Phytochemistry of Medicinal Plants

369 Pages·1995·10.2 MB·English

by  Hildebert K. M. Wagner (auth.)

recent advances in phytochemistry
volume 29
Phytochemistry of
Medicinal Plants
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
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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
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 978-1-4899-1780-5
1. Materia medica, Vegetable—Congresses. 2. Medicinal plants-
-Congresses. 3. Phytochemistry—Congresses. I. Arnason, J. T.,
1948- . II. Mata, Rachel. III. Romeo, John T. IV. Phytochemica1
Society of North America. Meeting (34th : 1994 .- Mexico City,
Mexico) V. Series.
RS164.P536 1995
615' .321—dc20 95-39616
CIP
Cover photograph: Comparative Molecular Field Analysis (CoMFA) model of the
germacranolide sesquiterpene lactone, parthenolide. Green areas indicate molecu
lar 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 978-1-4899-1780-5 ISBN 978-1-4899-1778-2 (eBook)
DOI 10.1007/978-1-4899-1778-2
© 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
1098765432
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
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 low
cost 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, 1994. 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
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 com
pounds, acetogenins and neo-c1erodane diterpenes.
We acknowledge the assistance of Ms. Diane Field for her skillful prepa
ration of the camera-ready manuscript.
Rachel Mata, Universidad Nacional Autonoma de Mexico
John Thor Amason, Universite d'Ottawa
John Romeo, University of South Florida
CONTENTS
1. Immunostimulants and Adaptogens from Plants
Hildebert K. M. Wagner
2. Natural Product Cancer Chemopreventive Agents ................. 19
John M. Pezzuto
3. Antiviral and Antitumor Plant Metabolites ....................... 47
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. . . . . . . . . . . . . . .. 65
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 .................. 113
A. J. Vlietinck, L. A. C. Pieters, and D. A. Vander Berghe
7. Biologically Active Compounds from Chilean Medicinal Plants ...... 137
Hermann M. Niemeyer
vii
viii CONTENTS
8. Phytochemicals Ingested in Traditional Diets and Medicines as
Modulators of Energy Metabolism ......................... 161
Timothy Johns and Laurie Chapman
9. Applications of Liquid Chromatography-Mass Spectrometry to the
Investigation of Medicinal Plants ........................... 189
Jean-Luc Wolfender and Kurt Hostettmann
10. Root Culture as a Source of Secondary Metabolites of Economic
Importance ............................................ 217
Victor M. Loyola-Vargas and Maria de Lourdes Miranda-Ham
11. Annonaceous Acetogenins: Potent Mitochondrial Inhibitors with
Diverse Applications ..................................... 249
Zhe-Ming Gu, Geng-Xian Zhao, Nicholas H. Oberiies, Lu Zeng,
and Jerry L. McLaughlin
12. Neo-Clerodane Diterpenoids from American Salvia Species ......... 311
Lydia Rodriguez-Hahn, Baldomero Esquivel, and Jorge Cardenas
13. Sesquiterpene Lactones Revisited: Recent Developments in the
Assessment of Biological Activities and Structure Relationships ... 333
Robin J. Maries, Liliana Pazos-Sanou, Cesar M. Compadre,
John M. Pezzuto, Elzbieta Bloszyk, and 1. Thor Amason
Index ........................................................ 357
Chapter One
IMMUNOSTIMULANTS AND ADAPTOGENS FROM
PLANTS
Hildebert K. M. Wagner
University of Munich
Institute of Pharmaceutical Biology
D-80333 Munich, Karlstrasse 29
Germany
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . I
Immunostimulants . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2
Currently Available Drugs. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2
Search for New Immunostimulating Drugs ...................... 5
Methods of Screening ..................... . . . . . . . . . . . . . . . . . . 5
Recent Results . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
Adaptogens ................................................... 9
The General Adaptation Syndrome. . . . . . . . . . . . . . . . . . . . . . . . . . . .. 10
Drugs with Putative Adaptogen Activities ....................... II
Verification Methods for Adaptogens . . . . . . . . . . . . . . . . . . . . . . . . . .. 16
Summary and Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 17
INTRODUCTION
The terms "immunostimulants" and "adaptogens" both describe drugs
capable of increasing the resistance of an organism against stressors of variable
origin. Both types of drugs achieve this enhancement primarily by nunspecific
mechanisms of actions. Immunostimulants generally stimulate, in a non-antigen
dependent manner, the function and efficiency of the nonspecific immune
system in order to counteract microbial infections or immunosuppressive states.
Adaptogens are believed to reinforce (increase) the non-specific power of
resistance of the body against physical, chemical or biological noxious agents.
With respect to the mechanisms of action immunostimulants influence primarily
the humoral and cellular immune system, whereas adaptogens are thought to