SAPONINS (k hostettmann et a marston 1995)

CAMBRIDGE UNIVERSITY PRESS This is the first comprehensive monograph to look in depth at saponins Saponins are glycosides oftriterpenes, steroids or steroid alkaloids which have a very wide distribution in plants and some marine organisms Their biological activity includes haemolysis and fish poisoning, and the steroid saponins are essential lor the manufacture of oral contraceptives and sex hormones Saponins have also been exploited commercially as soap substitutes and in several other industrial applications This book gives detailed information on the occurrence and distribution of saponins, their structural types, isolation, analysis and structure deter mination Biological and pharmacological activities are discussed, as are aspects of commercial and industrial use The volume provides a valuable source of data for the different classes of compound and includes an extensive list of references Chemstry and Pharmacology of Natural Products Saponins Saponins CHEMISTRY AND PHARMACOLOGY OF NATURAL PRODUCTS Series Editors: Professor J.D Phillipsoo, Department of Pharmacognosy, The School of Pharmacy, University of London; Dr D.C Ayres, Department of Chemistry, Queen Mary and Westfield College, University of London,, H Baxter, formerly at the Laboratory of ike K HOSTETTMANN Government Chemist, London Institute of Pharmacognosy and Phytochemistry School of Pharmacy, Lausanne University, Switzerland Also in this series and Edwin Haslam Plant polyphenols: vegetable tannins revisited AJ Pusztai Plant lectins D.C Ayres and J DXoike Llgnuns: chemical biological and clinical properties A MARSTON Institute of Pharmacognosy and Phytochemistry School of Pharmacy, Lausanne University, Switzerland I CAMBRIDGE UNIVERSITY PRESS Publisbed by die Press Syndicate of the University of Cambridge The Pitt Building, Trumpington Street, Cambridge CB2 IRP 40 West 20th Street, New York, NY 100U-42U, USA 10 Stamford Road, Oaklcigh, Melbourne 3166, Australia Contents © Cambridge University Press 1995 First published 1995 Printed in Great Britain at the University Press, Cambridge A catalogue recordfor this book is availablefrom the British Library Library of Congress cataloguing in publication data Hostettmann, K (Kurt), 1944- Saponins / K Hostettmann, A Marston p cm - (Chemistry and pharmacology or natural products) Includes bibliographical references and index ISBN 521 329701 Saponins I Marston A (Andrew), 1953, II Title III Scries QD325.H73 1995 547.7'83 - dc20 94-688 CIP ISBN 521 32970 hardback Glossary Introduction Page ix 1.1 General introduction 1.2 Definitions 1.3 Biosynthesis 1.4 Classes of aglycone 10 1.5 Nomenclature and stereochemistry 12 Occurrence and distribution 18 2.1 Tritcrpene saponins 19 22 Steroid saponins 76 23 Steroid alkaloid glycosidcs (glycoalkaloids, azasteroids) 2.4 Saponins from marine organisms Analyst and isolation 96 105 122 3.1 Analysis and quantitative determination 122 3.2 Isolation* 143 Structure determination 4.1 Cleavage reactions 175 177 4.2 Spectroscopic and other techniques for structure elucidation 197 Triterpene safonins - pharmacological and biolosical KW properties 232 5.1 General properties of saponins 232 viii Contents 5.2 Solubilizing properties 238 Glossary 5.3 Biological and pharmacological activities of triterpene saponins 239 5.4 Pharmacokinetics and metabolism * 283 5.5 Toxicity 284 Steroid saponins and steroid alkaloid saponins: pharmacological and biological properties 287 6.1 Biological and pharmacological activities 288 6.2 Toxicity 304 Commercially Important preparations and products 307 7.1 Sarsaparillae radix (sarsaparilla root) 310 7.2 Liquiritiae radix (glycyrrhiza, licorice root, licorice) 312 7.3 Hippocastani semen (aescine) 318 7.4 Hederae folium (ivy leaves) 321 7.5 Tea 322 7.6 Senegae radix (senega root) 323 7.7 Primulae radix (primula root) 323 7.8 Asiaticoside 324 7.9 Bupleuri radix 325 7.10 Gypsophila species 326 7.11 Quillaia bark 327 7.12 Ginseng 329 7.13 Eleutherococcus senticosus J37 Appendices 342 References 436 index of Latin names 539 General index 544 Ac acetyl ACTH adrenocortlcotrophin, corticotrophin All j5-D-allose Api Ara Bz Dta EBV j3-D-apiose a-L-arabinose benzyl 6-deoxy-a-L-talopyranose Epstein-Barr virus Fuc J5-o-fucose (6-deoxygalactose) Gal /J-D-galactose GalA GalNAc Glc GlcA GlcNAc HI p-D-galacturonic acid JV-acetyl-2-amino-2-deoxygalactose 0-D-gIucose /J-D-glucuronic acid iV-acetyl-2-amino-2-deoxyglucose haemolytic index HIV human immunodeficiency virus 5-HT 5-hydroxytryptamine Lp intraperitoneal i.v intravenous Ma malonyl Man a-L-mannose Me methyl PDE phosphodiestcrase p.o oral Rha a-L-rhamnose (6-deoxymannose) Rib 0-D-ribose Glossary p-D-quinovose (D-chinovose, Qui HETCOR 6-deoxygIucose) &c subcutaneous Ulo 6-deoxy-/J-r>xylo-hexos-4-ulo-pyranose Xyl /J-D-xylose l3C-1H heteronuclear correlated spectroscopy HMBC lH-detected heteronuclear multiple-bond spectroscopy HMQC furanose pyranose XI Glossary lH-detected heteronuclear one-bond spectroscopy HOHAHA homonuclear Hartmann-Hahn spectroscopy Techniques HPLC high-performance liquid chromatography internal diameter APT attached proton test I.D CA coUisional activation INADEQUATE CAMELSPIN cross-relaxation appropriate for minimolecules emulated by locked spins incredible natural abundance double quantum experiment INEPT insensitive nuclei enhanced by polarization transfer CD circular dichroism CF-FAB continuous-flow FAB-MS 1R Cl MS chemical ionization mass spcctromctry LC-MS liquid chromatography-mass spectrometry COLOC 13C-lH two-dimensional correlation 1X> laser desorption spectroscopy via long-range couplings LD/FTMS COSY two-dimensional *H correlation infra-red laser desorption/Fourkr transform mass spectrometry low-pressure liquid chromatography spectroscopy LPLC CPC centrifugal partition chromatography LSPD long-range selective proton decoupling CTLC centrifugal thin-layer chromatography MIKE/CAD mass-analysed ion kinetic DCCC droplet countercurrent chromatography D/CI-MS desorption-chemical ionization mass MPG microporous glass spectrometry MPLC medium-pressure liquid chromatography distortionless enhancement by polarization NMR nuclear magnetic resonance transfer NOE nuclear Overhauser enhancement double quantum-filtered, phase-sensitive NOESY nuclear Overhauser enhancement DEPT DQF-COSY (DQ-COSY) energy/collision-activated dissociation correlation spectroscopy COSY octadecylsilyl EI-MS electron impact mass spectrometry ODS ELISA enzyme-linked immunosorbent assay OPLC overpressure layer chromaiography FAB-MS fast atom bombardment mass spectrometry ORD optical rotatory dispersion FD-MS field desorption mass spectrometry PD-MS plasma desorption mass spectrometry long-range heteronuclear correlated PRFT partially relaxed Fourier transform FLOCK spectroscopy incorporating bilinear FRIT-FAB spectroscopy rotation decoupling pulses RCT relayed coherence transfer frit fast atom bombardment mass RIA radioimmunoassay spectrometry RLCC rotation locular countercurrent chromatography GC gas chromatography GC-FTIR gas chromatography-Fourier transform IR ROESY 2-D NOE in a rotating frame GC-MS gas chromatography-mass spectrometry RP reversed phase Glossary SIMS secondary ion mass spectrometry SINEPT selective INEPT TLC thin-layer chromatography TOCSY total correlation spectroscopy TSP thermospray uv ultra-violet VLC vacuum liquid chromatography XHCORR long-range 13C-1H correlation Introduction spectroscopy 1.1 General introduction Saponins are high-molecular-weight glycosides, consisting of a sugar moiety linked to a triterpene or steroid aglycone The classical definition of saponins is based on their surface activity; many saponins have detergent properties, give stable foams in water, show haemolytic activity, have a bitter taste and are toxic to fish (pisckidal) Such attributes, while not common to all saponins, have frequently been used to characterize this class of natural products However, because of the numerous exceptions which exist, saponins are now more conveniently defined on the basis of their molecular structure, namely as triterpene or steroid glycosides Some saponin-containing plants have been employed for hundreds of years as soaps and this fact is reflected in their common names: soapwort (Saponaria officinalis), soaproot (Chlorogalum pomeridianum), soapbark {Quillaja saponaria), soapberry {Sapindus saponaria\ soapnut (Sapindus mukurossi) Indeed, the name 'saponin' comes from the Latin word sapo (soap) Saponins are constituents of many plant drugs and folk medicines, especially from the Orient Consequently, great interest has been shown in their characterization and in the investigation of their pharmacological and biological properties Since the appearance of Kofler's book Die Saponine in 1927, the field has undergone a most remarkable transformation Kofler described in great detail the properties and pharmacological activities of saponins but at that time not a single saponin had been fully characterized In contrast, by 1987 the struaure of over 360 sapogenins and 750 triterpene glycosides had been elucidated (Bader and Hiller, 1987) This rapid progress is the result of the many dramatic advances in isolation and 1.2 Introduction Definitions structure elucidation techniques, a large number of which will be men tioned in this book The most common sources of saponins are the higher plants, but increasing numbers are being found in lower marine animals So far, they have only been found in the marine phylum Echinodennata and particu larly in species of the classes Holothuroidea (sea cucumbers) and Asteroidea (starfishes) Monodesmosidic 1.2 Definitions Bktesmosidic Fig 1.2 Monodesmosidic and bklesmosidic saponins The aglycone or non-saccharide portion of the saponin molecule is called the genin or sapogenin Depending on the type of genin present, the saponins can be divided into three major classes: (1) tritcrpene glycosides (2) steroid glycosides (3) steroid alkaloid glycosides The genins of these three classes can be depicted as shown in Fig 1.1 The aglycones are normally hydroxylated at C-3 and certain methyl groups are frequently oxidized to hydroxymethyl, aldehyde or carboxyl functionalities When an acid moiety is esterified to the aglycone, the term ester saponin is often used for the respective glycosides AH saponins have in common the attachment of one or more sugar chains to the aglycone Monodesmosidic saponins have a single sugar chain, normally attached at C-3 Bldesmosidic saponins have two sugar chains, often with one attached through an ether linkage at C-3 and one attached through an ester linkage (acyl glycoside) at C-28 (triterpene saponins) (Fig 1.2) or an ether linkage at C-26 (furostanol saponins) Tridesmosidic saponins have three sugar chains and are seldom found Bklesmosidic saponins are easily transformed into monodes mosidic saponins by, for example, hydrolysis of the esterified sugar at C-28 in triterpene saponins; they lack many of the characteristic properties and activities of monodesmosidic saponins The saccharide moiety may be linear or branched, with II being the highest number of monosaccharide units yet found in a saponin (Clematoside C from Clematis manshurica (Raminculaceae); Khorlin et al 1965) As a rule, however, most of the saponins so for isolated tend to have relatively short (and often unbranched) sugar chains, containing 2-5 monosaccharide residues Kochetkov and Khorlin (1966) have introduced the term oligoside for those glycosides containing more than 3-4 monosaccharides Triterpene class The most common monosaccharide moieties found, and the corre sponding abbreviations used in this book (according to IUPAC recom mendations; Pure Appl Ckem (1982) 54,1517-1522), are: D-glucose (Glc), D-galactose (Gal), D-glucuronic acid (GlcA), D-galacturonic acid (GalA), L-rhamnose (Rha), L-arabinose (Ara), D-xylose (Xyl) and D-fucose (Fuc) Saponins from marine organisms often contain D-quinovose (Qui) (some times written as D-chinovose) It is possible that D-fucose is present more often than generally thought, in view of its very similar chromatographic behaviour to L-rhamnose The glossary contains a full list of the abbrevia Steroid class Steroid alkaloid class Fig 1-1 Skeletal types of genin found in the three principal daises of saponin tions used in the book Unlike the cardiac glycoskles, unusual monosaccharides are seldom Introduction 1.3 Biosynthesis found, but it should be noted that uronic acids often occur in tritcrpene glycosides and that amino sugars may be present Glucose, arabinose, glucuronic acid and xylose are the monosaccharides most frequently attrached directly to the aglycone Squalene Acylated sugar moieties are also encountered In marine organisms, methylated and sulphated sugars are not uncommon Configurations of the intergjycosidic linkages are given by o and $ and the monosaccharides can be in the pyranose (p) or furanose (/) forms By virtue of carboxyl groups in the aglycone or sugar parts of a saponio, it can be rendered acidic 13 Biosynthesis A brief biosynthetic summary of triterpenes and steroids is shown in Fig 1.3 They are built up of six isoprene units and have a common biosynthetic origin in that they are all derived from squalene, presumably via ring opening of squalene-2(3-epoxide (oxidosqualene), followed by a concerted cyclization It is only recently that the corresponding cyciases have been characterized (Abe et at 1993) While the true triterpenes have 30 carbon atoms, the steroids have only 27 carbons by virtue of the oxidative cleavage of three methyl groups from a Cjo intermediate Other details of the biosynthesis of steroids have been reviewed (Heftmann, 1968; Takcda, 1972) Much work remains to be done to clarify the intermediates but at least the distinction between the cholesterol (C27) and the triterpene (C30) pathways is evident Figure 1.4 shows the cyclization of the chair-chair-chair-boat formation of squakne-2,3-epoxide Following the rearrangement of the tetracych'c carbonium ion, either a pentacyclic (eg 0-amyrin) or tetra- cychc (e.g dammarenol) tritcrpene is formed (Luckner, 1990) More details are to be found in a review article by Abe et aL (1993) In contrast, cyclization of the chair-boat-chair-boat conformation of squalene-2,3epoxide, followed by several 1,2-rearrangements, leads to the formation of either cycloartenol or lanosteroi (Fig 1.5) In the marigold {Calendula officinalis, Asteraceae), biosynthesis of oteanolic acid 3-O-glycosides occurs in the microsomes Stepwise oxid ation of jB-amyrin occurs, giving erythrodiol, oleanolaldehyde and oleanolic acid Finally the glycosides are formed (Wilkomirski and Kasprzyk, 1979) Other important classes of secondary metabolites such as phytosterols, cardenolides, cucurbitacins, quassinoids and fimonoids are also derived from squalene There are similarities in the biosynthesis of cardenolides Fig 1.3 Biosynthesis of triterpenes and steroids and steroid saponins Both can start with cholesterol, both go through a 3-keto intermediate and both processes occur actively in Digitalis spp (Heftmann, 1974) Like the saponins, many cardenolides give foams in aqueous solution but are classified separately because of their different biological activities The biosynthetic pathway to cholesterol in algae and green plants is via cycloartenol (Rees et at 1968; Goad and Goodwin, 1972; Goad, 1991), while fungi and non-photosynthctic organisms have lanosteroi as intermediate In keeping with these, biosynthetic findings, cycloartane triterpenes are found to be widely distributed throughout the plant kingdom (Boar and Romer, 1975) At first it was not certain that cholesterol could be a precursor of steroids because its distribution in the plant kingdom was not known In recent years it has been shown, however, that the occurrence of cholesterol izz 523 References Takcchi, M Shimada, S and Tanaka Y (1992), Time course and inhibition of saponin-induced hemolysis Pkmtu Mcdica, 58, 128-130 Takeda, K (1972) The steroidal sapogenins of the Dioscoreaceae In Progress in Phytochewistry, vol 3, cd L Reinhold and Y Liwschitz pp 287-333 Wiley Tannka R Nagao T., Okabe, H and Yamauchi, T (1990) Studies on the constituents of Aster tauricus U IV Structures of aster sapomns related frnm the herb Chem Pharm Bull., 38, 1153-1157 X T Kubo, M, Arich^ S and Kitagawa I U985) ^ Snins in siytens iClydne max meRr.,.l, seeds) Chan Tntcrscience New York Takeda, K., Hara S., Wada, A and Matsumcto, N (1963) A systematic simultaneous analysis of steroid sapogenins by thin-layer chromatography J Chromatogr., 11, 562-564 Takeda, O.7 Tanaka, S., Yamasaki, K_ Kchda, H-, Iwanaga, Y and Tsuji, M (1989) Screening for moljuscicidal activity in crude drugs Chem Pharm Bull 37, 1090-1091 Takernoto, T (1983) Saponins from Gynosteinma pentaphyllum Jap Pat 58 57,398 (Chem Abstr., 99, 76853) Takemoto, T and ICometani, K (1965) Triterpenglykoside (Mubenine) aus Samen von Stauntania hexaphylla Amtnten, 685, 237-246 Takemoto T, Kusano, G and Yamamoto, N (1970) Studies on the constituents of Cimicifuga spp VII Structure of cimicifugenoL Yakugaku Zasshi, 90,68-72 Takemoto, T., Nishimoto, N.r NakaL S etal (1983a) Pfaffic acid, a novel nortritcrpene from Pfajfia paniculate kuntze Terraliedron Lett., 24r 1057-1060 Takemoto, T., Arihara, S., Nakajima T and Okuhira, M (1983b) Studies on the constituents cfiGynostemnw pentaphyllum makino I Structures of gypenoside I XIV Yakugaku Zasshi, 103, 173-185 Takemoto, T, Arihara S-, Nakajima, T and Okuhira M (1983c) Studies on the constituents of Fnictus rnomordicae III Structure of mogrosides Yakugaku Zasshi 103, j 167 1173 Takemoto, T, Arihara, S., Yoshikawa, K , Kusumoto, K., Yano, I and Hayashi, T (1984) Studies on the constituents of Cucurbitaceae plants VI On the saponin constituents of Luffa cylindrica ROEM (1) Yakugaku Zasshi, 104 246-255 Takemoto, T., Arihara S., Yoshikawa, K., Tanaka, R and Hayashi, T (1985) Studies on the constituents of Cucurbitaceae plants XIII On the saponin constituents of Luffa cylindrica roem (2) Yakugaku Zasshi, 105, 834-839Takemoto, T., Arihara, S and Yoshikawa K H986) Studies on the constituents of Cucurbitaceae plants XIV On the saponin constituents of Gynosienmw pentaphyllum makino (9) Yakugaku Zasshi, 106, 664-670 Tamura, K Mizutani, K and Yamamoto, S (1990) Isolation of monodesmoside saponins from rind of Sapmdus trifoliatus or -mukorosii fruits as skin fungicides Jap Pat 02 160,798 (Chem Abatr., 113, 218226) Tanaka, M-, Mano, N., Akazai, E., Narni, Y-, Kato, F and Koyama, Y (1987) Inhibition of mutagenicity by glycyrrhiza extract and glycyrrhizin J Pharmacobio-Dyiu 10, 685-688 Tanaka, O (1985) Application of 13C-nuclear magnetic resonance specirometry to structural studies on glycosides: saponins of Panax spp and natural sweet glycosides Yakugaku Zasshi, 105, 323-351 Tanaka, O (1987) Solubilizing properties of ginseng saponins Korean J Ginseng ScL 11, 211-218 Tanaka O and Kasai, R (1984) Saponins of ginseng and related plants Prog Chem Org Nat Prods., 46, 1-76 * 2« Y, Yoshikawa, M and Kitagawa I (1988a) Saponin an^apog^ XLril Acetylso^aponins A., A, and A6 new a«n bisdesmosides of soyasapegenc A, from Japanese soybean, the seeds o Gtvane max MERR.IX Chem Pharm Bull., 36, 2S29-2839 Taniyama T Yoshikawa, M and Kitagawa, (1988b) Sapon.n and sapogenol XUV S^yasapomn composition in soybeans of vanous ongms and soya- faponin -men, in various organs of soybean Structure of soyasapomn V from soybean hypocotyl Yakugaku Zasshi, 108, 562-571 Tewan NC Ayengar, K.N.N and Rangaswami S (1970) Structure of sapo- %'Zo(CoJ,uaa,auca Caccigenin, caedgpnin actone and 23^eoxycaccicenin Indian J Chem., 8, 593 597 STlRM Lapa, A.I., Souccar, C and Valle, J.R^ (1984) Timb« Ichthyotoxic plams used by BraxiUan Indians J EthnophannacoL 10, Texier!S Ahond, A., Regerat, F and Poonal H (1984)-A*penoid saponin from Firarla rammcuhida tubers Phytcchemistry, 23, 290J HWS- Tian J Wu, F Qiu, M and Nie, R (1993a) Two mterpcnoid saponins from Wrocephalus bretsckneidri Phylochemislry, 32, 1539-1542 Tian" Wu F-, Qiu, M and Nie R- (1993b) Tnttrpenoid saporans from 'ptcrocephcihs hookeri Photochemistry, 32, • 535-1538 Tillekeratne, L.M.V., L.yanage, G.K., Ratnasoonya, W.D., KsebaU MB and Schmitz, F.J (1989) A new spermatostat.c glycoside from the sofl cor^l Smula,ia crtspa J Nat Prod 52, 1143-1145 Ttabekova, A.E and Abubakirov, N.K (1984) Tnterpene glycos.des of alfel a I Medicoside G - a novel bisdesmoside from Meilcagc salwa Klum Mr Timblkovt Axind Abubakirov, N.K (.985) Triterpene glycosides of alWfa II Medicoside C Khim Prir Soedm., 805 808 Timbckova, A.E and Abubakirov, N.K (1986) Tnterpene g.ycos.des of alfalfa III Medicoside I Khim Prir Scedin., 607-610 Timon-David, P., Mien, j, Gasquet, M, Balansard, G and Bernard P (1980) Recherche d'une activite antifongique de plusreurs pnncpes dCt.fs Extraits du lierre grimpant: Hedera helix L Am Phamvc Fr., 38, Tingey5W.M (1984) Glycoalkaloids as pest resistance factors Am Potato J., 61 TiJrfK^and Choudhary, R.N (1979) A new saponin from Wisteria anemh Indian J Chem 18B, 389-390 Tiwari, FLP.'and Masood, M (1980) Obtusilobicinin, a new saponin from Anemom obtusiloba Phytochenustry, 19, 1244-1247 rt, K.P and M.nocha, P.K (1980) Pavophylhne, a new sapon.n from he stem of Pavonla zeylanica Phylochemlslry, 19, 701-704 >i - — References Tiwaii, K.P., Srivastava, S.D and Srivasiava, S.K U980) a-i.-Rhamnopyranosy]3/?-hydroxy-Jup-20(29)-en-28-oic acid from the stem of Dittenia pentagyua haKhe R (1971) Advances in the chemistry of an.ibiotic substances fron, Hghcr plants In Plu.rnu.co^ end Pl.yu.Cemistry, ed H Wagner and Tokuda, R, Konoshima T Kozuka M and Kimura, T (1988) Inhibitory effccts of l2~0~tetradecanoyIphorboM3-acetate and tclcocidin B induced Epstein •techc° R and A»n U (1964) Tntcrpenes XV The cryptocsan qucst.cn Phywchemistry, 19, 980 981 Barr virus by saponin and its relaied compounds Cancer Leu 40.309 317 Tomas-Barbaren FA and Hostettmann, K (1988) A cytoioxic triterpenoid and flavonoids from Crossopteryx febiifuga, Planta Medico 54 266 267 Tornita, Y and Uomori, A £1971) Biosynthesis of sapogenins in tissue cultures of Dioscorea tokoro makino J Chan Soc Chem Comnun., 284 Tomowa M.P Panowa, D and Wulfson, N.S (1974) Steroid saponrns and sapogenins IV Saponins from Tributes tcrreslrh Planta Medico IS 231 -237 Tomowa, M Gyulemetova, R Zarkova S., Peeva, S., Pangarova, T and Simova, M (1981) Sieroidal saponins from Tributes terrestris L wiih a stimulating action on the sexual functions, Int Coif Chem Bioteclmol Biol Act Nat Prod X 298 302 Topping D.L Hood R.L., Illman R.J., Storer G.B and Oakenfuli, D-G (1978), Effects of dietary saponin on bile acid secretion and plasma cholesterol in ihe rat Prat Nutr Soc Ausu 68 [Chem Abstr,, 90, 85661) Topping, D.L., Illman R.J., Fen wick D.E and Oakenfull D.G (1980) Proc Nutr Soe Atau 195 Tori, K_ and Aono, K (1964) Ann Rept Shionogi Res, LaK 14, 136 Tori K Seo, S., Shimaoka, A and Tomita, Y (1974) Carbon-13 NMR spectra of olean-12-encs Full signal assignments including quaternary carbon signals assigned by use or direct I3C lH spin couplings Tetrahedron Lett., All! 4230 Tori, K., Yoshimura Y Seo S., Sakurawi K Tomita, Y and Ishii H (1976a) Carbon-13 NMR spectra of saikogenins Stereochernical dependence in hydroxylation effects upon carbon-13 chemical shifts of oleanene-iype triterpenoids Tetrahedron Leu., 4163 4166 Tori, K Scot S., Yoshimura Y Nakamura, M Tomita, Y and Ishii H (1976b) Carbon-13 NMR spectra of saikosaponins A C, D and F isolated from Bupleurum fdcotum L Tetrahedron Lett., 4167 4170 Tori, K., Seo, SM Terui, Y., Nishikawa, J and Yasuda, K (19^1) Carbon-13 NMR spectra of 5/?-sterordid sapogenins Reassignment of the F-ring carbon signals of [25S)-spirostans Tetrahedron Lett., 22 2405 -2408Toyota, M Msonthi J.D and Hostetlmann K (1990) A molluscicidal and antifungal trilerpenoid sapomn from the roots of Cteradendrum wildii Phjtochemhtry 29 2849-2851 Tripafhi, R.D and Tiwari, K.P (1980) Geniculatin a triterpenoid saponin from Euphorbia genicuhta Phytochenustry 19? 2163 2166 Trofimova, N.A., Romanova, G.A., Benson, NA and Dmitruk S.E (1985) Chemical composition of isolated tissue cultures and the intact Orthosiphon siantineus blnth plant Rastit Rcsur-, 21, 90-95 (Chem Ahstr 102, 128861) TsaL T.-H and Chen, C-F (1991) Determination of three active principles in licorice extract by reversed-phase high-performance liquid chrcmatography / Chromowgr-, 542, 521 525 L Horhammei pp 274 289 Springer Berlin, Naiurwisscnsctiaften, 51 359 360 -hesche R and Balle G (1963) Ucbcr Sapomne der SpirostanoJ-rcite X ' Zur Konstitution dcr Samcn Saponine von Digitalis lama fhrH Tetrahedwn 19 2323-2332 ■hesche R and Forstmann D (1957) Ueber Tnterpene IV Muscnnm em " Wurmw^rksames Saponin aus der Rinde von Alhizzia anthehmntic^ Chem Bt-r 90.2383 2394 chesche R and Gutwinski H (1975) Steroidsaponine imt mchr als cincr Zuctokcue, X Capsicosid, ein bisdesmosid.che^ 22-HydroxyfuroSianolGlycosid aus dem Samen von Capsicum annuum L Chem, Ber 108.265 111 schesche R and H«*h, A (1952) Ueber Tnterpene II Mittei ••G^-f' ™ Triterpenglykosid aus Gratiah officinahs L Chem Be,:, 85 "067-IU77 ■schesche, R and Hulpke; H (1966) Biosynihesis of plant steroids III Bio synthesis of sptrostanols from cholesterol giucoside / NatmjorscK 2I«- Tschclche^and Kammerer F,J f 1969) Ueber Tnterpene XXVII Die Siruklur von Musenmn und Desglucomusennm Annatcn, 724, ifcJ- IW Tschesche R and Richert K,H (1964) Ueber Saponine der SpirostanotahcsXI Nuatigenin, ein Cholegcnin-Analogon des Pilanzenreichcs Tetrahedron 7f\ ^R7— 19H Tschesche, R and Schultz, H (1974) Ueber Trherpenc, XXX Ueber das Haupisaponin der Kornrade (Agrcstemna githago LX Chem tiu lu/: 2710 2719 Tscteche R and Striegler H (1965) Trilerpene* XVI Identity of tenuiTofic acid with scnegenin NaturwissenscUafien 52, 303 Tschesche R and Wulff G (1963) Ueber Saponine der Spirosiano)retch Die Konstitulion des Digilonins Tetrahedron, 19 621 634 IX Tschesche R and Wulff, G (1964) ^Constitution und Eigenschaftcn der Saponine Planta Medica, 12 272 292 Tschesche R and Wulff G (1965) Ueber die antimikrobiclle Wirksamkeit von Saponincn Z Naiwforsch., 20B 543-546 , Tschesche R and Wulfl" G (1972) Chemie und Biologic der Saponine I rog Chem Org Nat Prods., 30, 462 606 Tsduachc R- and Ziegler F (1964) Ueber TrUcrpcne, XII Ueber die Saponine dcr Wurzeln von Primula elatior l, schreber Amwlen 674 185— 195 Tschesche, r! Duphorn J and Snatzke G (1963) Ueber Triterpene IX Ueber die Konstitution der Cincholsaure und die sauren Tnterpenglykos.de der Chinarinde Annalen 667 151-163 Tschesche R Inchaurrondo F and Wulff, G (1964) Ueber Trilerpene, XVII Das Aglykon des Cydamins Annalen 6Jft) 107 118 Tschocte R Schmidt W and Wulff, G (1965) Triterpenes XIX Ration and structure elucidation of ivy saponins {Redera helix) Z Naturjorseh., 20B 708 709 Tschesche, R., Striegler, H and Fehlhaber, H.-W (1966a) Ucber Triterpene XlX Die Struktur dcs Cydamiretins A Annalen, 691, 165-171 Tschesche, R., Kottler, R and Wulff, G (1956b) Ucbcr Saponfne der Spirostanolreihe, XII Ueber Parillin, ein Saponin mit stark verzweigter Zuckerkette Aimalen 699, 212-222 Tschesche, R., Tjoa B.T and Wulff, G (1966c) Ueber Triterpene, XXI Ueber die Sapcgenine aus den Wurzeln von Primula verts L Annalen, 696,160-179 Tschesche, R Tjoa, BX, WuIrT, G and Noronha, R.V (1968) Steroidsaponine mit mehr als einer Zuckerkette, III Convallamarosid, ein wcitcres 22Hydroxy-Furoslanolsaponin Tetrahedron Lett,, 5141 5144 Tschesche, R.? Weber, A and Wulff, G (1969a) Ueber Triterpene, XXV Ueber die Struktur des *Theasaponins\ eines Gemisches von Saponjncn aus Thea simnsis U mit stark antiexsudativer Wirksamkeit Annalen, 721, 209 219 Tschesche, R., Ludke, G and Wulff, G, (1969b) Steroidsaponine mit mehr als einer Zuckerkeltc, II Sarsaparillosid, ein hidesmosidisehes 22-Hydroxy- furostanol-saponin Chem Ber., 102, 1253-1269 Tschesche, R Mercker, H.-J and Wulff, G (1969c) Ueber Triterpene, XXIV Die Konstiiuiion der Zuckerkette des Cyclamins Anvalen, 721, 194-208 Tschesche, R., Tauscher, M., Fehlhaber, H.-W and Wulff, G (I969d) Steroid saponine mit mehr als einer Zuckerkette, IV Avcnacosid A, ein bisdesmosidisches Steroidsaponin aus Avena sativa Chem Ber., 102 2072 2082 Tschesche R., Rehkamper, H and WulfT, G (1969e) Ueber Triterpene, XXVIII Ueber die Saponinc des Spinats (Spiriacia aleraeea L.) Annalen, 726 125135 Tsuda Y Kiuchi, F and Liu H.-M (1989) Establishment of the structure of gymnemagenin by X-ray analysis and the structure of deacylgymnerrm; acid Tetrahedron Lett., 30, 361 -362- Tsuji, R, Osaka, S and Kiwada, H (1991) Targeting of Iiposomes surface" modified with glycyrrhizin to the liver Preparation and biological dis position Chem Pharm, Bull., 39, 1004-1008 Tsukamoto, T and Ueno, Y (1936) Glucosides of Dioscorea tckoro makino I Dioscin, dioscoreasapotoxin and diosgenin Yakugaku Zasshi, 56, 802 Tsukamoto,V Ueno, Y and Ohta, Z (1936) Constitution of diosgenin I Glucoside of Dioscorea wkoro makdjo J Pharm Soc Jpti., 56, 931-940 Tsukamoto, T, Kawasaki, T., Narakl A and Yamauchi, T (1954) Saponins of Japanese Dioscoreaceae II Waier-insoluble saponins from Dioscorea iiip- ponica makino, D gratillima miq^ and D tenutpes franc:h et sav Yakugaku Zas&hi, 74, 984 987 Tsukiiani, Y and Shoji, J (1973) Studies on the constituents of Senegae radix III The structures of senegin-III and -IV, saponins from Polygala senega linne var latifolia tokry et gray Chem, Pharm Bull 2h 1564 1574 Tsukiiani, Y-, Kawanishi S and Shoji J 0973) Studies on the constituents of Senegae radix II The structure of senegin-II, a saponin from Polygala senega linne var latijblia tqrrv et gray Chem Pharm Bull., 21, 791 799 Tsurumi S., Takagi, T and Hashimoto, T (1992) A y-pyronyl-triterpcnoid saponin from Pisum sativum Phytochemistry, 31, 2435-2438 Tursch, B., Tursch, E Harrison, I.T et al (1963) Terpenoids LIU Demonstration of ring conformation^ changes in tritcrpencs of the /j-amyrin class isolated Tschesche, R., Wulff, G., Weber, A and Schmidt, H (1970) Frasshemmende Wirkung von Saponinen auf Termiten {Isoptera, Reticulitermes), Z Naturfarsch 25B, 999-1000 Tschesche R Seidel, L., Sharma, S.C and Wulff, G (1972) Steroidsaponine mit mehr als einer Zuckerkette VI Ueber Lanatigosid und Lanagitosid, zwei bisdesmosidische 22-Hydroxy-FurastanoI-Glykoside aus den Blattern von from Stryphnodendron coriaceum J Org Chem., 28, 2390-2394 Tursch, B., Leclercq, J and Chiurdoglu, G (1965) Structurc-de I'acide mesembryanthemoidigenique, triterpene nouveau des cactacees Tetrahedron Lett,, Tscheschc, R., Hermann K.-R, Langlais, R., Tjoa, BX and Wulff G (1973) Steroidsaponine mit mehr ats einer Zuckerkette, VII Convallomarosid ein UniyaL, G.C, Agrawal, P.K., Thakur, R.S and Sati, O.P (1990) Steroidal Digitalis lanata ehrh Chem Ber., 105 3397-3406 trisdesmosidisches 22-HydroxyfurostanoI-Glycosid aus den Wurzeln von Convallaria majalts L Chem Ber., 106, 3010-3019 Tschesche, R_ Goossens, B and Topfer, A (1976) Zur Einfiihrung des StickstofTs und zura gemeinsamen Vorkommen von 2S(R)- and 25(S)-Steroidalkaloiden in Solanaceen Phytochemistry, 15, 1387-1389, Tschesche R Sepulveda, S and Braun, T.M (1980) Ueber Triterpene, XXXlH Ueber das Saponin der Bliiten von Verbascum phlomoides L Chem Ber., 113, 1754 1760 Tschesche R., Wagner, R and Widera, W U983) Saponine aus den Wurzeln von Primula claiior (L.) schreber Konstiiution eines Nebensaponins und Re vision der Zuckerkelte des Hauptsaponins Annalen 993-1000 Tsuda, Y., Kaneda, M., Vasufuku, N and Shirnizu, Y (1981) Lycopodim iriterpenoids, (II) The structures of imindoside-A, -B, -C, -D,, -D2, -E, -F and -G, tritcrpenoid-glycosides occurring in Lycopodium inundatum L Chem Phcmn Bull, 29, 2123-2134 4161-4166, Ujikawa K and Purchio A (1989) Substancias antifungicas, inhibidoras de Aspergitlus flaws e de oulras fungicas, isoladas de Agave sisalana (sisal) dene Cult (Sao Paulo), 41, 1218-1224 glycosides from Agave contain Phytochemistry, 79, 937-940 Uniyal, G.C Agrawal, P.K., Sati, O.P and Thakur, R.S (1991) Agaveside C, a steroidal glycoside from Agave cantata Phytochemistry, 30, 1336-1339 Uniyal, S.K and Sati, O.P- (1992) Triterpenoid saponins from roots of Clematis grata Phytocliemistry, 31, 1427-1428 Ushio, Y and Abe, H (1991) The effects of saikosaponin on macrophage functions and lymphocyte proliferation Planta Mcdica 57 511-514 Ushio, Y and Abe, H (1992) Inaciivation of measles virus and herpes simplex virus by saikosaponin a Planta Medka, 58 171-173 Usmanghani K H977) Isolation of sapogenin structures from the roots of Lysimachia mawitiana lam Pak J Sci Ind Res-, 20, 393-395 (Chem Abstr., 91 27215) Uvarova, N.I., Gorshkova, R.P and Elyakov, G B (1963) Preparation of the total glycoside preparation from ginseng by using sephadex Chem Abstr., 60,13099 Vagujfelvi, D (1965) Biogenesis of steroid glycoalkaloids in plants Herba Hung., 170-184 528 References References Valent B.S Darvill, A.G., McNeil, M., Robertsen, B.K and Albersheim, P (1980) A general and sensitive chemical method for sequencing the glycosyl residues of complex carbohydrates Carbohydr Res., 79, 165-192 van Antwerp, C.L., Eggert, H., Mcakins, G.D_ Miners J.O and Djerassi, C (1977) Addilivity relationships in carbon-13 nuclear magnetic resonance spectra of dihydroxy steroids J Org Chem., 42, 789 793 529 Vasyukova, N.I, Paseshnichenko, V.A-, Davydova, M.A and Chalenko G.I (1977) Study of the fungitoxic properties of steroid saponins from Dioscorcu dehoidea rhizomes PriU Biokhim Mikmhinl 13 172-176 (Chem Abstr., 87 33923) Vazquez M-I, Quinoa, E Riguera, R., San Martin, A and Daiias, J (1992) Sanliagosidc, the first asterosaponin from an Antarctic starfish {Neasmilaster ran Gelder, W.MX (1984) A new hydrolysis technique for steroid glyeoalkaloids with unstable aglycones from Solatium species J ScL Food Auric 35 Vech'erko, L.P., Kabanov, V.S and Zinkevich, E.P (1971) Structure of cal- Vanhaelen, M (1972) New saponoside from Bersama yaugambiemis Phyto- Vecherko, I.P., Zinkevich, E.P., Kogan, I.M (1973) Structure of caienduloside Vanhaelen M and Vanhaefen-Fastre, R (1984) Quantitative determination of biologically active constituents in crude extracts of medicinal plants by thin-layer chrotnatography-densitomctry II Eleuiheroccccus senticosus Vecherko, L.R, Sviridov, A.F., Zinkevich, E.P and Kogan, L.M (1975) Structure 487-494 chemhtry, II, 11111116 maxjm., Panax ginseng meyer and Picrorrhiza kurrva kovle J Chromotoar 312, 497 503 Vanhoutte, P.M (1986) Alpha-adrenergic effects oiRuscus acuhattts on cutaneous veins Modulation by local temperature In Advances in Medicinal Phytochemistry, ed D Barton and W,D OIlis, pp 187- 194, Libby, London van Kampen, EJ and Zijlstra, W.G (J961) Standardisation of hemoglobinometry II The hemiglobin cyanide method Clitt Chim Ada, 538-544 (Chem Abstr., 55, 27503) Varshney, I.R and Badhwar, G (1971) Saponins and sapogenins of Bassia hngifolia and Mimusops elengi Proc Natl Acad Set India, Sect A 4] 21-23 (Chem Absir., 77, 123778) Varshney, I.R and Beg M.F.A (1977) saponins from the seeds of Luffa aegyptiaca mill.: isolation of acgyplinin A and aegyptimn B Indian J Chem 15B, 394 Varshney, IP and Khan, M.S.Y (1961) Saponins and sapogenins VII Acid sapogenins isolated from Maharashtrian Aibizzia odoratissima seeds J Pharm ScL, 50, 923-925 Varshney, IP and Khan, M.S.Y (1962) Saponins and sapogenins XII Isolation of odoratissimin, a new saponin from the seeds of Albizzia odoratlssiim J ScL Indian Res., 21B, 30-33 (Chem Abstr., 57, 9938) ejcorgianus) Tetrahedron, 48, 6739-6746 enduloside B from Calendula officinalis roots Khim Prir Soed'w., 533 F from Calendula officinalis roots Khim Prir Soedin, 561-562 of calendulosides C and D from Calendula officinalis roots Khim Prir Soedin., 366 373 Vclieva, M.N., Iskenderov G.B Amiralieva U.A and Gazhieva, G.Ya (1988) Structure and hypochol^er6111^ properties of saponins from Gypsophila capitata Chem Abstt\ 109, 70410 Vereskovskii, V.V and Chekalinskaya, I.I (1980) Polyphenols and saponins of Rhapomicum canhamoides (willd) JUiN Chem Abstr., 92, 3212 Vidal-OIIivier, E., Babadjamian, A., Maillard, C, Elias, R and Balansard, G (1989a) Identification el dosage par chromatographie liquide haute per formance de six saponosides dans Ies fleurs de Calendula officinalis pharm Ada Heir,, 64, 156 159 Vidal-OIIivicr, E.? Balansard, G., Faure, R and Babadjamian, A (1989b) Revised structures of triterpenoid saponins from the flowers of Calendula officinalis J Nat Prad., 52, 1156 1159 Vidal-OIIivicr, E Babadjamian, A., Faure R et al (1989c) Two-dimensional NMR studies of triterpenoid glycosidcs II IH NMR assignment of arvensosidc A and B, calenduloside C and D Spectrosc Leti^ 22, 579-584 Vogel, G (1963) Zur Pharmakologie von Saponinen Planta Medica, II, 362-376 Vogel, G and Marek, M.-L (1962) Zur Pharmakologie einiger Saponine Arzneimittelforsch 12, 815-825 Vogel, G., Marek M.-L and Oertner, R (1968a) Zur Frage der Wertbestimmuny Varshney, I.R and Khanna, N (1978) Partial structure of a new saponin samanin-D from the flowers ofPithecohhium saman benth Indian J Pharmac antiexsudativ wirkender Pharmaka Arzneimitielfbrsch., 18, 426-429 Vogei, G Marek, M.-L and Oertner, R (1968b) Zur Pharmakologie des Tcesamen-Saponins, eines Saponingemisches aus Thea smensis L Arzitci- Varshney, IP and Shamsuddin, K.M (1962) Saponins and sapogenins XVI Echinocystic acid from the seeds of Albizzia amara J Sa Indian Res 21B Vogel, G., Marek, M.-U and Oertner, R (1970) Umersuchungen zum Mechanisraus der therapeuiischen und toxischen Wirkung des Rosskastanien- ScL, 40, 60-61 347 Varshney, IP and Sharma, S.C (1968) Saponins and sapogenins XXII Chemical investigation of seeds of Myristica fragrant Indian J Chem., 6, 474 Varshney, I.R, Jain, D.C, Beg; M.F-A and Srivastava, H.C (1985) Samanin-C and samanin-E, new saponins from Pithecclobtum saman Fitoterapia 56 281 -283 * ' Vasanth S., Kundu, A.B., Panda, S.K and Patra, A (1991) Vicosidc A, a 28-nortriterpenoid glucosidc from Vicoa indka Phytochemistry 30 3053- 3055 ' ' mitielforsch., 18, 1466-1467 Saponins Aescin Arzneimitxelforseh., 20, 699-703 Voigt, G and Hiller, K (1987) Neucre Ergebnisse zur Chemie und Biologie der Steroidsaponine ScL Pharm., 55, 201-227 Voigt, G., Thiel, P, Hiller, K., Franke, P and Habisch, D (1985) Zur Struktur des Hauptsaponins der Wurzeln von Eryngium ptotiutn I Pharmazie, 40, 656 Vora, P-S (1982) High-pressure liquid chromatographie determination of glycyrrhizic acid or glycyrrliizic acid sails in various licorice products: col laborative study J Assoc Off Anal Chem., 65, 572 574 Vugaltcr, M.M., Dekanosidze, G.E., Dzhikiya, O.D and KemerteJidze, E.P 0986) Triterpene glycosides of Caltha polypetala Glycosides A, B, D, E and F Khim Prir Sncditu, 712 716 Vugalier, M.M Dekanosidze, G.E., Dzhikiya, O.D and Kemertelidze, E.R (1987) Triterpene glycosides from Cahha polypetala Izv Akod Nauk Gruz SSR, Ser Khim., 13, 314-315 Wagner, H and Reger, H (1986a) Folium Hederae-Exlrakte: HPLC-Analyse DiscL Apoth Ztg., 126, 2613-2617 Wagner, H and Reger, H (1986b) Radix Primulae-Extrakte: HPLC-Analyse Dtsch Apoth Ztg,, 126, 1489-1493 Wagner, H., Ott, S., Jurcic, K., Morton, J and Neszmdyi, A (1983) Chemistry, 13C-NMR study and pharmacology of two saponins from Cohtbrtna asiatica Plama Medica, 48, 136-141 Wagner, H Bladt, S- and Zgainski, E.M (1984a) Plant Drug Analysis SpringerVerlag, Berlin Wagner, H., Nickl H and Aynehchi, Y (1984b) Molluscicidal saponins from Gundelia wuniefonii Phytochemistry, 23, 2505-2508 Wagner, H.T Roger, H and Bauer, R (1985) Saponinhaltige Drogen imd Fertigarzneirnittel: HPLC-Analyse am Beispiel von Rosskastaniensamen Dtsch Apoth Ztg., 125, 1513-1518 Wagner, H_, Ludwig, C, Grotjahn, L and Khan, M.S.Y (1987) Biologically active saponins from Dodonaea viscosa Phytochemistry, 26, 697-701Wagner, J and Hoffmann, FL (1967) Ueber Inhaltssloffe des Rosskastaniensamens, V Untersuchung an Triterpenglykosiden Z Physiol Chem., 348, 1697 1698 Wagner, J and Sternkopt, G (1958) Chemische und physiologische Untersuchungen uher das Saponin der Zuckerrube Nahrung, 2, 338-357 Wall, M.E and Serota, S (1959) Conversion of sleroidal sapogenins to pseudosapogenins US Patent 870 143 {Chan Abstr 53 16211) Wall, M.E, Eddy, C.R., McClennan, M.L and Klumpp M.E (1952) Detection and estimation of steroidal sapogenins in plant tissue Anal Chem 24 1337-1341 Wallcniels, K (1950) Ueber einen neuen Nachweis reduzierender Zuckcr im Papierchromatogramm und dessen quantitative Auswertung Naturwtssenschaften, 37, 491-492 Wallenfels, K., Bechtler, G., Kuhn, R., Trischmann, H and Egge, H (1963) Permelhylation of oligomeric and polymeric hydrocarbons and quantitative analysis of the cleavage products Angew Chem., 75, 1014-1022 Waller, D.P., Zaneveld, LJ.D and Fong, H.H.S (1980) In vitro spermicidal activity of gossypol Contraception 22 183-187 Walter, E.D (i960) Note on saponins and their sapogenins from strawberry clover J Am Pharm Assoc., 49, 735 736 Walter, E.D- (1961) Isolation of oleanolic acid saponin from trefoil (Lotus corniculatus var viking) J Pharm Set, 50, 173 Wallho, J.P., Williams, D.H., Mahato, S.B., Pal, B.C and Barna, J-C.J (1986) Structure elucidation of two triterpenoid tetrasaccharides from Androsace saxijragifolia J Chem Sac, Perkin 1, 1527-1531 Wang, B.Z., Wang, G.Z and Liu, AJ (1981) Antiinflarnmatory effect of saikosaponins Chvng-Kuo Yaoli Hsueh Pno, 2, 60-63 {Chem Abstr., 947 150447) , , Wang, H He, K., Ling, L and Li, H (1989a) Chemical study of Astragalus plant 11 Structures of asernestioside A and B, isolaied from Astragalus ernestu comb Huaxue Xuebao, 47, 583 -587 {Chem Abstr., lit, 2289651 Wang, H.K., He, K., Ji, L., Tezuka Y Kikuchi, T and Kitagawa, (1989b) Asernestioside C a new minor saponin from the roots of Astragalus ernesiii comb.: first example of negative nuclear Overhauser eflcci in the saponins Chan Pharm Bull, 37, 2041-2046 Wang H Yu, D., Liang, X., Watanabe, N., Tamai, M and Omura, S (1989c) Yemuosidc VM7) YMHl YM13 and YMl4: four nortriterpenoid saponins from Stavnlonia duuensis Planta Medica, SS, 303-306 Wang, M., Guan, X., Han, X and Hong S (1992) A new triterpenoid sapontn from Ardisia crenata Planta Medica, 58, 205-207 Wang, M.-K., Wu7 F.-E and Chen, Y.-Z (1993) Triterpenoid saponins from Anemone hupehensis Phytochemistry 34, 1395 1397 Warashina, T Miyase, T and Ueno A (1991) Novel acylated saponins from TragopoQon pomfolnts L Isolation and the structures of tragopogonsapomns A-R Chem Pharm Bui!., 39, 388-396 Wasicky, R and Wasicky, M (1961) Polygah brasiliensis L, cine saponmreiche Potygala-Art Brasilien* Qualitas Plant Mat Vegetables, 8, 65-79 Watanabe, K., Fujino R, Morita, T Kasai, R and Tanaka, O (1988) Solubilization of saponins of Bupleuri radix with ginseng saponins: cooperative cficct of dammarane saponins Planta Medica, 54, 405-409 Watanabe, N Saeki, J., SumimOto, M., Kondo, T and Kuroton S (1966) Antitermitic substance of Teinstwemia japonica wood I Nippon Mokuzm Gakkaishiy 12, 236 238 {Chem Abstr 66- 102477) Watanabe, Y., Sanada, S., Ida Y and Slioji, J (1983) Comparative studies on the constituents of Ophiopogonis tuber and its congeners II Studies on the constituents of the subterranean part of Ophiopogon planiscapus nakai Chem Pharm Bull, 31, 3486-3495 Weil, L (1901) Beitragc jut Kcnntnis der Sapomnsuhstanzen und ihrer Veibreitung Arch Pharm., 239, 363-373 Wdssenbcrg, M., Klein M., Meisner, J and Ascher, K.R.S (1986) Larval growth inhibition of the spiny bollworm, Eartas insulana, by some steroidal secondary plant compounds Eniomol Exp AppU 42, 213-217 Wenkert, E, Badddcy, G.V., Burfilt, I.R and Moreno L.N (1978) Carbon-13 nuclear magnetic resonance speclroscopy of naturally-occurring substances LVH Trilerpenes related to lupane and hopane Org Magn Reson., 11, 337 343 Weston, RJ Gottlieb H.E Hagaman, E.W and Wenkert, E (1977) Carbon-13 nuclear magnelic resonance speclroscopy of naturally occurring substances Aust.J C/mwi., 30, 917-921 Wierenga, J.M and Hollingworth, R.M (1992) Inhibition of insect acetylcholinestcrase by the potato glycoalkaloid a-chaconine Natural Toxins, 1,96 -99 Wilkins, A.L., Ronaldson, K.J., Jager, P.M and Bird, P.W (1987) A carbon-13 NMR study of some oxygenated hopane trilerpenes Ami, J Chem., 4U, 1713 1721 532 References References Wilkormrski, B and Kaspr^k, Z (1979) Free and ester-bound triterpene alcohol, 533 Triterpenoid saponins from the roots of Phvtolacca americana Planta Medico, 34, 87-9Z ^,« Tf LdbfrilZ'a ' C°^* assifinmen, and conformation! studies of tomatine and tomatidine Mag Res Chem 30 645-650 Wflluhn G and Kolhe U (1983) Das bil.ere Prinzip d'es Bhtemissen Nach,- scha tens, Solamun dulcmnara L - Isolierung und Struktur neuer Furostanolglykoside Arch Phann., 31.6, 678-687 Wilson, R.H., Poley, G.W and de Eds, F (1961) Some pharmacolcgic and toxicologic propert.es of tomatine and its derivatives Toxicol Ami Phar- macol 3, 39-48 ' Windaus A (1909) Ueber die EntgifUme der Saponine durch Cholesterir, Ber 42, 238-246 Windaus, A and Schneckcnburger, A (1913) Ueber Gilonin, ein neues DigtuHUGlykosid Ber., 46, 2628 2633 Wmicrstcin, A and Stein, G (1932) Un.ersuchungen in der Sapomnrdhc X Mittei ung Ueber die Oxy-trilerpensaure-glykoside der Araliaceen Z Phymol Chem 211, 18 Woitkc, H.-D., Kajwr, J.-R and Hiller, K (1970) Fortschriite in der Erforschung der Tnicrpensaponine Pharmazie, 25, 133-143 213-241 Wojciechowski, Z.A (1975) Biosynthesis of oleanolic acid glycosides by subcellular fractions of Calendula officmalLs seedlings Phytochemtstry, 14, 1749- Wojciechowski, Z.; Jdonkiewicz-Konador, A., Tomaszewski, M., Jankowski J and Kasprzyk, 7, (1970) Structure of glycosides of oleanolic acid' isolated from the roots of Calendula cffjcmalis Phytochemistry, 10, 1121 Woffender J.-U Maillard M, Marston, A and Hosteltrnann, K (1992) Mass !STCiUnderiVatiZed natlirH M2i4 i d* ik Wu, F., Koike, K., Ohmoto, T and Chen, W.-X (1989) Saponins from Chinese folk medicine, 'Zhu jie xiang fu\ Anemone raddeana regkl Chem Phann Bull., 37, 2445 Wu, J and Chen, J (1988) Depressan actions of Panax notoginseng saponins on vascular smooth muscle Zhongguo Yaoti Xuebao, 9, 147-152 (Chem Abstr., 108, 179841) Wulff G (1965) Determination of sugars in glycosides and oligosacchartdes by gas chromatography J Chromatogr,, 18, 285-296 Wulff, G (1968) Neuere Entwicklungen auf dem Sapcningebiel Dtsch Apoth Zty., 108, 797-808 Wulff, G and Tschesche, R (1969) Ueber Triterpene-XXVl Ueber die Struktur des Rosskaslaniensaponine (Aescin) und die Aglykone verwandtcr Glykosidc Tetrahedron, 25, 415^436 Xu: C-J and Lin, J,-T (1985) Comparison of silica- C18-, and NH2-HPLC columns for the separation of neutral steroid saponins from Dioscorea plants J Liq Chroinmogr» 361-368 Xu D., Zhang, B., Qi, Y and Ma, J (1983) Studies on alkaloids of Ping Bei Mu (Fritilhria usswiensis maxim.) II Isolation and identification of sipeimine glj'coside Zhvngcaoyav, 14, 55-56 {Chem Abstr., 98, 212853) Xu, D.-M., Xu, M.-L., Wang, S.-Q et al (1990) Two new steroidal alkaloids from Frittilaria usswiensis J Nat Prod., 53, 549-552, Xu, J.-R, Xu, R.-S., Luo, Z and Dong, J.-Y (1991) New triterpenoidal saponins from folk contraceptive medicine, Mussaenda pubescens Huaxue Xuebao 49, 621-624 (Chem Abstr., 115, 131997) Xu, J.-P., Xu, R.-S and Li, X-Y (1992a) Four new cycloartane saponins from Curculigo orchioides Planta Mcdica 58, 208-210 Xu, J.-R, Xu R.-S Luo Z Dong, J.-Y and Hu, H.-M (1992b) Mussaendosidcs Wolters, B (I965X Der Anteil der Steroidsaponioe an der anribfotischen Wirkunp M and N, new saponins from Mussaenda pubescens J Nat Prod., 55 Wolters B (1966a) Zur antimikroWeHen Wirksamkeit pflandicher Steroidc und Xu, S., Chen, Y., Cai, Z and Yao, X (1987) Chemical constituents of Panax quinquefolius unn Yaoxue Xuebao, 27, 750-755 (Chem Abstr., 108, von Solarium dulcamara, Phnta Medica, 13, 189-193 Tnlerpene Planta Medtca, 14, 392-401 Wolters, B (1966b) The action of various triterpene saponins on fungi Naturwssenschqften, 53 253 Wolters, B (1968a) The antibiotic action of saponfns HI Saponins as plant iungistatic compounds Planta (Berlin), 79, 77-83 1124-1128 72123) Xu, W.-H and Xue, Z (1986) Chemical investigation of glycosidal steroidal alkaloids of Nonhotiron hyacinthmwn Yaoxue Xuebao, 21 177-182 (Chem Ahstr., 105,21663) Wolters, B (1968b) Ueber die antibiotische Wirkung neutraler Steroidglykoside Xu, W.H and Xue, Z (1988) The chemical structure of neohyacimhoside Yaoxue Woo EH W00W.S, Chmurny, G.N and Hilton, B.D (1992)."Mclandnoside Xu, X and Zhong C (1988a) Chemical constituents of Chinese paris (Paris podophylla var chinensis) U Structural determination of sapogenin C mit und olinc Saponincharacter Planta Medico, 16 114-119 A, a saponm from Mehmdrium firmwn J Nat Prod 55 786-794 Woo W.S and Kang) SS (1977) The structure of phytolaccoside G Yakhak Hoe Clu, 21, 159-162 (Chan Abstr., 88, 191324) Woo, W.S Kang SS and Yooa M.M (1976) Phylochcmfcal study on donate Is 9^7) hWhakky0 Saemjyak YO"3USO °rf"^ 15> 1-4 (Chem Abstr,, Woo, W.S, Kang, S.S., Wagner, H., Seligmann, O and Chari, V.M (1978) Xuebao, 23, 61 63 {Chem Abstr^ 109, 51701) Zhongctwyuo, 19, 242-243 (Chem Abstr., 1095 226726) Xu, X and Zhong, C (1988b) The chemical constituents of Chinese pans (Paris palyphylla var ehinensis) Isolation and structural determination of sapo- genins A, B and D Zhongcaoyao, 19, 194 198 (Chem Abstr^ 109; 134875) Xue, S.-R., Liu J.-Q., Wang, G., Shi, J.-Q.: Wu, Q.-J and Hu, S.-Z (1992a) Triterpenoid saponin of Clinopodium chinense (benth.) o kuntze Yaoxue Xuebao, 27, 207-212 (Chem Abstr., 117, 86700) References Xue, S.-R Liu, J.-Q and Wang, G (1992b) Triterpenoid saponins from Cliimpodium polycephaium Phytochemistry, 31, 1049-1050 Yadav, N., Misra, G and Nigam S.K (1976) Triterpenoids of Adenaiithera pavonina bark Planta Medico, 29, 176-178 Yahara, S-, Murakami, N., Yamasaki, M, Hamada T., Kinjo, J and Nchara, T, (1985) A Hirostanol glucuronide from Solatium lyratum Phywchemistry 24 2748-2750 Yahara, S., Ernura, S., Feng, H and Nohara, T (1989a) Studies on the constituents of the bark of Dalbergia hupeana Chem Pharm Bull, 37, 2136-2138 Yahara, S Ohtsuka, M., Nakano, K and Nohara, T (1989b) Studies on the constituents of sotanaceous plants XIII A new steroidal gjucuronidc from Chinese Solanum lyratum Chem Pharm Bull., 37, 1802 1804 Yamada, H., Nishizawa, M and Katayama, C (1992) Osladin, a sweet principle of Polypodium vulgare Structure revision Tetrahedron Lett.^ 33, 40094010 Yaroaguchi, H-, Matsuura, H., Kasai R etai (1986) Application of borate ion-exchange mode high-performance liquid chromatography to separation of glycosides: saponins of ginseng, Sapindus mukurobsi caertn, and Anemone rivularis buch.-ham Chem Pharm Bull* 34, 2859-2867 Yamaguchi, H., Kasai, R., Malsuura, H., Tanaka, O and Fuwa, T (1988a) High-performance liquid chromatographic analysis of acidic saponins of ginseng and related plants Chem Pharm Bull., 36, 3468-3473 Yamaguchi H Matsuura, H., Kasai, R etai (1988b) Analysis of saponins of wild Panax giusetuj Chem Pharm Bull, 36, 4177-4181 Yamahara, I, Mibu, H., Sawada, T etai (1979) Anti-inflammatory effects of Mi-saponin Yakugaku Zasshi, 99, 612-617 Yamahara, J., Kubomura, Y., Miki, K and Fujimura, H (1987a) Anti-ulcer action of Patiax japomcus rhizome J Etlmopharmacol., 19, 95-101 Yarnahara, J., Kubomura, Y., Miki, K and Fujimura, H (1987b) Ami-ulcer action of chikusetsusaponin III Yakugaku Zasshi, 107, 135-139 Vamamoto, A., Mtyase, T., Ueno, A and Maeda, T (1991) Buddlejasaponins I-IV four new oleanane-iriterpene saponias from the aerial parts of Buddleja japonica hems., Chem Pharm Bull, 39, 2764-2766 Yamamoto, A., Suzuki, H., Miyase, T, Ueno, A and Maeda, T (1993) Clinoposaponins VI and VIII two oleanane-triterpene saponins from Ctwopodium micmnthum Phywchemistry 34, 485-488 Yamamoto, M and Uemura, T (1980) Endocrinological and metabolic actions of ginseng principles Proceedings of the Third international Ginseng Sym posium, pp 115-119 Korea Ginseng Research Institute, Seoul, Korea Yamamolo, M., Kumagai, A and Yamamura, Y (1975) Structure and actions of saikosaponins isolated from Bupleurum fafcatvm L I Anti-inflammator) action of saikosaponins Arzneimiuetforsch_, 25, 1021-1023 Yamanouchi, T (1943) ZooL Mag (Tokyo), 55, 87 Yamasaki Y- lto, K., Enomoto, Y and Sutko, J.L (1987) Alterations by saponins of passive calcium permeability and sodium-calcium exchange activity of canine cardiac sarcolemrnal vesicles Biochim Biophys Acta> 897, 481-487 Yamashila, T., Fujimura N., Yahara S Nohara, T., Kawanobu, S and Fujieda K (1990) Structures of three new sieroidal alkaloid glycosides, solaverines h 11 and III from Svlanum icxicorvm and S uerbascifotium Chem Vharm Bui}., 38,827-829 ^, , „ _ MnQli Yamashita, X, MatSumoto, T, Yahara, S, Yoshida N and NoharaJ-U»U Structures of two new steroida! 8lycoS.dcs, soladulcos.des A and B from Solmum dulcamara Chem Pharm Bull 39, 1626-1628 Yamauchi T (1959) Saponim of Japanese D.oscoreaceae IX Hydrous oi dio«Eenin plvcosides Chem Pharm Bull., 7, 343- J48 Yang C jTan^Z., Wu, M, Zhou, J and Tanaka, O (1984) S.ud.es on sapon.ns or rhizomes of Pamx ringttawsfa wu ht ,-hng Yacxue Xuebao, 19, 232-236 (Chem Ahstr., 103, 3686) , , Yang C Jiang Z Zhou, J., KaSai R and Tanaka, O (1985) Two new olcanohc add'type sapomns from Panax slipuleanatus Yuman 7.hlWu Yu,Vm, 103 108 (Chem Abstr., 102, 218350) Yang, D, Zhong, Z.C and Xic, Z.M (.992) Sweet ^f^I™^™* Cyclocarya palhnus (bataL.)hjinSKaya Yaoxue Xuebao 27 841-844(Chen JT^iluTl Yoshikawa K and Arihara, S (1993) Tri.erpeno.d saponins from Ilex Integra Phywchemiszry,3X 417-420 , ,_ Yasukawa K Takido, M., Takeuchi, M and Nakagawa, S., (1988) Inn.brtorj eflect'of glycyrrhizin and caffeine on two-slage carcinogeoes.s in m.ce Yakuqaku Zasshi, 108, 794-796 Yasumolo T, Tanaka M and Hashimoto, Y (1966) DimibuUon ofs»ponmm "hinodenns Nlppc, Sutom GakkaisH, 32,673-676 (CW Abxr.& 94029^ Yata N Sugihara N, Yamajo, R etai (1985) Enhanced reclal absorpfon of V—antibiotic in ra, by onodesmosides ^*°™£™^ °f Sapindus nmkurossi (Enmei-hi) J- Pharmacobio-Dyn "°«-1047 Yatsv™ Al Bclova, L.F., Lipkina, G.S Sokolov S.Ya and Trutneva, hA ' l978).Pharmacology of calenduloside B - a new triterpene gycos.de: from rhizomes of Calendula offiemalis Farmakol Toksikol (Moscow), 41 556-560 (Chem Ahstr 89, 209164) Yepez X.M/Lock dc Ugaz, O., Alvarez, CM «d glvcosides from Vncaria gukmensis Phytochamstry, 30, Yi Y.-H (1990) Esculentoside L and K: two new saponms from Phytohcca esculeraa Plcaaa Medka, 56, 301 303 Yi Y and Wang Z (1984) Active principle, of Phytolacca escutent* I IsclaUon and identification of the triterpene saponins Zhtnw#oyao IS 55-59 (Chan Yi, Y^-IL and Wang, C-L (1989) A new active saponin from Phytotacca escuknta Planta Medka 55- 551-552 , Yi, Y.-H and Da., F.-B (1991) A new triterpenoid and its glycoside irom Plntolacca esaitetua Planta Medka, 57, 162-164 Yi Y aodWu Z(1991).AnewtritcrPeneElycoSidcof ' Zitonaguo Yaoke Daxue Xuebao, 22, 270 274 (Chem Abstr., 117, Yokovan a H Ilmi S., Oura, H and Hayashi, T (1982a) Effects of total sapomns extracJedfrom several cr.de drugs on rat adrenocortical hormone secretion Yakuaaku Zasshi, 102, 555-559 Yo.™ H, Hiai S and Oura, H (1982b) Rat plasma corUcosterone secretion-inducing achvities of total saponin and prosapogenm methyl esters jjo References Kejerences JJ/ Yakugaku Zasshi 1(12, and a prosapogenol of seed kernels of Madhuca kmqifoUa L Tetrahedron, 30, Yokoyama, H, Hiai, S and Oura, H (1984) Effect of saikosaponins on dexamethasone suppression of the pituilary-adrenocortical system Chan Younes, MEG (1975) Chemical examination of local plants XIV Trrterpenoids from the leaves of Egypiian Calistcmon lanceoUttus Aust J Chem., 28 from the roots of Plutycodon qrandiflorum a.dc 1191 1194 Pharm Bull., 32, 1224-1227 Yoshikawa, K., Takcmoto, T and Arihara, S (1987a) Studies on the constituents of Cucurbitaceae plants XVI On the saponin constituents of Gynostemma penlaphytlum makino (II) Yakugaku Zasshi, 107, 262-267 Yoshikawa, K., Mitake, M., Takemoto T and Arihara, S (1987b) Studies on the constituents of Cucurbitaceae plants XVII On the sapontn stituents of Gytiostemma pcntaphyftum making (12) Yakugaku Zasshi 107 355-360 Yoshikawa, K., Amimoto, K., Arihara, S and Matsuura, K (1989a) Structure studies of new antiswcet constituents from Gymnema sylvestre Tetrahedron LetuSQ, 1103 1106 Yoshikawa, K., Amimolo, K,, Arihara, S and Matsuura, K (1989b) Gymnemic acid V, VI and VII from Gur-ma, the leaves of Gymnema sylvestre n br Chem Pharm Bull., 37, 852 854 Yoshikawa, K Arihara, S and Matsuura, K (1991a) A new type of anlisweet principle occurring in Gymnema sylvestre '/etrahedron Lett., 32, 789-792 Yoshikawa, K., Shimono, N and Arihara, S (1991b) Antisweet substances, jujubasaponins I 111 from Zizyphus jujuba Revised structure of ziziphjn Tetrahedron Leu., 32, 7059 7062 Yoshikawa, K., Arihara, S., Wang, J.-D., Narui, T and Okuyama, T (1991c) Studies of two new fibrinolytic saponins from the seed of Lujfa cyltndrica roem Chem Pharm Bull., 39, 1185-1188 Yoshikawa, M Wang, H.K., Kayakiri, H., Taniyama, X and Kitagawa, I (1985) Saponin and sapogenol XL Structure of sophoraflavosidc 1, a bisdesmoside of soyasapogenol B, from Sophorae radix, the root of Sophora flavescens AlTON Chan Pharm Bull., 33, 4267^4274 Yoshirmtsu, H Hayashi, K Shingu, K etal (1992) Two new cycloarlane glycosides, thaliciosides A and C from Thalictrum thunhergii D.c Chem Pharm Bull., 40, 2465-2468 Yoshimitsu, H., Hayashi, K., Kumabc, M and Nohara, T (1993) Two new cycloattanc glycosides from Thalictri lierba Chem Pharm Bull, 41,786-787 Yosioka, I., Fujio, M., Osamura, M and Kitagawa, (1966) A novel cleavage method of saponin with soil bacteria, intending to the genuine sapogenin: on Senega and Panax saponins Tetrahedron Lett., 6303 -6308 Yosioka, I Matsuda, A., Imai, K., Nishimura, T and Kitagawa, (1971) Saponin and sapogenol IV Seed sapogenols of Aescutus turbinaw blume On the configuration of hvdroxyl functions in ring E of aescigenin, protoaescigenin, and isoaescigenin in relation to barringtogenol C and thcasapogenol A Chcm Pharm BulL 19, 1200-1213 Yosioka, I., I lino, K_, Matsuda, A and Kitagawa, I (1972) Sapontn and sapogenol VI Sapogenol constituents of leaves of Piltosponmi tobira ait Chem Pharm Bull., 20, 1499-1506 Yosioka, I., Inada, A and Kitagawa, I (1974) Soil bacterial hydrolysis leading to genuine aglycone VIII Structures of a genuine sapogenol protobassic acid 707 714 221 224 Young IIS Park J.C and Choi, J.S (1987) Triicrpenoid glycosides from Rosa nupsa Arch )>harmaca! Res., 10, 219-222 (Chem Abstr., 108, 218989) Young, H.S, Park, J.C and Choi J.S (1988) Analytical separation of isomeric saponins by LC/MS Kor J Pharmacog., 19, 248-250 Yu, B.-Y Hirai Y.? Shoji, J and Xu, G.-J (1990) Comparative studies on the constituents of Ophiopogonis tuber and its congeners VI Studies on the constituents of the subterranean part of Liriope spicata var prolifera and L muscari (1) Chem Pharm Bull., 38, 1931 -1935 Yu, S.S and Xiao, Z.Y- (1992) The structures of yiyeliangwanoside III and IV from the bark of Nothnpanax davidii (FRANCS) harms Yaoxue Xuehao 27 42 47 {Chem Abstr., 116, 211140) Yu S Yu, D and Liang, X (1992) A new Lritcrpene saponin from the root of Aratia spimfolia Chin Chem Lett-, 3, 289-290 Yuchi, S and Uchida, Y (1988) Adzuki saponins from Vigna amjularis as hypolipemics Jap Pat 6.289,692 {Chem Abstr., 107, 233370) Yukananov D.K., Sokolskii, I.N., Zinkevich, R.P and Kuvaev, V.B (1971) Plants of the family Caryophyllaceae studied to determine the presence of the triterpenoid saponin, gypsoside Rust Resur., 7, 386-390 (Chem Abstr., 75, 121321) Zacharius, R.M and OsmanT S.F (1977) Glycoalkaloids in tissue culture of Solatium species Dehydrocommerscnine from cultured roots of Solatium chacoense Plant Sti Lett., 10, 283-287 Zakharov, A.M., Zinkevich, EP and Rankovskii, AJ (1968) Saponins of Primula turkestanka Khim Prir Socdin., 388-389 Zakharov, A.M., Zakharova, O.I., Pakalns D and Sokolskii, I.N (1971) Ti-ilerpenoiri glycoside from Primula macrocaiyx Khim Prir Soedin., 672 Zeng, L Zhang, R.-Y and Wang, X (1987) Studies on the constituents of Zizyphus spinoms HU Yaoxue Xuelxio, 22, 114-120 (Chem Abstr., 107, 12735) Zhang, B.7 Pan W., Feng, S and Shi, G (1985) Uffccls of saponins of Panax quinquefotium L on experimental arrhythmia Shenyang Yaoxueyuan Xuebao, 2, 273-275 (Chem Abstr., 104, 81750) Zhang, F and Chen, X (1987) Effects of ginsenosides on sympathetic neurctransmiUer release in pithed rats Zhangguo Yaoli Xuebao, 217-220 (Chem Abstr., 107, 32871) Zhang, J and Mao, Q (1984) Studies on the chemical constituents of Swertia cmeta BURKtLL Yaoxue Xuebao 19, 819-824 (Chem Abstr., 102, 109805) Zhang R- Zhang, J and Wang, M (1986) Saponins from the root of Glycyrrhiza uralensis nscH Yaoxue Huebao, 21, 510 515 (Chem Abstr., 105, 187603) Zhang, S and Hu, Z (1985) Effects of ginseng flower saponins and ginscnoside Re on experimentally-induced gastic ulcers Zhongyao Tongbao, 10, 331-332 (Cliem Abstr., 104, 512) Y Shcn, J Song J Wang Y and Li D (1984) Analgesic and *dalivc Index of Latin names ) Zhao L., Chen W and Fang Q (1990S Tn.erpeno.d sapomns from Ancnone fiueada Plania Medica, 56, 92-93 Zhou J (19S9) Some bioactive substance, from p|ams of West China Pure Appl Chan., 61, 457 -460 ' ' Zhou J Wu, M,Z Taniyasu, S et at (1981) Dammaranc^ponins of Sanchi- ginseng roots of Panax iioioginseng (burk.) r-.H chen (Araliaceae): structures ol new saponm-s notogimenosides-R, and -R2, and identification of einscno- sides-Rg2 and -Rh, Chem Pharm Bull., 29, 2844 2850 Zhou, X.-H Kasai R Ohtani K et al (1992) Oleanane and ursane glucosidcs from litibus species Phyiachemiairy, 3r 3642-3644 Zliu y,Z Lu S.H Okada, Y Takata, M.* and Okuyama T (1992) Two new cycloarlane-type glucosides, mongholicosidc i and II from the aerial pan of Astragalus nwngholit us bunge Chem Pharm, Bull 40 2230 223^ Zinova S.A., Isakov, V.V., Kalinov.skii, A.I., Uikova Z.I UlanovajK P and Olebko LJ (1992) Four new trilcrpcnc glycostdes from the roots of PulsatiUa thhurica Chem Nat Compd., 28, 306-311 Zollo F Finamore, E Minale L Laurent D and Bargibant G (1986) Starfish aponins 29 A novel steroidal glycosidc from the starfish Pentacerastcr atveohuus J Nat, Prod 49 919 921 Zollo F.f Finamore E and Minale, L (1987) Starfish saponins 31 Novel polyhydroxysleroids and slcroidal glycosides from the starfish Sphaemdiscus placenta J Nat Prod., 50 794 799 Zollo F., Finamore R, Riccio R and Minale, L (19«9) Starfish saponins part 37 Steroidal glycosidc sulfates from starfishes of the genus Pisaster J Nat Prod., 52, 693-700 ' " ' Zviadadze, L.D., Dekanosidze C.E Dzhikiya CD Kcmcndidze F.P and Shashkov A.S (1981) Triterpene glycosides of Cephahna gigantea II Structure of giganteasides D and G Bioorg Khim.y 7, 736-740 {them Abstr Sue also Appendix Ahnts fwiicvlasus 48, 281 Alnus scrmlatnides 49 Anagaliis arvensis 63, 193 245 4brus tnekmospnrm 313 Andrnsace saxifragifnlia 62, 221 Ahrus pnrawrius 48 28 K 313 Aiwmarrhetw asphotk'hides 90 303 Acacia auriculiformis 36 4nenwne fiarcida 246 Acanthaxter planci 116 117 291 299 Anctrume rivultitis 228 Acnnihopanax chiistmensis 282 341 Actmthopanax divaricaius 39, 341 Acamliopanax hypolettcus 29 Ardia mandschurica 268 278, 279 Avamhnpanax senticosus 38, 65, 66 Asparaqus adscciukas 90 Acer netjundo 24S Aitinvpytja agcs\tzi 111, 249 Asparagus CGchinchwensis 89, 90 Asparayus cttritius 91 295 Aainupyya echiniten 109 Asparagus officinal* W, 93, 237 243 287 Acfinapyqafiammea ill Avtinosictnma Uihaium 147 Ardisia craiuia 208 Ardisia crispa 280 290 298 Asparagus pukhcllus 313 Aesculus hippneastanum 61 272 275 318 Asparagus racemosa 90, 298 Acsculm indica 60 61 A>pidi.\ira elatinr 96 Ayavr cantata 298 A.\pilia kotschyi 32 At/ave sisatana 290, 309 Aster tutorials 225 Ayropyvtin repens 267 Aqromemma yiihago 2S5 Akcbia quUwta 273 Asterias amuivmis 112 116 117, 118 294 Asterias fnrbesi HZ 116, 118 119,291 302 Alhirr.in anthcimintira 31 266 Aftertax rubens 106 Aibizziu lebberk 279 Ahurinu pectimfci-a 112, 115, 116, 118,291 Alhhzio iucida 31 Alliunt cmpelaprasum 95 290 300 Astoropus sarasinosum 115, 291, 299 AUivm cepa 11 95 Astragalus ernestii 69 Ailium chincme 91 Astragalus galegijormis 68 Alltum Ailium Ailium Ailium eiuhcscev* 11 giga/ueum 77, S3 225 297 karataviense 77 parrum 297 Ailium aatirum 91 94 Astragalus mi'mhranacvus 19 68, 267 270 Astragalus orhiculaius 45 Astragalus sieversianus 68, 69 270 Astraaalui, taschkendtcus 68 Astragalus tngomts 45 Ailium mrenmomcum 11 Asmmiia tncjor 65 Ailium wutdstenii 77 A,\impi'iien indtrus 119 Ainus ptmdula 49 Ai'lhu sutii'0 70, 242 539 540 maex oj iMtm names Index of Latin names Balanites aeayptiaca 93, 227, 252, 291, 295, 299,303,330 Cucumahafraudatrix 111 Cutcita novaguinea 118 DaUwite* wxburyhii 297, 298 Curcutnaviajapomca 107, HI Bcesia caltlwefoliu 47 CwA'sonic bcrteii 280 Belfis perennis 67, 7(1 220 Cusiouia spicata 262 Beta vulgtiiLs 268 Cyclamen europacvm 23 191 Bt'tula pendula 267 liciula pubcscens 267 Desfnnrainia spiiiOSP 33 BHyhia welwitslichii 223 Boerhavia diffusa 274 Diantfius barbatus 276 Diamhus superbus 38, 276 Bohadschia argus 109 f>/flifflfc tonara 7, 91, 94, 96 Bohadschia bicittata 109 Digitalis purpwea 82 Bohadschia graeff'ei 109- II1 Diascorea alata 76 Bohadschia marmoraw 109 Dioscorea barbasco 309 Bottadschia citiettsis 109 Dioscorea baiaws 76 BaussingcmUia baseltoides 38, 282 Bulhastemma pamcuiatum 29, 239, 248 Diascorea cayeimensis 76 Buplcurum ch'weme 273, 277 Dioscorea composite 309 Buplcurum fakaium 10, !58, 164, 238, 245, Dioscorea deltoidca 290, 309 271 273,325 Dioscorea bulbifera 76 Dioscorea escuknta 76 Bupleuruin fauurtiitgeiise 35, 248 Dioscorea flnribimda 309 Bupfeurum rotundifolium 33 Dioscorea gracetlima 922 Dioscorea mexicana 309 Calendula arvensis 274 Calendula ojfidnatis 4, 9, 10, 18, 236, 246, 250, 268, 274 Ciotwssia cusickii 83 Camellia japomca 242, 263 Capsicum annuum 94, K)3 Castanopsrs cuspidal a 33 Cclmtsia petriei 38, 242 Centetla axalka 171, 226 Citcnopodnmt qtdnoa 180, 237 Chloroanlum pomeridiailum CNorophytum malaycnsc 91 O'cer arietinutn 42 Cimicifuga japoiiica 48 Dio.scorea opposila 76 Dioscorea septemhha 92 Dioscorea spiculifiora 309 Dioscorea lokora 8, 82 Dodotiaea viscosa 62, 273, 278 Dotichos falcatus 248, 276 Dofichos kilirnandsctiwicus 241 Dmcaena afrotnontana 89, 92, 299 Dracaena rnunnii 290 ?.9t Echinasier seposiws 112 Eleutherococcus senticosus 279, 337 Entada phasealnides 31, 247 linterolohiutn contentisUiqvwn 60 Cimicifuga racemose 275, 280 EquisL'tum urvctise 267 Cladolahes sp 110 Erylus letuteitfeldii 120 Gyinnema sylvestre 71, 245 274, 281 (jytrmacladw, dutmists 249 Cynvstcmmci pemaphyllum 49, 53, 249 275 Gypwphila altissinui 10 Gypsophila arrosti 326 Gypbophifa pactfica 29 Hactfia attetwaia 118 Mussatia sp 60 Mussaenda pithesrem 46 Jialityle regularis 116, H7, 118, 119 250,266,272,282,323 Nardoa novacaledonia 1(9 Hedera rhombca 56, 64 65 Neosimlaster geargianus 225 Hcloniopsis orientatis 83 Neothyane gibbo.w 109 Henricia laeviuscofa 117, 119, 244 Neoihynnidiutn muyiiwn 110 Herniara glabra 267 Nicotiana plwnbagimfolia 100, 101, 299 Herniara hirsuia 267 Nicotiana tabacum 290 Hvloihuiia airo 111 Notholirion btrfbifentm 103 Holorhuna edulh 109, 111 Noiholirion hyticinthimm; 103, 104 Hdothuria fomhuia 109, 110 Hotatlmriaforskati! 11 a 111, 225, 249 O/cq europea 12 Holoihuria grisea 110 OttonLs spinosti 267 Holoihuria leucaspiiota 107, 111 Ophiodenna loiUfkoudttm 120 Holothuria pcrvicax 109, 110 244 Ophiopogou hnermedius 298 Holothuria squatmfcra 111 Ophiopocjon planiscapuz 84, 92, 95, 96 Hovenia duicts 58 Oreaster rcticulafus 118 Hydrocotyle asiaticu 245, 273, 324 Oxytropis bicolor 49 Hydracotyle vultjaris 272 Paliurus ratHosissitnus 40 /fcrx conwta 6ft Panaxymheny 10, !8,53,163,249,279.329 //ex crenaia 40, 282 Patuuc japtmicus 53, 275, 279, 330 ffex opaca 263 Potkix noivginseng 53,269.271,276,280,33C J7ex pubestens 268 Panax pseudngin&eity 53 64, 33! //ex rotunda 263 Patiav quinquefolius 53, 269, 330 iseriia haenkeana 38 Panax trifalius 53, 333 Panax zmgiberensh 55, 331 Katapanax septemtobum 263 Collinsonia caneidemis 171 Irilillana thunbergii 103, 104 Colubrtiw asiaiica 59, 280 Fritiilaria ussurivmh 104, 105 Gleditsia japonica 249 Ohchidiott he\weamim 75 Coscinasurias tcnuisp'ma 117 CfwH/c max 42, 67, 203, 249 Cesrus specitrsus 298, 310 ciycyrrttiza glabra 10 40 275 312 O'ocraim'a crocozxniifiora 73, 248 GfyryrWiizfl inflata 41 Crocamna masaniorum 70 Glycyrrlnza urahnsis 41, 313 Crossaster papposus 291 Cuo/aa/M officinak 27, 37, 228 Crossopteryx febrifuge 249, 274, 276 Cueuarda ptaiypoda 246 Paracaudina ramonetti 110 Pardachirus marmoratus 288, 291 Lilitint pardaritwm 94, 95 Cnrmts fiorida 165 Nardoa gomophia 13 118, 119 Hcdera mpaleusis 65, 262 Fritilluria camtschaicensis 103 Cnnvallaria niajalis 83, 95 Myr.sme afiieana 247 //«fcra /idi* 34r 170, 205 239 240 247 Clerodctidrum wildii 243 Combretum indicium 60 Mimosa temtiftora 224 Mamurdka cocUmchinensis 75, 145, 282 Montordica yrosvenoni 57 L*tfs culinvris 42 Clnnatib itwndschwica M«eM« r/ifaK; 273, 276, 277 MarthaMerias ylacialis 106, 117 Medicaso satica 19, 216, 238 263 268 Gypsophila paniculaui 10 125 263 326 Eryiigium pianum 62; 272 Clematis chinensis 29 Madhuca longifoha 274 browntf 83, 100, 101, 105 Lilimn tcmifalium 77 Pardachirus pavaninus 288, 291 axinlis 201 polyphylia 92, 201, 299, 302, 303 Parw quadrifolia 84, 94 Uriape sracaia 95 Pflnfs rietnamensis 92, 303 Lonchocarpus cyaneu'em 274 Passiftora cdulis 46 Lonicera japntuca 18 65, 234 Passiflora qwdrangularis 46 iwMoj 55, 64 267 282 ffa operatluiu 56 mcculata 299 Lycopersicon iycopersicum 91, 98, 101 287 288 295 305 Patina pectinifira 118 Patrinia scabimaefolia 34, 65 279 Pentacerasler alveotatus 118 Periandra dukis 36, 73, 281, 282 Pctiliiiin cduardi 105 Ptiaseolus aureus 42 Madhuca bittyracea 251 Phaseclus cocdneus 42 C/*Tfv/rKi tvmcntnsu 246, 274 Phaseotus tunatus 42 Schefftera octopttytta 34 Stichopus chloroitotttl> 111,249 Phaseolus vulgnris 42 Schinm orgenlea 266 Siicltopus japoniats 110 Phywiacca doderandra 131, 157, 200, 252, Schima tnertertsiarta 251 Sivtffi/m rnuda/jascarieiisis 199, 253 Vtnatrum taliense 104 Securiilacc latigepedutKutata 274 Swcrtin cincia 274 Vcrhfu-cum phloinoideb 35 262, 274 Ficriu feltarrac 27 Serjania ferhalis 25! Pisaster brecispinus 116, 119 Sestfftmm atutum 39, 220 226 Piaster ochmceus 116, 118, 119 Sesbania seshan 262 Pisum sativwn 42 Silphium pcrfoliatutn 64 Pishecellobium aibaicum 30 Similaria nispa 12! Pithecelhbium cubense 30 Sm*7fl.x arixohchicefolia 83, 88 91, 94 Hatycodon grandifioritm 276 Smi/a.x spp 310 Potemonium caeruleum 111 Solarium avkulare 302 Poiycarpone loefUngiae 3(5 Solanum capskmtrum 104 Polygata chamaebuxus 173 Solomon dwcoeiise 98, 103 104 296 Polygata chinems 60 Solanum coinmersnrAi 104 Potygata senega 66, 67, 323 Solatium dasyphyllum 100, 101 Potygata temiifotia 66, 279 Solanum demlssum 101, 104 Pnlygtmdium cfficinale 93 So/onum dukamara 81.92,98,287.299.306 Polygonal urn sibiricum 93, 95 Poly podium gtycyrrhiza 86, 171 Polvpodium vulgare 86 Solatium eheagtujblium 305, 306 Solatium erianthum 99, 100, 103 Solarium liavanense 104 Poranio pidtitlus 118 Sotefium inoHiiiin 101 169, 298 303 Porastcr supcrbus 118, 119 Solatium japonense 100, 101 Primula acaulis 242 Primula elaiior 323 Primula vfficinafis 323 Primula icris 323 Protoreastcr iiodosus 118 Psolus fabric it 110 PyrenacoMha stavdtii 276 Quercus suhcr 274 (htillqja saponaria I, 70, 277, 285, 327 Rapanea metcmophtneos 243 Koso rugosu 138 Rubus coreamis 29 /?i«n« Qctjfcwm 95 290 302 Rust us hypoglossvin 298 Ruscus hyrcanus 299 Justus ponticua 95 Sofcimifn khasianwn 100, 310 Solatium laciniatum 310 Solanum lycapersicoides 101 Jyraium 91, 92, 96, 104 mammoswfi 295 maginatum 310 i melongena 91, 92 100 306 Solatium nigrum 98, 100 Solanum pamcutatum 83 So/fiHivHi peimelli fOl Solatium ptycanthum 99, 100, 103 Solanum ianctae-catharinae 100 Solatium sarrachaides 306 Solamim scabrum 100 Solanum sodomaeum 299 Sofeimwi lorumi 87 Solanum lOXiCOTUm 101 Sotouwn udxwsum 98 99, 101, 103, 288 304, 305, 306 Solatium verbasr.ifkirum 101 Sanguisorba officinalis 68 Scionum xanthocarpum 100 Saiiicula eurnpcca 70 272, 308 Soiidago canadensis 28, 267 Sapiitdux deiavcyi 65 Soiidago gigantea 28, 223, 267 Sapindus niukuro.ssi 1, 65, 238, 243 262, Solidatjo semiiiw 267 272, 282 Soiidago virgauraa 67, 242, 267, 272 Soutiea vagttmla 47 Sapindus saponaria I Sphaerodiscus placenta 118, 119 Sapindus trifirtiatus 262 Spinacia oteracea 240 Saponaria cfficmatis 1, 10, 247, 308 Stauntvnia chhnensis 38 Schejjleta impressa 65, 76 nifl araluicca 203 i aramaticutn 12 J-'ermmifl umyadatwa 77 23&, 287 Viciafaha 42 Tdinum tcnuissimwn 261 J-J«7«a arigutnris 268 Tenninalia Iwrnda 263 Viyna mungo 42 Terminalia ivorenws 274 I-'lffMfl 5H1PHSI.S 42 Tenmnafia safcea 275 Klo/o mungo 267 Temstraetnia japotiica 263 radiata 267 Tetrapanax papyriferum 273 «n«isijs 267 Tetrapleura teraptcra 30, 261, 274 Thaiktrum faetidum 44, 248 /rico/of 267, 308 album 12 Tiwlictrum minus 248 Thalictrum sqttarrosum 44 73km siJK-Fjsfe 61 263 272,322 Tiieknoia ananas 111, 249 r/iiw*w coriacea 251 Tlitadiantha dubia 148 Thtcdiamha gronenoru 57 Trachycarpus fortunei 93 Trachyairpus wagneriaws 96 Trayopogon pomfolius 64, 73 Tribulus terresiris 298 Tvidesmosietnon dnessenssi 202 Trigonetla foeman-graecum 92, 937 94, 298, 301,310 Trillium arandiflotum 290 7n//iu)>( kanuschaticum 84, 85, 90, 94, 95 Trillium tsdionaskii H4 H%tor(fl brachyhotrys 249 Xaitthoccas sorbljolia 61 yixtxv; armmica 309 JVcm brevifolia 76, 309 Yucca filamentosa 90 YMCa'filfora 309 yuccfl glonosa 94 yWc« schotti 301 Zizyphus jaazeiro 57, 59 Zizyphus jujuba 57 58, 269 279, 280, 281 Zteypftus ru$f»,a 276 BeUissaponins 220 General index Culubrinoside 213,280 Iktulintc acid 249 Contraceptive activity 262 Bidesmosidic saportins 3, 29 C'orticoslcrone 270, 309 Biosynthesis Countercurrent chromatograpfiy 164 cholesterol lanostcrol steroids steroid alkaloids trilerpenes Bitterness 77, 237, 287 centrifugal partition chromatography (CPC) 170 droplet counLercurrent climrruitography (DCCC) 164 rotation locular conntertiirrent chmmalograpliy (T?LCC) 169 Bivittoside D 243 Crocosmicffiides 73 Bnralc 137 Crossoptincs 274 Boussmgoside A 282 Cucumarioside A2-2 107 nromobenzoyiation 228 Cyclic saponins 29 4-Bromophenacyl derivatives 131 Cyclamin 191 Buplcuri radix 33, 325 Cyciamirctin A 23 Cycloartane glycosides 43, 270 Abrusosidcs 48 Antibacterial activity 244, 291 Absorption 283 Antiexudative activity 271, 319 Acaciaside 36 Antifeedanl activity 263, 295 Capillary fragility 274 302 Acetylafed glycoMde.1; set' N-Aceiylated Antifcrtilily activity 262, 298 Capsicastrine 303 glycosides see atst' Spermjcidal activity Calcndulosides 236, 274, 275 Camellidlns 196 216, 221 223, 242, 263 Caibenoxolonc 315 Aclin 280 Anlifimgal activity 7C, 24a 263, 288 Cardiovascular activities 269 Actinostemmosid.es 147 Antihepatoxic activity 303, 316 326 333 Adaptogenic activity 279, 332, 340 Anti-inflammatory activity 271, 274, 301, Caulosides 188 Chaconine 98, 295, 297, 304 Adjuvant* 277, 327 316,319,326,340 Chiisanosidc 282, 340 Cycloastragenol 27,43 Cytotoxic aelivity 247 249, 299 Dammarane saponinb 49 Uellonin 290 Delloside 290 Dcmissine 295 Deoxyoglycyiihclol 315 Deoxylrilknoside A 85 DcsfonlainosJdt; 33 Adrenocorlicotrophic system 270 Aniilcishmanial activity 282 Aescinc 272, 275, 318-21 Antimicrobial activity 239, 288 Cholesterol complexes 233, 237, 267 Afromonloside 89 299 Antimuiagenic activity 250, 316 Cholesterol metabolism 267 301 Agavcsidc B 178 Aniioedemalous activity 271, 274 Chromatography 146 Aginoside 297 Antipyretic activity 277 centrifugal thin-layer fCTLC) 152 Aglycor.cs 10 13.20,21.24 Aniitumour activity 247, 299 flash 152 cyclolanostane 27,43 Ant I-tumour-promotion 249, 316 high-pressure liquid (HPLC) 128.157,179 dammarcne 12, 16,49 Antilussive activity 266, 321 Sow-pressure liquid (LPLQ 153 lurosian U, 15,76,82,87 Antiukxr activity 275, 314 medium-pressure liquid (MPLC) 156 holostane 12, 107 Antiviral activity 245 291, 317 open-column 147 lanostane 12 49 Ardisiacrispim 216, 221, 280 overpressure liquid fOPLC) 171 oleanane II, 16, 21 Aridanin 29, 139, 261 polymeric supports 148 secodammaranc 49 Arjtmetin 138 reversed-phase 148 F.chinoricrmata 106 solanidan 12, 16, 9fi Arjungsnin 182 silica gel 14? Echinoidea 105 spirosolan 12 16, 98 spirostan 11, 15.76,79 Artifacts 23, 70, 78, 181 Ihin-layer 126, 180 Arvcnosidcs 273 vacuum liquid (VIjQ 171 Oiikusetsusaponin III 275 Dianosidefc 276 Diazomelhane degradation 196 Digiiogenin 78 Digitonin 204, 289, 301 Dimciic siiponins 29 DJORcin 290, 311 DiosECtiln 81 82, 190, 309 Diuretic activity 267, 3l2 Djvaroside 38 340 Dubiosidcs 14S Echinosides 243 Eleutherococcus 337-41 Akeboside 273 Asiaticoside 29, 36, 226, 273, 324 Alatosides 39 156 184,221 Asparagoside B 88 chromalography Gas FX1SA 140 Alditol acetates 228 Asteroidea 106 chromatography Emulsifying properties 233 Alkali metal cleavage 192 Asterosaponins 112, 115, 116, 288 291, 299 Chrysantellin A 224 Anagallisin A 193 Avenacins 70 242 Cimicifugoside 280 Erylosides 120 Circular dichroi&m 227 Ester saponins 60 Analgesic activity 276 Anemarsaponin B 303 Anodic oxidation 195 Anthelminlic activity 266 Bactericidal activity, see Antibacterial activity Balanifins 227 scr also Countercurrcnt Elcutherosides 337 Fpirnerization 182 Ciwujjanosides 338-9 Expectorant activity 266, 314, 323, 324 Clea\-age reactions 177 Extraction 144 Clcmaioside C 2b Antiallergic activity 282 Barbatosides 276 Colour reactions 123 Fibnnolytic activity 282 Anliarrythmic activity 269 Tkcsiosirics 47 Colubrin 280 Fish poisons 251, 295 544 (Jeherat index Foam formation 233 Isokmon 143 FunKicidal activity, see Aniifmiftai activity [vy 34, 321 Furustniiol saponir.s 76 87 Ciai chromalography (CiC) 179, 18 i Gas chromatography-mass spectrumelry /V-Aceiylaled glycosides 29 Nomenclature 12, 28 547 Primulagenin 323 Primulic acid A 323—4 Norlriterpenoid saponins 23, 37 Protobassk acid 184 Jujubogenin 57 Nuatigenin 82 83 Protopanaxadiol 52, 329 Jiijubogemn saponins 57, 280 Nuclear magnetic resonance 207 APT 213 Prolopanaxatriol 52, 329 Jurubine 87 (GC MS) 179 181.228 ISC-NMR 21(1 Proloprimulagsnin 195, 323 Pyridtne-acelic anhydride cleavage 196 Gen in Kslopanax saponin C 7.21 COLOC 221 Giganfcasaponins 223-4 Khaslanine 299 COSY 215 Ginseng 49, 329-37 Kizuta saponins 185, 188 DEPT 213 Quillaia bark 1, 70, 327-8 Gimenasidcs 49, 163 269 271 329 37 Kotschyioside 32 DQF-COSY 218 Quillaia saponins 196, 275 277, 285 Glochidiosidcs 75 Kryptoaescine 3IS—20 FLOCK 220 Quinosidc A 19 Glycoalkaloids 96, 134, 211 in 85 GlycyrrhuLinic acid 313-18 'H-NMR214 HMBC 220 Glycyrrhizin 40 245 275 281 313 18 Laeviuscoloside A 244 HMQC 220 Gyrnnema saponins 281 Lead tetraacetate oxidation 195 HOHAHA 218 Gymnemic acids 70, 281 Lenimatoxins 253, 262 NOE 221 Gypenoside 275 Lqitincs 295 Licorice 40, 3l2 2D-NOESY 221 PRFT 213 Liebermann-Burkhard test 124 126 RCT 222 Liquid chromatography-raass, ROESY 222 Gypsophiia 29, 326 GyprfKide A 29 234, 326 Haemolysis 124, 234, 312, 326 Hdemolytic index 234 Mecogcnin 309 spectrometry 138 SlNEPT 223 Lithium aluminium hydride cleavage 194 Quadra ngulosidc 46 Oleanoglyculoxin-A 253 262 Raccmoside 275 Radioimmunoassay 139 Relaxation times 213 Retro-DieLs Alder reaction 207 Rosamultin 138 Rolundiosidcs 33, 227 Rolungenoside 263 Ruscosidcs 301 Saikosaponini 35, 158, 164, 236, 238, 245, 271,273,325-6 Saniculosides 196 Hcderacosidc B 321 Lithium iodide cleavage 193 Ophiuroidea 106 HedcracosWe C 321 Longittiudosides 120 Osladin 86 Hetlcrasiiponin C 239, 240, 285 Lucyosidcs 267, 282 Ovaiian asterosaponins 112 a-Hedcrin 240, 266, 272, 282 321 Hololhurins 106, 236, 243, 249, 269, 285 Lupcroside I 194,216,221 Hololhuriodea 106 Holotoxins 107 Madecassoside 171, 325 Papyriogenins 273 Paril1in83f 89 289, 312 Marine organisms 105 Patisiflorine 46 Hovenosides Sarsasapogenin 309, 312 Mass spectrumetry 198 Pavonins 28R SaxifrngifoLiii A 221 , 280 Hydrolysis Sapogenin Saponaside D 326 Sarasinosides 115, 291, 300 Sarsaparilla 83, 88,3lO Sarsaparillcftide 88, 3l2 D/C1-MS 205 acidic 177, 191 Petiiniosides 300 Sea cucumbers 106 108 EI-MS 206 basic 185 Pcduncutoi>ide 263 Seco-iridoids 33 FAB-MS 199 enzymatic 187 Periandradiilcin 282 Sccotupane saponins 38 FD-MS 204 Periandrins 36 281 microbial 190 Secoursane saponins 39 Laser desorption 203 Penodate dcgj-adaiion 191 partial 186 Sedative action 279 MIKE/CAD 202 Permcthylalion 227 Hydro ihcnnolysk 187 Senega root 323 FD-MS 202 Pervicoside B 188 i lydroxyapatite 135 Scncgins 323 SIMS 203 Pfaffic acid 23 Sepositoside A 112 Hypoglycacmic activity 282 Metabolism 283, 335 Hypotension 269 270, 280 Pfaffosidcs 23, 248 Sericoside 275 22-Methoxyfurostanols 88, 145 Pharmacokinclics 283 Serjanosides 251 Microporous glass 137 Phascolide F 28 Shaiavarin-I 298 liexosides 39, 282 Mimonoside A 224 Phosphodiesterase inhibition 282 Smilagenin 312 Ilexsaponins 268 Mi-saponin A 243 Photochemical cleavage 195 Smith degradation 191 ImmunornoduJation 277, 327, 332 Mogroside V 57 Picfcltarracnin II 27 Smith-de Mayo degradation 192 lmperialine 105 Molecular optical rotation 227 Piscicidal activity 250, 291 Soaps 1, 307, 30S Indolizidincs 15 Molluscicidal activity 252, 291, 295 Plant growth inhibition 288 Soft cor;il 121 Inflammation 27 J Momordin 75, 145 Polycarponoside A 35 SoladukosideB81 Infra-red speclroscopy 226 Monodesmosidic sajxinins Polyhydroxylated steroids 106 Solamargine 169, 299, 3€3, 311 InscLlicidal activity 263 295 Monosaccharidcs 3, 28, 57 83 PolyphyJlin H 205 Solaninc 288, 295, 297, 304 Irritation 266 278 Moscsins 288 FolypodoMdes 86 Solaplumbine 299 Isochiisanosidc 340 Musennin 266 Primula root 323 Solasodine 3017 302, 309, 311 548 General index Solasonine 97, 169, 295, 298, 299, 30: Solubilizing properties 238, 284 Sophoraflavoside 195 Soyasapogcnols 181 215 311 rhladioMde 184 Thornasicrol A 112 Tomatinc 98, 225, 288, 295, 301, 302, 303, 304 Soyasaponins 42 Tomentosic acid 182 Spectrophotometry 123 Toxicity 284, 304, 321, 335 Spcctroscopy 197 Tridesmosidic saponins 3, 19 Spermicidal activity 262 264-5 298 Trillenoside A 85 Spinasaponins 240 Trillin 86, 299 Spirostanol saponins 77 Tragopogosaponjns 73 SquaIene-2;3-epoxidc Tubeiraosides 29, 212, 248 Starfish 105 Stereochemistry 12 Steroid hormones 308 Unsaturated sugars 32 Utero-contraction 280, 303 Stichoposides 249 Structure determination 175 Vasodilatation 269 Sulphatcd saponins 33, 57, 84, 96 Venous insufficiency 274, 302, 320 Sweetness 48, 86, 281, 314 Verbascosaponin 35 Sweetness inhibition 57, 71, 281 Vermicidal activity 266 Swericinctoside 274 Vernoniosides 77 238 287 Tannins 33 X-ray crystallography 226 Tea 322 Tenuifolioside A 77 Yamogemn 81 Teratogenieity 306 Ycmnosides 194 Thcasapogenin 322 Theasaponin 322 Ziziphm, 57,221, 231 ... data Hostettmann, K (Kurt), 1944- Saponins / K Hostettmann, A Marston p cm - (Chemistry and pharmacology or natural products) Includes bibliographical references and index ISBN 521 329701 Saponins. .. monosaccharide moiety or the C-22 sugar chain is j R1 R2 R2 acetylated (Kitagawa et al 1988b; Taniyama et al 1988a, 1988h; Shiraiwa et al 1991) It is very likely, therefore, that soyasaponins Aj,... only in the seed hypocotyl of soy- beans (Shiraiwa et al 1991) Very recently, a series of acetylated j saponins, acetyl-soyasaponins Aj-Ag and saponins Ac and Ad, have been j Group A isolated from