appendix saponin network for mass spectrometry …978-1-4899-1367-8/1.pdf · appendix saponin...

APPENDIX

SAPONIN NETWORK FOR MASS SPECTROMETRY AND NUCLEAR MAGNETIC RESONANCE SPECTROMETRY

The saponin 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 saponins 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 biomolecules, such as proteins and peptides by BioMagResBankl, or complex carbohydrates by

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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 classor 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. JCAMPDX 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 tagvalue 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).

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CONTRffiUTORS

H. Achenbach Institut fur Pharmazie und Lebensmittelchernie

der Friedrich-Alexander-Universitat Department of Pharmaceutical Chemistry D-91052 Erlangen SchuhstraBe 19 GERMANY

Khalid Aftab H.E.J. Institute of Chemistry University of Karachi Karachi 75270 PAKISTAN

Irina G. Agafonova Pacific Institute of Bioorganic

Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA

Suresht K. Aggarval College of Pharmacy University of Kentucky Lexington, KY 40536

Viqar Uddin Ahmad H.E.J. Institute of Chemistry University of Karachi Karachi 75270 PAKISTAN

Dmitry L. Aminin Pacific Institute of Bioorganic


Michail M. Anisimov Pacific Institute of Bioorganic


Magda Antal Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY

A. Aquino Dipartimento di Chimica delle Sostanze

Naturali via D.Montesano 49 Napoli 801211TALY

Y oshihisa Asada School of Pharmaceutical Sciences Kitasato University 5-9-1, Shirokane, Minato-ku Tokyo 108 JAPAN

Sergey A. A vilov Pacific Institute of Bioorganic


Manuel Balandrin NPS Pharmaceuticals, Inc. University Research Park Salt Lake City, UT 84108

Guy Balansard Laboratoire de Pharrnacognosie Faculte de Pharnacie Universite d'Aizmarseille II 27 Bd J. Moulin 13385 Marseille Cedex FRANCE

Perry Barboza University of New England Armidale, N.S.W. AUSTRALIA

NinaBerova Department of Chemistry Columbia University New York, NY 10027

Lojos Biro Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition 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 National Practical Science Center of Hygiene and

Epidemiology of the Health Ministry of the Moldova Republic

N. Testemitianu Chisinau State Medical University Chisinau 2002 MOLD A VIA

Paul Bowyer The Sainsbury Laboratory Norwich Research Park Colney Norwich NR4 7UH UNITED KINGDOM

G.N. Busuk Vitebsk Medical Institute Belorussia RUSSIA

I. Calis Department of Pharmacognosy Faculty of Pharmacy Hacettepe University Ankara TR-06100 TURKEY

V.Ya. Chirva Department of Organic Chemistry Simferopol State University Taltinskaya Str. 4 Simferopol, Crimea 333036 UKRAINE

Claus Cornett Royal Danish School of Pharmacy Department of Medicinal Chemistry Universitetparken 2, DK-2100 Copenhagen DENMARK

Michael J. Daniels The Sainsbury Laboratory Norwich Research Park Colney Norwich NR4 7UH UNITED KINGDOM

G.A. Drozd Department of Organic Chemistry Simferopol State University Taltinskaya Str. 4 Simferopol, Crimea 333036 UKRAINE

Olga A. Drozdova Pacific Institute of Bioorganic


580

Nguyen Minh Due Science-Production Union of Ginseng and

Medicinal Plants Ho Chi Minh City University of Medicine

and Pharmacy 41 Dinh Tien Hoang Street, District 1 Ho Chi Minh City, VIETNAM

Earnest Dworshak Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY

Y. Ebizuka Faculty of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113 JAPAN

Robert Faure URA1411 University Aix-Marseille III A v. Escadrille Normandi-Niemen 13997 Marseille Cedex 13 FRANCE

Tsutomu Furuya Faculty of Science Okayarna University of Science Okayarna 700 JAPAN

Odon Gaa! Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY

Monique Gasquet Laboratoire de Parasitology Faculte de Pharnacie Universite d'Aizmarseille II 27 Bd I. Moulin 13385 Marseille Cedex FRANCE

Sergey N. Gnedoi Pacific Institute of Bioorganic


Jack P. Goodman College of Pharmacy University of Kentucky Lexington, KY 40536

L.A. Gorbacheva Department of Organic Chemistry Sirnferopol State University Taltinskaya Str. 4 Sirnferopol, Crimea 333036 UKRAINE

V.I. Grishkovets Department of Organic Chemistry Sirnferopol State University Taltinskaya Str. 4 Sirnferopol, Crimea 333036 UKRAINE

Katalin Gruiz Technical University of Budapest Agricultural Chemical Technology H-1521, Budapest Szt. Gellert er 4 HUNGARY

T. Grushko National Practical Science Center of Hygiene and



Garner T. Haupert, Jr. Department of Chemistry Columbia University New York, NY 10027

Kurt Hostettmann Institut de Pharmacognosie et Phytochimie Universite De Lausanne BEP, CH-1015 Lausanne-Dorigny SWITZERLAND

Harald Hiibner Institut fur Pharmazie und Lebensmittelchemie


Kentaro Inoue Faculty of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113 JAPAN

M. lorizzi Department of Natural Products University of Naples Naples 80131 ITALY

Aiko Ito Institute of Pharmaceutical Sciences Hirostirna Univesity School of Medicine 1-2-3- Kasumi, Minarni-ku Hirostirna 734 JAPAN

D. lurea Institute of Biological Research Blvd. Copou 20A Iassy 6600 ROMANIA

M.M.Iwu Walter Reed Institute of Research Division of Experimental Therapeutics Walter Reed Medical Center Washington, DC 20307-5100

J.E. Jackson Walter Reed Institute of Research Division of Experimental Therapeutics Walter Reed Medical Center Washington, DC 20307-5100

Marian L. Jurzysta Department of Biochemistry Institute of Soil Science & Plant Cultivation Pulawy 24-1000 POLAND

Vladimir I. Kalinin Pacific Institute of Bioorganic


Molgorzata Kalinowska Department of Biochemistry Warsaw University 02-089 Warszawa ul. Zwirki i Wigury 93 POLAND

Geun Hyung Kang College of Pharmacy Chonnam National University Kwangju 500-757 KOREA

Ryoji Kasai Institute of Pharmaceutical Sciences Hirostirna University School of Medicine 1-2-3 Kasumi, Minarni-ku Hirostirna 734 JAPAN

Charlotte Kensil Cambridge Biotech Corporation Worcester, MA 01605

581

Dong Hyun Kim Faculty ofPhannaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113 JAPAN

Junei Kinjo Faculty ofPhannaceutical Sciences Kumamoto University Kumamoto 862 JAPAN

Dr. P. Kintia Institute of Genetics Academy of Sciences Padurii str. 20 Kishinev 277002 MOLDOVA

Takao Konoshirna Kyoto Phannaceutical University Misasagi, Yarnashina-Ku Kyoto 607 JAPAN

Maroufath Larnidi Laboratoire de Phannacognosie Faculte de Pharnacie Universite d'Aizmarseille II 27 Bd J. Moulin 13385 Marseille Cedex FRANCE

N.V. Lattserdis Institute of Genetics Academy of Sciences Padurii str. 20 Kishinev 277002 MOLDOVA

Ik-SooLee College of Pharmacy Chonnam National University Kwangju 500-757 KOREA

Else Lemmich Royal Danish School of Phannacy Department of Medicinal Chemistry Universitetparken 2, DK-2100 Copenhagen DENMARK

Xing-Cong Li Laboratory of Phytochemistry Kunming Institute of Botany Chinese Academy of Sciences Heilongtan, Kunrning 650204 CHINA

Galina N. Likhatskaya Pacific Institute of Bioorganic


582

Lee-Chiang Lo Department of Chemistry Columbia University New York, NY 10027

Maja Ja. Lovkova Bach Institute of Biochemistry Leninsky Prospekt, 33 Russian Academy of Science Moscow 117071 RUSSIA

James H. Ludens Department of Chemistry Columbia University New York, NY 10027

S.B. Mahato Indian Institute of Chemical Biology 4, Raja S.C. Mullick Road Jadavpur, Calcutta 700-032 INDIA

M. Maillard Institut de Phannacognosie et Phytochimie Universite De Lausanne BEP, CH-1015 Lausanne-Dorigny SWITZERLAN:

A Marston Institut de Phannacognosie et Phytochimie Universite De Lausanne BEP, CH-1015 Lausanne-Dorigny SWITZERLANl

Y oshihiro Mimaki SchoolofPhannacy Tokyo College of Pharmacy & Life Sciences 1423-1, Horinouchi Hachioji, Tokyo 192-03 JAPAN

L. Minale Department of Natural Products University of Naples Naples 80131 ITALY

Faryal Vali Mohammad H.E.J. Institute of Chemistry University of Karachi Karachi 75270 PAKISTAN

Tsuneatsu Nagao Faculty ofPhannaceutical Sciences Fukuoka University, Nanakurna 8-19-1, Jonan-ku, Fukuoka 814-01 JAPAN

Katalin Nagy Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a BudapestH-1097 HUNGARY

Mohamad A. Naibi Institute of Genetics Academy of Sciences Padurii str. 20 Kishinev 277002 MOLDOVA

Koji Nakanishi Department of Chemistry Columbia University New York, NY 10027

Nguyen Thoi Nham Science-Production Union of Ginseng and

Medicinal Plants Ho Chi Minh City University of Medicine

and Pharmacy 41 Dinh Tien Hoang Street District 1 Ho Chi Minh City VIETNAM

Toshihiro Nohara Faculty of Pharmaceutical Sciences Kumamoto University Kumamoto 862 JAPAN

Mushtaq Noorwala H.E.J. Institute of Chemistry University of Karachi Karachi 75270 PAKISTAN

Lucienne Nze-Ekekang Iphametra (Cenerest) Libreville B.P. 842 GABON

Kazuhiro Ohtani Institute of Pharmaceutical Sciences Hirostima University School of Medicine 1-2-3 Kasumi, Minarni-ku Hirostirna 734 JAPAN

HikamOkabe Faculty of Pharmaceutical Sciences Fukuoka University Nanakuma 8-19-1 Jonan-ku, Fukuoka 814-01 JAPAN

C.O. Okunji Walter Reed Institute of Research Division of Experimental Therapeutics Walter Reed Medical Center Washington, DC 20307-5100

Evelyne Ollivier Laboratoire de Pharmacognosie Faculte de Pharnacie Universite d'Aizmarseille II 27 Bd J. Moulin 13385 Marseille Cedex FRANCE

Anne Osborne The Sainsbury Laboratory Norwich Research Park Colney Norwich NR4 7UH UNITED KINGDOM

Cezary Paczkowski Department of Biochemistry Warsaw University 02-089 Warszawa ul. Zwirki i Wigury 93 POLAND

E. Palagiano Department of Natural Products University of Naples Naples 80131 ITALY

Valentina A. Paseshnichenko A.N. Bach Institute of Biochemistry Leninskiy pr. 33 Moscow 117071 RUSSIA

Jun-peng Peng Institute of Radiation Medicine, Beijing 27 Tai-ping Road Beijing 100850 CHINA

S. Piacente Dipartimento di Chimica delle Sostanze Naturali via D.Montesano 49 Napoli 80121 ITALY

C. Pizza Dipartimento di Chimica delle Sostanze Naturali via D. Montesano 49 Napoli 80121 ITALY

ltzhack Polacheck Department of Clinical Microbiology and Infectious Diseases The Hebrew University Jerusalem 91120 ISAREL

S.M. Ponomareva Bach Institute of Biochemistry Leninsky Prospekt, 33 Russian Academy of Science Moscow 117071 RUSSIA

Nina G. Prokofieva Pacific Institute of Bioorganic


583

GuoweiQin Shanghai Institute of Materia Medica Academia Sinica 319 Yue-yang Road Shanghai 200031 CHINA

A. Regoly-Merei Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY

Melchior Reiter lnstitut fur Pharmazie und Lebensmittelchemie


R. Riccio Department of Natural Products University of Naples Naples 80131 ITALY

J.G. Roddick Department of Biological Science University of Exeter Exeter EX4 4QG UNITED KINGDOM

Ushiro Sankawa Faculty of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113 JAPAN

Yutaka Sashida SchoolofPharmacy Tokyo College of Pharmacy & Life Science 1423-1, Horinouchi Hachioji, Tokyo 192-03 JAPAN

Elena B. Schentsova Pacific Institute of Bioorganic


Dirk C. van Setten National Institute of Public Health

& Environmental Protection Department of Molecular Spectroscopy P.O. Box 1 Bilthoven 3720 BA THE NETHERLANDS

584

Fehmeena Shaheen H.E.J. Institute of Chemistry University of Karachi Karachi 75270 PAKISTAN

Baoping Shao Shanghai Inst. of Materia Medica Academia Sinica 319 Yue-yang Road Shanghai 200031 CHINA

O.V. Shelepova N.Y. Tsitsin Main Botanical Garden Russian Academy of Science Moscow RUSSIA

Stepan A. Shvets Institute of Genetics Academy of Sciences Padurii str. 20 Kishinev 277002 MOLDOVA

F. DeSimone Dipartimento di Chimica delle Sostanze Naturali via D. Montesano 49 Napoli 80121 ITALY

P. Skofertsa National Practical Science Center of Hygiene and


N. Testemitianu Chisinau State Medical University Chisinau 2002 MOLDAVIA

S.M. Sokolova N.Y. Tsitsin Main Botanical Garden Russian Academy of Science Moscow RUSSIA

Sean Soltysik Cambridge Biotech Corporation Worcester, MA 01605

K. Spinu National Practical Science Center of Hygiene and



Jan St. Pyrek College of Pharmacy University of Kentucky Lexington, KY 40536

Otto Stieber Department of Pharmacy Swiss Deferal Institute of Technology

(ETH-Z) Zurich 8057 SWITZERLAND

Lybov I. Strigina Pacific Institute of Bioorganic


Chung Ki Sung College of Pharmacy Chonnam National University Kwangju 500-757 KOREA

J. Szepvolgyi Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY

J.D. Tally Walter Reed Institute of Research Division of Experimental Therapeutics Walter Reed Medical Center Washington, DC 20307-5100

Osamu Tanaka Suzugamine Women's College Inokuchi 4-chome 6-18 Nishi-ku Hiroshima 733 JAPAN

Ryuichiro Tanaka Faculty of Pharmaceutical Sciences Fukuoka University, Nanakuma 8-19-1, Jonan-ku, Fukuoka 814-01 JAPAN

Susan Thiilborg Royal Danish School of Pharmacy Department of Medicinal Chemistry Universitetparken 2, DK-2100 Copenhagen DENMARK

N. De Tommasi Dipartimento di Chimica delle Sostanze Naturali via D. Montesano 49 Napoli 80121 ITALY

Adrienne A. Tymiak Department of Chemistry Columbia University New York, NY 10027

C.V. Uglea Institute of Biological Research Blvd. Copou 20A lassy 6600 ROMANIA

Inessa S. Vasilvera A.N. Bach Institute of Biochemistry Leninskiy pr. 33 Moscow 117071 RUSSIA

V. Vorozhbit National Practical Science Center of Hygiene

and Epidemiology of the Health Ministry of the Moldova Republic


V. Vutkaryov National Practical Science Center of Hygiene and



George R. Waller Department of Biochemistry and Molecular Biology Oklahoma State University 246B Noble Research Center Stillwater, OK 74078-0454

Bethanne Warrack Department of Chemistry Columbia University New York, NY 10027

Gerrit van de Werken National Institute of Public Health

& Environmental Protection Department of Molecular Spectroscopy P.O. Box 1 Bilthoven 3720 BATHE NETHERLANDS

Deborah A. Wheeler Cambridge Biotech Corporation Worcester, MA 01605

J.L. Wofender Institut de Pharmacognosie et Phytochimie Universite De Lausanne BEP, Lausanne-Dorigny CH-1015 SWITZERLAND

Zdzislav A. Wojciechowski Department of Biochemistry Warsaw University 02-089 Warszawa ul. Zwirki i Wigury 93 POLAND

585

Roland Woldanski Department of Biochemistry Warsaw University 02-089 Warszawa ul. Zwirki i Wigury 93 POLAND

Jia-YanWu Cambridge Biotech Corporation Worcester, MA 01605

JunpingXu Pharmagenesis 3183 Porter Drive Palo Alto, CA 94304

Ren-sheng Xu Shanghai Inst. of Materia Medica Academia Sinica 319 Yue-yang Road Shanghai 200031 CHINA

and/or Pharmagenesis 3183 Porter Drive Palo Alto, CA 94304

Shoji Y ahara Faculty of Pharmaceutical Sciences Kumamoto University Kumamoto 862 JAPAN

Johji Y amahara Natural Medicinal Resources Division Research Institute for Production Development Kyoto 606 JAPAN

Kazuo Yamasaki Institute of Pharmaceutical Science Hiroshima University School of Medicine 1-2-3 Kasumi, Minami-ku Hiroshima 734 JAPAN

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

586

Pei-Ying Yang College of Pharmacy University of Kentucky Lexington, KY 40536

Xin-sheng Y ao Institute of Radiation Medicine, Beijing 27 Tai-ping Road Beijing 100850 CHINA

Sang Sun Y oon College of Pharmacy Chonnam National University Kwangju 500-757 KOREA

Masayuki Yoshikawa Kyoto Pharmaceutical University 5, Nakauchi-cho, Misasgi Yamashina-ku, Kyoto 607 JAPAN

UriZehavi The Hebrew University of Jerusalem Faculty of Agriculture Department of Biochemistry, Food Science,

and Nutrition P.O.B. 12, Rehovot 76100 ISRAEL

NingZhao Department of Chemistry Columbia University New York, NY 10027

WeiminZhao Shanghai Inst. of Materia Medica Academia Sinica 319 Yue-yang Road Shanghai 200031 CHINA

Jan Zimowski Department of Biochemistry Warsaw University Warszawa 02-089 POLAND

LATIN NAME INDEX

Abrus cantoniensis, 267, 271 Abrus precatorius, 271 Acacia auriculiformis, 173, 178 Acanthaster planci, 344 Acebia quinata, 239 Achillea millefolium, 7 Acorus calamus, 198 Aesculus hippocastanum, 5, 83, 85,207-208,

212,471 Agaricus bisporus, 31 Agathis philippinensis, 198 Agava americana, 310,313,323 Agava lecheguilla, 443 Agava sisalana, 3, 11 Agava spp., 11 Agrobacterium rhizogenes, 31 Albizzia julibrissin, 271 Alcyonum spp., 337-338 Aletris farinosa, 7 Allium albopilosum, 101 Allium ampeloprasum, 8, 511 Allium bakeri, 517 Allium cepa, 8, 310, 5ll Allium chinense, 107-108,512,517-518,

521-522 Allium macrostemon, 512-514,521-522 Allium narcissiflorum, 310, 314, 323 Allium porrum, 8 Allium sativum, 4, 8, 511-512, 520-522 Allium schoenoprasum, 8 Allium spp., 511 Allium vineale, 511 Aloe barbadensis, 4 Aloe vera, 4 Alternaria brassicicola, 287 Alternaria solani, 283, 553 Anemoclema glaucifolium, 229 Anthoplexaura dimorpha, 337-338 Arachis hypogaea, 9 Aralia elata, 83-84, 198, 207-208 Aralia racemosa, 7 Arcangelisiajlava, 198 Ardisia crenata, 494 Ardisia japonica, 403-404 Asparagus cochinchinensis, 408-409 Asparagus filicinus, 226-227

Asparagus mairei, 226-227 Asparagus officinalis, 8, 37,41-43,310,

314a,323 Asparagus plumosus, 37,41-43,45 Aspergillus fumigatus, 233-234 Aspergillus niger, 30, 31,536,565 Aspergillus spp., 120 Aspergillus wentii, 552 Aster scaber, 297, 299-301 Aster spp., 297 Aster tataricus, 297 Asterias amurensis, 342 Asterina pectinifera, 347-348 Asteropus sarasinosum, 335-336 Astragalus complanatus, 271 Astragalus falcatus, 83-84, Astragalus melanophrurius, 495 Astragalus membranaceus, 5, 225 Astragalus oleifolius, 495 Astragalus sinicus, 271 Astropecten indicus, 350 Atriplex canescens, 12 Atropa belladonna, 310,475,477,481-482 Aucuba japonica, 26 Avena longiglumis, 549 A vena sativa, 8-9

Bacillus subtilis, 328, 368 Bacteroides JY-6, 29-32, 35, Bacteroides fragilis, 27 Beshorneria yuccoides, 310 Beta vulgaris, 9, 208 Bifido-bacterium pseudo-longam, 27 Bifidobacterium breve, 27 Biomphalaria glabrata, 119-121, 152, 161,

426 Biomphalaria pfeifferi, 425-426 Blumea balsamifera, 198 Borago officinalis, 7 Borrelia burgdoiferi, 165 Botrytis cinerea, 553 Brachiaria decumbens, 443 Bufo spp., 219 Bulinusforskalii, 426 Bulinus globosus, 119, 425-426 Bupleurumfalcatum, 7, 28,30

587

Bupleurumfruticosum, 403,405

Caesalpinia sapan, 198 Caldocellum saccharolyticum, 30-31, Calendula arvensis, 403,404,407-408 Calendula officinalis, 5, 83-84, Caltha silvestris, 239 Camelliajaponica, 207-208, 213 Camellia sinensis, 9 Candida alba, 327 Candida albicans, 120, 233-234, 418, 565 Candida guilliermondii, 565 Candida krusli, 327,565 Candida lipol., 327 Candida parapsilosis, 565 Candida pelliculosa, 552 Candida pseudotropicalis, 565 Candida rugosa, 327 Candida tropicalis, 327, 418, 565 Candida utilis, 327 Capsicum annuum, 10,253,310,323, 325,

332 Capsicum frutescens, 10 Cassia tora, 30 Caulophyllum robustum, 239, 242 Caulophyllum thalictroides, 7 Centella asiatica, 6 Cephalosporium gramineum, 565 Chamaelirium luteum, 7 Charonia lampas, 347-348 Chenopodium quinoa, 9 Chlorogalum pomeridianum, 11 Chlorophytum malayense, 226, 228-229 Cicer arietinum, 9 Cimicifuga racemose, 6 Cinchona spp., 402 Cinnamomum mercadoi, 198 Citrullus vulgaris, 30, 198

· Cladosporium carrionii, 418, 420 Cladosporium cladosporioides, 420 Cladosporium cucumerinum, 120-121,420,

425 Cladosporium spp., 120 Cladosporium tenuissimum, 418,420,425 Clematis chinensis, 371, 373, 381 Clerodendrum wildii, 121 Codonopsis pilosula, 5 Codonopsis spp., 5 Codonopsis tangshen, 5 Coleus forskolii, 196 Cordia myxa, 198 Coriolus consors, 31 Coriolus versicolor, 31 Corticium rolfsii, 282 Corynebacterium sepedonicum, 283 Coscinasterias tenuispina, 344 Costus speciosus, 57, 59-62

588

Crataegus spp., 6 Crocosmia crocosmiiflora, 459-460, 464,

469 Crocosmia masoniorum, 459,464-465, 46~ Crotalaria albida, 271 Cryptococcus neoformans, 535,538,541,

543 Cucumaria echinata, 563 Cucumaria japonica, 557 Cucurbita moschata, 198 Culcita novaeguineae, 344 Cyclamen coum, 489,491-492,494 Cyclamen mirabile, 489,491,492

Dalbergia hupeana, 271 Datura stramonium, 310 Decaisnea fargesii, 229 Desmodium styracifolium, 271 Digitalis barbasco, 11 Digitalis deltoidea, 11 Digitalis lanata, 11 Digitalis macrostachya, 11 Digitalis purpurea, 1, 11,219,310,323,

325,332 Digitalis spiculiflora, 11 Digitalis tokoro, 11 Dioscorea batatus, 30 Dioscorea caucasica, 323 Dioscorea composita, 2, 11 Dioscorea deltoidea, 15-21, 83-84 Dioscorea floribunda, 2, 11, 59 Dioscorea mexicana, 2, 11 Dioscorea nipponica, 16, 18, 83-84 Dioscorea spp., 3, 10, 11, 15 Dioscorea terpinapensis, 11 Dioscorea tokoro, 30 Dioscorea villosa, 4 Diospyros kaki, 30 Diuranthera major, 226, 229 Dolichos kilimandscharicus, 120 Dolicusfalcata, 536 Dracaena arborea, 415,417,425 Dracaena mannii, 415-417 Dracaena spp., 415-426 Duasmodactyla kurilensis, 340-341

Echinaster sepositus, 342 Echinaster spp., 344-346, 353 Ejretia microphylla, 198 Eleutherococcus senticosus, 5 Entada phaseoloides, 198 Enterobacter cloacae, 31 Epidermophyton floccosum, 541 Equisetum arvense, 5 Eriobotrya japonica, 201 Escherichia coli, 328, 507

Eubacterium spp., 26, 28 Eupatorium perfoliatum, 1, 557 Eupentactafraudatrix, 340-341, 561 Exophialajeanselmei, 418

Fonsecaes pedrosoi, 418,420 Fritillaria camtschatcensis, 103 Fritillaria persica, 103 Fritillaria spp., 102 Funkia norata, 323 Funkia ovata, 310, 315, 316 Fusarium caeruleum, 283 Fusarium graminearum, 331 Fusarium oxysporum, 282-283, 536, 553, 565 Fusarium sambucinum; 283 Fusarium solani, 281, 283

Gaeumannomyces graminis, 548, 551, 565 Galega o.fficinalis, 7, 502 Gardenia ternifolia, 383 Geotrichum candidum, 418,565 Ginkgo biloba, 198 Glechoma hederacea, 198 Gleditsia japonica, 91, 93 Gloeoesporium frutctigenum, 282-283 Glycine max, 9, 208,502 Glycyrrhiza glabra, 3, 5, 12, 83-84 Glycyrrhiza spp., 27 Glycyrrhiza uralensis, 83, 84, 225, 371 Guaiacum o.fficinale, 9 Guettarda angelica, 390 Guettarda platypoda, 390, 402, 407-408 Guettarda spp., 402 Gymnema sylvestre, 7, 208 Gymnocladus chinensis, 92-93 Gynostemma pentaphyllum, 131, 405-406 Gypsophila paniculata, 12 Gypsophila spp., 12

Halityle regularis, 344 Hedera helix, 5 Heinsia crinata, 374 Helianthus annuus, 9 Heliothis zea, 284 Helix pomatia, 16 Heloniopsisjaponica, 272 Hemsleya macrosperma, 131 Henricia downeyae, 344, 352-353 Henricia laeviuscola, 344, 353 Hovenia dulcis, 208 Hydrangea arborescens, 7 Hydrocotyle asiatica, 6 Hyposoter exiguae, 284

/lex paraguariensis, 7

Klebsiella pneumoniae, 27 Kochia scoparia, 208

l.agerstroemia speciosa, 196, 198, 200-201 l.agotis stolonifera, 486 Larrea tridentata, 7 l.asiorhinus latifrons, 449, 451 Lebistes reticulatus, 529 Leishmania chagasi, 421 Leishmania donovani, 423 Leishmania panamensis, 423 Lens culinaris, 9 Leontice eversmanni, 435 Leptadenia hastata, 410-412 Leptinotarsa decemlineata, 283 Lilia henri, 310 Lilium pardarinum, 102 Lilium regale, 310,317-318 Liriope japonica, 225 Liriope platyphylla, 30 Lithospermum erythrorhizon, 41 Luidia clathrata, 342 Lupinus polyphyllus, 271 Lycopersicon esculentum, 10, 72,310,323,

326,332,505 Lymnaea natalensis, 426 Lyophyllum fusosum, 31

Manihot esculenta, 10 Marthasterias glacialis, 344 Medhuca butyracea, 237 Medicago arabica, 566,569-571 Medicago blancheana, 566,569-570 Medicago carstiensis, 566, 569-570 Medicago ciliaris, 566, 569-570 Medicago disciformis,.566, 569-571 Medicago doliata, 566,569-571 Medicago granadensis, 566, 569-570 Medicago heyniana, 566,569-571 Medicago hybrida, 566, 569-570 Medicago intenexta, 566,569-570 Medicago laciniata, 566, 569-571 Medicago lupulina, 536, 566, 569-570 Medicago minima, 566,569-570 Medicago murex, 566, 569-571 Medicago muruioleptis, 566, ·569-570 Medicago noeana, 566,569-571 Medicago polyceratia, 569-571 Medicago polymorpha, 566,569-570 Medicago praecox, 566,569-570 Medicago radiata, 566, 569-570 Medicago rotata, 566, 569-570 Medicago rugosa, 566, 569-570 Medicago sativa, 6, 9, 536, 565-567, 569-

571

589

Medicago sauvagei, 566, 569-571 Medicago scutellata, 566, 569-570 Medicago soleirolii, 566, 569-570 Medicago spp., 567-571, 573 Medicago tomata, 566, 569-570 Medicago truncatula, 566, 569-570 Medicago turbinata, 566, 569-570 Melilotus alba, 10 Melilotus officina/is, 10,310 Micoides citreum, 328 Microsporum audouinii, 418 Microsporum canis, 541 Microsporum grpseum, 418 Millettia spp., 10 Mitchella repens, 7 Momordica charantia, 198 Morinda Iucida, 383 Morus alba, 198 Muriceafruticosa, 336-337 Mussaendapubescens, 371-373,381 Myristica fragrans, 9

Nauclea diderrichii, 383, 385-386, 389-390, 392-393

Nauclea latifolia, 383 Nauclea orienta/is, 198 Nicandra spp., 264 Nicotiana plumbaginifolia, 285 Nicotiana rustic a, 310 Nicotiana tabacum, 310 Nigerian dracaena, 416 Nolina recurvata, 105-106 Nomuraea rileyi, 284

Ophipogon maglanthus, 226-227 Oplopanax elatus, 84 Oreaster reticulatus, 351 Oreosolen wattii, 237 Omithogalum saundersiae, 103-104, 108 Orthosiphon stamineus, 83-84

Pachastrella spp., 335 Paeonia lactiflora, 24 Paeonia suffruticosa, 24 Panax ginseng, 5, 84, 94-95, 97, 129, 132,

198,202,225,371 Panax japonica, 94-95,202,208 Panax notoginseng, 5, 94-99, 129, 132, 138,

202, 225-226 Panax pseudo-ginseng, 202 Panax quinquefolius, 3, 5, 129, 132, 202 Panax spp., 129, 131-132, 136, 138, 144,

202 Panax vietnamensis, 131-132, 138, 147,202 Panax zingiberensis, 202 Pandanus sp., 198

590

Panicum coloratum, 443 Panicum dichotomiflorum, 443 Panicum schinzii, 443 Pardachirus marmoratus, 338 Pardachirus pavoninus, 338 Pardachirus spp., 335 Passiflora incamata, 6 Patiria miniata, 344 Paullinia cupana, 6 Pavetta crassipes, 383 Peliosanthes sinica, 226-227, 229 Penicillium spp., 120 Pentacta australis, 340, 341 Peptostreptococcus intermedius, 27 Petunia hybrida, 251, 261, 310,480 Pfaffia paniculata, 5 Phaseolus aconitifolius, 9 Phaseolus acutifolius, 9 Phaseolus angularis, 9 Phaseolus aureus, 9 Phaseolus coccineus, 9 Phaseolus lunatus, 9 Phaseolus mungo, 9 Phaseolus vulgaris, 9 Phialophora verrucosa, 418 Phoma exigua, 283 Phoma medicaginis, 288 Physalis spp., 264 Phytolacca americana, 7, 487 Phytolacca dodecandra, 118-119, 125-126,

151-156, 160-161 Phytolacca spp., 152-153 Phytophthora cinnamomi, 536, 565 Phytophthora infestans, 21, 282-283, 324 Phytophthora spp., 281, 548 Pisum sativum, 9 Plasmodiumfalciparum, 385, 388, 394-397,

417,420 Pleurotus ostreatus, 31 Polemonium coeruleum, 83, 84 Polygala senega, 6, 207-208, 214 Polygonatum biflorum, 7 Polygonatum kingianum, 225-227 Polygonatum latofolium, 310, 327 Polygonatum multiflorum, 7 Polygonatum officinale, 7 Polygonatum pratti, 226-227 Primula elatior, 6 Primula officina/is, 6 Primulaceae auriculata, 487 Primulaceae elatior, 487 Primulaceae longipes, 487 Primulaceae megaseifolia, 487 Primulaceae veris, 487 Protoreaster nodosus, 344 Prunus armeniaca, 30

Prunus persica, 30 Prunus salicina, 30 Pseudoplexaura wagenaari, 337-338 Psolusfabricii, 340-341,557 Pueraria lobatta, 9, 266, 268, 271 Pueraria thunbergiana, 9 Pulsatilla campanella, 229 Pythium aphanidermatum, 536, 565 Pythium spp., 280, 548

Quercus alba, 5 Quillaja saponaria, 9, 12, 165, 167, 170,

185-191

ftamichloridium subulatum, 418, 425 Rapanea melanophloeos, 120-121 Rheum officinale, 25 Rheum palmatum, 25 Rheum spp., 25 Rhinanthus spp., 27 Rhizoctonia solani, 283, 536, 565 Rhizopus mucco, 536 Rhodotorula glutinis, 565 Rhodotorula spp., 418 Robinia pseudo-acacia, 271 Rosa canina, 6 Rubus fruticosus, 9 Ruscus aculeatus, 4, 1 04

Saccharomyces cerevisiae, 327 Saccharomycopsisfibuligera, 527, 552 Sapindus mukurossi, 12, 208, 211 Sap indus rarak, 12 Sapindus saponaria, 12 Saponaria officinalis , 12 Saprolegnia asterophora, 368 Sarcina lutea, 328 Schistosoma haematobium, 118 Schistosomajaponicum, 118 Schistosoma mansoni, 118 Schistosoma spp., 285 Scilla peruviana, 104, 107, 108 Sclerotium rolfsii, 536, 565 Scrophularia ilwensis, 486 Scrophularia spp., 486 Septaria lycopersici, 553 Sesamum indicum, 9 Setaria cervi, 177 Sinularia crispa, 337, 338 Smilacina racemosa, 7 Smilax aristolochiaefolia, 4, 8 Smilax febrifuga, 8 Smilax officinalis, 8 Smilax regelii, 8 Solanum abittiloides, 264, 266 Solanum achrolcucum, 264

Solanum aculeatissimum, 264 Solanum aethiopicum, 264 Solanum anguivi, 264 Solanum arundo, 286 Solanum bijlorum, 264 Solanum chacoense, 264, 283 Solanum cynathem, 264 Solanum demissum, 264 Solanum dubium, 286 Solanum dulcamara, 7, 263,264, 285 Solanum ferox, 263 Solanum gila, 264 Solanum incanum, 282 Solanum indicum, 264 Solanum integrifolum, 264 Solanum japonense, 264 Solanum jurpeva, 264 Solanum khasianum, 264 Solanum laciniatum, 47 Solanum lycocarpum, 264 Solanum lycopersicum, 10 Solanum lyratum, 263,264 Solanum macrocarpon, 264 Solanum mammosum, 264 Solanum melongena, 10,37-39,41-43,47,

264,310,319-321,327 Solanum nigrum, 263-264 Solanum paniculatum, 264 Solanum sanitwongsei, 264 Solanum sisymbrifolium, 263 Solanum sodomaeum, 285 Solanum spp., 47,285-286,445 Solanum stramonifolium, 264 Solanum surattense, 264 Solanum torvum, 264 Solanum toxicarium, 264 Solanum tuberosum, 10, 47, 71,264,310 Solanum vanhuerchii, 264 Solanum verbascifolium, 264 Solanum viarum, 264 Solanum xanthocarpum, 264 Solidago canadensis, 5 Solidago serotina, 5 Solidago virgaurea, 5 Sophora flavescens, 271, 503 Sophora japonica, 501-503 Sophora subprostrata, 271 Sorghum bicolor, 30 Spinacea oleracea, 9 Staphylococcus aureus, 328 Stellaria media, 5 Streptomyces scabies, 283 Strophanthus gratus, 219 Swartzia madagascariensis, 119, 123, 124 Symphytum officinale, 7, 429-431, 436, 439-

440

591

Tamus communis, 408-409 Taraxacum officinale, 5 Taxus cuspidata, 198 Tenebrio molitor, 529 Tetrapleura tetraptera, 119, 122, 124-125 Thalictrum spp., 273 Thea sinensis, 9, 208 Tinospora cordifolia, 198 Tinospora rumphii, 198 Torulopsis candida, 565 Torulopsis glabrata, 538, 565 Tremaster novaecaledonia, 350 Tribulus cistoides, 357, 358, 362-363, 367 Tribulus terrestris, 83-84, 310, 323, 329,

357 Trichoderma koningii, 530, 532 Trichoderma pseudokoningii, 530, 532 Trichoderma reesei, 530, 532, 552 Trichoderma viride, 527-530, 532-534, 536-

567,569,571 Trichophyton mentagrophytes, 233-234,

418,535,538,541 Trichophyton rub rum, 418 Trichophyton soudanense, 418, 425 Trichophyton tonsurans, 418 Trichosporon cutaneum, 418 Trichosurus vulpecula, 449 Trifolium pratense, 6 Trifolium repens, 63 Trigonellafoenum-graecum, 4, 8, 310,444 Trillium erectum, 7

592

Trillium spp., 7 Triplostegia grandiflora, 229 Tubocapsicum spp., 264 Tupistra wattii, 226-227

Uncaria guianensis, 390, 402 Uncaria tomentose, 6, 390,402,407-408

Verbascum thapsus, 7 Verticillium albo-atrum, 283, 324, 326, 553 Vibrio vulnificus, 31 Vicia faba, 9 Vigna aconitifolia, 9 Vigna angularis, 9, 208, 502-503 Vigna radiata, 9 Vigna sinensis, 9 Vigna umbellata, 9 Viola tricolor, 84 Vitex negundo, 198 Vombatus ursinus, 449-450, 453

Wistaria brachybotrys, 87-90, 271 Withania somnifera, 7

Yucca brevifolia, 4, 11 Yuccafilamentosa, 310, 322, 325 Yucca gloriosa, 83-84 Yucca mohavensis, 11 Yucca schidigera, 4, 11

Zizyphus jujuba, 9

SUBJECT INDEX

Abrisapogenols, 265-268 Abrisaponin I, 268-269 Abrisaponins, from Abri Herba, 269 Abutiloside A, 266 Acaciasides, 174-176, 178-182 Acacic acid lactones, 17 4-17 5, 177, 179-

180 Acacigenin A, 175-177, 181-182 Acetylcholinesterase, 281 Acetyllycopsamine acetylintermedine

(diasteroisomers), 430 Acovenosigenin, 220 Acrosome reaction, 342 Acute gastroenteritis, 371 Aculeoside A, 104-105 Acyl group in crocosmiosides, 469

enhanced inhibiting activity, 469 26-0-Acylated furostanol saponins, 102 Adjuvant activity of QS-21, 171 Adriamycin, 108,233 Adzukisaponins, 502-503 Aescin (see escin), 527, 533 Afromosin, 89-91 Agave, 4, 11 Agavosides

conversion, 310-313 hypocholesterolemic activity, 312-

313,325 fungicidal activity, 325

Aglycone distribution from Medicago spp., 570

AJ[)S, 120,535,416 AI+3 82-83 Alcoholism, treatment with saponin drugs,

207-215, 266-267 Alfalfa, 535

herbs, 472 juice, 528 meal, 528 plant resistant to molds, 527 roots, 472 saponins with antimycotic activity, 535 seed, 472

Alkannin, 430 Allelopathic activity, 324

Alliumosides, 310, 314, 323 Aloeresin, 26 Aloesin, 26 American ginseng, 129 Ames test, 154 cAMP phosphodiesterase inhibition, 101,

107-108 2H-cAMP incorporation, 241 3H-cAMP uptake, 245 Amphotericin B, 233-234, 544 Anaemia, 429 Anagalligenin, 488-489 Analgesic, 240, 373, 429, 495 Analysis of plant extracts for saponins by

LC (HPLC) and mass spectrometry, 121-127

Anemoclemosides, 230-231 Anthraquinone, 25 Anthrone glycosides, 25 Anthroquinone and anthrone glycosides,

25-26 Antiacetylcholinesterase activity, 277 Antiallergic, 27 Antiarthritic, 4-6, 208 Antibacterial activity, 324, 328, 423 Antibiotics, 535 Antibody response, 168 Anticancer agents ,1, 12, 99, 109,263,

289,410 Antidiabetic response, 101, 198, 208 Antifertility, 475,494 Antifilarial activity of saponins, 173, 177-

178 Antifungal activity of steroid saponins,

233, 286-288, 324-326 Antifungal compounds, 12, 120, 233-234,

368,416,475,511,535,557,565 extracts of fruit pulp, 425

Antiinflammatory, 1, 4-6,27-28, 173,212-213,240,373,381,402,404,429-430, 487,495

Antiedematous, 212 Antileishmanial activity, 415, 420, 423 Antimalarial activity, 392,415,417 Antimicrobial, 111, 251, 415, 420, 423,

475

593

Antimycotic, 535, 544 Antioxidative properties, 251, 324, 329,

475 Antiperspirant, 268, 495 Antiphlogistic, 25, 371, 381 Antiprotozoal, 416 Antipyretic, 268, 371,381,404 Antirheumatic, 4-5 Antiseptic, 429 Antispasmodic, 268 Antithrombotic agents, 511 Antitumor activity, 98, 101, 111, 119,251,

263,285,311,373,402,411,430 of cholestane glycosides from

Omithogalum saundersiae, 108-109 of clinically used anticancer agents,

109 promoting activities of triterpenoid

glycosides, 87-99 of Solanum species, 263-264, 285 of steroid saponins from Moldovian

plants, 311-312 of tomatoside modified by oxidation,

114-116 water extract of gladiolus corms, 459

inhibitors, 101 Antitussive inhibitors, 101 Antiulcer, 27 Antiulcer properties, 27, 429 Antiviral activity, 28, 37, 111,402, 505-

509 agents, 115 chemotherapy, Ill effect, 324 Human Immunodeficiency Virus

(HIV), 407 in vitro, 407, 505 in vivo, 505 of interferons, 506 of steroidal glycosides, 324 of tomatoside, 506, 508 of tomatoside modified by oxidation,

111-112, 114-116 varicella-zoster virus, 407

Antiyeast activity, 327 API mass spectrometer, 127 Ardisicrenosides, utero-contracting, 494 Arvenin, 486 Aspafiliosides, 234 Asparagosides, 310, 323, 325 Asterogenic acid, 297 Astersaponins, 297, 300, 342, 344 Asthma, 429 Astragalosides, 495 Astrasieversianin, 495 Astringent, 5 Atroposides, 310,476-477,479,482 Aucubin and degradation products, 26-27

594

Avenacin, fungal activity, 548-550 A venacinase

determinant of pathogenicity, 552 ~-glucosyl hydrolases, 552 gene isolation, 550, 552

Ayurvedic medicine, 357 Azoles, 535

Bacteroides QY-6 ~-glucosidase activity for various saikosaponins, 32 gene, cloning, 32-33 localization of, 33 transformants of, 33-35

Bacteriostatic activity (bacterioside), 415, 521

Banaba, as source of glucose transporter, 200-201, 204-205 antidiabetic, 200 tea leaves, 204

Barbaloin, 26 Barley seed, 453 Bayogenin, 152, 156 Baytan, 331 Benzoylation and naphthylation of sugar

moieties, 221-222 Bergenin, 26 Beshomosides, 210 Bilayer lipid membrane, 241 Bioautography for fungicidal saponins,

120 Biochemical characteristics for rats

after horse-chestnut saponins administered, 473

Biosynthesis of steroid glycosides by Dioscorea cells, 18-21

Birinetorenol, 82 Bisdesmodic forms stored as

inactive form, 547 Blood coagulation, 524, 525 Blood ethanol concentration, 208, 210 Blood hemolysis, 529 Bovine hypothalamus, 220, 221 Brasiliensoside, 345 Broad-spectrum antibiotics, 535, 538 Bronchitis, 429 Buddlejasaponins, 230, 235 Bufalin, 219 Bums,429 Butyrosides, 230, 235, 237 45Ca2+ uptake, 241, 245

Caffeic acid, 430 Calorimetry, 240 Camelliasaponins, 207, 213-214 Camptothecin, 1 08 Cancer, skin, 2859 Cancer chemopreventive agents, 87, 99 Candidiosis, 535 Capillary-protective properties, 212

Capsicosides, 253,310,323,325 effect on sex ratio in cucumber plants,

330 effect on yield of apple trees, 330

13-Carbolines, 383 Carbon tetrachloride, 267 Cardenolides, 104, 219-220 Cardiac glycosides, 108 Cardioactivity

dependance on carbonyl group at C-12, 368 on sugar moiety, 368

Cardiotonic glycosides, 6, 223,426 Cardiovascular diseases, 6, 471 Cardiovascular drug

adenosine, 524 blood coagulation, 524 platelet aggregation, 524 fibrinolysis, 524 steroidal saponins, 524

Casein, 453 Caulodiac glycosides, 219-223 Caulosides, 230, 235, 239, 242 Cardoside C

cytotoxicity, 240, 243-244 effect on 45Ca2+ uptake, 241, 245-247 effect on cell membrane, 241-242,

244-248 effect on cell proliferation, 242, 247 effect on [3H]-CAMP uptake, 241,

246 . effect on microviscosity of liposomal

membranes, 241,244-245 formation of pH-dependent channels,

239-248 hemolytic effect, 240, 242-243

+ . K release by cells, 241-243 structure, 239

Carotene, 10 Cayenne peppers, 10 Cell cultures

Dioscorea spp., 15 Cell proliferation determination, 242, 247 Cellobiose, 549, 552 Cell membranes effects of cauloside C,

240 Central nervous system depressant activity,

173 CER cell cultures, 407 Ceveratrum alkaloids, 103 CF-FAB LC-MS, 124 Chaconine,47,265,278,280,286-289 Channels formed by cauloside C, 247-248 Chemical carcinogenesis mechanism, 87,

99 Chemical defense agents, 282,338,342 Chemotaxonomic significance of steroid

saponins, 129,229,237

Chemotherapy, 425,538 Chestnut saponins, 530 Chikusetsusaponins, 203-204, 209-210 Chinenosides, 517-520, 522, 525 Chinese traditional medicine, 23, 28, 81,

91-92,202,207-208,225,371 Chlorambucil, 285 Chlorogenic acid, 430 Chlorogenin, 522 Chloromalosides, 228-229, 233, 234 Cholegenic and novel bile acids

Australian opossum, 449 Wombats, 449

Cholegenic acid methyl ester, 452 Cholegenin 444, 453 Cholestane bidesmosides, 105-106 Cholestane and lanostane glycosides,

rearranged, 103-104 Cholestane-type glycosides, 363 Cholesterol, 10-11, 19, 49, 53-54, 71, 78

biosynthetic intermediate, 19 level of serum, 456

Chronic alcoholics cyanamide,207 disulfiram, 207

Chronic wounds, 429 C/D-cis-polyoxypregnane esters and

glycosides, 410 cytotoxic, 410 tumoricidal, 410

Cisplatin, 108 Cistocardin, 258,361-362,367-368

cardioactive, 360 Clofibrate, 207 Cloning of avenacinase gene 13-

glucosidase, 551 from bacteriosides JY -6, 32 hydrolysis mechanism of saikosapon-

in-c, 30 Clotrimazole, 233, 234 Co+3, 81,83 Cold, common, 429 Comfrey, 429 Commercial utilization of saponins, 1-14 Compartmentalized in plant cell

convert plant glycosyl hydrolases, 548 monodesmodic forms, 548

Complex with membrane sterols, 547 Concavalin, 60 Consolicin, 430 Consolidin, 430 Constipation, 25 Contraceptives, 2-3, 5, 15, 324 Contusion, 404 Conversion of protodioscin

to dioscin, 59 to coprostanol, 444

Coronilla plant resistant to molds, 527

595

Corosolic acid, 200-201 Corticosteroids, 15, 426 Cortisone, 426 Q-+3, 83-84 Critical micellar concentration (CMC), 170 Crocosmioside, 459-460, 468 Crude starfish extracts Cryptococcosis, 538 eu+2, 83-84 Cucumariosides, 340-341, 557, 559-561

desulfated derivative, 557 Cucumber, effect ofpetuniosides on, 257-

259 Cucurbitacin glycosides, 487 Curaderm,285,289 Custom-made saponins within plants, 289 Cuvier's tubules, 340 Cyclacoumin, 490, 492 Cyclamin, 490, 492 Cyclaminorin, 490, 492 Cyclamiretin, 404,491 Cycloartane-type saponins, 273 Cycloartane-type triterpenoid glycosides,

495 Cyclocanthoside, 495 Cytochalasin B, 196 Cymarose, 410 Cytoplasmic leakage, 426 Cytoprotective effect

carbon tetrachloride-induced hepatic injury, 208

Cytosensor®, 415,423 Cytostatic activity, 37, 109, 233

cholestane glycosides with acyl groups, 108

Cytotoxic T lymphocyte response, 165 Cytotoxicities, 234, 243, 265

of acylated saponins, 468 of dioscin, protodioscin, and a-

chaconine, 265 of embryos, 240 of modified tomatosides, 114 of sea urchin eggs, 240 of solamargines and solasodine, 265 of spirostane glycosides, 409 of steroid saponins, 233-234

D-Cymarose, 410

Dammar resin with triterpenes from trees and resinous exudates, 144

Dammarane saponins, 95, 129-133, 136, 138-139,141,143-144,147,235,237,

406 biogenesis, 130, 144-147

Daturosides, 210 Deacetylmetaplexigenin, 410 Decaisosides, 230 Decne,410 Deglucocyclamin dodecaacetate, 491 Deglucocyclamin, 490, 494

596

Dehydrosoyasaponin, 89,269 Delphinidin acid, 430 Deltonin, 233, 234 Deltoside, 16-21 Deltostim, 21 Demissine, 281 Demissidine, 78 2-Deoxy-D-glucose (2-DG), 197-199 201-

205 ' 5-Deoxyisonodoside, 349-350 DEPT,389 pH-Dependency on

cauloside C, 239 Dermatiaceous fungi, 420 Dermatophytes, 538

infections of hair, nail, and skin 425 535 ' '

Desacylcamelliasaponin, 213 Desacylcrocosmioside, 461,465, 468 Desacylescin, 212 Desacylmasonoside, 465,468 Desacylsaponin from QS-21, 167-168

characterization, 167-168 lack of antibody stimulation, 168-170

Desacylsenegasaponin, 214 Desacylsenegin, 214 Designer saponins, 10, 12 Detergents, effects on enzymes, 51-52,54

in the textile industry, 11 D~toxication mushroom poisons, 371, 381 Dtabetes, 495 Diaphoretic, 371, 381 Diarrhea, 371 Diazomethane degradation, 189 449 Diderroside, 383 ' Dietary origin, 453 Digitonins, 323, 325 Digitoxigenin, digoxigenin, 215-220 2~,23-Dihydroxyacacic acid, 93 Dimethylbenz[ a ]anthracene, 90 Dimorphosides, 337 Dioscin, 57, 233, 408 Dioscine, 57-58, 65, 265, 323 2,6-trans-2,6-Dimethyl-8-hydroxyoctane-

2,6-dienoic acid, 174-175 Dioscorea, 2-4, 10-11,30, 82

cell cultures, 15-21 Diosgenin, 2-3, 11, 15-18, 20, 37-39,47-

54,57,66,82,310,409,443,475,479-480 progesterone, 2

Diosgenin glycosidic peracetate, 481 Disruption of membrane systems

a-chaconine and a-solanine, 280 Diuranthoside, 228, 229, 233-235 Diuretic, 5, 6, 91, 240, 371, 373, 381, 495 Diversity of Southwest China for saponins

225 ' Drug development

thoracic pain, 525

stenocardia, 525 heart asthma, 525

Drug permeation enhancement, 170 N-Docosanoyltyramine, 258, 369

Eagle's culture medium, 507 Echimidine, 430 Echinocystic acids, 93, 119, 297-298 Ecostim®, 332 Eczema, 429 Edema, 371 Effect on isolated guinea-pig atria, 435 Effect on isolated guinea-pig ileum and rat

uterus, 435 Eggplants, 10 Ehrlich ascites tumor (EAT), 196-197,

199,201,204-205,244 Ehrlich reagent, 476 Elatosides, 207-210 Elemental composition of plants

synthesizing saponins, 83 Emetic, 497 Emulsification agents, 11 Endod, 151, 157, 160-161 Endod plant, 118, 426

berries, 161 endod S, 153 molluscicidal saponins, 151 pericarp, 153 seeds, 153

Enzymes activity as a-rhamnosidases and ~-

glucosidases of bacteria, 31 commercial, 31 , 66 crude hesperidinase, 463-464 glycosylation oftomatidine, 71-79 of higher plants, 30 of hydrolysis, 34, 450 of mushrooms, 31, 35 naringinase, 461, 464

Eosin, 242 3-Epidigitoxigenin, 220 Epiosarsapogenin, 444 Epi-smilagenin, 444

~-D-g1ucuronide, 443 Epstein-Barr virus, 87-89, 93-96 Ergosterol, 532-534

fatty acid composition, 533 without saponin, 530 with saponin, 530

Eruboside, 521 Erylosides, 336 Erythrocyte K +

loss of, 559 dependence on the sulfate group in the

carbohydrate chain, 559 presence of the 3- 0-methyl group in a

terminal monosaccharide required, 559

Escape reaction, 340 Escins, 207, 212-213, 527, 533 Esculentoside, 487 Ethanol absorption, inhibition, 210-215

by methanol extracts of natural medicines, 208

by saponins, 207-215 Eukaryotic organisms, 279 Exciton-coupled circular dichroism, 221 Exogenously added sterols and fatty acids

fungal membrane composition, 532 Expectorant, 5, 6, 91, 92, 487

mollusks, 340 sea anemones, 340 sea urchins, 340 starfishes, 340

Extract of Panax notoginseng, 97-99

FAB~S, 189,388,404,459,465,467 FAB MS~S, 189 Fascioliasis, 426 Fast atom bombardment (FAB), 123 Fatty acid composition

saponin-sensitive, 531 nonsensitive trichoderma strains, 532

Fatty acid domain of QS-21, 166-171 fu+3, 81,83-84 Feeding furostanol saponins

dogs, fecal excretion, 444 epi-srnilagenin, 444 epi-sarsapogenin, 444 srnilagenin, 444 diosgenin, 444 gitogenin, 444

Feeding-deterrent properties, 342 Fermentation, 3 Fever, 383 Fibrinolysis, 524, 525 Fire extinguisher, 11 Fish poisons, 431 Fish test, 529 Flavor agent, 4, 5 Flavor-modifying substances, 1 Fluconazole, 233-234 Foaming agent

baked goods, 185 beverages, 185 confectionery, 185 dairy desserts, 185

Foetidissimoside, 299-301 Food and beverage plants containing

saponins, 8-10 Formononetin, 81 Forskolin, 196-198, 204 Fouling, 336, 342 Fragmentation product of

elucidated sugar sequences, 127 Froth forming, 101 Fruit extract of S. japonica, 501 Fructose, 107

597

Fungicidal activity, 21, 37, 111, 117, 120, 251,281,415,475,487,527,529-530, 565 plant pathogens, 535 human dermatophytes, 535 medically important yeasts, 535

Funkiosides, 210,233,234,315,316 Furostanol glycosides

26-0-acylated, 102 biological activity, 21 biosythesis, 20 conversion to spirostanol glycosides,

312 from various plants, 314,316,321 26-0-~-glucosidases (E-26G)

assay, 59 occurrence, 60-61 properties, 60-61, 66-68 purification, 61-63 specificity, 64-66

substrate specificity, 64, 65 N-terminal amino acid sequence, 63-64 tetraglycosides, 409

Garlic, 520 Gastrointestinal absorption

inhibition, 10 Gastrointestinal indigestion, 25 GenBank, 552 Gene disruption, 551 Geniposide and relatives, 27 Ginseng, 225

extract, effect on 2-DG uptake, 202 saponins, 205 varieties, 202

Ginseng extract, 207 Ginseng root, 472 Ginsenosides, 95-97, 130-133, 135, 146,

202-205,232-233,235,237 Gi taloxigenin, 219-220 Gitogenin, 252-254,255-256, 310,323,

325,44 Gleditsia saponins, 92-94 Glucose transport systems, 195-205

inhibitors, 196 location, 195

~-Glucosidases, 23 converter furostanol glycosides to

spirostanol glycosides, 57 Glucosylrheinanthrone, rheinanthrone,

rhein, 25-26 ~-D-Glucuronides

hepatic formation, 444 GLUT family, 195 Glycoalkaloids, steroid, 10, 47, 54, 277-

289 consequencesforhumans,284-285

mechanism, 279-281 symptoms, 280

create 'pores' in membranes, 280

598

inhibitors of acetylcholinesterase, 281 role in chemical defense, 282-283 structures, 278 synergistic interactions, 286-289 toxicity, 279-282, 284

Glycosidases, 348, 402 Glycosidases converting natural glycosides

to bioactive compounds, 23-35 Glycyrrhiza, 82 Glycyrrhetic acid, 82, 89-90, 94, 96-97 Glycyrrhizin, 407

glycyrrhetyl monoglucuronide, g1ycyrrhetic acid, 27-28

Gomophioside, 349-350 Gracillin, 57-59, 66, 330,409 Granulatoside, 349-350 Green peppers, 10 Growth-enhancing ability of plants

petuniosides, 257-259, 261 Growth inhibitor of rice, 272 Growth inhibition of a diatom, 336 Guinea pigs

curing skin lesions in, 535 Gum tragacanth

foodstuff, 495 pharmaceutical emulsifier, 495

Gymnocladus saponins, 92-94 Gypanoside, 131 Gypsogenin, 191 Gypsogenic acid, 191

Halityloside, 349-350 Haikomari's method, 460 Heart ailments

Chinese medicine, 107 Heart asthma, 517 Hecogenin,39,42,313,323,330 Hederagenin, 120, 152, 156, 210, 237, 432,

528,565,568,571 glycosides, 211, 240 hemolytic and fungistatic glycosides,

571,573 Heinsiagenin, 374 HeLA cells, 407 Helojaposide, 272 Hematological examinations for horse

chestnut saponins, 472 Hematopoesis, 114 Hemolysis and rate of K +, 561 Hemolytic activity, 101, 115, 160-162,

170-171,240,340,382,538,557,559, 565-573

Hemorrhoids 429 Hemostatic drug, 94 Hemsloside-Ma3, 131 Hepatic hydroxylation, 457 Hepatitis, 94 Hepatoprotective action, 28 Herbal medicinal products, 3-7, 485 Hexadecanoic acid, 531

HL-60 cells inhibiting activity of acylated saponins, 468

Holostane, 339 Holothurin, 339 Home and garden fungicidal applications,

12 22-Homo-23-norcholestane skeleton, 22-

homo-23-norlanostane skeleton, 104 Homologous recombination, 552 Hormones, 2 Homoorientin, 26 Horse-chestnut saponins, 472, 530 HPLC,

coupled with mass spectral analysis, 117

for analysis of saponins, 121-122, 225-226

for cell cultures, 18 profiles of derivatives of ouabain,

OLC, and HIP, 222-223 Human basophils, 25 Human blood platelet aggregation, 513-

517 Human inflammatory fungal infections,

538 Human interferons, 505 Human platelet aggregation, 513 Human promyelocytic leukemia HL-60

cells, 108 Human spermatozoa, 235, 236 Human vaccines, 186 Hydrolysis with NaHC03

masonoside A, 468 Hydroxycholegenic acid, 447 Hydroxycholegenin, 447 2a-Hydroxy-heinsiagenin, 374 (S)-3-Hydroxy-3-methylglutaryl (HMG)

group, 101-102 Hydroxy protobassic acid, 237 5'-(Hydroxysulfonyloxy)jasmonic acid,

358,362,369 2~-Hydroxyoleanolic acid, 152, 156 Hypercholesterolemia, 1, 313, 320, 472 Hyperplasia of liver

in mice, 98 Hyperplastic nodules, 99 Hypertension, 220 Hypocholesterolemic activity, 4-6, 10, 37,

323 Hypotensive effects, 431, 440, 495

leontoside-A, 435a symphytoxide-A, 435a

Hypothalamic inhibitory factor, 220

Ichthyotoxicity, 340 Ilwensisaponin, 486 Immune stimulating, 1 Immunization studies, 167 Immunoadjuvant properties, 185 Immunocytochemical studies, 68

Immunodeficency syndrome (AIDS), 416 Immunological adjuvant, 165 Immunological assays, 167 Immunomodulatory action, 21, 28

sea cucumber glycosides, 340 Immunopromotive, 382 Immunosuppressive drugs in transplant

patients, 535 mycoses, 538

In vitro antimalarial test, 388 In vitro culture of C. speciosus, 59-68 Indicoside, 349-350 Indolepyridines, 383 Induced hypercholesterolemia, 472 Inducing immune interferon ,487 Infectious hepatitis, 267 Infertility, 489 Inflammatory agent, 404 Inhibition

butyrosides, 237 mimengoside A, 237 of cAMP phosphodiesterase, 101 motility of human spermatozoa, 237 replication of some DNA and RNA

viruses in vitro, 407 settlement of larvae barnacles and

bryozoans, 342 triplosides B, 237

Inotropic cardioactivity effect, 357, 367-368

Inotropic drugs, 107 Insecticidal agent, 373, 381, 383 Interferon-inducing activity, 408 Interferons, 505, 508

antiviral activity, 506 Intestinal flora, 444 Ion permeability of mycelia

Trichoderma strains, 531 Iridoid glycosides, 26-27 Ischemic heart diseases

Hungarian population, 471 Isocholegenin, 38-45, 444, 453 Isocyclamin, 490, 492-493 Isoeruboside, 521-522

blood ocagulation inhibitory effect, 525 firinolysis-promoting effect, 525

Isonodoside, 349-350 Isonuatigenin, 39, 42, 445

Jaundice, 25 Jones' oxidation reagent, 449, 455-456 Julibrosides, 271-272,274

Kampferol acid, 430 Kaikasaponins, 266, 269 Kalopanax saponin, 230 Kampferol-3-sulfate, 200-201 KB cells

inhibitory activity of acylated saponins, 468

599

Ketoconazole, 418, 425 Kidney diseases, 429 Kingianosides, 233 Killing kinetics

leakage of potassium, 544 leakage of magnesium, 544 phosphate ions, 544

Koryoginsenosides, 233 Kudzusaponins, 269,270 Kurilosides, 340-341 Kuroyurinidine, 103

Lachrymal glands, 382 Laryngopharyngitis, 371 Lasiocapine, 430 Laxative, 25 Laxogenin, 517,521 Laxoside, 522

blood coagulation, 525 Lectins, 264 Leishmania species/strains, 421 Leishmaniasis, 416 Leontoside, 230,235,429,431,435

hederagenin 429 Leptine, 281, 286 Leucocytosis, 114 Leukemia, 495 Licorice, 225 Life cycle of Schistosoma, 118 Liliaceous plants, species containing

steroid saponins 226, 227 medical uses, 226-227

Lilioglycosides, 310, 317-318 Linoleic acid, 430, 531 Liposome, 240, 280 Liquid chromatography-mass spectrometry

(LC-MS), 121-122 comparison of methods, 124-125

Lithium aluminum hydride reduction, 452 Lithospermic acid, 430 Livers

triglycerides, 472 cholesterol, 472

Livestock feed and forage plants and crops, 10

Longevity, ginseng aids, 202 Low-saponin alfalfa

breeding of cultivars, 529 Lowering effect in plasma, 185 Lycopsamine/intermedine

(diastereoisomers), 430 Lysis, 547

Macrophase-phagocyte liposomal system, 543

liposomal G2, 543 Macrophyllogenin, 498 Macrophyllosaponin, 496, 498 Macrostemonoside, 513-516,522,525 Maize, 453

600

Majonoside-R2, 130-131, 133, 138, 143 Malaria, 416

people attacked annually, 383 Malignant neoplasms

cholesterol reduction, 475 Malignant tumor cells, 109 Malvidin acid, 430 Mammalian erythrocytes, 286 Mangiferin, 26 Marsupials, bile, 445 Marthasterosides, 343-344 Maslinic acid, 200-201 Masonoside, 466 Mass spectrometry (MS), 124, 157, 387

chemical ionization (NH3), 363 mono- or bidesmosidic structure, 363

Mass spectral (MS) interfaces, 122-123 comparisons of methods, 123-124

Mass spectrometry for structural studies, 157, 298, 302-303

Mechanism of action antisera recognised, 553 anti-avenacinase, 553 tomatinase, 553

Medicagenic acid, 120, 528, 535-536, 565, 568

hemolytic and fungistatic, 573 Medicago spp. for commercial

development, 573 Medicinal plants

medical uses, 230 as sources of triterpenoid saponins,

229-230 Melanoma, 285 Melilotosides, 310 Melongosides, 38,310,319,330 Membranes, 241-248,280-281 Membrane-lytic properties, 277 Menstrual disorders, 494 Metabolites of nuatigenin, 454 Methotrexate, 108 Methyl a-linolenate, 207 Methyl polygalactate, 468 Methylallyl trisulfide, 512 Methylation of atroposides, 482 Metropolis Monte Carlo method, 105 Miconazole, 418, 425 Microencapsulation, 11 Microviscosity, 241, 244 Mimengosides, 230, 235, 237 Mirabilin, 490,494 Mirabilin lactone, 490, 494 Mirabilin methyl ester, 490 Mitomycin, 108 Mn+2, 83-84 Moldstim®-type and Pavstim®-type

saponins, 112-113, 331-332 Molecular dynamics

computations, 105-106 Molluscicidal activity, 117, 160-161,285,

415,426,487

extracts of fruit pulp, 425 Molluscicidal potency test, 425 Molluscicidal saponins, 118-119, 125,

151-154, 160-162 Monodesmodic formation, 548 Mosaic virus, 326 Mosesins, 338 Mold cell chemical composition, 531 MS-III, 211 MS/MS, 127 Muricins, 337 Murine cryptococcosis, 535

among AIDS patients, 541 Mussaendosides, 375-376, 382 Myristic acid, 531

N aringinase, 221 Natural detergents, 431 Naucledal, 383 Necic acid 430 Necine, 430 Nematocide activity, 21, 282 Neochlorogenin, 522 Neogitogenin, 368-369 Neoglycolipid synthesis, 274 Neohecogenin, 229, 358, 368-369 (25S)-Neospirost-4-en-3-one, 366 Neotigogenin, 229, 310,358,367-369 Nephritis, 495 Neurological-type toxicity, 291 Nicaphipalin, 266 Nicaphysalins, 266 Nicotianosides, 312 4-Nitroquinoline N-oxide, 98 N-Nitrosodiethylamine, 98 NMR, use in structure studies, 157, 233,

302,304 of aglycone moieties, 134 COLOC, 410-411 COSY, 158,388,404,410-411,432, 452,461,463,480,497

COSY and TOCSY, 137, 150, 158, 233,254,305,374,463,468

HETCOR, 404,410-411 HOHAHA, 404, 411 HMBC, 374, 388,433,498,516 HMQC, 374, 388 ID lH, ID proton-decoupled Be, 158 J-resolved lH, NOESY lH, 158, 235 NOE, 302-303,305 NOEs and lH-BC long-range

correlations, 141, 159, 233, 363, 365,376,402,405

NOESY, 159, 233, 374 13C-NMR, 362-363, 374, 389, 401,

404 l3C-NMR chemical shift

BC-NMR spectra, 174, 180, 182, 189, 201,252-253,410-411,431-432, 434,438,452,461,463-465,467-468,475

2D-NMR, 388, 402, 410 lH NMR, 189, 351,360, 362-363,

365,404,410-411,431,434,438, 459, 464-465, 467

lH-lH DQF COSY, 138,305,374 Refocused INEPT Be, 160 ROED lH, 303-304 ROESY lH, 254, 374, 404-405,480 of sugar moieties, 135, 138

NMR coupling constants, 137, 139, 142-143,253-254,256,298,303,305-306

Nodososides cytotoxicity from starfish, 342-343

Nonoxynol-9, 234 Norlanostane, 335 Notoginsenosides, 130, 138, 233 Nuatigenin, 37, 39,445 Nystatin, 233, 234, 544

Oat pathogenic, 548 Oat seeds and sprouts, 453 Octillol-type saponins, 130, 133, 136, 138,

143, 146-147 Oleanane saponins, 229-230, 235-236, 271 Oleandrose, 410 Oleanen-28-oic acid, 208-210, 271 Oleanolic acid, 82, 119-120, 131, 133,

152-153,156,202,208-209,297-298, 430,565,568

desmosides, 208, 236 Oleanolic glycosides, 403

inhibitory effect against VSV, 407 Oleic acid, 531 Ononin, 89 Oomycete fungi, 548 Ophydianosides, 342 Opportunistic pathogens of humans, 425 Oral contraceptives, 2, 426 Oreasterosides, 351 Ouabagenin, 219-220, 223 Ouabain "OLC", "HIF", 220-222 Ouabain-like compound, 220 Ouabain pentanaphthoate, 222 OVA, antibodies to, 167-170 Ovarian cancer, 285 Ovulation process, 2, 21, 251 Oxoquinovic acid, 385, 392-393

Pachastrellosides, 336 inhibition cell division of fertilized starfish eggs, 335

Paeoniflorin, paeoninmetabolins, 24 Palmitic acid, 461 20(S)-Panaxadiol, 140, 147

601

Panax:ynol, 96 Panax:ytriol, 95-96, 147 Papaverine, 107 Papillary muscle

guinea pigs, 367 Papillomas, 91, 93-94, 97 Pardanosides,

see 26-0-Acylated furostanol saponins

Partial hydrolysis of atroposides, 482 Patiriosides, 343-344 Pavstim®, 332 Pavonins, 338 Pectiniosides, 345, 347-348 Peliosanthosides, 228 Penaustrosides, 340-341 Pentanaphthoate, 222 Peripheral vascular disorders, 212 Periplogenin, 220 Permethylation of desacylcrocosmioside,

462 Persicanidine A, 103 Pesticides, 289, 309 Petuniosides, 251-261, 266, 310,480

determination of structure, 252-257 hydrolysis, 260 methylation, 260 purification and properties, 259-260 sugar components, 252-257

Pharmacological activity of dammarane triterpenoids, 129

Phaseoside, 219, 269 Phenobarbital, 98 Phospholipids, effect on glycosy lation, 51,

54 Photoeruboside, 521 Photographic chemicals and emulsions, 11 Photoisoeruboside, 521-522

fibrinolysis, 525 Photosensitization

hepatic dysfunction, 443 kleingrass, 443 lambs, 443

Phytoalexins, 547 Phytoanticipin, 547 Phytolaccasaponin, 487 Phytopathogenic fungi, 324 Phytosterols, 74 Pinitol, 358, 362-363 Pisasteroside, 349-350 Piscicidal activity, 160 Plant glycosyl hydrolases

bidesmodic and monodesmodic forms, 548

Plant pathogens, 536-543, 547-553 Plasmid, 33-35 Platelet aggregation, 101, 524

assay, 522 Polyclonal antibody, 68 Polygalacic acid 3-0-vicianoside, 463

602

Polygonatosides, 310, 329 Polyhydroxypregnane derivatives, 412 Polisaponin, 323 Potato Y -virus, 326 Potato glycoalkaloids, 281, 284 Potatoes, 10 Pratioside, 233, 234 Pregnane17 (20)-ene-type glycoside, 369 Pregnane-type glycosides, 363 Presenegenin, 214, 215 Primacrosaponin, 487, 488 Primulasaponin, 487, 488 Priverogenin, 489 Priverosaponin, 487, 488 Priverosaponin B-monoacetate, 487 Proacaciasides, 174-175

isolation, 178-179 permethylation and hydrolysis, 179,

181 properties, 178-180

Progenins from petuniosides, 252, 256, 260

Promastigotes, 421 Prophylactic effects, 407

chronic viral hepatitis, 407 Prosaikogenin, 9, 29, 35 Prosapogenin, 191,361,461,463 Prosapogenin of butyroside, 235 Prosapogenin of diocin, 233-235 Prosapogenol,347 Protein concentrates, alfalfa, 528 Protobassic acid saponins, 121, 237 Protobioside, 16-20 Protodescigenin, 82 Protodigitonin, 325 Protodioscin, 16-18-21, 57, 64-65, 265 Protoeruboside, 521 Protogracillin, 57, 64-66 Protoisoeruboside, 522 Protopanax:adiol, 57, 82, 130, 144, 202,

205 Protopanax:atriols, 130-131, 133, 136, 139-

140,144-145,147,202,205 20(S)-Protopanax:atriol oxides, 136, 140-

144 Protopolygonatoside, 329, 330 Protoprimulagenin and relatives, 120-121,

488-489 Protozoan infections

immunodeficiency syndrome (AIDS), 416

immunosuppressed patients, 416 morbidity, 416 mortality, 416

Psolusosides, 340, 341, 559 desulfated derivative, 557

Pulsatilosides, 230, 235, 237 Purpureagitoside, 210, 325, 329

QS-ill structure, 186-187

QS-21, an acylated triterpene glycoside deacylation and fatty acid domain,

166-170 stimulation of cytotoxic and

lypmphocyte response, 165, 171 structure, 166-168

Quercetin, 25 Quillaic acid, 191 Quillaja saponins, 185-192

molecular structure, 186-192 aglycones of, 191 by cleavage and analysis of

products, 188-192 reported, 186-188

Quil A and QS-21 fractions, 185-186 Quinovic acid, 385, 393 Quinovic acid, 3-0-a-lr

rhamnopyranoside, 392 Quinovic acid, 3-0-glycosides, 383, 385 Quinovic acid glycosides, 383

inhibitory effect against VSV, 407 Quinquenosides, 130 Quinquina, 383 Quis, 345

Rabbits, 445 Radiorespirometry, 415 Raji cells, 88-90, 93, 95-96 RAM drug test procedure, 416, 420-421 Recombinant analysis, 552-553 Recurvosides, 106-107 Reductive cleavage of permethylated

acaciaside C, 181 Red ginseng, 94 K+ release, 241 Renal sodium excretion, 220 Resistance of alfalfa cotyledons to molds,

529 Resistance to saponin action, 548 Respiratory tract infections, 494 Restriction map, 34 Reverse genetics approach, 550 a-Rhamnosidase, 31 Rhein, 26 Rheinanthrone, 26 Rheumatic arthritis, 404, 431 Rheumatic diseases, 431 Rhinovirus type, 407 Robinioside E, 269 Rockogenin, rockosides, 323, 325 Robinioside, 269 Rosmarinic acid, 430 Rumen content, 444 Rutin, 24-25

Saikosaponins, 28-32, 35, 237 Salivary glands, 382 Sanchi ginseng, 129 Sapindosides, 211

Saponins as fungicides, 120 as molluscicides, 118-119, 125, 151-

154, 160-162 of P. dodecandra, 125-127

Saponin-containing herbs, 7 Saponin-detoxifying enzymes, 548

pathogens of oat and tomato, 553 Saponin Network

Mass Spectrometry, 575 Nuclear Magnetic Resonance

Spectrometry, 575 Saponinases, 548 Sarasinosides, 211,335-336 Sarcosine, 410-411 Sarsasapogenin, 37, 39,41-42,310,323,

443 Sativoside, 521 Scaberoside, 298 Scaberoside methyl esters

determination of structure, 298 NMR data, 298 mass spectra, 298

isolation, 299 structures, 300-301, 306

Schistosomes in the bladder or intestines, 118

Schistosome, schistosomiasis, 118-119, 151, 153-155, 161,285

Sclerotium rolfsii from snails, 118, 119, 161 insoluble complexes with sterols, 536 high cholesterol, 536 lower cholesterol, 536

Screening of plant extracts for GT uptake, 198-199

Sea cucumbers, 335, 339, 557 Secoiridoids, 383 Sedative effect, 6, 495 Senegae radix, 214-215

effect on ethanol absorption, 214 Senegasaponins, 207, 214-215 Senegines, 214-215 Sennoside A and degradation products, 25-

26 Sepositosides, 343 Sex hormones, 15,426 Sex ratio shifts in cucumbers, 330 Shampoo liquids, 11 Shark antifeedant, 339 Shark-repellent secretions and

peptidic pardaxins, 338 steroid glycosides, mosesins, 338

pavonins, 338 Shark's olfactory sense, 339 Sheep erythrocytes, 196-197, 202, 204

effect of ginseng, 202 Shikonin, 430 Shionane, 297 Shoot tip cultures, 57

603

Sister Chromatid Exchange, I 54 Sitosterol, 75, 78, 430 ~-Sitosteryl, 3-0- ~-D-glucopyranoside,

I30 Skin cancer, 285 Smilagenin, 39, 4I-42, 433,52 I Soap substitute, II8 ~-Solamargine, 285 Solamarines, solamargine, 285-286, 289 Solanaceous plants,

antitumor activity, 263-264 chemical constituents, 263-264

Solanidane, 47-52, 278 Solanidine, 47-52, 7I, 78-79,286 Solanine, 47-52, 28I, 286 Solanine/chaconine, 28I Solasonine/solamargine, 28I Solaplumbin, 285 Solasodine, 47-52, 7I, 78,265,285-286 Solamins,278,280,286,289 Sophoraflavosides, 269 Sophorose, 549 ~-Sophorosyl moiety, 136 Southern blot analysis, 552-553 Soyasapogenol B substituted, 502 Soyasapogenols, 565, 568 Soyasaponins, 268-270, 502-503 Spawning inhibitors, 340 Spermicidal activity, 2I, 330

of steroid saponins, 234-235, 239 of triterpenoid saponins, 235-236

Spinasaponins, 209-210 Spiroconazole, 4I5, 4I7-4I8, 425-427 Spirostane glycosides, 409 Spirostanol biosynthesis, 44 Spirostanol saponins

biosynthesis 37-45 formation from furostanol glycosides,

57, IOI, 312 from various plants, 313-315, 317,

319-320,322 polyhydroxylated, 106, 107 with an HMG group, 10I-102

Starfishes, 335, 339 Steamed ginseng, 94 Stearic acid, 531 Steroid glycosides in bacterial tests, 328 Steroid glycosides as bioregulators, 331 Steroid hormones, I,2 Steroid sapogenins,

precursors of drugs and hormones, 2 structure and biosynthesis, 43-45

Steroidal glycosides

604

antifungal activity, 233-234 cytotoxicity, 233-234 isolation from plants, 3II of Allium chinensis, 107 -I 08 of lilaceous plants, medical uses,

isolated ones, and structures thereof, 226-228, 3I8

spermicidal activity, 239, 330 spirostanes and furostanes, 228 stimulating action on plants, 251

Steroidal saponins in food and beverage plants, 8

Steroidal saponins, botanical sources, II Sterol binding by glycoalkaloids, 28I Sterol metabolism by demethylases, 28I Stenocardia, 517 Stichlorosides, 339 Stichopodidae, 340 Stigmasterol, 430 Stimulant beverage, 6 Stipuleanoside R, 209-210 Stomach ache, 202, 213, 273 Streptomycin, 425 Strophanthidin, 2I9-220 Structure-activity relationship

antitumor activity, 4I3 dendrochirotid a order, 557-563 ethanol absorption, 210-2I5 glycosides of medicagenic acid, 407,

535 protopanaxatriol, 205 quinoic acid derivatives, 403 spermicidal activity, 234-237

Subprosides, 269 Sulfated digitogenin, 330 Sulfated neotigogenin trioside, 330 Sunflower oil, 533 Surface activity, 170-17I Surfactant, I2 Suspension stabilizer in pharmacuetical

additive, I85 Suspension cultures of Dioscorea

deltoidea cells, 15-2I Symphitine, 430 Symphytocynoglossin, 420 Symphytoxide, 429-43I, 436-439 Synergistic interactions

chaconine/solamargine, 286 detoxification mechanisms of

pathogens or predators, 287 solanine/chaconine, 296 solasonine/solamargine, 286 significance to man, 287-289

Synthetic medicagenic acid glycosides treatment of fungal infections, 543

Synthetic molluscicides, 151

Tannin, 20I Tarasaponin, 209 Taxol, I08 Taxonomic relationship, I38, 229, 277 Tenuifolin, 214-215 N-Tetracosanoyltyramine, 358 I2- 0-Tetradecanoylphorbol-13-acetate,

87-88, 90-91, 93-97 3a,5a-Tetrahydrodesoxycordifoline, 392,

393

Tenuispinosides, 343, 344 Termination early pregnancy, 371, 381 Thalictoside, 273 Therapeutic effects on viral hepatitis, 407 Thermal burn, 25 Thermotropic behavior of liposomes, 244,

246 Thoracic pain, 525 Thornasterol, 344 Thornasterosides, 343, 344 Thrombosis

cure effect from saponins from Allium plants, 522

Tigogenins, 39,41-42,47,252,255-256, 325,475,479,517,521

Tigogenin glucogalactopyranoside, 479 Tigogenin glycosidic peracetate, 481 Tigogenin monoside, 479 Tigogenin trioside, 479 Tomatidine, 47-48

glycosylation, 71-79 a-Tomatine, 71-72,281,283,285,323,

325,549,550,553 molecular complex with 3f3-hydroxy

steroids, 279 role in plant self-defense, 71 tomato pathogens detoxification, 552

Tomatinases hydrolysus sugar molecules, 553

Tomato, 10, 548 Tomato bronzetop, 326 Tomatoside saponins, 112-116, 310, 323,

325,330 antiviral activity, 505-508 modified biological effects, 114-116

Tonic,4,5,6,202,208 Toxicity

antiprotozoal drugs, 416 complex with membrane sterols, 547 glycoalkaloids, 279, 284 humans, 279, 284 potatoes, 284 sapogenols, 456 starfishes, 340

Traditional medicine, 401, 415 Brazilian, 402 Peruvian, 402 percent of the population using, 383 developing countries, 383

Transglycosylation, 274-275 Tremasterols, 350 Tribulosides, 310 Tribulosin, 358, 360-363, 367-369 Tribulus toxicity

bladder, 357 kidney, 357 leaf extract, 367 malaria, 357 sheep toxicity, 357

Trichoderma strains growth inhibition, 569 ion permeability, 531, 532 nonsensitive, 530, 534 resistant to saponins, 534 sensitive, 530, 534

Trichophyton mentagrophytes long life, 535 C.neoformans,535 liposomes, 535

Trichophyton soudanense, 425 Trigonellosides, 310 Trilline, 323 Triplosides, 230-232, 235, 237 Triterpene saponins

in food and beverage plants, 9, 12 of Scilla pervians, 107-108 spermicidal activity, 235 structures, 229-232

Triterpenoid acids of dietary origin, 453

Triton X-100, 51-52,74,76 Tuberculosis, 429 Tuberosides, 310, 320-321 Tubocaposide B, 266 Tumor necrosis factor, 487 Two-stage carcinogenesis test, 90, 94, 97

UDP-galactose, UDP-glucose, 71-78 UDP-galactose: tomatidine

galactosy ltransferases activity, 74, 79 assay, 73 molecular weight, 73 purification, 72-73, 76-77 specificity, 78

UDP-glucose: diosgenin/solasodine glucosyltransferases, 47-54

assay for, 49 occurrence, 48 molecular weight 49 phospholipids, 53 purification, 52

UDP-glucose: diosgenin/tigogenin glucosyltransferases, 37-45

assay for, 38-39 occurrence, 39 properties, 42-43, 47-51, 54 purification, 38-42 specificity, 41-42

UDP-glucuronic acid, 77-78 Ulcers, 431 Ursane, 205 Uterine cancer, 495 Utero-contracting saponins

ardisicrenosides, 494 Uzarigenin, 220

Varicella-zoster virus, 263

605

Vegetarians European and Asiatic countries, 472

Vesicular stomatitis virus, 407 Veterinary vaccines

anti parasite vaccines for malaria, babesiosis, and trypanosomiasis, 185

foot-and-mouth disease, 185 Vietnamese ginseng, 129

discovery and distribution, 129-130 saponins

extraction, 130 structure, 133-136 varieties, 130-132

Vina-ginsenosides, 131-133, 136, 138, 139, 142, 144, 147

Vinblastine, 285 Vincristine, 108 Virucidal effects, 251 Virus-infected cells, 410 Vulpecholic acid, 449

Walker tumor, 115 Warts,285 Western blot analysis, 68 Wheat

606

pathogens, 548 White ginseng, 94 Wistariasaponins, 89, 269 Wistin, 89 Wrinkles, 429 Wound-healing activities, 4, 430-431,495

Xiebai, drugs use, 512

Yamogenin, 37, 39,41-42,45,310,433 Yeast, 538 Yield of saponin from Dracaena spp for

commerce, 426 Yucca,4, 11 Yuccosides, 310, 322

Zanhic acid, 565, 568 Zimbabwean-Danish project

agronomic investigations, 154 biological activities, 160 chemical and analytical investigations,

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