7/23/2019 3-Hydroxybutanolide derivatives and flavonoid glucosides from Anoectochilus roxburghii http://slidepdf.com/reader/full/3-hydroxybutanolide-derivatives-and-avonoid-glucosides-from-anoectochilus 1/54 Triterpenoids Joseph D. Connolly and Robert A. Hill * Received 26th August 2009 First published as an Advance Article on the web 26th November 2009 DOI: 10.1039/b808530g Covering: January 2007 to December 2008. Previous review: Nat. Prod. Rep. , 2008, 25, 794 This review covers the isolation and structure determination of triterpenoids including squalene derivatives, protostanes, lanostanes, holostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, lupanes, oleananes, friedelanes, ursanes, hopanes, isomalabaricanes and saponins; 574 references are cited. 1 Int rod uc ti on 2 The squalene group 3 The lanostane group 4 The dammarane group 4.1 Tetranortriterpenoids 5 The lupane group 6 The oleanane group 7 The ursane group 8 The hopane group 9 Miscellaneous compounds 10 References 1 Introduction Interest in the pharmaceutical activities of triterpenoids continues to increase. 1 Reviews have appeared on the triterpe- noid constituents of Boswellia serrata, 2 Lantana camara, 3 Lysimachia species 4 and Maytenus species. 5 The classification and occurrence 6 and extraction 7 of plant triterpenoid saponins have been surveyed. Further reviews include the pharmaceutical activities of pentacyclic triterpenoid saponins, 8 the biological activities of triterpenoid saponins containing monoterpenoid moieties 9 and central nervous system activities of triterpenoid saponins. 10 2 The squalene group Tetrahydroxysqualene 1, from the leaves and twigs of Rhus taitensis, is active against Mycobacterium tuberculosis. 11 Ekeber- ins D 1 –D 5 2–6 are antiplasmodial squalene derivatives from the stem bark of Ekebergia capensis. 12 The absolute configuration of intricatetraol 7, from Laurencia intricata, has been determined by total synthesis. 13 Several squalene-derived polyethers have been reported from marine organisms. These include aplysiols A 8 and B 9 from the mantle of the sea hare Aplysia dactylomela, 14 laurenmariannol 10, together with compound 8, fromthered alga Laurencia mariannensis 15 and omaezakianol 11 and 15,16-anhy- drothyrsiferol 12 from Laurencia omaezakiana. 16 The condensation of C 32 and C 34 macrocyclic aldehydes with the methylated squalene diols 13 and 14 gives rise to the braunicetals (e.g. 15 and 16), an inseparable mixture of compounds from the green microalga Botryococcus braunii . 17 An enantioselective total synthesis of achilleol B 17 has led to the revision of its C-18 configuration. 18 Oxidosqualene cyclase homologues from Arabidopsis thaliana continue to attract attention. At1g78955 (CAMS1) converted oxidosqualene almost entirely (98%) into the monocyclic product camelliol C 18, with only traces of achilleol A (2%) and b-amyrin (0.2%) being formed. 19 This enzyme appears to have evolved from the enzymes which lead to pentacyclic products. A lano- sterol synthase-deficient yeast strain At1g78500 afforded the two 8,14-seco-derivatives 19 and 20 of a-amyrin and b-amyrin. 20 The C-14 configuration of arabidiol 21, produced by At4g15340, has been established as R. 21 The stereochemistry of the addition of water to triterpenoid cationic intermediates is also discussed. Replacement of Phe699 by threonine in the oxidosqualene-lan- osterol cyclase ERG7 from Saccharomyces cerevisiae resulted in the formation of protosta-13(17),24-dien-3b-ol 22 instead of lanosterol. 22 Calculations suggest that the biosynthesis of friedelin is a non-stop process which involves pentacyclisation of squalene oxide to the lupanyl cation followed by ten supra- facial 1,2-shifts of methyls and hydrogens. 23 Several reviews have appeared covering aspects of oxidosqualene-lanosterol cyclase, 24 engineering squalene cyclising enzymes 25 and the properties of oxidosqualene cyclases. 26,27 3 The lanostane group The marine-derived fungus Aspergillus sydowii produces the new protostane triterpenoid 23, a hydrate of the known helvolic acid. 28 In the original paper this compound is described as a nordammarane. 1,2-Dihydrohelvolic acid 24 has been found in the entomopathogenic fungus Metarhizium anisopliae. 29 Aliso- lide 25, alisol O 26 and alisol P 27 are new compounds from the rhizome of Alisma orientale , a rich source of protostanes. 30 Unfortunately the name alisol O has already been used. The X-ray crystal structure of the known alisol B 23-acetate is also reported in this paper. Other new compounds from Alisma ori- entale include 25-anhydroalisol F 28 and 11-anhydroalisol F 29 31 and 11,25-bisanhydroalisol F 30. 32 Compound 29 has also been named 24-deacetylalisol O, referring to the original alisol O structure. 33 Department of Chemistry, Glasgow University, Glasgow, G12 8QQ, UK This journal is ª The Royal Society of Chemistry 2010 Nat. Prod. Rep. , 2010, 27, 79–132 | 79 REVIEW www.rsc.org/npr | Natural Product Reports View Article Online / Journal Homepage / Table of Contents for this issue
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7/23/2019 3-Hydroxybutanolide derivatives and flavonoid glucosides from Anoectochilus roxburghii
Acanthopanaxoside E Acanthopanax senticosus 400Achyranthosides G and H Achyranthes fauriei 401Aesculiosides IIe–IIk and IIIa–IIIf Aesculus pavia 402Akebosides La and Lb Akebia quinata 403Ardisiacrenoside I Ardisia crenata 404Arganins L and O–R Argania spinosa 405Assamicins VI–VIII Aesculus assamica 406Asteratoidesoside A Aster souliei 407Bodinierin C Elsholtzia bodinieri 408Brevifoliasaponin Calliandra brevifolia 409
Cauloside H Caulophyllum thalictroides 410Cernuasides A–D Pulsatilla cernua 411,412Chakasaponins V and VI Camellia sinensis 413Chionaeosides A–D Paronychia chionaea 414Clematiganoside A Clematis ganpiniana 415Codonolasides I–III Codonopsis lanceolata 416,417Congmuyanoside I Aralia elata 418Dexylosyltubeimoside III Bolbostemma paniculatum 419Dipterosides A–E Dipteronia dyeriana 420Floratheasaponins D–I Camellia sinensis 421Foliatheasaponins I–V Camellia sinensis 422Giganteasaponins 5 and 6 Solidago gigantea 423Giganteosides L–N Cephalaria gigantea 424Gleditzsioside Z Gleditisia sinensis 425Gummiferaosides A–C Albizia gummifera 426Gymnemosides W1 and W2 Gymnema sylvestre 427Gypsosaponins A (Gypoldoside A) –C Gypsophila oldhamiana 428,429
Hehuanoside A Albizia julibrissin 430Helianthosides 4 and 5 Helianthus annuus 431Hydrocosisaponins A–F Hydrocotyle sibthorpioides 432Ilexpernoside F Ilex pernyi 433Ilexsaponin C Ilex pubescens 434Impatiprins A–C Impatiens pritzellii var. hupehensis 435Isoescins VIa–VIIa Aesculus turbinata 436Lancemasides B–G Codonopsis lanceolata 437,438Lonicerosides D and E Lonicera japonica 439Lysichrisides A and B Lysimachia christinae 440Montanosides 1 and 2 Clematis montana 441Nigellosides A–D Nigella damascena 442Oblonganosides L–M Ilex oblonga 443Onjisaponins Polygala tenuifolia 444,445Perennisaponins A–F Bellis perennis 446Perennisosides I–VII Bellis perennis 447
Pharbitosides A and B Pharbitis nil 448Pithelucosides A–C Pithecellobium lucidum 449Puberosides A and B Glochidion puberum 450Raddeanoside R19 Anemone raddeana 451Repensosides A–F Gypsophila repens 452Sapinmusaponins K–N Sapindus mukorossi 217Serrulatins A–E Photinia serrulata 453Sigmoiside E Erythrina sigmoidea 454Stauntoside A Suantonia chinensis 455Stryphnosides A–F Stryphnodendron fissuratum 456Theasaponins A6, A7 and B5 Camellia sinensis 457Tenuifoside A Polygala tenuifolia 458Vaccaroside I Vaccaria segetalis 459Xanifolias Y0, Y2, Y3 and Y7 Xanthoceras sorbifolia 460Yemuosides YM21 –YM25 Stauntonia chinensis 461
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