recent advances in phytochemistry volume 29 Phytochemistry of Medicinal Plants

Transcription

1 recent advances in phytochemistry volume 29 Phytochemistry of Medicinal Plants

2 RECENT ADVANCES IN PHYTOCHEMISTRY Proceedings of the Phytochemical Society of North America General Editor: John T. Romeo, University of South Florida, Tampa, Florida Recent Volumes in the Series: Volume 20 The Shikimic Acid Pathway Proceedings of the Twenty-fifth Annual Meeting of the Phytochemical Society of North America, Pacific Grove, California, June, 1985 Volume 21 The Phytochemical Effects of Environmental Compounds Proceedings of the Twenty-sixth Annual Meeting of the Phytochemical Society of North America, College Park, Maryland, July, 1986 Volume 22 Opportunities for Phytochemistry in Plant Biotechnology Proceedings of the Twenty-seventh Annual Meeting of the Phytochemical Society of North America, Tampa, Florida, June, 1987 Volume 23 Plant Nitrogen Metabolism Proceedings of the Twenty-eighth Annual Meeting of the Phytochemical Society of North America, Iowa City, Iowa, June, 1988 Volume 24 Biochemistry of the Mevalonic Acid Pathway to Terpenoids Proceedings of the Twenty-ninth Annual Meeting of the Phytochemical Society of North America, Vancouver, British Columbia, Canada, June, 1989 Volume 25 Modern Phytochemical Methods Proceedings of the Thirtieth Annual Meeting of the Phytochemical Society of North America, Quebec City, Quebec, Canada, August, 1990 Volume 26 Phenolic Metabolism in Plants Proceedings of the Thirty-first Annual Meeting of the Phytochemical Society of North America, Fort Collins, Colorado, June, 1991 Volume 27 Phytochemical Potential of Tropical Plants Proceedings of the Thirty-second Annual Meeting of the Phytochemical Society of North America, Miami Beach, Florida, August, 1992 Volume 28 Genetic Engineering of Plant Secondary Metabolism Proceedings of the Thirty-third Annual Meeting of the Phytochemical Society of North America, Pacific Grove, California, June.July, 1993 Volume 29 Phytochemistry of Medicinal Plants Proceedings of the Thirty-fourth Annual Meeting of the Phytochemical Society of North America, August, 1994, Mexico City, Mexico A Continuation Order Plan is available for this series. A continuation order will bring delivery of each new volume immediately upon publication. Volumes are billed only upon actual shipment. For further information please contact the publisher.

3 recent advances in phytochemistry volume 29 Phytochemistry of Medicinal Plants Edited by John T. Arnason Universite d' Ottawa Ottawa, Ontario, Canada Rachel Mata Universidad Nacional Autonoma de Mexico Coyoacan, Mexico and John T. Romeo University of South Florida Tampa, Florida SPRINGER SCIENCE+BUSINESS MEDIA, LLC

4 Library of Congress Catalog1ng-1n-PublIcatIon Data Phytochemistry of medicinal plants / edited by John T. Arnason, Rachel Mata, and John T. Romeo. p. cm. (Recent advances in phytochemistry ; v. 29) "Proceedings of the Thirty-fourth Annual Meeting of the Phytochemica1 Society of North America on phytochemistry of medical plants, held August 15-19, 1994, in Mexico City, Mexico"--T.p. verso. Includes bibliographical references and index. ISBN Materia medica, Vegetable Congresses. 2. Medicinal plants- -Congresses. 3. Phytochemistry Congresses. I. Arnason, J. T., II. Mata, Rachel. III. Romeo, John T. IV. Phytochemica1 Society of North America. Meeting (34th : Mexico City, Mexico) V. Series. RS164.P '.321 dc CIP Cover photograph: Comparative Molecular Field Analysis (CoMFA) model of the germacranolide sesquiterpene lactone, parthenolide. Green areas indicate molecular regions where activity would be enhanced by greater steric bulk. Yellow areas indicate molecular regions where activity would be enhanced by less steric bulk. Red areas indicate molecular regions where activity would be enhanced by greater negative electrostatic potential. Blue areas indicate molecular regions where activity would be enhanced by greater positive electrostatic potential. Such models aid the rational design of natural product derivatives with enhanced activity and specificity. Proceedings of the Thirty-Fourth Annual Meeting of the Phytochemical Society of North America on Phytochemistry of Medicinal Plants, held August 15-19, 1994, in Mexico City, Mexico ISBN ISBN (ebook) DOI / Springer Science+Business Media New York 1995 Originally published by Plenum Press, New York in 1995 Softcover reprint of the hardcover 1st edition 1995 All rights reserved No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permission from the Publisher

5 PREFACE Phytochemicals from medicinal plants are receiving ever greater attention in the scientific literature, in medicine, and in the world economy in general. For example, the global value of plant-derived pharmaceuticals will reach $500 billion in the year 2000 in the OECD countries. In the developing countries, over-the-counter remedies and "ethical phytomedicines," which are standardized toxicologically and clinically defined crude drugs, are seen as a promising lowcost alternatives in primary health care. The field also has benefited greatly in recent years from the interaction of the study of traditional ethnobotanical knowledge and the application of modem phytochemical analysis and biological activity studies to medicinal plants. The papers on this topic assembled in the present volume were presented at the annual meeting of the Phytochemical Society of North America, held in Mexico City, August 15-19, This meeting location was chosen at the time of entry of Mexico into the North American Free Trade Agreement as another way to celebrate the closer ties between Mexico, the United States, and Canada. The meeting site was the historic Calinda Geneve Hotel in Mexico City, a most appropriate site to host a group of phytochemists, since it was the address of Russel Marker. Marker lived at the hotel, and his famous papers on steroidal saponins from Dioscorea composita, which launched the birth control pill, bear the address of the hotel. The meeting was organized by Rachel Mata, Jose Calderon, Rogelio Pereda-Miranda, Guillermo Delgado, and Jose Antonio Serratos in Mexico, and by John Amason and Dennis Awang in Canada. We are grateful to the Facultad de Quimica, Universidad Nacional Autonoma de Mexico for assistance and to the many students who assisted at the meeting. The papers presented in this volume are representative of the new trends in medicinal plants research. Wagner, Pezzuto, and Beutler et at. provide chapters that demonstrate the importance of such plant-based medicinals as adaptogens, immunostimulants, cancer preventatives, and anti-aids or anti-cancer agents. Bye et al., Pereda-Miranda, Vlietinck et al., Niemeyer, and Johns and Chapman provide insight into ethnobotanical traditions, and how these can lead to new phytochemical and biological activity discoveries. As is appropriate for a meeting v

6 vi PREFACE held in Mexico, the rich tradition of medicinal plants of Latin America is emphasized. The two chapters by Wolfender and Hostettmann and Loyola-Vargas and Miranda-Ham describe state-of-the-art techniques of phytochemical analysis and root culture in medicinal plant studies, while MarIes et al. apply the latest modeling techniques to study antimigraine activity of sesquiterpene lactones. Finally Rodriguez-Hahn and Gu et al. provide in-depth reviews covering the phytochemistry and biological activity of two highly interesting groups of compounds, acetogenins and neo-c1erodane diterpenes. We acknowledge the assistance of Ms. Diane Field for her skillful preparation of the camera-ready manuscript. Rachel Mata, Universidad Nacional Autonoma de Mexico John Thor Amason, Universite d'ottawa John Romeo, University of South Florida

7 CONTENTS 1. Immunostimulants and Adaptogens from Plants Hildebert K. M. Wagner 2. Natural Product Cancer Chemopreventive Agents John M. Pezzuto 3. Antiviral and Antitumor Plant Metabolites John A. Beutler, John H. Cardellina II, James B. McMahon, Robert H. Shoemaker, and Michael R. Boyd 4. Biological Diversity of Medicinal Plants in Mexico Robert Bye, Edelmira Linares, and Eric Estrada 5. Bioactive Natural Products from Traditionally Used Mexican Plants.. 83 Rogelio Pereda-Miranda 6. Bioassay-Guided Isolation and Structure Elucidation of Pharmacologically Active Plant Substances A. J. Vlietinck, L. A. C. Pieters, and D. A. Vander Berghe 7. Biologically Active Compounds from Chilean Medicinal Plants Hermann M. Niemeyer vii

8 viii CONTENTS 8. Phytochemicals Ingested in Traditional Diets and Medicines as Modulators of Energy Metabolism Timothy Johns and Laurie Chapman 9. Applications of Liquid Chromatography-Mass Spectrometry to the Investigation of Medicinal Plants Jean-Luc Wolfender and Kurt Hostettmann 10. Root Culture as a Source of Secondary Metabolites of Economic Importance Victor M. Loyola-Vargas and Maria de Lourdes Miranda-Ham 11. Annonaceous Acetogenins: Potent Mitochondrial Inhibitors with Diverse Applications Zhe-Ming Gu, Geng-Xian Zhao, Nicholas H. Oberiies, Lu Zeng, and Jerry L. McLaughlin 12. Neo-Clerodane Diterpenoids from American Salvia Species Lydia Rodriguez-Hahn, Baldomero Esquivel, and Jorge Cardenas 13. Sesquiterpene Lactones Revisited: Recent Developments in the Assessment of Biological Activities and Structure Relationships Robin J. Maries, Liliana Pazos-Sanou, Cesar M. Compadre, John M. Pezzuto, Elzbieta Bloszyk, and 1. Thor Amason Index