Triterpenoids. 2011.pdf

View Article Online / Journal Homepage / Table of Contents for this issue C NPR Dynamic Article Links < Cite this: Nat. Prod. Rep., 2011, 28, 1087 REVIEW Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. www.rsc.org/npr Triterpenoids Robert A. Hill* and Joseph D. Connolly Received 8th February 2011 DOI: 10.1039/c1np00012h Covering: January 2009 to December 2009. Previous review: Nat. Prod. Rep., 2010, 27, 79–132. This review covers the isolation and structure determination of triterpenoids, including squalene derivatives, protostanes, lanostanes, holostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, serratanes and saponins; 278 references are cited. 1 2 3 4 4.1 4.2 5 6 7 8 9 10 Introduction The squalene group The lanostane group The dammarane group Tetranortriterpenoids Quassinoids The lupane group The oleanane group The ursane group The hopane group Miscellaneous compounds References 1. Introduction The pharmacological properties of triterpenoids continue to be of interest with reviews appearing on their antitumour,1,2 antiHIV3 and antiviral activities.4 Triterpenoid saponins with antitumour5 and apoptosis-inducing6 activities have been surveyed, as have the biological activities of triterpenoid saponins from Chenopodium quinoa,7 Pulsatilla species8 and the Leguminosae family.9 The interest in saponins has prompted reviews of their synthesis10,11 and biosynthesis.12 Further reviews have covered the biological activities of frankincense-derived triterpenoids,13 oleanane triterpenoids from soy14 and pentacyclic triterpenoids from the medicinal plants Centella asiatica15 and Terminalia arjuna.16 2. The squalene group Aplysqualenols A 1 and B 2, squalene-derived polyethers from the Caribbean sea slug Aplysia dactylomela, show antiviral and antitumour activity.17 Protostadienol synthase, the cyclase that transforms squalene oxide into protosta-17(20)E,24-dien-3b-ol 3, Department of Chemistry, Glasgow University, Glasgow, UK G12 8QQ This journal is ª The Royal Society of Chemistry 2011 the precursor of helvolic acid 4, has been isolated from the pathogenic fungus Aspergillus fumigatus.18 Compound 3 is the major product of the reaction (90%), with 5% of the 13(17)-isomer also being produced. 3. The lanostane group The highly oxygenated lanostanes, ganoderic acids GS-1 5, GS2 6, GS-3 7, 20-dehydrolucidenic acid N 8 and 20-hydroxylucidenic acid A 9, from the fruiting bodies of Ganoderma sinense, show anti-human immunodeficiency virus-1 protease activity.19 3-O-Acetylganoderic acid B 10, 8b,9a-dihydroganoderic acid C 11 and 3-O-acetylganoderic acid K 12 are further constituents of the mycelium of Ganoderma. lucidum cultured by submerged fermentation.20 Two ethyl esters of known ganoderic acids were also obtained. Three unusual lanostane-farnesylhydroquinone conjugates, ganosinensins A–C 13–15, have been isolated from the fruiting bodies of Ganoderma. sinense.21 Igniarens A–D 16–19 are constituents of the fruiting bodies of Phellinus igniarius.22 The fungus Phellinus gilvus contains gilvsins A–D 20–23.23 The structure of gilvsin A 20 was confirmed by X-ray analysis. Two ring A-cleaved derivatives, poricoic acids AE 24 and CE 25, have been isolated from the surface layer of Poria cocos.24 The antitumourpromoting effects of a series of lanostane acids from Poria cocos have been investigated.25 These compounds include 16a,27-dihydroxytrametenoic acid 26, 25-hydroxy-3-epitumulosic acid 27, 16a,25-dihydroxyeburicoic acid 28, 25methoxyporicoic acid A 29, 26-hydroxyporicoic acid DM 30, 25-hydroxyporicoic acid C 31, poricoic acid GM 32, poricoic acid HM 33 and 6,7-didehydroporicoic acid H 34. Two antibacterial compounds 35 and 36 have been obtained from the wood-rotting fungus Fomitopsis rosea.26 Other new compounds from fungal sources include fomefficinic acids F 37 and G 38 and fomefficinols A 39 and B 40 from Fomes officinalis27 and inoterpenes A–F 41–46 from the sclerotia of Inonotus obliquus.28 Nat. Prod. Rep., 2011, 28, 1087–1117 | 1087 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. 1088 | Nat. Prod. Rep., 2011, 28, 1087–1117 View Article Online This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. This journal is ª The Royal Society of Chemistry 2011 View Article Online Nat. Prod. Rep., 2011, 28, 1087–1117 | 1089 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. 1090 | Nat. Prod. Rep., 2011, 28, 1087–1117 View Article Online This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online Other lanostanes reported this year include neoabieslactones A–F 47–52 from Abies chinensis,29 coccinones A–D 53–56 and coccinilactone B 5730 and secococcinic acid F 5831 from the roots of Kadsura coccinea, cashmirols A 59 and B 60 from Sorbus cashmiriana,32 3b-acetoxylanosta-7,24-diene 61, lanosta-7,24dien-3-one 62, 3b-acetoxylanosta-7,25-dien-24-ol 63 (epimeric mixture) and 3b-acetoxylanosta-8,25-dien-24-ol 64 (epimeric mixture) from Mikania aff. jeffreyi,33 the 29-nor-derivatives This journal is ª The Royal Society of Chemistry 2011 65 and 66 from the leaves of Freycinetia formosana34 and 24methyllanost-25-ene-3b,24S-diol 67 from the aerial parts of Skimmia laureola.35 Schisanlactone H 6836 and schisanlactone G 6937 are new constituents of Schisandra sphenanthera. The leaves of Markhamia lutea afforded the cycloartanes musambins A–C 70–72 and the corresponding xylosides musambiosides A–C 73–75.38 The compounds showed antiplasmodial and antitrypanosomal activity. Wild chimpanzees Nat. Prod. Rep., 2011, 28, 1087–1117 | 1091 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online include this plant in their diet. Musambin B 71 has also been isolated from Combretum leprosum together with 3b,16adihydroxycycloart-24-en-28-oic acid 76.39 Dikamali gum, the resin of Gardenia gummifera and G. lucida, contains dikamaliartanes A–F 77–82.40 Dikamaliartane B has already been reported from Gardenia aubryi.41 Sootepins A–E 83–87 are cytotoxic constituents of Gardenia sootepensis.42 The structure of sootepin A 83 was confirmed by X-ray analysis. Sootepin E 87 is the known compound coccinelane A. The spirocycloartane derivatives 88–90 have been isolated from Kleinhovia hospita together with cycloarta-1,24-diene-3,23dione 91.43 Several more variants of complex cycloartane derivates from Schisandra species have been reported. Schigrandilactones A–C 92–94 were obtained from Schisandra grandiflora.44 The structures of schigrandilactones A 92 and C 94 were confirmed by X-ray analyses. The structure of schilancidilactone A 95, from Schisandra lancifolia, was also confirmed by X-ray analysis.45 It was accompanied by its 20-epi-derivative, schilancidilactone B 96. Propindilactones K–O 97–101, from Schisandra propinqua var. propinqua,46 are based on an 18(13 / 14)-abeoschiartane skeleton. The shiartane skeleton is a 3,4:9,10-disecocycloartane 1092 | Nat. Prod. Rep., 2011, 28, 1087–1117 skeleton that is found in many of the Schisandra terpenoids. The ring A-cleaved cycloartanes, schisanbilactones A 102 and B 103 have been isolated from stems of Schisandra bicolour.47 The cycloartane derivatives 104 and 105, from Cretan propolis,48 and 106 and 107, from Myanmar propolis,49 show antimicrobial and cytotoxic activity, respectively. Other simple cycloartanes include 25-hydroxycycloart-22E-en-3-one 108 and cycloart-23Z-ene-3a,25-diol 109 from the leaves and stems of Fritillaria hupehensis,50 the formate 110 and the decadienoate 111 from Euphorbia retusa,51 cycloeucalenol linolenate 112 from Brassica rapa pollen,52 cycloartane-1a,2a,3b,25-tetrol, neomyrrhaol 113, from the resin of Commiphora myrrha,53 sabajal acetate 114 from Artemisia princeps54 and the nor-derivative 115 from Quercus variabilis.55 Cyclomacroside C 116,56 the corresponding 24,25-acetonide cyclomacroside A 117,57 cyclomacroside D 11858 and cyclomacroside D 11959 are new glycosides from Astragalus macrocarpus. The diglucoside SU3 120 has been isolated from Sutherlandia humilis.60 Three new glycosides have been obtained from the rhizomes of Cimicifuga foetida.61 Two of them, 121 and 122, have new genins. Further cycloartane xylosides with new genins 123 and 124 have been isolated from the rhizomes of This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. This journal is ª The Royal Society of Chemistry 2011 View Article Online Nat. Prod. Rep., 2011, 28, 1087–1117 | 1093 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online Cimicifuga yunnanensis, together with the cimigenol derivatives 125 and 126.62 Cycloartane glycosides with known genins have been reported from Astragalus amblolepis63 and Actaea asiatica.64 The holostane saponins achlioniceosides A1, A2 and A3, from the Antarctic sea cucumber Achlionice violaecuspidata (¼ Rhipidothuria racowitzai) have the new genins 127–129, respectively.65 Marmoratoside A, 17a-hydroxyimpatienside A, marmoratoside B and 25-acetoxybivittoside D are new antifungal holostane saponins from the sea cucumber Bohadschia marmorata.66 Marmoratoside A and B have the new genins 130 and 129, respectively. A detailed study of the saponins of Holothuria forskali resulted in the identification of thirteen holostanes, provisionally named holothurinosides E, F, G, H, I, A1, C1, E1, F1, G1, H1, I1 and desholothurin A1.67 Holothurinoside E is the known 17-dehydroxyholothurinol A. All the saponins have known genins apart from C1, E1 F1 and H1, which have the new genin 131. Other holostanes with known genins include 1094 | Nat. Prod. Rep., 2011, 28, 1087–1117 leucospilotaside B from Holothuria leucospilota,68 scabrasides A and B from Holothuria scabra69 and arguside F, impatienside B and pervicoside D from Holothuria axiloga.70 New cucurbitanes and their glycosides continue to be reported. Balsaminapentaol A 132, cucurbalsaminols A 133 and B 134 and balsaminols A 135 and B 136 are constituents of Momordica balsamina.71 Nine new compounds 137–145 were obtained from the stems of Cucucumis melo72 while wilbrandisides A 146 and B 147 were isolated from Wilbrandia species.73 Further investigation of Momordica charantia, a rich source of cucurbitanes,74 afforded kuguacins F–S 148–16175 and charantadiol A 162.76 Two new saponins, xuedanglycosides A 163 and B 164, have been isolated from the rhizomes of Hemsleya chinensis.77 Both have new genins. A glycoside from the fruit of Momordica cymbalaria has the new genin 165.78 New glycosides with known genins have been reported from the roots of Siraitia grosvenor79 and the stems of Dendrosicyos socotrana (socotroside).80 This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. This journal is ª The Royal Society of Chemistry 2011 View Article Online Nat. Prod. Rep., 2011, 28, 1087–1117 | 1095 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online 4. The dammarane group Silvaglenamin 166 is an interesting dimeric nitrogen-containing dammarane from Aglaia silvestris. Silvaglenamin 166 may be an artefact formed during the isolation and purification, however, the authors claim that no ammonia was used in the process. Other new dammaranes include panaxadione 167 from the seeds of Panax ginseng,81 3b,28-diacetoxydammar-23-ene-1a,2a,25triol 168 from the resin of Commiphora holtziana82 and 169 from the hydrolysate of Panax ginseng.83 The structure 169 was confirmed by X-ray analysis. Ginsenoside Ki 170 and ginsenoside Km 171 are new saponins from the leaves of Panax ginseng with new dammarane genins.84 Other new saponins with known genins include floranotoginsenosides A–D from Panax notoginseng,85 quinquefoloside Lc86 and quinquenosides L1687 and L1788 from Panax quinquefolium, ginsenoside Rz1 from heat-processed ginseng,89 a saponin from Oncoba manii,90 bacopasides IX–XII91,92,93 from Bacopa monniera and gynosaponins I–VI from Gynostemma pentaphyllum.94 Reviews have appeared on the bioactive constituents of ginseng95 and on the biosynthesis96 and production97 of ginsenosides. Toosendanone A 172 is an unusual euphane derivative with a cyclopentane ring in the side chain.98 It was isolated from the 1096 | Nat. Prod. Rep., 2011, 28, 1087–1117 bark of Melia toosendan and was accompanied by toosendanic acids A 173 and B 174. Dysoxyhainic acid A 175 is a tirucallane derivative from Dysoxylum hainanense.99 Its structure was confirmed by X-ray analysis. Constituents of Toona ciliata include the tirucallanes toonaciliatins K 176 and L 177 and three further nor-limonoids, toonaciliatins H 178, I 179 and C 180.100 It is unfortunate that these authors failed to notice that they had previously used the names toonaciliatins H and I for different compounds.101 Seven tirucallanes 181–187 and two euphanes 188–189 have been reported as minor constituents of the roots of Euphorbia micractina.102 The tirucallane ester 190 has been isolated from Euphorbia retusa.51 The tirucallane bruceajavaninone A 191 and the apotirucallane derivatives bruceajavanone A 192, the corresponding 7-acetate 193 and bruceajavanones B 194 and C 195 are cytotoxic constituents of Vietnamese Brucea javanica.103 Bruceajavanin C 196 is a further constituent of Brucea javanica.104 Other apotirucallanes include the ring A-cleaved derivatives acutaxylines A 197 and B 198 from Dysoxylum acutangulum,105 protoxylocarpins F–H 199–201106 (the proposed structure of protoxylocarpin H 201 contains an unlikely a-hydroxyepoxide), chisiamols A–F 202–207107 and protoxylogranatin A 208 from the seeds of Xylocarpus granatum.108 The structures proposed for compound 209 from Nepeta suavis109 and myrrhasin 210 from resin of Commiphora myrrha110 This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. This journal is ª The Royal Society of Chemistry 2011 View Article Online Nat. Prod. Rep., 2011, 28, 1087–1117 | 1097 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. 1098 | Nat. Prod. Rep., 2011, 28, 1087–1117 View Article Online This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online are biogenetically unusual since they lack the functionalisation at C-7 and, in the case of 209, at C-14, expected as a result of the apo-rearrangement. Protoxylocarpins A–E 211–215 have been reported from the fruit of Xylocarpus granatum.111 Protoxylocarpin D is a known compound, holstinone B.112 The cyclopropane derivatives dichapetalin M 216 and 217 have been isolated from Dichapetalum madagascariensis113 and the stems of Spathelia excelsa,114 respectively. 4.1 Tetranortriterpenoids Three new limonoids 218–220 have been obtained from the root bark of Melia toosendan.115 The methyl angolensate derivatives sandoripins A 221 and B 222 are constituents of the leaves of Sandoricum koetjape.116 Seven new ring C-cleaved limonoids, This journal is ª The Royal Society of Chemistry 2011 chisonimbolinins A–G 223–229, have been reported from Chisocheton paniculatus.117 The structure of chisonimbolinin A 223 was confirmed by X-ray analysis. Hemiacetal formation between the C-6 hydroxyl group and the C-1 ketone accounts for the new framework of khayalenoid A 230 and B 231 from Khaya senegalensis.118 The structure of khayalenoid A 230 was confirmed by X-ray analysis. The skeletal diversity of limonoids continues to impress, especially from Cipadessa cinerascens, a prolific source of interesting new compounds. Recent additions include cipadonoid A 232,119 cineracipadesins A–F 233–238120 and cipadonoids B–G 239–244.121 The structure of cipadonoid B 239, the simplest of the compounds, was confirmed by X-ray analysis. Trichilin B 245 has an impressive polycyclic skeleton. It was isolated from Trichilia connaroides together with its complex congener trichilin A 246.122 Nat. Prod. Rep., 2011, 28, 1087–1117 | 1099 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online Chukvelutins A–C 247–249123 and chukvelutilides A–F 250– 255,124 from Chukrassia tabularis var. velutina, clearly arise from C-15-acylated precursors. New compounds from Khaya species include 256–259 from Khaya ivorensis125 and 6-deoxykhayanolide E 260 from Khaya senegalensis.126 Many new phragmalin derivatives have been reported this year, including swietephragmins H–J 261–263 and swietemacophine 264 from Swietenia macrophylla127 and sixteen ring D-opened derivatives, 1100 | Nat. Prod. Rep., 2011, 28, 1087–1117 swietenitins A–M 265–277, 2-acetoxylswietenialide D 278, 2,11diacetoxyswietenialide D 279 and 11-deoxyswietenialide D 280 also from Swietenia macrophylla.128 The structures of swietenitins A 265 and B 266 were confirmed by X-ray analyses. Moluccensins A–G 281–287 are phragmalin derivatives with a conjugated C-30 ketone from the seeds of an Indian mangrove, Xylocarpus moluccencis.129 The structure of moluccensin A 281 was confirmed by X-ray analysis. Granatumins A–G 288–294 have This journal is ª The Royal Society of Chemistry 2011 View Article Online Xylocarpus species has been published.132 Swietmanins A–J 299– 308, 2-hydroxy-3-O-isobutyrylproceranolide 309 and 2-hydroxy3-O-benzoylproceranolide 310 are further assorted limonoids from the fruit of Swietenia mahogani.133 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. been isolated from the related species Xylocarpus granatum.130 Other compounds from Xylocarpus granatum include xylomexicanins A 295 and B 296 from the seeds131 and xylocarpins J 297 and K 298 from the fruit.111 A review of the constituents of This journal is ª The Royal Society of Chemistry 2011 Nat. Prod. Rep., 2011, 28, 1087–1117 | 1101 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online 4.2 Quassinoids Delaumonones A 311 and B 312 are antiplasmodial quassinoids from Laumoniera bruceadelpha.134 Delaumone A is the carboxylic acid corresponding to isobrucein A 313. The rearranged structure 314 has been assigned to AECHL-1, an antitumour quassinoid 1102 | Nat. Prod. Rep., 2011, 28, 1087–1117 from the root bark of Ailanthus excelsa.135 Further constituents of Eurycoma longifolia, a well-known source of quassinoids, include 13b,18-dihydro-14-epieurycomanone 315, 12,15-diacetyl-13b,18dihydroeurycomanone 316, 6a,14b,15b-trihydroxyklaineonone 317, 14b,15b-dihydroxyailanquassin A 318, 3a,4a-epoxyeurycomalide B 319, 3,4-epoxy-5,6-didehydroeurycomalactone 320, This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online 5a-hydroxyeurycomalactone 321, D4-7b-hydroxy-6-oxoeurycolactone E 322, D4(28)-eurycolactone E 323 and 6ahydroxyeurycolactone E 324.136 5 The lupane group The anticancer activities of betulinic acid have been highlighted in a recent review.137 Zizyberanal acid 325138 and dysoxyhainol This journal is ª The Royal Society of Chemistry 2011 32699 are ring-A contracted lupane derivatives from Zizyphus jujuba and Dysoxylum hainanense, respectively. The 3,4-secolupane derivatives 327 and 328 have been isolated from the fruits of Acanthopanax sessiliflorus.139 A further 3,4-secolupane 329 has been found in Maytenus apurimacensis where it occurs with lup20(29)-ene-3a,16b,28-triol 330, lup-12-ene-3a,16b-diol 331 and its 3b-epimer 332.140 Other simple lupane derivatives isolated recently include 15a-hydroxylup-20(29)-en-3-one 333 from Nat. Prod. Rep., 2011, 28, 1087–1117 | 1103 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online Ricinus communis,141 28-hydroxy-3-oxolupan-29-oic acid 334 from Salacia chinensis,142 9a-hydroxylup-20(29)-en-28-oic acid 335 from Zizyphus jujuba143 and 29-hydroxyalphitolic acid 336 from Callistemon lanceolatus.144 Perrottetia arisanensis is the source of several lupane coumaroyl esters 337–342 together with 1104 | Nat. Prod. Rep., 2011, 28, 1087–1117 7b-hydroxybetulinaldehyde 343 and 28-norlup-20(29)-ene3a,17b-diol 344.145 Lup-20(29)-ene-3b,6a-diol 345 and the corresponding 3-acetate 346 and 3-E-caffeate 347 esters are constituents of Drypetes inaequalis.146 Other new lupane esters include diospyrolide acetate 348 from the liverwort Ptilidium This journal is ª The Royal Society of Chemistry 2011 View Article Online Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. pulcherrimum147 and 3b-acetoxy-2a-hydroxylup-20(29)-en-28-oic 349 acid from Garcinia hanburyi.148 Acankoreoside I is a lupane saponin with a new genin 350, isolated from Acanthopanax koreanum,149 and rubuside I 351 from Rubus ellipticus var. obcordatus also has a new genin.150 6 The oleanane group Sculponeatic acid 352 is a ring A-contracted oleanane derivative from Isodon sculponeata.151 Further examples of ring A-contracted oleananes are dysoxyhainic acids B 353 and C 354 from Dysoxylum hainanense where they occur with the 2,3-secoderivatives dysoxyhainic acids D 355 and C 356.99 Microtropis japonica is the source of another 2,3-seco oleanane 357.152 The This journal is ª The Royal Society of Chemistry 2011 structure of the 3b-hydroxy-27-noroleanan-28,13b-olide 358, from Uncaria hirsuta, was established by X-ray analysis.153 The structures of falcatins A 359 and B 360 and of 3-oxoazukisapogenol 361, from the roots of Oxytropis falcata, were also established by X-ray analysis.154 Falcatin A 359 is the genin of soyasaponin Bh, which is found in soybeans, Glycine max.155 Other recent isolations of simple oleanane derivatives include atricins A 362 and B 363 from Perovskia atripicifolia,156 6ahydroxyhederagenic acid 364 from Cephalaria ambrosioides,157 3b,6b,7a-trihydroxyolean-12-en-27-oic acid 365158 and four further 27-carboxylic acid derivatives 366–369159 from Astilbe chinensis, 2b,3b,16a,28-tetrahydroxyolean-12-en-23-oic acid 370 from Gladiolus segetum160 and paeonenolide H 371, an acetonide of a known dinoroleanane, from Paeonia anomala ssp. veitchii.161 Nat. Prod. Rep., 2011, 28, 1087–1117 | 1105 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online Racemosol A 372 and isoracemosal A 373 are esters of barrigenol R1 from Barringtonia racemosa.162 Seven oleanane derivatives, aceriphyllic acids C–I 374–380, were isolated from roots of Aceriphyllum rossii163 and nine new derivatives of 23-hydroxyimberbic acid, including the diacetate 381, the methyl ester 382 and a-L-rhamnosyl derivatives have been found in Combretum sundaicum.164 Verbesinosides A–F, from Verbesina virginica, are 15,27cyclooleanane saponins with the genin 383 and various aromatic esters of the C-21 alcohol.165 Glochieriosides A and B are 1106 | Nat. Prod. Rep., 2011, 28, 1087–1117 saponins from Glochidion eriocarpum with the new genin 384.166 In an independent study, glochierioside B has been isolated from the same species and named glochidioside E.167 Ilexhainanoside C 385, with a new genin, is accompanied by ilexhaonosides D and E that have known genins in Ilex hainanensis168 and incarvilloside B 386, with a new genin, is found in Incarvillea delavayi.169 Other simple oleanane glycosides with new genins include 387 and 388 from Terminalia superba,170 389 from Gymnema inodorum,171 390 from celery (Apium graveolens),172 391 from leaves of Actinidia kolomikta,173 392 from leaves of Callicarpa japonica174 and 393 This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online and 394 from underground parts of Caulophyllum thalictroides.175 Clinopodoside H is a saponin from Clinopodium chinense with a new oleanane genin 395176 and polybosaponin A, from Hedysarum polybotrys, has the new genin 396.177 The new genins of unnamed saponins include 397178 and the 28-noroleanane derivative 398179 from Nigella sativa and olean-12-ene3b,28,30-triol 399 from Ardisia pusilla.180 New oleanane saponins with known genins that have been assigned trivial names are listed in Table 1. The sources of new oleanane saponins with known genins that have not been assigned trivial names are listed in Table 2. Pterospermum heterophyllum is the source of taraxer-14-ene1a,3b-diol 400 and the corresponding 1-ketone 401,236 and This journal is ª The Royal Society of Chemistry 2011 14a,15a-epoxytaraxeran-3b-ol 402 is found in Helmiopsis sphaerocarpa.237 Three glutinane derivatives with unusual oxygenation patterns, glutin-5-en-19a-ol 403, glutin-11-ene2b,15a,21b-triol 404 and glutina-7,21-diene-2b,19a-diol 405, have been isolated from Euonymus hamiltonianus.238 3b-Hydroxyglutin-5-en-28-oic acid 406 is a constituent of Garcinia cymosa239 and 7b,25-epoxy-3b-hydroperoxyglutin-5-ene 407 has been identified in Maytenus apurimacensis.140 Itoaic acid 408 is a 3,4-secofriedelane derivative from Itoa orientalis240 and the 2,3-secofriedelane lobatanhydride 409 has been isolated from Crossopetalum lobatum together with 3a,25dihydroxyfriedelan-2-one 410 and 1b,25-dihydroxyfriedelan-3one 411.241 Other new friedelane triterpenoidss include Nat. Prod. Rep., 2011, 28, 1087–1117 | 1107 View Article Online Table 2 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. Table 1 Trivial name Plant species Reference Plant species Reference Albizosides A–C Arboreasides A, C–E Ardipusilloside III Ardipusillosides IV and V Arjunglucoside Brachyposides A and B Albizia chinensis Cussonia arborea Ardisia pusilla Ardisia pusilla Cornus kousa Acanthopanax brachypus Camellia sinensis Chiococca alba Clematis chinensis Albizia coriaria Cyclamen adzharicum Dianthus versicolor Dodonaea viscosa Camellia sinensis Impatiens siculifer Lysimachia foenum-graecum Lysimachia foenum-graecum Ilex paraguariensis Akebia trifoliate var. australis Clematis parviloba Alternanthera philoxeroides Physena sessiliflora Phytolacca acinosa Anemone raddeana Anemone raddeana Sapindus rarak 181 182 183 184 185 186 Acanthopanax sessilflorus Anemone coronaria Anemone hupehensis var. japonica Bougainvillea spectabilis Callicarpa japonica var. luxurians Cassia angustifolia Combretum olivaeforme Drypetes inaequalis Gordonia chrysandra Gypsophila trichotoma Ilex pernyi Lonicera dasystyla Medicago arabica Parthenium hysterophorus Patrinia saniculaefolia Phytolacca americana Phytolacca bogotensis Psammosilene tunicoides Pulsatilla cernua Sechium mexicanum Sideroxylon foetidissimum ssp. gaumeri Xanthoceras sorbifolia Xerospermum noronhianum 139 216 217 218 174 219 220 146 221 222 223 224 225 226 227 228 229 230 231 232 233 234 235 Chakasaponins I–III Chiococcasaponins I, II Clematichinenoside AR2 Coriariosides A and B Cyclamen F Dianversicosides A–G Dodoneasides A and B Floratheasaponin J Impatienosides A–G Lysimachiagenoside A Lysimachiagenosides C and D Mateglycoside A Mutongsaponin F Parvilobaside A Philoxeroidesides A–D Physenosides S1–S8 Phytolacacinoside A Raddeanoside R19 Raddeanoside R20 and R21 Rarasaponins I–III and Raraoside A Rarasaponins IV–VI Sativosides A and B Securidacasides A and B Stauntoside C1 Stellarinpin A Tetrapterosides A and B Undulatoside Xuedanglycoside C Yemuosides YM26–YM35 Yuchasaponins A–D Sapindus rarak Nigella sativa Securidaca longepedunculata Stauntonia chinensis Stellaria media Tetrapleura tetraptera Anchusa undulata ssp. hybrida Hemsleya chinensis Stauntonia chinensis Camellia oleifera 187 188 189 190 191 192 193 194 195 196 197 198 199 200 201 202 203 204 205 206 207 208 209 210 211 212 213 77 214 215 1b-hydroxyfriedelin 412 from sclerotia of Polyporus umbellatus,242 12a-hydroxyfriedelane-3,15-dione 413 and 3bhydroxyfriedelan-25-al 414 from Drypetes paxii,243 28-hydroxy3-oxofriedelan-29-oic acid 415 from Euonymus hederaceus244 and the 24,29-dinorfriedelane 416 from Euonymus japonicus.245 7 The ursane group The 28-norursanes changyediyuines I 417 and II 418 and the 27,28-dinorursane changyediyuine III 419, with aromatic E-rings, have been isolated from Sanguisorba longifolia.246 The related 28-norursane kakidiol 420 has been found in leaves of Diospyros kaki together with the 18,19-secoursane glucosyl esters kakisaponins B 421 and C 422.247 The 18,19-seco derivative 3-episwinhoeic acid 423 and the 18,19-epoxide 424 are constituents of Duchesnea indica.248 A range of ursane triterpenoids has been isolated from Microcarpis japonica, including 425–429 and the 24-norursane 430.152 The unusually named a-neriursate 431 and b-neriursate 432 have been claimed from leaves of Nerium 1108 | Nat. Prod. Rep., 2011, 28, 1087–1117 oleander.249 The ursen-28,30-olides 433 and 434 have been isolated from the roots of Actinidia chinensis,250 while 11a,12aepoxy-3-oxoursan-28,13b-olide 435 is from leaves of Hymenodictyon excelsum.251 Other simple ursane derivatives include 3b,15a-dihydroxyurs9(11)-en-12-one 436 from Photinia serrulata,252 2a,3a,24-trihydroxy-23-oxours-12-en-28-oic acid 437 from Saurauia napaulensis,253 the enone 438 from Canthium multiflorum,254 2a,3b,20b-trihydroxyursa-12,19(29)-dien-28-oic acid 439 from Salvia chinensis,255 2b,3a,24-trihydroxyurs-12-en-28-oic acid 440 from Actinidia rufa,256 3b,6b,7a-trihydroxyurs-12-en-27-oic acid 441,158 3b,6b,24-trihydroxyurs-12-en-27-oic acid 442 and the acetate 443159 from Astilbe chinensis and the 23-methyl esters 444–446 from Commiphora holtziana oleo-gum resin.82 Uncariaside A 447 is a 27-norursane diglucoside from Uncaria hirsuta and is accompanied by 22a-hydroxy-3-oxours-12-ene27,28-dioic acid 448.153 The related diglucoside asphorodin 449 is a constituent of Asphodelus tenuifolius.257 Melissa officinalis is the source of the 23-sulfate 450 and its 28-glucosyl ester 451258 and incarvilloside A 452 is found in Incarvillea delavayi.169 An unusual dimeric ursane diglucoside triumfettosaponin 453 has been isolated from Triumfetta cordifolia.259 Kudinoside LZ2, from Ilex kudincha (also known as Ilex kudingcha), is an ursane saponin with a new genin 454, which was erroneously drawn in its enantiomeric form in the ref. 260. Ilekudinosides T, U and V, from the same source, have the related genins 455–457, respectively.261 Rubusides A–H and J are ursane saponins from Rubus ellipticus var. obcordatus; rubusides C 458, F 459, G 460, H 461 and J 462 all have new genins.150 Other saponins with new genins include zygopylosides Q 463 and R 464 from Zygophyllum fabago,262 two saponins 465 and 466 from celery (Apium graveolens)172 and four saponins from Ilex pernyi including the genin 467.223 Ursane saponins with know genins include acetylilexsaponin A1 from Ilex hainanensis,263 arboreaside B from Cussonia This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. This journal is ª The Royal Society of Chemistry 2011 View Article Online Nat. Prod. Rep., 2011, 28, 1087–1117 | 1109 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. 1110 | Nat. Prod. Rep., 2011, 28, 1087–1117 View Article Online This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. This journal is ª The Royal Society of Chemistry 2011 View Article Online Nat. Prod. Rep., 2011, 28, 1087–1117 | 1111 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online arborea,182 mateglycosides B and C from Ilex paraguariensis198 and saponins from Bourgainvillea spectabilis,218 Licania arianeae,264 Premna microphylla265 and Rhaponticum uniflorum.266 New taraxastane derivatives 468 and 469 have been isolated from Tolpis species267 and procerursenyl acetate 470 is from Calotropis procera.268 Two taraxastane saponins with the new genin 471 have been isolated from Morina kokonorica269 and two saponins from Caulophyllum thalictroides have known taraxastane genins.175 1112 | Nat. Prod. Rep., 2011, 28, 1087–1117 8 The hopane group The structure of 2-hydroxydiplopterol 472, a metabolite of halotolerant Aspergillus variecolor B-17, has been confirmed as hopane-2a,22-diol by X-ray analysis.270 Hopane-21b,22-diol 473 and hopane-6a,11a.22-triol 474 have been identified in Marchantia polymorpha.271 A saponin from Launaea pinnatifida has the known dinorhopane spergulatriol as genin.272 Lobariolides A 475, B 476 and C 477 are fernane derivatives from the lichen This journal is ª The Royal Society of Chemistry 2011 Published on 28 April 2011. Downloaded by Universidad Nacional Agraria La Molina on 10/06/2016 15:41:29. View Article Online Lobaria kurokawae.273 The structure of lobarialide A 475 was confirmed by X-ray analysis. The lichen Pyxine berteriana is the source of fern-9(19)-ene-3,19-dione 478 and the corresponding 3b-acetoxy derivative 479.274 Two 2,3-secofernanes, alstonic acids A 480 and B 481, have been isolated from Alsonia scholaris.275 The structure of alstonic acid A 480 was confirmed by X-ray analysis and a biosynthetic pathway to alstonic acid B 481 has been proposed. 9 Miscellaneous compounds Serratan-3-one 482 has been isolated from Ficus benjamina var. comosa276 and seven new serratane derivatives 483–489 have This journal is ª The Royal Society of Chemistry 2011 been found in Palhinhaea cernua var. sikkimensis.277 Aristolochia gibertii is the source of onocerane-8,14-diol 490, which has been drawn with the wrong absolute configuration in the paper.278 10 References 1 A. Petronelli, G. Pannitteri and U. Testa, Anti-Cancer Drugs, 2009, 20, 880–892. 2 M. N. Laszczyk, Planta Med., 2009, 75, 1549–1560. 3 R.-Y. Kuo, K. Qian, S. L. Morris-Natschke and K.-H. Lee, Nat. Prod. 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