilancitrilactones were confirmed by X-ray analyses. New structures from Schisandra sphenanthera include preschisanartanins E 102–J 107 and sphenadilactones D 108–F 110.⁴⁷ Isoschicagenin C 111, preschisanartanins K 112–M 114, schisdilactones A 115–G 121 and schinesdilactones A 122 and B 123 constitute an impressive array of new derivatives from Schisandra chinensis.⁴⁸ Schiglausins K 124–O 128 are simple ring A-cleaved cycloartanes from Schisandra glaucescens.⁴⁹

An interesting approach to the “dereplication, residual complexity and rational naming” of the Actea triterpenoids has the potential to be applied to other groups of natural products with the same inherent problems.⁵⁰ Pseudolaridimers A 129 and B 130, from Pseudolarix amabilis, appear to have arisen by a Diels–Alder reaction involving a cycloartane and a labdane.⁵¹ The structure of 129 was confirmed by an X-ray analysis of the corresponding methyl ester. The cycloartanes lygodipenoids A 131 and B 132, from Lygodium japonicum, have an additional cyclopropane in their side chains.⁵² Thirty new cycloartane proteasome inhibitors 133–162 have been reported from Neoboutonia melleri.⁵³ An interesting UV light-induced inversion of the configurations at C-9 and C-10 was observed in this series. Caloncobic acids A 163 and B 164 and caloncobalactones A 165 and B 166 are constituents of the leaves of Caloncoba glauca.⁵⁴ Compounds 167–172 are new cycloartanes from the leaves of Homonoia riparia.⁵⁵ Neoabiestrines G 173–I 175 have been reported from Abies recurvata.¹⁸ The structure of neoabiestrine H 174 was confirmed by X-ray analysis. Other new cycloartanes include the trinor derivatives 176 and 177 from Abies holophylla,²⁰ rotundusolide C 178 from the rhizomes of Cyperus rotundus,⁵⁶179–182 from the aerial parts of Atemisia lagocephala,⁵⁷ three esters 183–185 of cyclomargenol from Krameria pauciflora,⁵⁸ euphonerins A 186–G 192 from the leaves of Euphorbia neriifolia,⁵⁹ cycloccidentalic acids A 193 and B 194 and the related saponins cycloccidentalisides I 195–V 199 from Cassia occidentalis,⁶⁰ glaucartanoic acids A 200 and B 201 from the fruit of Caloncoba glauca⁶¹ and 202 from the leaves of Aglaia exima.⁶² Compounds 203, 204 and the acetonide 205, a likely artefact, have been obtained from the resin of Commiphora opobalsamum.⁶³ The structures of 203 and 205 were confirmed by X-ray analyses.

New cycloartanes continue to be isolated from Cimicifuga species. Cimicifuga foetida is the source of compounds 206–209 (ref. 70) and of 24-epi-cimigenol-3-one 210 and the xyloside foetinoside 211.⁶⁴ The ring A-cleaved derivative 212, the cimigenol arabinosides 213–215, the 25-dehydrocimigenol arabinoside 216, compounds 217–219 and the shengmanol arabinoside 220 have all been isolated from the roots of Cimicifuga heracleifolia.⁶⁵ Other new compounds include the galactopyranosides 221–223, all with new genins, from the roots of Cimicifuga simplex⁶⁶ and isocimipodocarpaside 224 from Cimicifuga racemosa.⁶⁷

Six cycloartane saponins with the new genins 225–228 have been obtained from Astragalus angustifolius.⁶⁸ Cycloquivinoside A 229 is a new saponin from Astragalus chivensis.⁶⁹ The new genin cycloartane-3β,6α,16β,20S,24R,25-hexol 230 has been identified in the saponins of Astragalus stereocalyx⁷⁰ and in saponins from Astragalus schottianus.⁷¹ Nervisides A 231–C 233, from Nervilia fordii, all have new genins.⁷² Other cycloartane saponins with new genins include curculigosaponins N and O from Curculigo orchioides with the genin 234 (ref. 73) and two saponins from Thalictrum fortune with the genins 235 and 236.⁷⁴ The ring-A cleaved cycloartanes sootependial 237 and sootepenoic acid 238 have been isolated from the exudates of Gardenia sootepensis.⁷⁵ Novel cycloartane saponins with known genins include cycloascidoside from Astragalus mucidus,⁷⁶ cyclogaleginoside C from Astragalus galegiformis and cycloascauloside D from Astragalus caucasicus,⁷⁷ hareftosides A–D from Astragalus hareftae,⁷⁸ neoastragaloside I from Astragalus membranaceus⁷⁹ and unnamed saponins from Astragalus erinaceus.⁸⁰

A new nitrogen-containing cucurbitane, endecaphyllacin C 239, has been reported from the tubers of Hemsleya endecaphylla.⁸¹ Eleaocarpucins A 240–H 247 are 16,23-epoxy derivatives from Eleaocarpus chinensis.⁸² The new cucurbitanes jinfushanencins A 248 and B 249 occur in the tubers of Hemsleya penxianensis, together with the glycosides jinfushanosides E−K.⁸³ Jinfushanoside K has the new genin 250. Other new cucurbitanes include 251–253 from the fruit of Momordica charantia,⁸⁴ 10β-hydroxybryodulcosigenin 254 from Saniculiphyllum guangxiense,⁸⁵ six new compounds 255–260 from the leaves of Momordica charantia⁸⁶ and isoarvenin III 261 from the fruit of Trichosanthes kirilowii.⁸⁷ The 3,4-seco-cucurbitane 262 is a constituent of Russula lepida and Russula amarissima.⁸⁸ The unlikely 10α-methyl lanostane structure 263 has been proposed for a compound from Momordica charantia.⁸⁹ Perhaps the compound is a cucurbitane! Reviews have appeared on cucurbitacins and bottle gourd toxicity,⁹⁰ medicinally important plants of the Cucurbitaceae⁹¹ and the anticancer activity of the cucurbitacins.^92,93

4. The dammarane group

A review of ginsenoside derivatives and their antitumour activity has been published.⁹⁴ New saponins from the stems and leaves of Panax ginseng include ginsenosides Rh₁₄–Rh₁₇ with the new genins 264 (Rh₁₅₎ and 265 (Rh₁₇)⁹⁵ and ginsenosides Rh₁₈– Rh₂₀.⁹⁶ The new genin 266 of ginsenoside Rh₁₈ was also isolated together with the dammarane 267.⁹⁶ Two new saponins of 20S-protopanaxatriol have also been found in Panax ginseng together with the dammarane 268.⁹⁷ The biological activity of an artefact 269 from the acid hydrolysate of Panax ginseng has been investigated.⁹⁸ The hexanordammarane saponin, ginsenoside R₁₀270, has been isolated from the stems and leaves of Panax quinquefolium.⁹⁹

Saponins with the new genins 271 and 272 (ref. 100) and 273 (ref. 101) have been isolated from Gynostemma pentaphyllum. Cyclocariosides D–G, with the new genins 274 and 275, cyclocarioside H, with a known genin, and the dammarane cyclocarin A 276 are constituents of the leaves of Cyclocarya paliurus.¹⁰² Dammarane saponins with known genins have been isolated from the roots of Machilus yaoshansis.¹⁰³ This paper also reports a revision the C-23 configuration of Gynostemma pentaphylla saponins as in 277.

New dammaranes include the rearranged aglinone 278 and aglinin E 279 from the bark of Aglaia smithii,¹⁰⁴ the nor-derivatives 280–283 from Dysoxylum hainanense,¹⁰⁵ the 27-nor-derivative 284 from Dipterocarpus obtusifolius¹⁰⁶ and the two probable artefacts 285 and 286 from the leaves of Aglaia odorata.¹⁵

Novel dammarane saponins with known genins include acerbosides A and B from Hovenia acerba,¹⁰⁷ chikusetsusaponins FK₁–FK₇, FH₁, FH₂, FM and FT₁–FT₄ from Panax japonicus,^108,109 gypenbiosides A and B from Gynostemma pentaphyllum,¹¹⁰ 20R-pseudoginsenoside F₁₁ (ref. 111) and quinquenosides Ja and Jb¹¹² from Panax quinquefolium.

New compounds from the stem bark of Aphanamixis grandifolia include the tautomeric tirucallane cyclopentenones 287 and 288 (ref. 113) and the tirucallanes 289 and 290.¹¹⁴ Compounds 287 and 288 were originally named aphragranins A and B, names used by the authors for previous compounds. Their names have been changed to aphagraones A and B.¹¹⁵ Two further derivatives 291 and 292 were obtained from the leaves and twigs of Aphanamixis grandifolia.¹¹⁶ Some of these compounds clearly incorporate the extraction solvent. Aphanamgrandins A 293–J 302 constitute a series of 2,3-seco- and 3,4-seco-tirucallanes from the stems of Aphanamixis grandifolia.¹¹⁷ They were accompanied by the ring-A intact derivatives aphanamgrandin J 303 and the dienone 304. The structures of aphanamgramins A 293 and B 294 were confirmed by X-ray analyses. Other new tirucallanes include the 21-nor-derivative dysoxylentin A 305 from Dysoxylum lenticellatum,¹¹⁸ ixoroid 306 from the flowers of Ixora coccinea,¹¹⁹307 and 308 from the stem bark of Araliopsis synopsis,¹²⁰ capulin 309 from Capuronianthus mahafalensis,¹²¹310–312 from the stem bark of Melia toosendan,¹²² dysohainanin F 313 from Dysoxylum hainanense¹²³ and 24,25,26-trihydroxytirucall-7-en-3-one 314 from Salacia hainanensis.¹²⁴ The 19(10 → 9)-abeotirucallane 315 has been reported from Euphorbia mellifera.¹²⁵

Chisiamols G 316 and H 317 (ref. 126) and chisopanins L 318–O 321 (ref. 108 and 127) are new apotirucallanes from Chisocheton paniculatus. A series of compounds from the leaves and twigs of Melia toosendan includes the apoeuphane mesendanin K 322, the euphanes mesendanins L 323–P 327, the tirucallanes mesendanins Q 328–T 331 and the apotirucallane mesendanin U 332.¹²⁸ The apotirucallane 332 was also isolated from Dysoxylum hainanense and named dysohainanin E.¹²³ Other new apotirucallanes include piscidinones A 333 and B 334 from Walsura trifoliata,¹²⁹ agladorals A 335–E 339 from Aglaia odorata var. microphyllina¹³⁰ and trichostemonate 340 from the roots of Walsura trichostemon.¹³¹ The structure of 340 was confirmed by X-ray analysis. Toonaciliatavarins A 341–H 348 are constituents of Toona ciliata.¹³²

4.1 Tetranortriterpenoids

A review of the structures and biological activities of limonoids from Cipadessa species has been published.¹³³ Walsucochinoids A 349 and B 350 are rearranged limonoids, with an aromatic ring D, from Walsura cochinchinensis.¹³⁴ Andhraxylocarpins A 351, B 352, C 353 and E 354 are new skeletal types from Xylocarpus granatum.¹³⁵ The structures of 349, 351 and 353 were confirmed by X-ray analyses. Andhraxylocarpin D 355 is the same as chisomicin A, published in 2011. Hortia oreadica is the source of the interesting rearranged limonoids 356–363, related to the known hortiolide A.¹³⁶ The structure of hortiolide C 358 was confirmed by X-ray analysis. The configurations at C-5 and C-10 of hortiolide E 362 and 12-hydroxyhortiolide E 363 are wrongly drawn in the paper. Carapanolides A 364 and B 365 are 9,10-seco mexicanolide derivatives from the seeds of Carapa guianensis.¹³⁷ Other new structural types include citriolide A 366 from the seeds of Citrus reticulate,¹³⁸ aphanamixoid A 367 from Aphanamixis polystachya¹³⁹ and chukrasones A 368 and B 369 from Chukrasia tabularis.¹⁴⁰ The structure of aphanamixoid A 367 was confirmed by X-ray analysis. It was accompanied in the extract by aphanamixoid B 370.

Toonayunnanins A 371–L 382 constitute a group of assorted limonoids from the leaves of Toona ciliata var. yunnanensis.¹⁴¹ Toonayunnanin I 378 is the same as toonaciliatin P, published in 2011. Another group of compounds, toonaciliatones B 383–F 387, has been obtained from the seeds of Toona ciliata.¹⁴² Meliatoosenins E 388, F 389, I 390, J 391, L 392–N 394 and P 395–S 398 are new compounds from the fruit of Melia toosendan.¹⁴³ Meliatoosenins G, H, K and O, claimed as new compounds, have all been published previously. Other new compounds include andirolides H 399–P 407 from Carapa guianensis flowers,¹⁴⁴ ceramicines J 408–L 410 from Chisocheton ceramicus¹⁴⁵ and walsuranins A 411–C 413 from Walsura yunnanensis.¹⁴⁶

The ring A-cleaved compounds, aphanalides A 414–H 421, have been reported from the fruit of Aphanamixis polystachya.¹⁴⁷ The structures of aphanalides A 414 and C 416 were confirmed by X-ray analyses. Aphanagranins A 422–D 425 are constituents of Aphanamixis grandifolia.¹⁴⁸ Other species producing multiple new compounds include Munronia unifoliata with munronoids A 426–J 435 (ref. 149) and K 436–O 440 (ref. 150) and Dysoxylum hainanense with dysohainanins A 441–D 444.¹²³ 6-O-Deacetylseverinolide 445 is a constituent of Atalantia buxifolia.¹⁵¹

The seemingly unending flow of phragmalin/bussein derivatives and variants continues and is matched only by the proliferation of confusing trivial names. These points are well illustrated by Chukrasia tabularis and Chukrasia tabularis var. velutina, the sources of chubularisins A 446–R 463,¹⁵² chuktabrins C 464–J 471 and chuktabularins U 472–X 475,¹⁵³ tabulalins G 476–I 478,¹⁵⁴ chukvelutins D 479–F 481 (ref. 155) and R310B8 482 and velutinalides A 483 and B 484.¹⁵⁶ Chabularisin O 460 is the same as chuktabularin V 474. The structure of chuktabrin C 464 was confirmed by X-ray analysis. Heytrijumalins A 485–I 493 have been isolated from the twigs and leaves of Heynea trijuga.¹⁵⁷ Other new compounds in this group include hisomicines D 494 and E 495 from Chisocheton ceramicus,¹⁵⁸ malayanines A 496 and B 497 from Chisocheton erythrocarpus,¹⁵⁹ senegalensions A 498–C 500 from Khaya senegalensis,¹⁶⁰ kotschyins D 501–H 505 from Pseudocedrela kotschyi,¹⁶¹ soymidins A 506 and B 507 from Soymida febrifuga¹⁶² and swietenin J 508 from Swietenia macrophylla.¹⁶³ Five new mexicanolide derivatives, heytrijunolides A 509–E 513, have been obtained from Heynea trijuga.¹⁶⁴ Mollucensins R 514–Y 521 are new mexicanolide and phragmalin derivatives from the seeds of Xylocarpus moluccensis.¹⁶⁵

4.2 Quassinoids

The compounds isolated from Brucea javanica and their pharmacology have been reviewed.¹⁶⁶ Bruceanic acids E 522 and F 523, buruceanic acid E methyl ester 524, javanic acids A 525 and B 526 and javanicolide H 527 are new compounds from the seeds of Brucea javanica.¹⁶⁷ Other new quassinoids include picrasin K 528 from Quassin amara¹⁶⁸ and odyendanol 529 from the fruit of Odyendyea gabonensis.¹⁶⁹

5. The lupane group

Reviews covering the sources and biological properties of betulinic acid¹⁷⁰ and the antineoplastic effects of lupeol¹⁷¹ have appeared. The 3,4-secolupane derivatives acanthosessiligenins I 530 and II 531 and acanthosessiliosides A 532–F 537 have been isolated from the fruit of Acanthopanax sessiliflorus.¹⁷² The 17,18-secolupane 538 has been found in the roots of Taraxacum platycarpum together with 3β-acetoxylup-18-en-21-one 539, the neolupane derivatives 540–542 and the migrated lupane 543.¹⁷³ Lup-20(29)-ene-2β,3β-diol 544 is a constituent of Salacia hainanensis¹²⁴ and the related ketones 545 and 546 have be found in Fagus hayatae.¹⁷⁴ Other simple lupane derivatives include glochitriol 547 from Glochidion lanceolarium,¹⁷⁵ bengalensinone 548 from Ficus bengalensis,¹⁷⁶ 3β-hydroxylupane-28,29-dioic acid 549 from Aglaia duperreana¹⁷⁷ and the norlupane derivatives 550, 551 and 552 from Dipterocarpus obtusifolius.¹⁰⁶

Two lupane saponins with the new genin 553 have been isolated from Schefflera venulosa.¹⁷⁸ New lupane saponins with known genins include ilekudinchoside E from Ilex kudincha,¹⁷⁹ stellatosides C, D and E, the methyl esters of stellatosides B and C and thurberoside A from Stenocereus eruca¹⁸⁰ and unnamed saponins from Liquidambar formosana¹⁸¹ and Cichorium intybus.¹⁸²

Oleanderocioic acid 554, a lupane ester with the unusual cis-4-acetylcinnamic acid, is claimed to be a constituent of Nerium oleander.¹⁸³ Other new lupane esters include the nonanoyl ester of lupeol 555 from Dorstenia harmsiana,¹⁸⁴ kurramanoic acid 556 from Nepeta clarkei,¹⁸⁵ the myristoyl esters 557 from Glochidion wrightii¹⁸⁶ and 558 from Sinocalamus affinis,¹⁸⁷ the cis-feruloyl ester 559 from Panax ginseng,¹⁸⁸ the palmitoyl ester 560 from Cichorium intybus¹⁸² and the stearoyl ester 561 from Ocimum sanctum.¹⁸⁹

6. The oleanane group

Reviews have appeared on the origins, biosynthesis and biological activity of oleanolic acid¹⁹⁰ and the beneficial effects of arjunolic acid in type 1 diabetes.¹⁹¹Fagus hayatae is the source of the 1,10-secooleanane derivative 562 where it is found with 3α,23-dihydroxy-3-oxoolean-12-en-28-oic acid 563 and 3β,12α,23-trihydroxyoleanan-28,13β-olide 564.¹⁷⁴ Sentulic acid from Sandoricum koetjape has been identified as 3,4-secooleana-4(23),12-diene-3,27-dioic acid 565.¹⁹² The 17,22-secooleanenol 566, from Pyrenacantha kaurabassana, has the unusual 18αH-configuration.¹⁹³ Zizimauritic acids A 567, B 568 and C 569 are ring-A contracted 20,21-secooleanane derivatives from Ziziphus mauritiana.¹⁹⁴ The zizimauritic acids also have the 18αH-configuration. A ring-E contracted oleanane derivative 570 has been isolated from the bark of Diospyros decandra.¹⁹⁵ Platycodonoids A 571 and B 572 are 28-noroleanane derivatives from the roots of Platycodon grandiflorum.¹⁹⁶ The 30-nor derivatives euscaphic acids G 573 and H 574, together with their likely precursor euscaphic acid I 575, are present in Euscaphis japonica.¹⁹⁷ Further noroleanane derivatives include 30-noroleanolic acid 576 from Olea europea,¹⁹⁸ the 24,30-dinor derivatives 577 and 578 and the 24-nor compounds 579 and 580 from the roots of Paeonia emodi¹⁹⁹ and 581 from Pilea cavaleriei.²⁰⁰ A 4900 year old oak wood sample found in a freshwater sediment has produced six noroleanane derivatives 582–587 all lacking oxygenation at C-3.²⁰¹

Several olean-18-ene derivatives have been identified including olean-18-ene-1β,2α,3β-triol 588 from Salvia atropatana,²⁰²589–596 from Cassine xylocarpa, 597 from Maytenus jelskii,²⁰³ olean-18-ene-1α,3β-diol 598 from Juglans sinensis²⁰⁴ and 2α,3α,24-trihydroxyolean-18-en-28-oic acid 599 from Eucalyptus exserta.²⁰⁵ The stem bark of Terminalia arjuna is the source of oleaterminaloic acids A 600, B 601 and C 602 together with the 3-glucoside oleaterminalide 603.²⁰⁶ Other new simple oleanane derivatives include pseuderanic acid 604 from Pseuderanthemum carruthersii,²⁰⁷ punicaone 605 from Punica granatum,²⁰⁸ turformosinic acid 606 from Turpinia formosana,²⁰⁹ 3β,23,28-trihydroxyolean-12-en-11-one 607 from Aster yomena,²¹⁰ 3α,29-dihydroxyolean-12-ene-23,28-dioic acid 608 from Schefflera farinosa,²¹¹ oleana-9(11),12-diene-1β,3β-diol 609 from Salvia xanthocheila,²¹² 1-epi-castanopsol 610 from Simira glaziovii,²¹³ the 29,22-olide 611 from Celastrus orbiculatus²¹⁴ and the epoxy aldehyde 612 from Tetraena mongolica.²¹⁵

New oleanane esters include the caffeoyl derivatives 613–615, from Tetraena mongolica,²¹⁵ the coumaroyl ester 616 from Rubia schumanniana,²¹⁶ the ferruloyl ester 617 from Saniculiphyllum guangxiense,⁸⁵ the palmitates 618 from Anemone rivularis,²¹⁷619 from Barringtonia asiatica²¹⁸ and 620 from Lobelia sessilifolia.²¹⁹ Four esters 621–624 of the 19(18 → 17)-abeo-28-noroleanane phlomstetraol B have been isolated from Leonurus heterophyllus.²²⁰

Two oleanane saponins, with the new genin olean-12-ene2β,15α,23-triol 625, have been isolated from Ammannia auriculata.²²¹ Antoniosides E–J are oleanane saponins from Antonia ovata.²²² Antioniosides E–H have new genins that are esters of olean-12-ene-3β,15α,16α,21β,22α,23,28-heptol 626. Sorbifoliasides G–J, from Xanthoceras sorbifolia, have known genins and sorbifoliaside K has the new genin oleana-12,15-diene-3β,21β,22α,28-tetrol 627.²²³ A variety of new 30-noroleanane genins, 628–631, are included in akemisaponins A–K from Akebia trifoliate.²²⁴ Two saponins from Camellia japonica have been assigned the names camelliosides E and F that have been used previously.²²⁵ Camellioside E has the new genin 28-norolean-12-ene-3β,16α,17β-triol 632. Four saponins have been isolated from Astragallus angustifolius including the new genin olean-12-ene-3β,21β,22α,24,29-pentol 633.⁶⁸

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

Table 1

Trivial name	Plant species	Ref.
Aesculiosides G1–G16	Aesculus glabra	226
Afrocyclamins A and B	Cyclamen africanum	227
Anemonerivulariside A	Anemone rivularis	228
Asperosaponins A–C	Dipsacus Asper	229
Besylvosides I–VI	Aegilops geniculata	230
Bigeloviis A and B	Salicornia bigelovii	231
Bodiniosides C and D	Elsholtzia bodinieri	232
Bonarienosides A–E	Hydrocotyle bonariensis	233
Bunkankasaponin F	Xanthoceras sorbifolia	234
Centelloside D	Centella asiatica	235
Chakasaponin IV	Camellia sinensis	236
Dumortierinoside A methyl ester	Isolatocereus dumortieri	237
Elmalienosides A–C	Cephalaria elmaliensis	238
Entadosides A–D	Entada phaseoloides	239
Gardenisides A–C	Gardenia jasminoides	240
Guaianin P	Guaiacum officinale	241
Gummososide A, gummososide A methyl ester	Stenocereus alamosensis	237
Hareftoside E	Astragalus hareftae	78
Hederifoliosides A–E	Cyclamen hederifolium	242
Ilexsaponins D–F	Ilex pubescens	243
Ilexsaponin D (duplicate name)	Ilex pubescens	244
Kalopanaxsaponins L and M	Kalopanax pictus	245
Lobatosides L and M	Actinostemma lobatum	246
Lonimacranthoides IV and V	Lonicera macranthoides	247
Mimengosides H and I	Buddleja lindleyana	248
Oleiferasaponin A1	Camellia oleifera	249
Paviosides A–H	Aesculus pavia	250
Pleurosaponins A–K	Pleurospermum kamtschaticum	251
Polygalasaponins LI–LIII	Polygala japonica	252
Raddeanosides R20–R22	Anemone raddeana	253
Sanchakasaponins A–D	Camellia japonica	254
Sanchakasaponins E–H	Camellia japonica	255
Sandrosaponin XI	Ferula hermonis	256
Senaciapittosides A and B	Pittosporum senacia	257
Silenoviscoside F	Silene viscidula	258
Sorbifoliasides A–F	Xanthoceras sorbifolia	234
Teaseedsaponins A–L	Camellia sinensis	259
Treleaseside A	Stenocereus eruca	180

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

Table 2

Plant species	Ref.
Abrus precatorius	260
Abuta grandifolia	261
Acanthopanax senticosus	262
Acanthophyllum gypsophiloides	263
Alhagi maurorum	264
Anemone amurensis	265
Aralia elata	266
Aralia taibaiensis	267
Ardisia gigantifolia	268
Callicarpa integerrima	269
Chenopodium foliosum	270
Clematis argentilucida	271 and 272
Cyperus rotundus	273
Dizygotheca elegantissima	274
Eragrostis tef	275
Grangea maderaspatana	276
Gymnema sylvestre	277
Gymnocladus chinensis	278
Gypsophila trichotoma	279
Kalopanax pictus	245
Kalopanax septemlobus	280
Maesa lanceolata	281
Patrinia scabiosifolia	282
Pometia pinnata	283
Salicornia europaea	284
Salicornia herbacea	285
Samanea saman	286
Sideroxylon obtusifolium	287
Tarenna grevei	288
Wedelia chinensis	289
Xanthoceras sorbifolia	290

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Pachanosides I1 and D1 are pachanane saponins with known genins from Isolatocereus dumortieri.²³⁷ The structures of the 13,27-cyclized oleananes donellanic acids A 634, B 635 and C 636, from Donella ubanguiensis, were all established by X-ray analyses.²⁹¹ The donellanic acids are accompanied by two further 13,17-cyclized compounds that have been assigned the tentative structures 637 and 638. Ilelic acid B 639 is a rearranged oleanane with a seven-membered C-ring from Ilex latifolia.²⁹² Four taraxerane derivatives 640–643 have been identified in Saussurea graminea.²⁹³

Cassinolide 644, from Cassine xylocarpa, is a 2,3-secofriedelan-3,24-olide derivative.²⁹⁴Maytenus robusta is the source of the 3,4-secofriedelan-3,11β-olide 645 (ref. 295) and friedelane-3β,11β-diol 646.²⁹⁶ Reissantiadiol, from Reisantia grahamii, has been identified as friedelane-2α,3α-diol 647.²⁹⁷ Other simple friedelane triterpenoids include 30-hydroxyfriedel-1-en-3-one 648 from Salacia hainanensis,¹²⁴649–653 from Celastrus vulcanicola and 654–658 from Maytenus jelskii²⁹⁸ and glaucalactone 659 from Caloncoba glauca.⁶¹

A review of the pharmacology of celastrol, a norfriedlane derivative, has been published.²⁹⁹ Hypoglaside A 660 is a dinorfriedelane glucoside from Tryperygium hypoglaucum.³⁰⁰Celastrus orbiculatus is the source of a range of norfriedelane and methyl-migrated derivatives.³⁰¹ The 25(9 → 8)-abeo norfriedelane 661 and the 25(9 → 7)-abeo derivative 662 are accompanied by the 8,14-seco compounds 663 and 664. A biosynthetic pathway to these rearranged friedelane derivatives has been proposed. Also present in Celastrus orbiculatus are the “dimeric” norfriedelanes celastrolines Aα 665 and Aβ 666 and isocelastroline Aα 667, together with celastrolines Bα 668 and Bβ 669 that have a linkage to a podocarpane derivative.

7. The ursane group

Ursane triterpenoids have shown potential as anticancer drugs.³⁰² Reviews on the anticancer activities of ursolic acid³⁰³ and acetyl-11-keto-β-boswellic acid (AKBA)³⁰⁴ have been published.

The 18,19-secoursane derivative 670 has been isolated from the bark of Diospyros decandra together with 671.¹⁹⁵ The 17,22-seco derivative 672 has been found in both Salvia palaestina and Salvia syriaca.³⁰⁵ Euscaphic acids J 673, K 674 and L 675 have been isolated from Euscaphis japonica.¹⁹⁷ Euscaphic acid L 675 has a contracted ring-A. Negundonorins A 676 and B 677, from Vitex negundo, are 24-nor and 28-noruranes, respectively.³⁰⁶ Further 24-norursanes include ulmoidol A 678 from Eucommia ulmoides³⁰⁷ and the related compounds 679 and 680 from Dipsacus chinensis.³⁰⁸ 30-Norurs-11-en-3α-ol 681 has been identified in the roots of Alhagi camelorum.³⁰⁹

6β,20β-Dihydroxyurs-12-en-28-oic acid 682, from leaves of Psidium guajava, is unusual as it lacks oxygenation at C-3.³¹⁰ The structure of 3β,19α,23,24-tetrahydroxyurs-12-en-28-oic acid 683, from Nauclea officinalis, was confirmed by X-ray analysis.³¹¹ It is accompanied by the corresponding 2β,3β,19α,24-tetrahydroxy compound 684. Further simple ursane derivatives include the acetal 685 from Juglans sinensis,²⁰⁴ rhododendric acid A 686 from Rhododendron brachycarpum,³¹² uncariursanic acid 687 from Uncaria macrophylla,³¹³ 2α,3β,6β,23-tetrahydroxyursa-12,18-dien-28-oic acid 688 from Kadsura marmorata,³¹⁴ 2α,3β,6β,20β,23,30-hexahydroxyurs-12-en-28-oic acid 689 and psiguanins B 690, C 691 and D 692 from Psidium guajava,³¹⁵ the 2α,3β,21α-trihydroxy derivative 693 and the 24-aldehyde 694 from Berberis koreana,³¹⁶ the 1α,3α-dihydroxy derivatives 695–697 from Euphorbia kansuensis,³¹⁷ the 3-ketone 698 from Albizzia lebbeck,³¹⁸ loxanic acid 699 and its acetate 700 from Eucalyptus loxophleba³¹⁹ and tolpidiol B 701 from Tolpis proustii and Tolpis lagopoda.³²⁰

Kirmanoic acid 702, from Nepeta clarkei, is an unusual alkylphenyl ether.¹⁸⁵ New ursane esters include the isoferuloyl ester 703 from Eucalyptus exserta,²⁰⁵ ehretiolide 704 from Ehretia longifolia,³²¹ the 30-cis-coumaryl ester 705 from Rubia schumanniana,²¹⁶ 3β-tetradecanoyloxyurs-12-en-28,19β-olide 706 from Lysimachia clethroides³²² and 3-epi-cecropic acid 707 from Dipterocarpus obtusifolius.¹⁰⁶

Sanguisoside A is an ursane saponin from Sanguisorba officinalis with the new 18,19-seco-ursane genin 708.³²³ Centelloside E from Centella asiatica has the new genin 709 (ref. 235) and the genins 710 and 711 are present in saponins from Actinidia valvata.³²⁴

Ursane saponins with known genins include asphorins A and B from Asphodelus tenuifolius,³²⁵ asprellanosides A and B from Ilex asprella,³²⁶ elasticoside from Ficus elastica,³²⁷ ilekudinchosides F and G from Ilex kudincha,³²⁸ ilemaminosides A and B from Ilex mamillata,³²⁹ ilexasosides A–H from Ilex asprella,³³⁰ phillyriside A from Stenocereus eruca,¹⁸⁰ and unnamed saponins from Diospyros decandra,¹⁹⁵Juglans sinensis,²⁰⁴Lantana camara³³¹ and Psidium guajava.³³²

The taraxastane hydroperoxide derivatives 712 and 713 have been isolated from the roots of Taraxacum platycarpum.¹⁷³ Psiguanin A, which is 2α,3β-dihydroxytaraxast-20-en-28-oic acid 714, has been found in the leaves of Psidium guajava.³¹⁵ Other new taraxastane derivatives include chlorotolpidiol 715 and tolpidiol A 716 from Tolpis proustii and Tolpis lagopoda,³²⁰ pergularines A 717 and B 718 from Pergularia tomentosa³³³ and calotroprocerol A 719, calotroprocerone A 720 and calotroproceryl acetates A 721 and B 722 from Calotropis procera.³³⁴ Two taraxastane saponins with known genins have been found in the roots of Ilex pubescens.³³⁵

The 27(14 → 13)-abeo-urs-14-enone derivative 723, from Rubia schumanniana, has the unusual β-configuration for the migrated methyl.²¹⁶ The rearranged ursanes ilelic acids A 724, C 725 and D 726 have been isolated from Ilex latifolia.²⁹² The structure of ilelic acid D 726 was confirmed by X-ray analysis.

8. The hopane group

3,4-Secohop-22(29)-en-3-oic acid 727 has been isolated from Maytenus robusta.²⁹⁵ The scale insect pathogenic fungus Aschersonia calendulina is the source of two hopane metabolites 728 and 729.³³⁶ The leaves of Hybanthus austro-caledonicus produce 3-epiwoodwardinic acid 730.³³⁷ Plakohopanoid 731, a C₃₂ hopanoid ester of a manosyl myoinostol, has been isolated from the sponge Plakortis cf. lita.³³⁸ The structure of plakohopanoid 731 implies that it is of bacterial origin. This is the first example of a biologically produced C₃₂ hopanoic acid. Such acids were considered to only be geohopanoids formed by abiotic degradation of bacteriohopanoids. Oppositifolone 732, from Glinus oppositifolius, has a 29(22 → 21)-abeo-hopane skeleton and is the 3-ketone of spergulagenin A.³³⁹

Pteroxygonumnol 733, from the roots of Pteroxygonum giraldii, has been identified as 2β,25 : 19β,28-diepoxyarborin-9(11)-ene-3β,7β-diol.³⁴⁰ Five 25-norarborinane derivatives 734–738 have been isolated from bamboo stems, Sinocalamus affinis.¹⁸⁷ The structure of 734 was confirmed by X-ray analysis. Atalantia retusa is the source of the 17,21-seco-arborane derivative retusinol 739.³⁴¹ Peniciside 740 is a fernane metabolite of Penicillium sp.169³⁴² and 3β-acetoxyfern-7-en-6-one 741 is a constituent of Scorzonera latifolia.³⁴³

9. Miscellaneous compounds

The unlikely structure 742 has been proposed for erucaoic acid from Sonchus eruca.³⁴⁴ The club moss Lycopodium phlegmaria is the source of the serratane esters lycophlegmariols A 743–D 746 (ref. 345) and four esters 747–750 have been found in Palhinhaea cernua (syn. Lycopodium cernuum).³⁴⁶ The D:B-friedobaccharane derivatives leonatriol 751 and the corresponding ketone leonatriolone 752 have been isolated from Cassine xylocarpa and Celastrus vulcanicola, respectively.²⁹⁴ Globostelletins J 753–S 761, from the marine sponge Rhabdastrella globostellata, are isomalabaricanes with cyclopentane side chains.³⁴⁷

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