Handbook of Natural Toxins Toxicology of Plant and Fungal

Compounds 1st Edition

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 Page ii
Disclaimer:
This book is part of a volume set. netLibrary may or may not have
all the companion volumes in eBook format.
Library of Congress Cataloging-in-Publication Data
Toxicology of plant and fungal compounds/edited by Richard F.
Keeler, Anthony T. Tu.
p. cm. (Handbook of natural toxins; v. 6)
Includes bibliographical references and index.
ISBN 0-8247-8375-1
1. Plant toxinsToxicology. 2. MycotoxinsToxicology.
I. Keeler, Richard F. II. Tu, Anthony T. III. Series.
RA1250.T69 1991
615.9'52dc20 90-28581
CIP
This book is printed on acid-free paper.
Copyright © 1991 by MARCEL DEKKER, INC. All Rights
Reserved
Neither this book nor any part may be reproduced or transmitted in
any form or by any means, electronic or mechanical, including
photocopying, microfilming, and recording, or by any information
storage and retrieval system, without permission in writing from
the publisher.
MARCEL DEKKER, INC.
270 Madison Avenue, New York, New York 10016
Current printing (last digit):
10 9 8 7 6 5 4 3 2 1
PRINTED IN THE UNITED STATES OF AMERICA
 Page iii

This volume is dedicated to the memory of Ivar Tidestrom, one of several

plant taxonomists traversing the western United States in the early 1900s.
Without the systematic identification and description of plants and fungi,
study of their toxins would be difficult, confirmatory experiments on sepa-
rate accessions would be impossible, and much valuable research time would
be lost. Those who study natural toxins owe a great deal to taxonomists.
Ivar Tidestrom made several botanical journeys in the early twentieth century
in the western United States from Colorado to California and from southern
Arizona to central Idaho. By 1925 he had described and deposited in the
U.S. National Herbarium nearly 8000 specimens. His book Flora of Utah and
Nevada, published in 1925, has been a valuable aid to many researchers since
that time. In this photo Ivar Tidestrom is shown on one of his many bota-
nizing trips, but in this instance with a handful of kittens rather than plants
(photograph used with permission of the Journal of Natural Products).
 Page v

PREFACE TO THE HANDBOOK

Natural toxins are unique toxins which possess some common
properties, whether they are obtained from plants, microorganisms,
or animals. One common characteristic is that they exert a
pronounced effect on the metabolism and biological functions of
the intoxicated animals with just a minute quantity. Since ancient
times human beings have pondered the physiological effects of
various toxins and venoms. How do these natural poisons work?
Despite possessing some common nature, each toxin, however, has
its unique mode of action and its own characteristic structure.
Drugs are compounds that have specific beneficial effects with a
minute quantity. Usually, natural toxins also have very specific
effects. Therefore, it is not surprising that many natural toxins are
potentially good drugs.
Heretofore, the study of each field of toxins has been taking an
independent pathway. Scientists in a specific toxin field are often
unaware of the activity in other toxin fields. It is thus desirable to
have a primary source of information on all natural toxins so that
scientists in a specific discipline of toxin research can easily obtain
useful information from other toxin researchers.
This seven-volume handbook of toxins includes the following
volumes:
1. Plant and Fungal Toxins
2. Insect Poisons, Allergens, and Other Invertebrate Venoms
3. Marine Toxins and Venoms
4. Bacterial Toxins
5. Reptile Venoms and Toxins
6. Toxicology of Plant and Fungal Compounds
7. Food Poisoning
The editor expresses sincere thanks to Maurits Dekker, Chairman
of the Board of Marcel Dekker, Inc., for initiating this project.
ANTHONY T. TU
 Page vii

PREFACE TO VOLUME 6
Toxicology has blossomed as a science during the last two decades.
That development has been stimulated by a variety of laws passed
to protect human populations from careless use and disposal of
synthetic chemical compounds such as pesticides, herbicides, and
industrial solvents. Naturally occurring toxins also represent
hazards of significant magnitude to humans and animals, although
they are less frequently the subject of popular press reports.
Natural toxins, including those from plants and fungi, have been
responsible for toxicosis of epidemic proportions in humans and
animals throughout history. The problems are particularly frequent
in domestic livestock. These animals are often fed grains and other
feeds that have been improperly dried, cured or stored and on
which there is obvious fungal activity with potential toxin
production. Furthermore, millions of livestock graze on native
plants many of which are poisonous because of contained toxins.
Since the publication, in 1983, of Volume 1 of this series, which
was subtitled Plant and Fungal Toxins, a great deal of exciting
research has been published. We have assembled in this volume 29
chapters describing some of that research. A few chapters update
topics previously treated, but most of the chapters describe in depth
the toxicologic and chemical aspects of other topics. Accordingly,
Volumes 1 and 6 together will provide readers with wide coverage
of the general area of plant and fungal toxins.
Chapters in this volume are assembled into three groups: a group
on plant toxins, a group on fungal toxins, and a group related to
epidemiologic and response considerations. Readers of this
volume, as with Volume 1, will see the diversity of chemical
classes represented among toxins, the range of effects upon
biologic systems, and the variety of expressions of toxicoses.
Research on plant and fungal toxins has yielded significant
solutions to practical toxicoses problems, provided insight into
fundamental chemistry and biology related to the toxicoses, and
generated much useful spinoff in the areas of potential drugs,
pesticides, and herbicides.
 Page viii
The responsibility for the scientific content of each chapter rests
with the individual authors. Any opinions, findings, conclusions, or
recommendations expressed in this publication are those of the
authors and do not necessarily reflect the view of the U.S.
Department of Agriculture, Colorado State University, or any other
organization.
RICHARD F. KEELER
ANTHONY T. TU
 Page ix

CONTENTS
Preface to the Handbook v
Preface to Volume 6 vii
Contributors xiii
Contents of Previous Volumes xvii
Part I. Nature and Toxicity of Plant Toxins
A. Alkaloidal Class
1. Metabolism of Pyrrolizidine Alkaloids 3
H. J. Segall, D. W. Wilson, M. W. Lamé, D. Morin, and
C. K. Winter
2. Teratogenicity of Rangeland Lupinus: Crooked Calf 27
Disease
Richard H. Finnell, Clive C. Gay, and Louise C. Abbott
3. Investigations of the Teratogenic Potential of the 41
Lupine Alkaloid Anagyrine
James E. Meeker and Wendell W. Kilgore
4. Myopathy in Cattle Caused by Thermopsis Montana 61
Dale C. Baker and Richard F. Keeler
5. Toxicosis from Steroidal Alkaloids of Solanum 71
Species
Dale C. Baker, Richard F. Keeler, and William Gaffield
6. Teratogenic Solanum Species and the Responsible 83
Teratogens
Richard F. Keeler, Dale C. Baker, and William Gaffield
 Page x

7. Steroidal Glycoalkaloids in Solanum: Consequences 101

for Potato Breeding and for Food Safety
W. M. J. Van Gelder
8. Solanum Glycoalkaloids: Plant Toxins Possessing 135
Disparate Physiologically Active Structural Entities
William Gaffield, Richard F. Keeler, and Dale C. Baker
9. Swainsonine: A Toxic Indolizidine Alkaloid from the 159
Australian Swainsona Species
Steven M. Colegate, Peter R. Dorling, and Clive R.
Huxtable
10. Swainsonine, the Locoweed Toxin: Analysis and 191
Distribution
Russell J. Molyneux and Lynn F. James
B. Other Classes
11. New Techniques for the Isolation and Identification 217
of Phorbol Esters and Structurally Related Diterpenes
A. Douglas Kinghorn
12. Ricin and Related Plant Toxins: Mechanism of 243
Action and Neurobiological Applications
Ronald G. Wiley and T. N. Oeltmann
13. Plant Terpenoids as Pesticides 269
Stephen O. Duke
14. Poisoning of Livestock by Lantana Plants 297
Michael A. Pass
 15. Role of Phenol Glycosides in Plant-Herbivore 313
Interactions
Paul B. Reichardt, Thomas P. Clausen, and John P.
Bryant
16. Cassia-Induced Myopathy 335
Loyd D. Rowe
17. Position of Perilla Ketone Metabolism by Lung 353
Cytochromes P450: Evidence for the Mechanism of
Bioactivation through Design of an In Vivo Inhibitor of
Toxicity
John E. Garst and William C. Wilson
Part II. Nature and Toxicity of Fungal Toxins
18. Phomopsins: Antimicrotubule Mycotoxins 371
John A. Edgar
 Page xi

19. Phytotoxins from Fungi Attacking Weedy Plants 397

Gary A. Strobel, Doug Kenfield, Greg Bunkers, and
Fumio Sugawara
20. Phytotoxins of Microbial Origin 411
Horace G. Cutler
21. Fungal Elicitors of Plant Phytoalexins 439
Jack D. Paxton
22. Cyclic Peptide Hepatotoxins from Cyanobacteria 459
Val Richard Beasley, Randall A. Lovell, Andrew M.
Dahlem, Wanda M. Haschek, and Stephen B. Hooser
23. Human Poisoning by Mushrooms of the Genus 497
Cortinarius
Kenneth F. Lampe
24. Trichothecene Mycotoxins 523
William B. Buck and Louise-Marie Côté
Part III. Epidemiology and Responses
25. Epidemiology of Plant Poisoning in Humans 559
D. Jesse Wagstaff
26. Antineoplastic Potential and Other Possible Uses of 575
Swainsonine and Related Compounds
Kenneth Olden, Sandra L. White, Sheila A. Newton,
Russell J. Molyneux, and Martin J. Humphries
27. Ultrasonographic Studies on the Fetotoxic Effects of 589
Poisonous Plants on Livestock
 Kip E. Panter, Terrie L. Wierenga, and Thomas D. Bunch
28. Cutaneous Responses to Plant Toxins 611
William L. Epstein
29. Congestive Right-Heart Failure in Cattle: High 635
Mountain Disease and Factors Influencing Incidence
Lynn F. James, Russell J. Molyneux, and A. F. Alexander
Index 645
 Page xiii

CONTRIBUTORS
Louise C. Abbott Department of Veterinary Biosciences, College of
Veterinary Medicine, University of Illinois at Urbana-Champaign,
Urbana, Illinois
A. F. Alexander College of Veterinary Medicine, Colorado State
University, Fort Collins, Colorado
Dale C. Baker Department of Pathology, Colorado State University,
Fort Collins, Colorado
Val Richard Beasley Department of Veterinary Biosciences,
College of Veterinary Medicine, University of Illinois at Urbana-
Champaign, Urbana, Illinois
John P. Bryant Institute of Arctic Biology, University of Alaska,
Fairbanks, Fairbanks, Alaska
William B. Buck Department of Veterinary Biosciences, College of
Veterinary Medicine, University of Illinois at Urbana-Champaign,
Urbana, Illinois
Thomas D. Bunch Utah State University, Logan, Utah
Greg Bunkers Plant Pathology Department, Montana State
University, Bozeman, Montana
Thomas P. Clausen Department of Chemistry, University of Alaska,
Fairbanks, Fairbanks, Alaska
Steven M. Colegate Department of Toxicology and Pharmacology,
School of Veterinary Studies, Murdoch University, Perth, Murdoch,