APPENDIX

SAPONIN NETWORK FOR MASS SPECTROMETRY AND NUCLEAR MAGNETIC RESONANCE SPECTROMETRY

The network for MS and NMR spectra is a part of the Databases of Carbohydrate Spectra which was conceived August 18-20, 1995 in Seattle, Washington for the Complex Carbohydrate Center, The University of Georgia, Athens, GA, by Prof. Peter Albersheim, and by the Department of Bio-Organic Chemistry, The Utrecht University, Utrecht, The Netherlands by Prof. Johannes F.G. Vliegenthart, and sponsored by the U.S. Department of Energy. The curator of the mass spectra and NMR spectra for is:

Dr. Tadahiro Takeda Professor of Kyoritsu College of Pharmacy 1-5-30, Shiba-Kouen, Minato-ku Tokyo 105 JAPAN Tel: +81-3-5400-2696 Fax: +81-3-5400-2666

At this time Dr. Takeda has just accepted the responsibility for collecting and disseminating the spectra of saponins, and he does not have his organizational scheme set-up as yet. The mass spectra would include fast atom bombardment (FAB), electrospray ionization (ESI), tandem MS/MS with collision-induced decomposition, matrix-assisted laser-desoription (MALDI), electron impact and/or chemical ionization spectrometry, and liquid chromatography/mass spectrometry (LC/MS). To be of value to all who use the mass spectra database the details of the instrument settings and experimental conditions used to acquire each spectrum must be submitted. These guidelines will be available from Dr. Takeda or published in the letters to the editors of the leading journals in the field. Although there has not been time enough to prepare a proposal on mass spectrometry, Dr. J. Albert van Kuik and Professor Johannes F.G. Vliegenthart have put together a proposal on a NMR spectra database gathering and dissemination for complex carbohydrates and it is presented below:

Proposal on standardized information-exchange formats for spectral databases of complex carbohydrates. J. Albert van Kuik and Johannes F.G. Vliegenthart Department of Bio-Organic Chemistry, University of Utrecht, P.O. Box 80.075, 3508 T Butrecht, The Netherlands, Tel: +31-30-253-5184, Fax: +31-30-254-0980

Currently, no general database format exists for the storage of spectral data for these classes of bio-molecules. Some efforts have been made to collect NMR data for specific types of bio• molecules, such as proteins and peptides by BioMagResBankl, or complex carbohydrates by

575 SUGABASE2. These collections typically contain chemical-shift assignments, a description of the molecule, and experimental conditions, but no original spectral data. One major obstacle associated with collecting original spectral data is the variety of formats in which spectra are stored. Even with one NMR-instrument manufacturer, different machines and different generations of software result in many incompatible formats. Collections of chemical-shift assignments bring their own compatibility problems. To unequivocally assign a chemical shift in an arbitrary bio-molecule, this molecule needs a unique identifier, and, additionally, each atom in this molecule requires a unique identifier too. These identifiers must be universal and not class• or database-dependent. The lack of standards in this field leads to a specialized nomenclature for sub-classes of bio-molecules, e.g. proteins, carbohydrates, or saponins thereby excluding other classes, and making the inclusion of combined classes, e.g. glycoproteins or saponins, virtually impossible.

Fortunately some solutions for these problems are currently emerging3. To store spectral data of carbohydrate-containing bio-molecules in a format that is compatible with databases of other classes of biomolecules, we propose to extend current examples in the field, and to keep to the recommendations of IUPAC whenever possible.

Original spectral data should be stored in JCAMP-DX4,5, a computer-readable exchange format, originally designed for infrared spectral data exchange. Data are represented as printable ASCII characters. This format has specific extensions for NMR data, and is recommended by IUPAC. It is, or will soon be, supported by major NMR manufacturers Broker, Varian and Jeol. JCAMP• DX can also be used to store experimental conditions, e.g. type of instrument, solvent, concentration, original standard, conversion shift, temperature, and quality of the data.

Structures are to be submitted in the Standard Molecular Data (SMD) format6, an organic structural information exchange format, which is currently under development by the IUPAC Committee of Chemical Databases (CCDB) and others in collaboration with the United States of America standards organization ASTM. This format will be supported by major organizations, e.g. Chemical Abstracts and Beilstein Institute.

For the electronic handling of data, in particular electronic submission of spectral data and storage of these data in a computer database, not a single clear-cut standard is available. For electronic handling, we propose to adopt the format used by crystallographers and by BioMagResBank. This Self-defining Text Archival and Retrieval (STAR) format utilizes tag• value pairs, and is suitable for electronic data submission and subsequent processing by the computer. It is also the format of choice to represent lists of chemical shift assignments. For each database, a specific data dictionary is required to clearly define each data tag and associated attribute. Crystallographers have developed CIF, the Crystallographic Information File Data Dictionary. This is now the format in which structure papers are submitted to Acta Crystallographica. BioMagResBank has defined a Data Disposition Form for submission of NMR spectra for their database. This form is specific for data stemming from proteins and peptides, but could in principle be extended to handle other bio-molecules as well. At the moment it does not handle complex branched structures such as some carbohydrates, and it doesn't mention JCAMP-DX or SMD formats.

REFERENCES

I. B.R. Seavey, E.A. Farr, W.M. Westler, and J.L. Markley, A Relational Database for Sequence-Specific Protein NMR Data, J.Biomolecular NMR 1, 217-236 (1991).

2. J.A. van Kuik and J.F.G. Vliegenthart, A NMR Spectroscopic Database of Complex Carbohydrate Structures, Carbohydr. Europe 10, 31-32 (1994).

3. C.L. Wilkins, Guidelines on Nuclear Magnetic Resonance Computerized Databases, Pure & Appl. Chem. 67, 593-596 (1995).

4. J.G. Grasselli, JCAMP-DX, A Standard Format for Exchange of Infrared Spectra in Computer Readable Form, Pure & Appli Chem., 63, 1781-1792 (1991).

576 5. A.N. Davies and P. Lampen, JCAMP-DX for NMR, Appl. Spectrosc. 41, 1093 (1993). 6. F.H. Allen, J.M. Barnard, A.P.F. Cook and S.R. Hall, The Molecular Information File (MIF): Core Specifications of a New Standard Format for Chemical Data, J. Chem. Inf. Comput. Sci. 35, 412-427 (1995).

577 CONTRffiUTORS

H. Achenbach A. Aquino Institut fur Pharmazie und Lebensmittelchernie Dipartimento di Chimica delle Sostanze der Friedrich-Alexander-Universitat Naturali Department of Pharmaceutical Chemistry via D.Montesano 49 D-91052 Erlangen Napoli 801211TALY SchuhstraBe 19 GERMANY Y oshihisa Asada Khalid Aftab School of Pharmaceutical Sciences H.E.J. Institute of Chemistry Kitasato University University of Karachi 5-9-1, Shirokane, Minato-ku Karachi 75270 PAKISTAN Tokyo 108 JAPAN

Irina G. Agafonova Sergey A. A vilov Pacific Institute of Bioorganic Pacific Institute of Bioorganic Chemistry of Far East Chemistry of Far East Division of Russian Academy of Sciences Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA Vladivostok 690022 RUSSIA

Suresht K. Aggarval Manuel Balandrin College of Pharmacy NPS Pharmaceuticals, Inc. University of Kentucky University Research Park Lexington, KY 40536 Salt Lake City, UT 84108

Viqar Uddin Ahmad Guy Balansard H.E.J. Institute of Chemistry Laboratoire de Pharrnacognosie University of Karachi Faculte de Pharnacie Karachi 75270 PAKISTAN Universite d'Aizmarseille II 27 Bd J. Moulin 13385 Marseille Cedex FRANCE Dmitry L. Aminin Pacific Institute of Bioorganic Perry Barboza Chemistry of Far East University of New England Division of Russian Academy of Sciences Armidale, N.S.W. AUSTRALIA Vladivostok 690022 RUSSIA NinaBerova Michail M. Anisimov Department of Chemistry Pacific Institute of Bioorganic Columbia University Chemistry of Far East New York, NY 10027 Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA Lojos Biro Department of Protein and Vitamin Research Magda Antal Institute of Food-Hygiene and Nutrition Department of Protein and Vitamin Research Gyali ut 3/a Institute of Food-Hygiene and Nutrition Budapest H-1097 HUNGARY Gyali ut 3/a Budapest H-1097 HUNGARY G. Biro Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY

579 V. Bologa Nguyen Minh Due National Practical Science Center of Hygiene and Science-Production Union of Ginseng and Epidemiology of the Health Ministry of the Medicinal Plants Moldova Republic Ho Chi Minh City University of Medicine N. Testemitianu Chisinau State Medical University and Pharmacy Chisinau 2002 MOLD A VIA 41 Dinh Tien Hoang Street, District 1 Ho Chi Minh City, VIETNAM Paul Bowyer The Sainsbury Laboratory Earnest Dworshak Norwich Research Park Department of Protein and Vitamin Research Colney Norwich NR4 7UH Institute of Food-Hygiene and Nutrition UNITED KINGDOM Gyali ut 3/a Budapest H-1097 HUNGARY G.N. Busuk Vitebsk Medical Institute Y. Ebizuka Belorussia RUSSIA Faculty of Pharmaceutical Sciences The University of Tokyo I. Calis 7-3-1 Hongo, Bunkyo-ku Department of Pharmacognosy Tokyo 113 JAPAN Faculty of Pharmacy Hacettepe University Robert Faure Ankara TR-06100 TURKEY URA1411 University Aix-Marseille III V.Ya. Chirva A v. Escadrille Department of Organic Chemistry Normandi-Niemen Simferopol State University 13997 Marseille Cedex 13 FRANCE Taltinskaya Str. 4 Simferopol, Crimea 333036 UKRAINE Tsutomu Furuya Faculty of Science Claus Cornett Okayarna University of Science Royal Danish School of Pharmacy Okayarna 700 JAPAN Department of Medicinal Chemistry Universitetparken 2, DK-2100 Odon Gaa! Copenhagen DENMARK Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Michael J. Daniels Gyali ut 3/a The Sainsbury Laboratory Budapest H-1097 HUNGARY Norwich Research Park Colney Norwich NR4 7UH Monique Gasquet UNITED KINGDOM Laboratoire de Parasitology Faculte de Pharnacie G.A. Drozd Universite d'Aizmarseille II Department of Organic Chemistry 27 Bd I. Moulin 13385 Marseille Cedex FRANCE Simferopol State University Taltinskaya Str. 4 Sergey N. Gnedoi Simferopol, Crimea 333036 UKRAINE Pacific Institute of Bioorganic Chemistry of Far East Olga A. Drozdova Division of Russian Academy of Sciences Pacific Institute of Bioorganic Vladivostok 690022 RUSSIA Chemistry of Far East Division of Russian Academy of Sciences Jack P. Goodman Vladivostok 690022 RUSSIA College of Pharmacy University of Kentucky Lexington, KY 40536

580 L.A. Gorbacheva Aiko Ito Department of Organic Chemistry Institute of Pharmaceutical Sciences Sirnferopol State University Hirostirna Univesity School of Medicine Taltinskaya Str. 4 1-2-3- Kasumi, Minarni-ku Sirnferopol, Crimea 333036 UKRAINE Hirostirna 734 JAPAN

V.I. Grishkovets D. lurea Department of Organic Chemistry Institute of Biological Research Sirnferopol State University Blvd. Copou 20A Taltinskaya Str. 4 Iassy 6600 ROMANIA Sirnferopol, Crimea 333036 UKRAINE M.M.Iwu Katalin Gruiz Walter Reed Institute of Research Technical University of Budapest Division of Experimental Therapeutics Agricultural Chemical Technology Walter Reed Medical Center H-1521, Budapest Washington, DC 20307-5100 Szt. Gellert er 4 HUNGARY J.E. Jackson T. Grushko Walter Reed Institute of Research National Practical Science Center of Hygiene and Division of Experimental Therapeutics Epidemiology of the Health Ministry of the Walter Reed Medical Center Moldova Republic Washington, DC 20307-5100 N. Testemitianu Chisinau State Medical University Chisinau 2002 MOLDA VIA Marian L. Jurzysta Department of Biochemistry Garner T. Haupert, Jr. Institute of Soil Science & Plant Cultivation Department of Chemistry Pulawy 24-1000 POLAND Columbia University New York, NY 10027 Vladimir I. Kalinin Pacific Institute of Bioorganic Kurt Hostettmann Chemistry of Far East Institut de Pharmacognosie et Phytochimie Division of Russian Academy of Sciences Universite De Lausanne Vladivostok 690022 RUSSIA BEP, CH-1015 Lausanne-Dorigny SWITZERLAND Molgorzata Kalinowska Harald Hiibner Department of Biochemistry Institut fur Pharmazie und Lebensmittelchemie Warsaw University der Friedrich-Alexander-Universitat 02-089 Warszawa Department of Pharmaceutical Chemistry ul. Zwirki i Wigury 93 POLAND D-91052 Erlangen SchuhstraBe 19 GERMANY Geun Hyung Kang College of Pharmacy Kentaro Inoue Chonnam National University Faculty of Pharmaceutical Sciences Kwangju 500-757 KOREA The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Ryoji Kasai Tokyo 113 JAPAN Institute of Pharmaceutical Sciences Hirostirna University School of Medicine M. lorizzi 1-2-3 Kasumi, Minarni-ku Department of Natural Products Hirostirna 734 JAPAN University of Naples Naples 80131 ITALY Charlotte Kensil Cambridge Biotech Corporation Worcester, MA 01605

581 Dong Hyun Kim Lee-Chiang Lo Faculty ofPhannaceutical Sciences Department of Chemistry The University of Tokyo Columbia University 7-3-1 Hongo, Bunkyo-ku New York, NY 10027 Tokyo 113 JAPAN Maja Ja. Lovkova Junei Kinjo Bach Institute of Biochemistry Faculty ofPhannaceutical Sciences Leninsky Prospekt, 33 Kumamoto University Russian Academy of Science Kumamoto 862 JAPAN Moscow 117071 RUSSIA

Dr. P. Kintia James H. Ludens Institute of Genetics Department of Chemistry Academy of Sciences Columbia University Padurii str. 20 New York, NY 10027 Kishinev 277002 MOLDOVA S.B. Mahato Takao Konoshirna Indian Institute of Chemical Biology Kyoto Phannaceutical University 4, Raja S.C. Mullick Road Misasagi, Yarnashina-Ku Jadavpur, Calcutta 700-032 INDIA Kyoto 607 JAPAN M. Maillard Maroufath Larnidi Institut de Phannacognosie et Phytochimie Laboratoire de Phannacognosie Universite De Lausanne Faculte de Pharnacie BEP, CH-1015 Lausanne-Dorigny SWITZERLAN: Universite d'Aizmarseille II 27 Bd J. Moulin 13385 Marseille Cedex FRANCE A Marston Institut de Phannacognosie et Phytochimie N.V. Lattserdis Universite De Lausanne Institute of Genetics BEP, CH-1015 Lausanne-Dorigny SWITZERLANl Academy of Sciences Padurii str. 20 Y oshihiro Mimaki Kishinev 277002 MOLDOVA SchoolofPhannacy Tokyo College of Pharmacy & Life Sciences Ik-SooLee 1423-1, Horinouchi College of Pharmacy Hachioji, Tokyo 192-03 JAPAN Chonnam National University Kwangju 500-757 KOREA L. Minale Department of Natural Products Else Lemmich University of Naples Royal Danish School of Phannacy Naples 80131 ITALY Department of Medicinal Chemistry Universitetparken 2, DK-2100 Faryal Vali Mohammad Copenhagen DENMARK H.E.J. Institute of Chemistry University of Karachi Xing-Cong Li Karachi 75270 PAKISTAN Laboratory of Phytochemistry Kunming Institute of Botany Tsuneatsu Nagao Chinese Academy of Sciences Faculty ofPhannaceutical Sciences Heilongtan, Kunrning 650204 CHINA Fukuoka University, Nanakurna 8-19-1, Jonan-ku, Fukuoka 814-01 JAPAN Galina N. Likhatskaya Pacific Institute of Bioorganic Katalin Nagy Chemistry of Far East Department of Protein and Vitamin Research Division of Russian Academy of Sciences Institute of Food-Hygiene and Nutrition Vladivostok 690022 RUSSIA Gyali ut 3/a BudapestH-1097 HUNGARY

582 Mohamad A. Naibi Anne Osborne Institute of Genetics The Sainsbury Laboratory Academy of Sciences Norwich Research Park Padurii str. 20 Colney Norwich NR4 7UH UNITED KINGDOM Kishinev 277002 MOLDOVA Cezary Paczkowski Koji Nakanishi Department of Biochemistry Department of Chemistry Warsaw University Columbia University 02-089 Warszawa New York, NY 10027 ul. Zwirki i Wigury 93 POLAND

Nguyen Thoi Nham E. Palagiano Science-Production Union of Ginseng and Department of Natural Products Medicinal Plants University of Naples Ho Chi Minh City University of Medicine Naples 80131 ITALY and Pharmacy 41 Dinh Tien Hoang Street District 1 Valentina A. Paseshnichenko Ho Chi Minh City VIETNAM A.N. Bach Institute of Biochemistry Leninskiy pr. 33 Toshihiro Nohara Moscow 117071 RUSSIA Faculty of Pharmaceutical Sciences Kumamoto University Jun-peng Peng Kumamoto 862 JAPAN Institute of Radiation Medicine, Beijing 27 Tai-ping Road Mushtaq Noorwala Beijing 100850 CHINA H.E.J. Institute of Chemistry University of Karachi S. Piacente Karachi 75270 PAKISTAN Dipartimento di Chimica delle Sostanze Naturali via D.Montesano 49 Lucienne Nze-Ekekang Napoli 80121 ITALY Iphametra (Cenerest) Libreville B.P. 842 GABON C. Pizza Dipartimento di Chimica delle Sostanze Naturali Kazuhiro Ohtani via D. Montesano 49 Institute of Pharmaceutical Sciences Napoli 80121 ITALY Hirostima University School of Medicine 1-2-3 Kasumi, Minarni-ku ltzhack Polacheck Hirostirna 734 JAPAN Department of Clinical Microbiology and Infectious Diseases HikamOkabe The Hebrew University Faculty of Pharmaceutical Sciences Jerusalem 91120 ISAREL Fukuoka University Nanakuma 8-19-1 S.M. Ponomareva Jonan-ku, Fukuoka 814-01 JAPAN Bach Institute of Biochemistry Leninsky Prospekt, 33 C.O. Okunji Russian Academy of Science Walter Reed Institute of Research Moscow 117071 RUSSIA Division of Experimental Therapeutics Walter Reed Medical Center Nina G. Prokofieva Washington, DC 20307-5100 Pacific Institute of Bioorganic Chemistry of Far East Evelyne Ollivier Division of Russian Academy of Sciences Laboratoire de Pharmacognosie Vladivostok 690022 RUSSIA Faculte de Pharnacie Universite d'Aizmarseille II 27 Bd J. Moulin 13385 Marseille Cedex FRANCE

583 GuoweiQin Fehmeena Shaheen Shanghai Institute of Materia Medica H.E.J. Institute of Chemistry Academia Sinica University of Karachi 319 Yue-yang Road Karachi 75270 PAKISTAN Shanghai 200031 CHINA Baoping Shao A. Regoly-Merei Shanghai Inst. of Materia Medica Department of Protein and Vitamin Research Academia Sinica Institute of Food-Hygiene and Nutrition 319 Yue-yang Road Gyali ut 3/a Shanghai 200031 CHINA Budapest H-1097 HUNGARY O.V. Shelepova Melchior Reiter N.Y. Tsitsin Main Botanical Garden lnstitut fur Pharmazie und Lebensmittelchemie Russian Academy of Science der Friedrich-Alexander-Universitat Moscow RUSSIA Department of Pharmaceutical Chemistry D-91052 Erlangen Stepan A. Shvets SchuhstraBe 19 GERMANY Institute of Genetics Academy of Sciences R. Riccio Padurii str. 20 Department of Natural Products Kishinev 277002 MOLDOVA University of Naples Naples 80131 ITALY F. DeSimone Dipartimento di Chimica delle Sostanze Naturali J.G. Roddick via D. Montesano 49 Department of Biological Science Napoli 80121 ITALY University of Exeter Exeter EX4 4QG UNITED KINGDOM P. Skofertsa National Practical Science Center of Hygiene and Ushiro Sankawa Epidemiology of the Health Ministry of the Faculty of Pharmaceutical Sciences Moldova Republic The University of Tokyo N. Testemitianu Chisinau State Medical University 7-3-1 Hongo, Bunkyo-ku Chisinau 2002 MOLDAVIA Tokyo 113 JAPAN S.M. Sokolova Yutaka Sashida N.Y. Tsitsin Main Botanical Garden SchoolofPharmacy Russian Academy of Science Tokyo College of Pharmacy & Life Science Moscow RUSSIA 1423-1, Horinouchi Hachioji, Tokyo 192-03 JAPAN Sean Soltysik Cambridge Biotech Corporation Elena B. Schentsova Worcester, MA 01605 Pacific Institute of Bioorganic Chemistry of Far East K. Spinu Division of Russian Academy of Sciences National Practical Science Center of Hygiene and Vladivostok 690022 RUSSIA Epidemiology of the Health Ministry of the Moldova Republic Dirk C. van Setten N. Testemitianu Chisinau State Medical University National Institute of Public Health Chisinau 2002 MOLDAVIA & Environmental Protection Department of Molecular Spectroscopy Jan St. Pyrek P.O. Box 1 College of Pharmacy Bilthoven 3720 BA THE NETHERLANDS University of Kentucky Lexington, KY 40536

584 Otto Stieber C.V. Uglea Department of Pharmacy Institute of Biological Research Swiss Deferal Institute of Technology Blvd. Copou 20A (ETH-Z) lassy 6600 ROMANIA Zurich 8057 SWITZERLAND Inessa S. Vasilvera Lybov I. Strigina A.N. Bach Institute of Biochemistry Pacific Institute of Bioorganic Leninskiy pr. 33 Chemistry of Far East Moscow 117071 Division of Russian Academy of Sciences RUSSIA Vladivostok 690022 RUSSIA V. Vorozhbit Chung Ki Sung National Practical Science Center of Hygiene College of Pharmacy and Epidemiology of the Health Ministry of the Chonnam National University Moldova Republic Kwangju 500-757 KOREA N. Testemitianu Chisinau State Medical University Chisinau 2002 MOLDA VIA J. Szepvolgyi Department of Protein and Vitamin Research V. Vutkaryov Institute of Food-Hygiene and Nutrition National Practical Science Center of Hygiene and Gyali ut 3/a Epidemiology of the Health Ministry of the Budapest H-1097 HUNGARY Moldova Republic N. Testemitianu Chisinau State Medical University J.D. Tally Chisinau 2002 MOLDAVIA Walter Reed Institute of Research Division of Experimental Therapeutics George R. Waller Walter Reed Medical Center Department of Biochemistry and Molecular Biology Washington, DC 20307-5100 Oklahoma State University 246B Noble Research Center Osamu Tanaka Stillwater, OK 74078-0454 Suzugamine Women's College Inokuchi 4-chome 6-18 Bethanne Warrack Nishi-ku Department of Chemistry Hiroshima 733 JAPAN Columbia University New York, NY 10027 Ryuichiro Tanaka Faculty of Pharmaceutical Sciences Gerrit van de Werken Fukuoka University, National Institute of Public Health Nanakuma 8-19-1, & Environmental Protection Jonan-ku, Fukuoka 814-01 JAPAN Department of Molecular Spectroscopy P.O. Box 1 Susan Thiilborg Bilthoven 3720 BATHE NETHERLANDS Royal Danish School of Pharmacy Department of Medicinal Chemistry Deborah A. Wheeler Universitetparken 2, DK-2100 Cambridge Biotech Corporation Copenhagen DENMARK Worcester, MA 01605

N. De Tommasi J.L. Wofender Dipartimento di Chimica delle Sostanze Naturali Institut de Pharmacognosie et Phytochimie via D. Montesano 49 Universite De Lausanne Napoli 80121 ITALY BEP, Lausanne-Dorigny CH-1015 SWITZERLAND

Adrienne A. Tymiak Zdzislav A. Wojciechowski Department of Chemistry Department of Biochemistry Columbia University Warsaw University New York, NY 10027 02-089 Warszawa ul. Zwirki i Wigury 93 POLAND

585 Roland Woldanski Pei-Ying Yang Department of Biochemistry College of Pharmacy Warsaw University University of Kentucky 02-089 Warszawa Lexington, KY 40536 ul. Zwirki i Wigury 93 POLAND Xin-sheng Yao Jia-YanWu Institute of Radiation Medicine, Beijing Cambridge Biotech Corporation 27 Tai-ping Road Worcester, MA 01605 Beijing 100850 CHINA

JunpingXu Sang Sun Yoon Pharmagenesis College of Pharmacy 3183 Porter Drive Chonnam National University Palo Alto, CA 94304 Kwangju 500-757 KOREA

Ren-sheng Xu Masayuki Yoshikawa Shanghai Inst. of Materia Medica Kyoto Pharmaceutical University Academia Sinica 5, Nakauchi-cho, Misasgi 319 Yue-yang Road Yamashina-ku, Kyoto 607 JAPAN Shanghai 200031 CHINA UriZehavi and/or The Hebrew University of Jerusalem Pharmagenesis Faculty of Agriculture 3183 Porter Drive Department of Biochemistry, Food Science, Palo Alto, CA 94304 and Nutrition P.O.B. 12, Rehovot 76100 ISRAEL Shoji Yahara Faculty of Pharmaceutical Sciences NingZhao Kumamoto University Department of Chemistry Kumamoto 862 JAPAN Columbia University New York, NY 10027 Johji Yamahara Natural Medicinal Resources Division WeiminZhao Research Institute for Production Development Shanghai Inst. of Materia Medica Kyoto 606 JAPAN Academia Sinica 319 Yue-yang Road Kazuo Yamasaki Shanghai 200031 CHINA Institute of Pharmaceutical Science Hiroshima University Jan Zimowski School of Medicine Department of Biochemistry 1-2-3 Kasumi, Minami-ku Warsaw University Hiroshima 734 JAPAN Warszawa 02-089 POLAND

Chong-Ren Yang Laboratory of Phytochemistry Kunming Institute of Botany Chinese Academy of Sciences Heilongtan, Kunming 650204 CHINA

586 LATIN NAME INDEX

Abrus cantoniensis, 267, 271 Asparagus mairei, 226-227 Abrus precatorius, 271 Asparagus officinalis, 8, 37,41-43,310, Acacia auriculiformis, 173, 178 314a,323 Acanthaster planci, 344 Asparagus plumosus, 37,41-43,45 Acebia quinata, 239 Aspergillus fumigatus, 233-234 Achillea millefolium, 7 Aspergillus niger, 30, 31,536,565 Acorus calamus, 198 Aspergillus spp., 120 Aesculus hippocastanum, 5, 83, 85,207-208, Aspergillus wentii, 552 212,471 Aster scaber, 297, 299-301 Agaricus bisporus, 31 Aster spp., 297 Agathis philippinensis, 198 Aster tataricus, 297 Agava americana, 310,313,323 Asterias amurensis, 342 Agava lecheguilla, 443 Asterina pectinifera, 347-348 Agava sisalana, 3, 11 Asteropus sarasinosum, 335-336 Agava spp., 11 Astragalus complanatus, 271 Agrobacterium rhizogenes, 31 Astragalus falcatus, 83-84, Albizzia julibrissin, 271 Astragalus melanophrurius, 495 Alcyonum spp., 337-338 Astragalus membranaceus, 5, 225 Aletris farinosa, 7 Astragalus oleifolius, 495 Allium albopilosum, 101 Astragalus sinicus, 271 Allium ampeloprasum, 8, 511 Astropecten indicus, 350 Allium bakeri, 517 Atriplex canescens, 12 Allium cepa, 8, 310, 5ll Atropa belladonna, 310,475,477,481-482 Allium chinense, 107-108,512,517-518, Aucuba japonica, 26 521-522 Avena longiglumis, 549 Allium macrostemon, 512-514,521-522 A vena sativa, 8-9 Allium narcissiflorum, 310, 314, 323 Allium porrum, 8 Bacillus subtilis, 328, 368 Allium sativum, 4, 8, 511-512, 520-522 Bacteroides JY-6, 29-32, 35, Allium schoenoprasum, 8 Bacteroides fragilis, 27 Allium spp., 511 Beshorneria yuccoides, 310 Allium vineale, 511 Beta vulgaris, 9, 208 Aloe barbadensis, 4 Bifido-bacterium pseudo-longam, 27 Aloe vera, 4 Bifidobacterium breve, 27 Alternaria brassicicola, 287 Biomphalaria glabrata, 119-121, 152, 161, Alternaria solani, 283, 553 426 Anemoclema glaucifolium, 229 Biomphalaria pfeifferi, 425-426 Anthoplexaura dimorpha, 337-338 Blumea balsamifera, 198 Arachis hypogaea, 9 Borago officinalis, 7 Aralia elata, 83-84, 198, 207-208 Borrelia burgdoiferi, 165 Aralia racemosa, 7 Botrytis cinerea, 553 Arcangelisiajlava, 198 Brachiaria decumbens, 443 Ardisia crenata, 494 Bufo spp., 219 Ardisia japonica, 403-404 Bulinusforskalii, 426 Asparagus cochinchinensis, 408-409 Bulinus globosus, 119, 425-426 Asparagus filicinus, 226-227 Bupleurumfalcatum, 7, 28,30

587 Bupleurumfruticosum, 403,405 Crataegus spp., 6 Crocosmia crocosmiiflora, 459-460, 464, Caesalpinia sapan, 198 469 Caldocellum saccharolyticum, 30-31, Crocosmia masoniorum, 459,464-465, 46~ Calendula arvensis, 403,404,407-408 Crotalaria albida, 271 Calendula officinalis, 5, 83-84, Cryptococcus neoformans, 535,538,541, Caltha silvestris, 239 543 Camelliajaponica, 207-208, 213 Cucumaria echinata, 563 Camellia sinensis, 9 Cucumaria japonica, 557 Candida alba, 327 Cucurbita moschata, 198 Candida albicans, 120, 233-234, 418, 565 Culcita novaeguineae, 344 Candida guilliermondii, 565 Cyclamen coum, 489,491-492,494 Candida krusli, 327,565 Cyclamen mirabile, 489,491,492 Candida lipol., 327 Candida parapsilosis, 565 Dalbergia hupeana, 271 552 Candida pelliculosa, Datura stramonium, 310 Candida pseudotropicalis, 565 Decaisnea fargesii, 229 Candida rugosa, 327 Desmodium styracifolium, 271 Candida tropicalis, 327, 418, 565 Digitalis barbasco, 11 Candida utilis, 327 Digitalis deltoidea, 11 Capsicum annuum, 10,253,310,323, 325, Digitalis lanata, 11 332 Digitalis macrostachya, 11 10 Capsicum frutescens, Digitalis purpurea, 1, 11,219,310,323, Cassia tora, 30 325,332 239, 242 Caulophyllum robustum, Digitalis spiculiflora, 11 Caulophyllum thalictroides, 7 Digitalis tokoro, 11 Centella asiatica, 6 batatus, 30 565 Dioscorea Cephalosporium gramineum, Dioscorea caucasica, 323 Chamaelirium luteum, 7 Dioscorea composita, 2, 11 Charonia lampas, 347-348 Dioscorea deltoidea, 15-21, 83-84 quinoa, 9 Chenopodium floribunda, 2, 11, 59 11 Dioscorea Chlorogalum pomeridianum, Dioscorea mexicana, 2, 11 226, 228-229 Chlorophytum malayense, Dioscorea nipponica, 16, 18, 83-84 Cicer arietinum, 9 Dioscorea spp., 3, 10, 11, 15 Cimicifuga racemose, 6 Dioscorea terpinapensis, 11 Cinchona spp., 402 Dioscorea tokoro, 30 198 Cinnamomum mercadoi, Dioscorea villosa, 4 Citrullus vulgaris, 30, 198 Diospyros kaki, 30 · Cladosporium carrionii, 418, 420 Diuranthera major, 226, 229 420 Cladosporium cladosporioides, Dolichos kilimandscharicus, 120 Cladosporium cucumerinum, 120-121,420, Dolicusfalcata, 536 425 Dracaena arborea, 415,417,425 spp., 120 Cladosporium Dracaena mannii, 415-417 418,420,425 Cladosporium tenuissimum, Dracaena spp., 415-426 371, 373, 381 Clematis chinensis, Duasmodactyla kurilensis, 340-341 Clerodendrum wildii, 121 Codonopsis pilosula, 5 Codonopsis spp., 5 Echinaster sepositus, 342 Codonopsis tangshen, 5 Echinaster spp., 344-346, 353 Coleus forskolii, 196 Ejretia microphylla, 198 Cordia myxa, 198 Eleutherococcus senticosus, 5 Coriolus consors, 31 Entada phaseoloides, 198 Coriolus versicolor, 31 Enterobacter cloacae, 31 Corticium rolfsii, 282 Epidermophyton floccosum, 541 Corynebacterium sepedonicum, 283 Equisetum arvense, 5 Coscinasterias tenuispina, 344 Eriobotrya japonica, 201 Costus speciosus, 57, 59-62 Escherichia coli, 328, 507

588 Eubacterium spp., 26, 28 Klebsiella pneumoniae, 27 Eupatorium perfoliatum, 1, 557 Kochia scoparia, 208 Eupentactafraudatrix, 340-341, 561 Exophialajeanselmei, 418 l.agerstroemia speciosa, 196, 198, 200-201 l.agotis stolonifera, 486 Fonsecaes pedrosoi, 418,420 Larrea tridentata, 7 Fritillaria camtschatcensis, 103 l.asiorhinus latifrons, 449, 451 Fritillaria persica, 103 Lebistes reticulatus, 529 Fritillaria spp., 102 Leishmania chagasi, 421 Funkia norata, 323 Leishmania donovani, 423 Funkia ovata, 310, 315, 316 Leishmania panamensis, 423 Fusarium caeruleum, 283 Lens culinaris, 9 Fusarium graminearum, 331 Leontice eversmanni, 435 Fusarium oxysporum, 282-283, 536, 553, 565 Leptadenia hastata, 410-412 Fusarium sambucinum; 283 Leptinotarsa decemlineata, 283 Fusarium solani, 281, 283 Lilia henri, 310 Lilium pardarinum, 102 Gaeumannomyces graminis, 548, 551, 565 Lilium regale, 310,317-318 Galega o.fficinalis, 7, 502 Liriope japonica, 225 Gardenia ternifolia, 383 Liriope platyphylla, 30 Geotrichum candidum, 418,565 Lithospermum erythrorhizon, 41 Ginkgo biloba, 198 Luidia clathrata, 342 Glechoma hederacea, 198 Lupinus polyphyllus, 271 Gleditsia japonica, 91, 93 Lycopersicon esculentum, 10, 72,310,323, Gloeoesporium frutctigenum, 282-283 326,332,505 Glycine max, 9, 208,502 Lymnaea natalensis, 426 Glycyrrhiza glabra, 3, 5, 12, 83-84 Lyophyllum fusosum, 31 Glycyrrhiza spp., 27 Glycyrrhiza uralensis, 83, 84, 225, 371 Manihot esculenta, 10 Guaiacum o.fficinale, 9 Marthasterias glacialis, 344 Guettarda angelica, 390 Medhuca butyracea, 237 Guettarda platypoda, 390, 402, 407-408 Medicago arabica, 566,569-571 Guettarda spp., 402 Medicago blancheana, 566,569-570 Gymnema sylvestre, 7, 208 Medicago carstiensis, 566, 569-570 Gymnocladus chinensis, 92-93 Medicago ciliaris, 566, 569-570 Gynostemma pentaphyllum, 131, 405-406 Medicago disciformis,.566, 569-571 Gypsophila paniculata, 12 Medicago doliata, 566,569-571 Gypsophila spp., 12 Medicago granadensis, 566, 569-570 Medicago heyniana, 566,569-571 Halityle regularis, 344 Medicago hybrida, 566, 569-570 Hedera helix, 5 Medicago intenexta, 566,569-570 Heinsia crinata, 374 Medicago laciniata, 566, 569-571 Helianthus annuus, 9 Medicago lupulina, 536, 566, 569-570 Heliothis zea, 284 Medicago minima, 566,569-570 Helix pomatia, 16 Medicago murex, 566, 569-571 Heloniopsisjaponica, 272 Medicago muruioleptis, 566, ·569-570 Hemsleya macrosperma, 131 Medicago noeana, 566,569-571 Henricia downeyae, 344, 352-353 Medicago polyceratia, 569-571 Henricia laeviuscola, 344, 353 Medicago polymorpha, 566,569-570 Hovenia dulcis, 208 Medicago praecox, 566,569-570 Hydrangea arborescens, 7 Medicago radiata, 566, 569-570 Hydrocotyle asiatica, 6 Medicago rotata, 566, 569-570 Hyposoter exiguae, 284 Medicago rugosa, 566, 569-570 Medicago sativa, 6, 9, 536, 565-567, 569- /lex paraguariensis, 7 571

589 Medicago sauvagei, 566, 569-571 Panicum coloratum, 443 Medicago scutellata, 566, 569-570 Panicum dichotomiflorum, 443 Medicago soleirolii, 566, 569-570 Panicum schinzii, 443 Medicago spp., 567-571, 573 Pardachirus marmoratus, 338 Medicago tomata, 566, 569-570 Pardachirus pavoninus, 338 Medicago truncatula, 566, 569-570 Pardachirus spp., 335 Medicago turbinata, 566, 569-570 Passiflora incamata, 6 Melilotus alba, 10 Patiria miniata, 344 Melilotus officina/is, 10,310 Paullinia cupana, 6 Micoides citreum, 328 Pavetta crassipes, 383 Microsporum audouinii, 418 Peliosanthes sinica, 226-227, 229 Microsporum canis, 541 Penicillium spp., 120 Microsporum grpseum, 418 Pentacta australis, 340, 341 Millettia spp., 10 Peptostreptococcus intermedius, 27 Mitchella repens, 7 Petunia hybrida, 251, 261, 310,480 Momordica charantia, 198 Pfaffia paniculata, 5 Morinda Iucida, 383 Phaseolus aconitifolius, 9 Morus alba, 198 Phaseolus acutifolius, 9 Muriceafruticosa, 336-337 Phaseolus angularis, 9 Mussaendapubescens, 371-373,381 Phaseolus aureus, 9 Myristica fragrans, 9 Phaseolus coccineus, 9 Phaseolus lunatus, 9 Nauclea diderrichii, 383, 385-386, 389-390, Phaseolus mungo, 9 392-393 Phaseolus vulgaris, 9 Nauclea latifolia, 383 Phialophora verrucosa, 418 Nauclea orienta/is, 198 Phoma exigua, 283 Nicandra spp., 264 Phoma medicaginis, 288 Nicotiana plumbaginifolia, 285 Physalis spp., 264 Nicotiana rustica, 310 Phytolacca americana, 7, 487 Nicotiana tabacum, 310 Phytolacca dodecandra, 118-119, 125-126, Nigerian dracaena, 416 151-156, 160-161 Nolina recurvata, 105-106 Phytolacca spp., 152-153 Nomuraea rileyi, 284 Phytophthora cinnamomi, 536, 565 Phytophthora infestans, 21, 282-283, 324 Ophipogon maglanthus, 226-227 Phytophthora spp., 281, 548 Oplopanax elatus, 84 Pisum sativum, 9 Oreaster reticulatus, 351 Plasmodiumfalciparum, 385, 388, 394-397, Oreosolen wattii, 237 417,420 Omithogalum saundersiae, 103-104, 108 Pleurotus ostreatus, 31 Orthosiphon stamineus, 83-84 Polemonium coeruleum, 83, 84 Polygala senega, 6, 207-208, 214 Pachastrella spp., 335 Polygonatum biflorum, 7 Paeonia lactiflora, 24 Polygonatum kingianum, 225-227 Paeonia suffruticosa, 24 Polygonatum latofolium, 310, 327 Panax ginseng, 5, 84, 94-95, 97, 129, 132, Polygonatum multiflorum, 7 198,202,225,371 Polygonatum officinale, 7 Panax japonica, 94-95,202,208 Polygonatum pratti, 226-227 Panax notoginseng, 5, 94-99, 129, 132, 138, Primula elatior, 6 202, 225-226 Primula officina/is, 6 Panax pseudo-ginseng, 202 Primulaceae auriculata, 487 Panax quinquefolius, 3, 5, 129, 132, 202 Primulaceae elatior, 487 Panax spp., 129, 131-132, 136, 138, 144, Primulaceae longipes, 487 202 Primulaceae megaseifolia, 487 Panax vietnamensis, 131-132, 138, 147,202 Primulaceae veris, 487 Panax zingiberensis, 202 Protoreaster nodosus, 344 Pandanus sp., 198 Prunus armeniaca, 30

590 Prunus persica, 30 Solanum aculeatissimum, 264 Prunus salicina, 30 Solanum aethiopicum, 264 Pseudoplexaura wagenaari, 337-338 Solanum anguivi, 264 Psolusfabricii, 340-341,557 Solanum arundo, 286 Pueraria lobatta, 9, 266, 268, 271 Solanum bijlorum, 264 Pueraria thunbergiana, 9 Solanum chacoense, 264, 283 Pulsatilla campanella, 229 Solanum cynathem, 264 Pythium aphanidermatum, 536, 565 Solanum demissum, 264 Pythium spp., 280, 548 Solanum dubium, 286 Solanum dulcamara, 7, 263,264, 285 Quercus alba, 5 Solanum ferox, 263 Quillaja saponaria, 9, 12, 165, 167, 170, Solanum gila, 264 185-191 Solanum incanum, 282 Solanum indicum, 264 ftamichloridium subulatum, 418, 425 Solanum integrifolum, 264 Rapanea melanophloeos, 120-121 Solanum japonense, 264 Rheum officinale, 25 Solanum jurpeva, 264 Rheum palmatum, 25 Solanum khasianum, 264 Rheum spp., 25 Solanum laciniatum, 47 Rhinanthus spp., 27 Solanum lycocarpum, 264 Rhizoctonia solani, 283, 536, 565 Solanum lycopersicum, 10 Rhizopus mucco, 536 Solanum lyratum, 263,264 Rhodotorula glutinis, 565 Solanum macrocarpon, 264 Rhodotorula spp., 418 Solanum mammosum, 264 Robinia pseudo-acacia, 271 Solanum melongena, 10,37-39,41-43,47, Rosa canina, 6 264,310,319-321,327 Rubus fruticosus, 9 Solanum nigrum, 263-264 Ruscus aculeatus, 4, 104 Solanum paniculatum, 264 Solanum sanitwongsei, 264 Saccharomyces cerevisiae, 327 Solanum sisymbrifolium, 263 Saccharomycopsisfibuligera, 527, 552 Solanum sodomaeum, 285 Sapindus mukurossi, 12, 208, 211 Solanum spp., 47,285-286,445 Sap indus rarak, 12 Solanum stramonifolium, 264 Sapindus saponaria, 12 Solanum surattense, 264 Saponaria officinalis , 12 Solanum torvum, 264 Saprolegnia asterophora, 368 Solanum toxicarium, 264 Sarcina lutea, 328 Solanum tuberosum, 10, 47, 71,264,310 Schistosoma haematobium, 118 Solanum vanhuerchii, 264 Schistosomajaponicum, 118 Solanum verbascifolium, 264 Schistosoma mansoni, 118 Solanum viarum, 264 Schistosoma spp., 285 Solanum xanthocarpum, 264 Scilla peruviana, 104, 107, 108 Solidago canadensis, 5 Sclerotium rolfsii, 536, 565 Solidago serotina, 5 Scrophularia ilwensis, 486 Solidago virgaurea, 5 Scrophularia spp., 486 Sophora flavescens, 271, 503 Septaria lycopersici, 553 Sophora japonica, 501-503 Sesamum indicum, 9 Sophora subprostrata, 271 Setaria cervi, 177 Sorghum bicolor, 30 Sinularia crispa, 337, 338 Spinacea oleracea, 9 Smilacina racemosa, 7 Staphylococcus aureus, 328 Smilax aristolochiaefolia, 4, 8 Stellaria media, 5 Smilax febrifuga, 8 Streptomyces scabies, 283 Smilax officinalis, 8 Strophanthus gratus, 219 Smilax regelii, 8 Swartzia madagascariensis, 119, 123, 124 Solanum abittiloides, 264, 266 Symphytum officinale, 7, 429-431, 436, 439- Solanum achrolcucum, 264 440

591 Tamus communis, 408-409 Trillium spp., 7 Taraxacum officinale, 5 Triplostegia grandiflora, 229 Taxus cuspidata, 198 Tubocapsicum spp., 264 Tenebrio molitor, 529 Tupistra wattii, 226-227 Tetrapleura tetraptera, 119, 122, 124-125 Thalictrum spp., 273 Uncaria guianensis, 390, 402 Thea sinensis, 9, 208 Uncaria tomentose, 6, 390,402,407-408 Tinospora cordifolia, 198 Tinospora rumphii, 198 Verbascum thapsus, 7 Torulopsis candida, 565 Verticillium albo-atrum, 283, 324, 326, 553 Torulopsis glabrata, 538, 565 Vibrio vulnificus, 31 Tremaster novaecaledonia, 350 Vicia faba, 9 Tribulus cistoides, 357, 358, 362-363, 367 Vigna aconitifolia, 9 Tribulus terrestris, 83-84, 310, 323, 329, Vigna angularis, 9, 208, 502-503 357 Vigna radiata, 9 Trichoderma koningii, 530, 532 Vigna sinensis, 9 Trichoderma pseudokoningii, 530, 532 Vigna umbellata, 9 Trichoderma reesei, 530, 532, 552 Viola tricolor, 84 Trichoderma viride, 527-530, 532-534, 536- Vitex negundo, 198 567,569,571 Vombatus ursinus, 449-450, 453 Trichophyton mentagrophytes, 233-234, 418,535,538,541 Wistaria brachybotrys, 87-90, 271 Trichophyton rub rum, 418 Withania somnifera, 7 Trichophyton soudanense, 418, 425 Trichophyton tonsurans, 418 Yucca brevifolia, 4, 11 Trichosporon cutaneum, 418 Yuccafilamentosa, 310, 322, 325 Trichosurus vulpecula, 449 Yucca gloriosa, 83-84 Trifolium pratense, 6 Yucca mohavensis, 11 Trifolium repens, 63 Yucca schidigera, 4, 11 Trigonellafoenum-graecum, 4, 8, 310,444 Trillium erectum, 7 Zizyphus jujuba, 9

592 SUBJECT INDEX

Abrisapogenols, 265-268 Alliumosides, 310, 314, 323 Abrisaponin I, 268-269 Aloeresin, 26 Abrisaponins, from Abri Herba, 269 Aloesin, 26 Abutiloside A, 266 American ginseng, 129 Acaciasides, 174-176, 178-182 Ames test, 154 Acacic acid lactones, 17 4-17 5, 177, 179- cAMP phosphodiesterase inhibition, 101, 180 107-108 Acacigenin A, 175-177, 181-182 2H-cAMP incorporation, 241 Acetylcholinesterase, 281 3H-cAMP uptake, 245 Acetyllycopsamine acetylintermedine Amphotericin B, 233-234, 544 (diasteroisomers), 430 Anaemia, 429 Acovenosigenin, 220 Anagalligenin, 488-489 Acrosome reaction, 342 Analgesic, 240, 373, 429, 495 Acute gastroenteritis, 371 Analysis of plant extracts for saponins by Aculeoside A, 104-105 LC (HPLC) and mass spectrometry, Acyl group in crocosmiosides, 469 121-127 enhanced inhibiting activity, 469 Anemoclemosides, 230-231 26-0-Acylated furostanol saponins, 102 Anthraquinone, 25 Adjuvant activity of QS-21, 171 Anthrone , 25 Adriamycin, 108,233 Anthroquinone and anthrone glycosides, Adzukisaponins, 502-503 25-26 Aescin (see escin), 527, 533 Antiacetylcholinesterase activity, 277 Afromosin, 89-91 Antiallergic, 27 Agave, 4, 11 Antiarthritic, 4-6, 208 Agavosides Antibacterial activity, 324, 328, 423 conversion, 310-313 Antibiotics, 535 hypocholesterolemic activity, 312- Antibody response, 168 313,325 Anticancer agents ,1, 12, 99, 109,263, fungicidal activity, 325 289,410 Aglycone distribution from Medicago spp., Antidiabetic response, 101, 198, 208 570 Antifertility, 475,494 AJ[)S, 120,535,416 Antifilarial activity of saponins, 173, 177- AI+3 82-83 178 Alcoholism, treatment with saponin drugs, Antifungal activity of saponins, 207-215, 266-267 233, 286-288, 324-326 Alfalfa, 535 Antifungal compounds, 12, 120, 233-234, herbs, 472 368,416,475,511,535,557,565 juice, 528 extracts of fruit pulp, 425 meal, 528 Antiinflammatory, 1, 4-6,27-28, 173,212- plant resistant to molds, 527 213,240,373,381,402,404,429-430, roots, 472 487,495 saponins with antimycotic activity, 535 Antiedematous, 212 seed, 472 Antileishmanial activity, 415, 420, 423 Alkannin, 430 Antimalarial activity, 392,415,417 Allelopathic activity, 324 Antimicrobial, 111, 251, 415, 420, 423, 475

593 Antimycotic, 535, 544 Avenacin, fungal activity, 548-550 Antioxidative properties, 251, 324, 329, A venacinase 475 determinant of pathogenicity, 552 Antiperspirant, 268, 495 ~-glucosyl hydrolases, 552 Antiphlogistic, 25, 371, 381 gene isolation, 550, 552 Antiprotozoal, 416 Ayurvedic medicine, 357 Antipyretic, 268, 371,381,404 Azoles, 535 Antirheumatic, 4-5 Antiseptic, 429 Bacteroides QY-6 ~-glucosidase Antispasmodic, 268 activity for various saikosaponins, 32 Antithrombotic agents, 511 gene, cloning, 32-33 Antitumor activity, 98, 101, 111, 119,251, localization of, 33 263,285,311,373,402,411,430 transformants of, 33-35 of cholestane glycosides from Bacteriostatic activity (bacterioside), 415, Omithogalum saundersiae, 108-109 521 of clinically used anticancer agents, Banaba, as source of glucose transporter, 109 200-201, 204-205 promoting activities of triterpenoid antidiabetic, 200 glycosides, 87-99 tea leaves, 204 of Solanum species, 263-264, 285 Barbaloin, 26 of steroid saponins from Moldovian Barley seed, 453 plants, 311-312 Bayogenin, 152, 156 of tomatoside modified by oxidation, Baytan, 331 114-116 Benzoylation and naphthylation of sugar water extract of gladiolus corms, 459 moieties, 221-222 inhibitors, 101 Bergenin, 26 Antitussive inhibitors, 101 Beshomosides, 210 Antiulcer, 27 Bilayer lipid membrane, 241 Antiulcer properties, 27, 429 Bioautography for fungicidal saponins, Antiviral activity, 28, 37, 111,402, 505- 120 509 Biochemical characteristics for rats agents, 115 after horse-chestnut saponins chemotherapy, Ill administered, 473 effect, 324 Biosynthesis of steroid glycosides by Human Immunodeficiency Virus Dioscorea cells, 18-21 (HIV), 407 Birinetorenol, 82 in vitro, 407, 505 Bisdesmodic forms stored as in vivo, 505 inactive form, 547 of interferons, 506 Blood coagulation, 524, 525 of steroidal glycosides, 324 Blood ethanol concentration, 208, 210 of tomatoside, 506, 508 Blood hemolysis, 529 of tomatoside modified by oxidation, Bovine hypothalamus, 220, 221 111-112, 114-116 Brasiliensoside, 345 varicella-zoster virus, 407 Broad-spectrum antibiotics, 535, 538 Antiyeast activity, 327 Bronchitis, 429 API mass spectrometer, 127 Buddlejasaponins, 230, 235 Ardisicrenosides, utero-contracting, 494 Bufalin, 219 Arvenin, 486 Bums,429 Aspafiliosides, 234 Butyrosides, 230, 235, 237 Asparagosides, 310, 323, 325 45Ca2+ uptake, 241, 245 Asterogenic acid, 297 Astersaponins, 297, 300, 342, 344 Caffeic acid, 430 Asthma, 429 Calorimetry, 240 Astragalosides, 495 Camelliasaponins, 207, 213-214 Astrasieversianin, 495 Camptothecin, 108 Astringent, 5 Cancer, skin, 2859 Atroposides, 310,476-477,479,482 Cancer chemopreventive agents, 87, 99 Aucubin and degradation products, 26-27 Candidiosis, 535 Capillary-protective properties, 212

594 Capsicosides, 253,310,323,325 Chemotherapy, 425,538 effect on sex ratio in cucumber plants, Chestnut saponins, 530 330 Chikusetsusaponins, 203-204, 209-210 effect on yield of apple trees, 330 Chinenosides, 517-520, 522, 525 13-Carbolines, 383 Chinese traditional medicine, 23, 28, 81, Carbon tetrachloride, 267 91-92,202,207-208,225,371 Cardenolides, 104, 219-220 Chlorambucil, 285 Cardiac glycosides, 108 Chlorogenic acid, 430 Cardioactivity Chlorogenin, 522 dependance on carbonyl group at C-12, Chloromalosides, 228-229, 233, 234 368 Cholegenic and novel bile acids on sugar moiety, 368 Australian opossum, 449 Cardiotonic glycosides, 6, 223,426 Wombats, 449 Cardiovascular diseases, 6, 471 Cholegenic acid methyl ester, 452 Cardiovascular drug Cholegenin 444, 453 adenosine, 524 Cholestane bidesmosides, 105-106 blood coagulation, 524 Cholestane and glycosides, platelet aggregation, 524 rearranged, 103-104 fibrinolysis, 524 Cholestane-type glycosides, 363 steroidal saponins, 524 Cholesterol, 10-11, 19, 49, 53-54, 71, 78 Casein, 453 biosynthetic intermediate, 19 Caulodiac glycosides, 219-223 level of serum, 456 Caulosides, 230, 235, 239, 242 Chronic alcoholics Cardoside C cyanamide,207 cytotoxicity, 240, 243-244 disulfiram, 207 effect on 45Ca2+ uptake, 241, 245-247 Chronic wounds, 429 effect on cell membrane, 241-242, C/D-cis-polyoxypregnane esters and 244-248 glycosides, 410 effect on cell proliferation, 242, 247 cytotoxic, 410 effect on [3H]-CAMP uptake, 241, tumoricidal, 410 246 . Cisplatin, 108 effect on microviscosity of liposomal Cistocardin, 258,361-362,367-368 membranes, 241,244-245 cardioactive, 360 formation of pH-dependent channels, Clofibrate, 207 239-248 Cloning of avenacinase gene 13- hemolytic effect, 240, 242-243 glucosidase, 551 + . K release by cells, 241-243 from bacteriosides JY-6, 32 structure, 239 hydrolysis mechanism of saikosapon- Carotene, 10 in-c, 30 233, 234 Cayenne peppers, 10 Clotrimazole, Cell cultures Co+3, 81,83 Dioscorea spp., 15 Cold, common, 429 Cell proliferation determination, 242, 247 Comfrey, 429 Cellobiose, 549, 552 Commercial utilization of saponins, 1-14 Cell membranes effects of cauloside C, Compartmentalized in plant cell 240 convert plant glycosyl hydrolases, 548 Central nervous system depressant activity, monodesmodic forms, 548 173 Complex with membrane sterols, 547 CER cell cultures, 407 Concavalin, 60 Ceveratrum alkaloids, 103 Consolicin, 430 CF-FAB LC-MS, 124 Consolidin, 430 Chaconine,47,265,278,280,286-289 Constipation, 25 Channels formed by cauloside C, 247-248 Contraceptives, 2-3, 5, 15, 324 Chemical carcinogenesis mechanism, 87, Contusion, 404 99 Conversion of protodioscin Chemical defense agents, 282,338,342 to dioscin, 59 Chemotaxonomic significance of steroid to coprostanol, 444 saponins, 129,229,237 Coronilla plant resistant to molds, 527

595 Corosolic acid, 200-201 Dehydrosoyasaponin, 89,269 Corticosteroids, 15, 426 Delphinidin acid, 430 Cortisone, 426 Deltonin, 233, 234 Q-+3, 83-84 Deltoside, 16-21 Critical micellar concentration (CMC), 170 Deltostim, 21 Crocosmioside, 459-460, 468 Demissine, 281 Crude starfish extracts Demissidine, 78 Cryptococcosis, 538 2-Deoxy-D-glucose (2-DG), 197-199 201- eu+2, 83-84 205 ' Cucumariosides, 340-341, 557, 559-561 5-Deoxyisonodoside, 349-350 desulfated derivative, 557 DEPT,389 Cucumber, effect ofpetuniosides on, 257- pH-Dependency on 259 cauloside C, 239 Cucurbitacin glycosides, 487 Dermatiaceous fungi, 420 Curaderm,285,289 Dermatophytes, 538 Custom-made saponins within plants, 289 infections of hair, nail, and skin 425 ' ' Cuvier's tubules, 340 535 Cyclacoumin, 490, 492 Desacylcamelliasaponin, 213 Cyclamin, 490, 492 Desacylcrocosmioside, 461,465, 468 Cyclaminorin, 490, 492 Desacylescin, 212 Cyclamiretin, 404,491 Desacylmasonoside, 465,468 Cycloartane-type saponins, 273 Desacylsaponin from QS-21, 167-168 Cycloartane-type triterpenoid glycosides, characterization, 167-168 495 lack of antibody stimulation, 168-170 Cyclocanthoside, 495 Desacylsenegasaponin, 214 Cytochalasin B, 196 Desacylsenegin, 214 Cymarose, 410 Designer saponins, 10, 12 Cytoplasmic leakage, 426 Detergents, effects on enzymes, 51-52,54 Cytoprotective effect in the textile industry, 11 carbon tetrachloride-induced hepatic D~toxication mushroom poisons, 371, 381 injury, 208 Dtabetes, 495 Cytosensor®, 415,423 Diaphoretic, 371, 381 Cytostatic activity, 37, 109, 233 Diarrhea, 371 cholestane glycosides with acyl groups, Diazomethane degradation, 189 449 108 Diderroside, 383 ' Cytotoxic T lymphocyte response, 165 Dietary origin, 453 Cytotoxicities, 234, 243, 265 Digitonins, 323, 325 of acylated saponins, 468 Digitoxigenin, digoxigenin, 215-220 of dioscin, protodioscin, and a- 2~,23-Dihydroxyacacic acid, 93 chaconine, 265 Dimethylbenz[ a ]anthracene, 90 of embryos, 240 Dimorphosides, 337 of modified tomatosides, 114 Dioscin, 57, 233, 408 of sea urchin eggs, 240 Dioscine, 57-58, 65, 265, 323 of solamargines and solasodine, 265 2,6-trans-2,6-Dimethyl-8-hydroxyoctane- of spirostane glycosides, 409 2,6-dienoic acid, 174-175 of steroid saponins, 233-234 Dioscorea, 2-4, 10-11,30, 82 D-Cymarose, 410 cell cultures, 15-21 , 2-3, 11, 15-18, 20, 37-39,47- Dammar resin with 54,57,66,82,310,409,443,475,479- from trees and resinous exudates, 144 480 saponins, 95, 129-133, 136, progesterone, 2 peracetate, 481 138-139,141,143-144,147,235,237, Diosgenin glycosidic Disruption of membrane systems 406 and a-solanine, 280 biogenesis, 130, 144-147 a-chaconine Diuranthoside, 228, 229, 233-235 Daturosides, 210 Diuretic, 6, 91, 240, 371, 373, 381, 495 Deacetylmetaplexigenin, 410 5, Diversity of Southwest China for saponins Decaisosides, 230 225 ' Decne,410 Deglucocyclamin dodecaacetate, 491 Drug development pain, 525 Deglucocyclamin, 490, 494 thoracic

596 stenocardia, 525 Escape reaction, 340 heart asthma, 525 Escins, 207, 212-213, 527, 533 Drug permeation enhancement, 170 Esculentoside, 487 N-Docosanoyltyramine, 258, 369 Ethanol absorption, inhibition, 210-215 by methanol extracts of natural Eagle's culture medium, 507 medicines, 208 Echimidine, 430 by saponins, 207-215 Echinocystic acids, 93, 119, 297-298 Eukaryotic organisms, 279 Ecostim®, 332 Exciton-coupled circular dichroism, 221 Eczema, 429 Exogenously added sterols and fatty acids Edema, 371 fungal membrane composition, 532 Effect on isolated guinea-pig atria, 435 Expectorant, 5, 6, 91, 92, 487 Effect on isolated guinea-pig ileum and rat mollusks, 340 uterus, 435 sea anemones, 340 Eggplants, 10 sea urchins, 340 Ehrlich ascites tumor (EAT), 196-197, starfishes, 340 199,201,204-205,244 Extract of Panax notoginseng, 97-99 Ehrlich reagent, 476 Elatosides, 207-210 FAB~S, 189,388,404,459,465,467 Elemental composition of plants FAB MS~S, 189 synthesizing saponins, 83 Fascioliasis, 426 Emetic, 497 Fast atom bombardment (FAB), 123 Emulsification agents, 11 Fatty acid composition Endod, 151, 157, 160-161 saponin-sensitive, 531 Endod plant, 118, 426 nonsensitive trichoderma strains, 532 berries, 161 Fatty acid domain of QS-21, 166-171 endod S, 153 fu+3, 81,83-84 molluscicidal saponins, 151 Feeding furostanol saponins pericarp, 153 dogs, fecal excretion, 444 seeds, 153 epi-srnilagenin, 444 Enzymes epi-sarsapogenin, 444 activity as a-rhamnosidases and ~- srnilagenin, 444 glucosidases diosgenin, 444 of bacteria, 31 gitogenin, 444 commercial, 31 , 66 Feeding-deterrent properties, 342 crude hesperidinase, 463-464 Fermentation, 3 glycosylation oftomatidine, 71-79 Fever, 383 of higher plants, 30 Fibrinolysis, 524, 525 of hydrolysis, 34, 450 Fire extinguisher, 11 of mushrooms, 31, 35 Fish poisons, 431 naringinase, 461, 464 Fish test, 529 Eosin, 242 Flavor agent, 4, 5 3-Epidigitoxigenin, 220 Flavor-modifying substances, 1 Epiosarsapogenin, 444 Fluconazole, 233-234 Epi-smilagenin, 444 Foaming agent ~-D-g1ucuronide, 443 baked goods, 185 Epstein-Barr virus, 87-89, 93-96 beverages, 185 Ergosterol, 532-534 confectionery, 185 fatty acid composition, 533 dairy desserts, 185 without saponin, 530 Foetidissimoside, 299-301 with saponin, 530 Food and beverage plants containing Eruboside, 521 saponins, 8-10 Erylosides, 336 Formononetin, 81 Erythrocyte K + Forskolin, 196-198, 204 loss of, 559 Fouling, 336, 342 dependence on the sulfate group in the Fragmentation product of carbohydrate chain, 559 elucidated sugar sequences, 127 presence of the 3- 0-methyl group in a Froth forming, 101 terminal monosaccharide required, Fruit extract of S. japonica, 501 559 Fructose, 107

597 Fungicidal activity, 21, 37, 111, 117, 120, inhibitors of acetylcholinesterase, 281 251,281,415,475,487,527,529-530, role in chemical defense, 282-283 565 structures, 278 plant pathogens, 535 synergistic interactions, 286-289 human dermatophytes, 535 toxicity, 279-282, 284 medically important yeasts, 535 Glycosidases, 348, 402 Funkiosides, 210,233,234,315,316 Glycosidases converting natural glycosides Furostanol glycosides to bioactive compounds, 23-35 26-0-acylated, 102 Glycyrrhiza, 82 biological activity, 21 Glycyrrhetic acid, 82, 89-90, 94, 96-97 biosythesis, 20 Glycyrrhizin, 407 conversion to spirostanol glycosides, glycyrrhetyl monoglucuronide, 312 g1ycyrrhetic acid, 27-28 from various plants, 314,316,321 Gomophioside, 349-350 26-0-~-glucosidases (E-26G) Gracillin, 57-59, 66, 330,409 assay, 59 Granulatoside, 349-350 occurrence, 60-61 Green peppers, 10 properties, 60-61, 66-68 Growth-enhancing ability of plants purification, 61-63 petuniosides, 257-259, 261 specificity, 64-66 Growth inhibitor of rice, 272 substrate specificity, 64, 65 Growth inhibition of a diatom, 336 N-terminal amino acid sequence, 63-64 Guinea pigs tetraglycosides, 409 curing skin lesions in, 535 Gum tragacanth Garlic, 520 foodstuff, 495 Gastrointestinal absorption pharmaceutical emulsifier, 495 inhibition, 10 Gymnocladus saponins, 92-94 Gastrointestinal indigestion, 25 Gypanoside, 131 GenBank, 552 Gypsogenin, 191 Gene disruption, 551 Gypsogenic acid, 191 Geniposide and relatives, 27 Ginseng, 225 Halityloside, 349-350 extract, effect on 2-DG uptake, 202 Haikomari's method, 460 saponins, 205 Heart ailments varieties, 202 Chinese medicine, 107 Ginseng extract, 207 Heart asthma, 517 Ginseng root, 472 Hecogenin,39,42,313,323,330 Ginsenosides, 95-97, 130-133, 135, 146, , 120, 152, 156, 210, 237, 432, 202-205,232-233,235,237 528,565,568,571 Gi taloxigenin, 219-220 glycosides, 211, 240 Gitogenin, 252-254,255-256, 310,323, hemolytic and fungistatic glycosides, 325,44 571,573 Gleditsia saponins, 92-94 Heinsiagenin, 374 Glucose transport systems, 195-205 HeLA cells, 407 inhibitors, 196 Helojaposide, 272 location, 195 Hematological examinations for horse ~-Glucosidases, 23 chestnut saponins, 472 converter furostanol glycosides to Hematopoesis, 114 spirostanol glycosides, 57 Hemolysis and rate of K+, 561 Glucosylrheinanthrone, rheinanthrone, Hemolytic activity, 101, 115, 160-162, rhein, 25-26 170-171,240,340,382,538,557,559, ~-D-Glucuronides 565-573 hepatic formation, 444 Hemorrhoids 429 GLUT family, 195 Hemostatic drug, 94 Glycoalkaloids, steroid, 10, 47, 54, 277- Hemsloside-Ma3, 131 289 Hepatic hydroxylation, 457 consequencesforhumans,284-285 Hepatitis, 94 mechanism, 279-281 Hepatoprotective action, 28 symptoms, 280 Herbal medicinal products, 3-7, 485 create 'pores' in membranes, 280 Hexadecanoic acid, 531

598 HL-60 cells Immunodeficency syndrome (AIDS), 416 inhibiting activity of acylated saponins, Immunological adjuvant, 165 468 Immunological assays, 167 Holostane, 339 Immunomodulatory action, 21, 28 Holothurin, 339 sea cucumber glycosides, 340 Home and garden fungicidal applications, Immunopromotive, 382 12 Immunosuppressive drugs in transplant 22-Homo-23-norcholestane skeleton, 22- patients, 535 homo-23-norlanostane skeleton, 104 mycoses, 538 Homologous recombination, 552 In vitro antimalarial test, 388 Hormones, 2 In vitro culture of C. speciosus, 59-68 Homoorientin, 26 Indicoside, 349-350 Horse-chestnut saponins, 472, 530 Indolepyridines, 383 HPLC, Induced hypercholesterolemia, 472 coupled with mass spectral analysis, Inducing immune interferon ,487 117 Infectious hepatitis, 267 for analysis of saponins, 121-122, 225- Infertility, 489 226 Inflammatory agent, 404 for cell cultures, 18 Inhibition profiles of derivatives of ouabain, butyrosides, 237 OLC, and HIP, 222-223 mimengoside A, 237 Human basophils, 25 of cAMP phosphodiesterase, 101 Human blood platelet aggregation, 513- motility of human spermatozoa, 237 517 replication of some DNA and RNA Human inflammatory fungal infections, viruses in vitro, 407 538 settlement of larvae barnacles and Human interferons, 505 bryozoans, 342 Human platelet aggregation, 513 triplosides B, 237 Human promyelocytic leukemia HL-60 Inotropic cardioactivity effect, 357, 367- cells, 108 368 Human spermatozoa, 235, 236 Inotropic drugs, 107 Human vaccines, 186 Insecticidal agent, 373, 381, 383 Hydrolysis with NaHC03 Interferon-inducing activity, 408 masonoside A, 468 Interferons, 505, 508 Hydroxycholegenic acid, 447 antiviral activity, 506 Hydroxycholegenin, 447 Intestinal flora, 444 2a-Hydroxy-heinsiagenin, 374 Ion permeability of mycelia (S)-3-Hydroxy-3-methylglutaryl (HMG) Trichoderma strains, 531 group, 101-102 Iridoid glycosides, 26-27 Hydroxy protobassic acid, 237 Ischemic heart diseases 5'-(Hydroxysulfonyloxy)jasmonic acid, Hungarian population, 471 358,362,369 Isocholegenin, 38-45, 444, 453 2~-Hydroxyoleanolic acid, 152, 156 Isocyclamin, 490, 492-493 Hypercholesterolemia, 1, 313, 320, 472 Isoeruboside, 521-522 Hyperplasia of liver blood ocagulation inhibitory effect, 525 in mice, 98 firinolysis-promoting effect, 525 Hyperplastic nodules, 99 Isonodoside, 349-350 Hypertension, 220 Isonuatigenin, 39, 42, 445 Hypocholesterolemic activity, 4-6, 10, 37, 323 Hypotensive effects, 431, 440, 495 Jaundice, 25 leontoside-A, 435a Jones' oxidation reagent, 449, 455-456 symphytoxide-A, 435a Julibrosides, 271-272,274 Hypothalamic inhibitory factor, 220 Kampferol acid, 430 Ichthyotoxicity, 340 Kaikasaponins, 266, 269 Ilwensisaponin, 486 Kalopanax saponin, 230 Immune stimulating, 1 Kampferol-3-sulfate, 200-201 Immunization studies, 167 KB cells Immunoadjuvant properties, 185 inhibitory activity of acylated saponins, Immunocytochemical studies, 68 468

599 Ketoconazole, 418, 425 Majonoside-R2, 130-131, 133, 138, 143 Kidney diseases, 429 Malaria, 416 Kingianosides, 233 people attacked annually, 383 Killing kinetics Malignant neoplasms leakage of potassium, 544 cholesterol reduction, 475 leakage of magnesium, 544 Malignant tumor cells, 109 phosphate ions, 544 Malvidin acid, 430 Koryoginsenosides, 233 Mammalian erythrocytes, 286 Kudzusaponins, 269,270 Mangiferin, 26 Kurilosides, 340-341 Marsupials, bile, 445 Kuroyurinidine, 103 Marthasterosides, 343-344 , 200-201 Lachrymal glands, 382 Masonoside, 466 Laryngopharyngitis, 371 Mass spectrometry (MS), 124, 157, 387 Lasiocapine, 430 chemical ionization (NH3), 363 Laxative, 25 mono- or bidesmosidic structure, 363 Laxogenin, 517,521 Mass spectral (MS) interfaces, 122-123 Laxoside, 522 comparisons of methods, 123-124 blood coagulation, 525 Mass spectrometry for structural studies, Lectins, 264 157, 298, 302-303 Leishmania species/strains, 421 Mechanism of action Leishmaniasis, 416 antisera recognised, 553 Leontoside, 230,235,429,431,435 anti-avenacinase, 553 hederagenin 429 tomatinase, 553 Leptine, 281, 286 Medicagenic acid, 120, 528, 535-536, 565, Leucocytosis, 114 568 Leukemia, 495 hemolytic and fungistatic, 573 Licorice, 225 Medicago spp. for commercial Life cycle of Schistosoma, 118 development, 573 Liliaceous plants, species containing Medicinal plants steroid saponins 226, 227 medical uses, 230 medical uses, 226-227 as sources of triterpenoid saponins, Lilioglycosides, 310, 317-318 229-230 Linoleic acid, 430, 531 Melanoma, 285 Liposome, 240, 280 Melilotosides, 310 Liquid chromatography-mass spectrometry Melongosides, 38,310,319,330 (LC-MS), 121-122 Membranes, 241-248,280-281 comparison of methods, 124-125 Membrane-lytic properties, 277 Lithium aluminum hydride reduction, 452 Menstrual disorders, 494 Lithospermic acid, 430 Metabolites of nuatigenin, 454 Livers Methotrexate, 108 triglycerides, 472 Methyl a-linolenate, 207 cholesterol, 472 Methyl polygalactate, 468 Livestock feed and forage plants and Methylallyl trisulfide, 512 crops, 10 Methylation of atroposides, 482 Longevity, ginseng aids, 202 Metropolis Monte Carlo method, 105 Low-saponin alfalfa Miconazole, 418, 425 breeding of cultivars, 529 Microencapsulation, 11 Lowering effect in plasma, 185 Microviscosity, 241, 244 Lycopsamine/intermedine Mimengosides, 230, 235, 237 (diastereoisomers), 430 Mirabilin, 490,494 Lysis, 547 Mirabilin lactone, 490, 494 Mirabilin methyl ester, 490 Mitomycin, 108 Macrophase-phagocyte liposomal system, Mn+2, 83-84 543 Moldstim®-type and Pavstim®-type liposomal G2, 543 saponins, 112-113, 331-332 Macrophyllogenin, 498 Molecular dynamics Macrophyllosaponin, 496, 498 computations, 105-106 Macrostemonoside, 513-516,522,525 Molluscicidal activity, 117, 160-161,285, Maize, 453 415,426,487

600 extracts of fruit pulp, 425 BC-NMR spectra, 174, 180, 182, 189, Molluscicidal potency test, 425 201,252-253,410-411,431-432, Molluscicidal saponins, 118-119, 125, 434,438,452,461,463-465,467- 151-154, 160-162 468,475 Monodesmodic formation, 548 2D-NMR, 388, 402, 410 Mosaic virus, 326 lH NMR, 189, 351,360, 362-363, Mosesins, 338 365,404,410-411,431,434,438, Mold cell chemical composition, 531 459, 464-465, 467 MS-III, 211 lH-lH DQF COSY, 138,305,374 MS/MS, 127 Refocused INEPT Be, 160 Muricins, 337 Murine cryptococcosis, 535 ROED lH, 303-304 among AIDS patients, 541 ROESY lH, 254, 374, 404-405,480 Mussaendosides, 375-376, 382 of sugar moieties, 135, 138 Myristic acid, 531 NMR coupling constants, 137, 139, 142- 143,253-254,256,298,303,305-306 Nodososides cytotoxicity from starfish, N aringinase, 221 342-343 Natural detergents, 431 Nonoxynol-9, 234 Naucledal, 383 Norlanostane, 335 Necic acid 430 Notoginsenosides, 130, 138, 233 Necine, 430 Nuatigenin, 37, 39,445 Nematocide activity, 21, 282 Nystatin, 233, 234, 544 Neochlorogenin, 522 Neogitogenin, 368-369 Oat pathogenic, 548 Neoglycolipid synthesis, 274 Oat seeds and sprouts, 453 Neohecogenin, 229, 358, 368-369 Octillol-type saponins, 130, 133, 136, 138, (25S)-Neospirost-4-en-3-one, 366 143, 146-147 Neotigogenin, 229, 310,358,367-369 Oleanane saponins, 229-230, 235-236, 271 Nephritis, 495 Oleandrose, 410 Neurological-type toxicity, 291 Oleanen-28-oic acid, 208-210, 271 Nicaphipalin, 266 , 82, 119-120, 131, 133, Nicaphysalins, 266 152-153,156,202,208-209,297-298, Nicotianosides, 312 430,565,568 4-Nitroquinoline N-oxide, 98 desmosides, 208, 236 N-Nitrosodiethylamine, 98 Oleanolic glycosides, 403 NMR, use in structure studies, 157, 233, inhibitory effect against VSV, 407 302,304 Oleic acid, 531 of aglycone moieties, 134 Ononin, 89 COLOC, 410-411 Oomycete fungi, 548 COSY, 158,388,404,410-411,432, Ophydianosides, 342 452,461,463,480,497 Opportunistic pathogens of humans, 425 COSY and TOCSY, 137, 150, 158, Oral contraceptives, 2, 426 233,254,305,374,463,468 Oreasterosides, 351 HETCOR, 404,410-411 Ouabagenin, 219-220, 223 HOHAHA, 404, 411 Ouabain "OLC", "HIF", 220-222 HMBC, 374, 388,433,498,516 Ouabain-like compound, 220 HMQC, 374, 388 Ouabain pentanaphthoate, 222 ID lH, ID proton-decoupled Be, 158 OVA, antibodies to, 167-170 Ovarian cancer, 285 J-resolved lH, NOESY lH, 158, 235 Ovulation process, 2, 21, 251 NOE, 302-303,305 Oxoquinovic acid, 385, 392-393 NOEs and lH-BC long-range correlations, 141, 159, 233, 363, Pachastrellosides, 336 365,376,402,405 inhibition cell division of fertilized NOESY, 159, 233, 374 starfish eggs, 335 13C-NMR, 362-363, 374, 389, 401, Paeoniflorin, paeoninmetabolins, 24 404 Palmitic acid, 461 l3C-NMR chemical shift 20(S)-Panaxadiol, 140, 147

601 Panax:ynol, 96 Polygonatosides, 310, 329 Panax:ytriol, 95-96, 147 Polyhydroxypregnane derivatives, 412 Papaverine, 107 Polisaponin, 323 Papillary muscle Potato Y -virus, 326 guinea pigs, 367 Potato glycoalkaloids, 281, 284 Papillomas, 91, 93-94, 97 Potatoes, 10 Pardanosides, Pratioside, 233, 234 see 26-0-Acylated furostanol Pregnane17 (20)-ene-type , 369 saponins Pregnane-type glycosides, 363 Partial hydrolysis of atroposides, 482 Presenegenin, 214, 215 Patiriosides, 343-344 Primacrosaponin, 487, 488 Pavstim®, 332 Primulasaponin, 487, 488 Pavonins, 338 Priverogenin, 489 Pectiniosides, 345, 347-348 Priverosaponin, 487, 488 Peliosanthosides, 228 Priverosaponin B-monoacetate, 487 Penaustrosides, 340-341 Proacaciasides, 174-175 Pentanaphthoate, 222 isolation, 178-179 Peripheral vascular disorders, 212 permethylation and hydrolysis, 179, Periplogenin, 220 181 Permethylation of desacylcrocosmioside, properties, 178-180 462 Progenins from petuniosides, 252, 256, Persicanidine A, 103 260 Pesticides, 289, 309 Promastigotes, 421 Petuniosides, 251-261, 266, 310,480 Prophylactic effects, 407 determination of structure, 252-257 chronic viral hepatitis, 407 hydrolysis, 260 Prosaikogenin, 9, 29, 35 methylation, 260 Prosapogenin, 191,361,461,463 purification and properties, 259-260 Prosapogenin of butyroside, 235 sugar components, 252-257 Prosapogenin of diocin, 233-235 Pharmacological activity of dammarane Prosapogenol,347 triterpenoids, 129 Protein concentrates, alfalfa, 528 Phaseoside, 219, 269 Protobassic acid saponins, 121, 237 Phenobarbital, 98 Protobioside, 16-20 Phospholipids, effect on glycosy lation, 51, Protodescigenin, 82 54 Protodigitonin, 325 Photoeruboside, 521 Protodioscin, 16-18-21, 57, 64-65, 265 Photographic chemicals and emulsions, 11 Protoeruboside, 521 Photoisoeruboside, 521-522 Protogracillin, 57, 64-66 fibrinolysis, 525 Protoisoeruboside, 522 Photosensitization Protopanax:adiol, 57, 82, 130, 144, 202, hepatic dysfunction, 443 205 kleingrass, 443 Protopanax:atriols, 130-131, 133, 136, 139- lambs, 443 140,144-145,147,202,205 Phytoalexins, 547 20(S)-Protopanax:atriol oxides, 136, 140- Phytoanticipin, 547 144 Phytolaccasaponin, 487 Protopolygonatoside, 329, 330 Phytopathogenic fungi, 324 Protoprimulagenin and relatives, 120-121, Phytosterols, 74 488-489 Pinitol, 358, 362-363 Protozoan infections Pisasteroside, 349-350 immunodeficiency syndrome (AIDS), Piscicidal activity, 160 416 Plant glycosyl hydrolases immunosuppressed patients, 416 bidesmodic and monodesmodic forms, morbidity, 416 548 mortality, 416 Plant pathogens, 536-543, 547-553 Psolusosides, 340, 341, 559 Plasmid, 33-35 desulfated derivative, 557 Platelet aggregation, 101, 524 Pulsatilosides, 230, 235, 237 assay, 522 Purpureagitoside, 210, 325, 329 Polyclonal antibody, 68 Polygalacic acid 3-0-vicianoside, 463 QS-ill structure, 186-187

602 QS-21, an acylated glycoside Saponins deacylation and fatty acid domain, as fungicides, 120 166-170 as molluscicides, 118-119, 125, 151- stimulation of cytotoxic and 154, 160-162 lypmphocyte response, 165, 171 of P. dodecandra, 125-127 structure, 166-168 Saponin-containing herbs, 7 Quercetin, 25 Saponin-detoxifying enzymes, 548 Quillaic acid, 191 pathogens of oat and tomato, 553 Quillaja saponins, 185-192 Saponin Network molecular structure, 186-192 Mass Spectrometry, 575 aglycones of, 191 Nuclear Magnetic Resonance by cleavage and analysis of Spectrometry, 575 products, 188-192 Saponinases, 548 reported, 186-188 Sarasinosides, 211,335-336 Quil A and QS-21 fractions, 185-186 Sarcosine, 410-411 Quinovic acid, 385, 393 , 37, 39,41-42,310,323, Quinovic acid, 3-0-a-lr 443 rhamnopyranoside, 392 Sativoside, 521 Quinovic acid, 3-0-glycosides, 383, 385 Scaberoside, 298 Quinovic acid glycosides, 383 Scaberoside methyl esters inhibitory effect against VSV, 407 determination of structure, 298 Quinquenosides, 130 NMR data, 298 Quinquina, 383 mass spectra, 298 Quis, 345 isolation, 299 structures, 300-301, 306 Rabbits, 445 Schistosomes in the bladder or intestines, Radiorespirometry, 415 118 Raji cells, 88-90, 93, 95-96 Schistosome, schistosomiasis, 118-119, RAM drug test procedure, 416, 420-421 151, 153-155, 161,285 Recombinant analysis, 552-553 Sclerotium rolfsii from snails, 118, 119, Recurvosides, 106-107 161 Reductive cleavage of permethylated insoluble complexes with sterols, 536 acaciaside C, 181 high cholesterol, 536 Red ginseng, 94 lower cholesterol, 536 K+ release, 241 Screening of plant extracts for GT uptake, Renal sodium excretion, 220 198-199 Resistance of alfalfa cotyledons to molds, Sea cucumbers, 335, 339, 557 529 Secoiridoids, 383 Resistance to saponin action, 548 Sedative effect, 6, 495 Respiratory tract infections, 494 Senegae radix, 214-215 Restriction map, 34 effect on ethanol absorption, 214 Reverse genetics approach, 550 Senegasaponins, 207, 214-215 a-Rhamnosidase, 31 Senegines, 214-215 Rhein, 26 Sennoside A and degradation products, 25- Rheinanthrone, 26 26 Rheumatic arthritis, 404, 431 Sepositosides, 343 Rheumatic diseases, 431 Sex hormones, 15,426 Rhinovirus type, 407 Sex ratio shifts in cucumbers, 330 Robinioside E, 269 Shampoo liquids, 11 Rockogenin, rockosides, 323, 325 Shark antifeedant, 339 Robinioside, 269 Shark-repellent secretions and Rosmarinic acid, 430 peptidic pardaxins, 338 Rumen content, 444 steroid glycosides, mosesins, 338 Rutin, 24-25 pavonins, 338 Shark's olfactory sense, 339 Sheep erythrocytes, 196-197, 202, 204 Saikosaponins, 28-32, 35, 237 effect of ginseng, 202 Salivary glands, 382 Shikonin, 430 Sanchi ginseng, 129 Shionane, 297 Sapindosides, 211 Shoot tip cultures, 57

603 Sister Chromatid Exchange, I 54 spermicidal activity, 239, 330 Sitosterol, 75, 78, 430 spirostanes and furostanes, 228 ~-Sitosteryl, 3-0- ~-D-glucopyranoside, stimulating action on plants, 251 I30 Steroidal saponins in food and beverage Skin cancer, 285 plants, 8 Smilagenin, 39, 4I-42, 433,52 I Steroidal saponins, botanical sources, II Soap substitute, II8 Sterol binding by glycoalkaloids, 28I ~-Solamargine, 285 Sterol metabolism by demethylases, 28I Solamarines, solamargine, 285-286, 289 Stenocardia, 517 Solanaceous plants, Stichlorosides, 339 antitumor activity, 263-264 Stichopodidae, 340 chemical constituents, 263-264 Stigmasterol, 430 Solanidane, 47-52, 278 Stimulant beverage, 6 Solanidine, 47-52, 7I, 78-79,286 Stipuleanoside R, 209-210 Solanine, 47-52, 28I, 286 Stomach ache, 202, 213, 273 Solanine/chaconine, 28I Streptomycin, 425 Solasonine/solamargine, 28I Strophanthidin, 2I9-220 Solaplumbin, 285 Structure-activity relationship Solasodine, 47-52, 7I, 78,265,285-286 antitumor activity, 4I3 Solamins,278,280,286,289 dendrochirotid a order, 557-563 Sophoraflavosides, 269 ethanol absorption, 210-2I5 Sophorose, 549 glycosides of medicagenic acid, 407, ~-Sophorosyl moiety, 136 535 Southern blot analysis, 552-553 protopanaxatriol, 205 Soyasapogenol B substituted, 502 quinoic acid derivatives, 403 Soyasapogenols, 565, 568 spermicidal activity, 234-237 Soyasaponins, 268-270, 502-503 Subprosides, 269 Spawning inhibitors, 340 Sulfated digitogenin, 330 Spermicidal activity, 2I, 330 Sulfated neotigogenin trioside, 330 of steroid saponins, 234-235, 239 Sunflower oil, 533 of triterpenoid saponins, 235-236 Surface activity, 170-17I Spinasaponins, 209-210 Surfactant, I2 Spiroconazole, 4I5, 4I7-4I8, 425-427 Suspension stabilizer in pharmacuetical Spirostane glycosides, 409 additive, I85 Spirostanol biosynthesis, 44 Suspension cultures of Dioscorea Spirostanol saponins deltoidea cells, 15-2I biosynthesis 37-45 Symphitine, 430 formation from furostanol glycosides, Symphytocynoglossin, 420 57, IOI, 312 Symphytoxide, 429-43I, 436-439 from various plants, 313-315, 317, Synergistic interactions 319-320,322 chaconine/solamargine, 286 polyhydroxylated, 106, 107 detoxification mechanisms of with an HMG group, 10I-102 pathogens or predators, 287 Starfishes, 335, 339 solanine/chaconine, 296 Steamed ginseng, 94 solasonine/solamargine, 286 Stearic acid, 531 significance to man, 287-289 Steroid glycosides in bacterial tests, 328 Synthetic medicagenic acid glycosides Steroid glycosides as bioregulators, 331 treatment of fungal infections, 543 Steroid hormones, I,2 Synthetic molluscicides, 151 Steroid , precursors of drugs and hormones, 2 Tannin, 20I structure and biosynthesis, 43-45 Tarasaponin, 209 Steroidal glycosides Taxol, I08 antifungal activity, 233-234 Taxonomic relationship, I38, 229, 277 cytotoxicity, 233-234 Tenuifolin, 214-215 isolation from plants, 3II N-Tetracosanoyltyramine, 358 of Allium chinensis, 107 -I 08 I2- 0-Tetradecanoylphorbol-13-acetate, of lilaceous plants, medical uses, 87-88, 90-91, 93-97 isolated ones, and structures thereof, 3a,5a-Tetrahydrodesoxycordifoline, 392, 226-228, 3I8 393

604 Tenuispinosides, 343, 344 Trichoderma strains Termination early pregnancy, 371, 381 growth inhibition, 569 Thalictoside, 273 ion permeability, 531, 532 Therapeutic effects on viral hepatitis, 407 nonsensitive, 530, 534 Thermal burn, 25 resistant to saponins, 534 Thermotropic behavior of liposomes, 244, sensitive, 530, 534 246 Trichophyton mentagrophytes Thoracic pain, 525 long life, 535 Thornasterol, 344 C.neoformans,535 Thornasterosides, 343, 344 liposomes, 535 Thrombosis Trichophyton soudanense, 425 cure effect from saponins from Allium Trigonellosides, 310 plants, 522 Trilline, 323 Tigogenins, 39,41-42,47,252,255-256, Triplosides, 230-232, 235, 237 325,475,479,517,521 Triterpene saponins Tigogenin glucogalactopyranoside, 479 in food and beverage plants, 9, 12 Tigogenin glycosidic peracetate, 481 of Scilla pervians, 107-108 Tigogenin monoside, 479 spermicidal activity, 235 Tigogenin trioside, 479 structures, 229-232 Tomatidine, 47-48 Triterpenoid acids of glycosylation, 71-79 dietary origin, 453 a-Tomatine, 71-72,281,283,285,323, Triton X-100, 51-52,74,76 325,549,550,553 Tuberculosis, 429 molecular complex with 3f3-hydroxy Tuberosides, 310, 320-321 , 279 Tubocaposide B, 266 role in plant self-defense, 71 Tumor necrosis factor, 487 tomato pathogens detoxification, 552 Two-stage carcinogenesis test, 90, 94, 97 Tomatinases hydrolysus sugar molecules, 553 UDP-galactose, UDP-glucose, 71-78 Tomato, 10, 548 UDP-galactose: tomatidine Tomato bronzetop, 326 galactosy ltransferases Tomatoside saponins, 112-116, 310, 323, activity, 74, 79 325,330 assay, 73 antiviral activity, 505-508 molecular weight, 73 modified biological effects, 114-116 purification, 72-73, 76-77 Tonic,4,5,6,202,208 specificity, 78 Toxicity UDP-glucose: diosgenin/solasodine antiprotozoal drugs, 416 glucosyltransferases, 47-54 complex with membrane sterols, 547 assay for, 49 glycoalkaloids, 279, 284 occurrence, 48 humans, 279, 284 molecular weight 49 potatoes, 284 phospholipids, 53 sapogenols, 456 purification, 52 starfishes, 340 UDP-glucose: diosgenin/tigogenin Traditional medicine, 401, 415 glucosyltransferases, 37-45 Brazilian, 402 assay for, 38-39 Peruvian, 402 occurrence, 39 percent of the population using, 383 properties, 42-43, 47-51, 54 developing countries, 383 purification, 38-42 Transglycosylation, 274-275 specificity, 41-42 Tremasterols, 350 UDP-glucuronic acid, 77-78 Tribulosides, 310 Ulcers, 431 Tribulosin, 358, 360-363, 367-369 Ursane, 205 Tribulus toxicity Uterine cancer, 495 bladder, 357 Utero-contracting saponins kidney, 357 ardisicrenosides, 494 leaf extract, 367 Uzarigenin, 220 malaria, 357 sheep toxicity, 357 Varicella-zoster virus, 263

605 Vegetarians pathogens, 548 European and Asiatic countries, 472 White ginseng, 94 Vesicular stomatitis virus, 407 Wistariasaponins, 89, 269 Veterinary vaccines Wistin, 89 anti parasite vaccines for malaria, Wrinkles, 429 babesiosis, and trypanosomiasis, 185 Wound-healing activities, 4, 430-431,495 foot-and-mouth disease, 185 Vietnamese ginseng, 129 Xiebai, drugs use, 512 discovery and distribution, 129-130 saponins , 37, 39,41-42,45,310,433 extraction, 130 Yeast, 538 structure, 133-136 Yield of saponin from Dracaena spp for varieties, 130-132 commerce, 426 Vina-ginsenosides, 131-133, 136, 138, Yucca,4, 11 139, 142, 144, 147 Yuccosides, 310, 322 Vinblastine, 285 Vincristine, 108 Zanhic acid, 565, 568 Virucidal effects, 251 Zimbabwean-Danish project Virus-infected cells, 410 agronomic investigations, 154 Vulpecholic acid, 449 biological activities, 160 chemical and analytical investigations, Walker tumor, 115 155 Warts,285 structure elucidation, 157 Western blot analysis, 68 Zingibroside R 1, 204 Wheat Zn+2, 83-84

606