Alkaloids: Biochemistry, Ecology, and Medicinal Applications

492 Pages·1998·12.29 MB·English

by  Margaret F. Roberts

Alkaloids
Biochemistry, Ecology, and
Medicinal Applications
Alkaloids
Biochemistry, Ecology, and
Medicinal Applications
Edited by
Margaret F. Roberts
TheUniversityofLondon
London, England
and
Michael Wink
UniversityofHeidelberg
Heidelberg,Germany
Springer Science+Business Media, LLC
Library of Congress Cataloging-in-Publication Data
Alkaloids biochemistry. ecology. and medicinal applications I edited
by Margaret F. Roberts and Michael Hink.
p. em.
Includes bibliographical references and index.
1. Alkaloids. I. Roberts. M. F. (Margaret F.) II. Hink.
Michael.
QP801.A34A44 1998
572' .549-·-dc21 98-17602
CIP
ISBN 978-1-4419-3263-1 ISBN 978-1-4757-2905-4 (eBook)
DOI 10.1007/978-1-4757-2905-4
© 1998 Springer Science+Business Media New York
Originally published by Plenum Press, New York 1998.
Softcover reprint of the hardcover 1s t edition 1998
http://www.plenum.com
1098765432 1
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
Contributors
J. C.Braekman • Laboratory of Bio-Organic Chemistry, Free University of Brussels,
50-1050 Brussels, Belgium
D. Daloze • Laboratoryof Bio-OrganicChemistry,FreeUniversityof Brussels,50-1050
Brussels, Belgium
RainerEbel • Julius von Sachs Institute for Biological Sciences, Department of Phar
maceutical Biology, University of Wtirzburg,D-97082 Wiirzburg, Germany
U. Eilert • Institute for Pharmaceutical Biology, Technical University of Braun
schweig, D-38106 Braunschweig, Germany
A. H. C. Hoult • Department of Agronomy and Soil Science, University of New
England, Armidale, NSW 2351, Australia
J. V. Lovett • Grains Research and Development Corporation, Kingston, ACT 2604,
Australia
Isamu Murakoshi • Faculty of Pharmaceutical Sciences, Laboratory of Molecular Bi
ology and Biotechnology, Research Center of Medicinal Resources, Chiba Univer
sity, Inage-ku, Chiba 263, Japan
H. D. Neuwinger • Department of Chemistry, University of Heidelberg, D-69120
Heidelberg, Germany (Retired). Present address: Hauptstrasse 190, D-68789 St.
Leon-Rot, Germany
J.M.Pasteels • Laboratory of Animal andCellular Biology,Free University of Brus
sels, 50-1050 Brussels, Belgium
Peter Proksch • Julius von Sachs Institute for Biological Sciences, Department of
Pharmaceutical Biology, University of Wtirzburg, D-97082 Wtirzburg, Germany
MargaretF. Roberts • TheCentreforPharmacognosy,SchoolofPharmacy, University
of London, London WCIN lAX, England
RichardJ.Robins • Laboratoire d'Analyse Isotopique et Electrochimique de Metabo
lismes, CNRS UPRES-A 6006, University of Nantes, BP 92208, F-44322 Nantes
Cedex 03, France
v
vi Contributors
Kazuki Saito • Faculty of Pharmaceutical Sciences, Laboratory of Molecular Biology
and Biotechnology, Research Center of Medicinal Resources, Chiba University,
Inage-ku, Chiba 263, Japan
T. Schmeller • Institutefor Pharmaceutical Biology, Universityof Heidelberg,D-69l20
Heidelberg, Germany
F. R. Stermitz • Department of Chemistry, Colorado State University, Fort Collins,
Colorado 80523
R. Verpoorte • Division of Pharmacognosy, LeidenlAmsterdam Center for Drug Re
search, University of Leiden, 2300 RA Leiden, The Netherlands
Peter G. Waterman • Phytochemistry Research Laboratories, University of Strath
clyde, Glasgow G1 lXW, Scotland
Michael Wink • Institute for Pharmaceutical Biology, University of Heidelberg,
D-69120 Heidelerg, Germany
Preface
Wehave tried, inthis book, toprovideasurvey ofrecent scientificthinkingon thebiology
of that heterogenous group of secondary metabolites, the alkaloids. To this end, we have
prevailed on scientists who are specialists in their particular areas to define the current
thinking in their areas of expertise. G. R. Waller and E. K. Nowacki edited Alkaloid
Biology and Metabolism in Plants in 1978. The present volume can be regarded as a
sequel.
The book is designed for use by advanced students and professional workers in the
agricultural, biological, and pharmaceutical sciences, natural products chemistry, bio
chemistry,and botany. Each chapterisreferencedwith itsown setofreview and specialist
references.Chaptersarearrangedinfourparts:PartIisanintroductioncoveringsomeofthe
historical uses of alkaloids; Part II considers the biochemistry of alkaloid production in
plants; Part III discusses ecology and includes marine invertebrates, animals, and plant
parasites;andPartIVstudies alkaloidsasantimicrobialsandreviews thecurrentmedicinal
use. The volumeis an attempt toput into one bookcurrentthoughts inthese areas and as
such cannot be exhaustive on such a large and diverse group of constituents. For other
details the reader should consult such reviews as The Alkaloids, first edited by R. H.
Manske, later by A. Brossi and G. A. Cordell, 1952-1996, Academic Press, New York;
Alkaloids: Chemical and Biological Perspectives, edited by S. W.Pelletier, 1983-1996,
PergamonPress,Oxford;andTheChemicalSocietySpecialistReports onNatural Products.
This bookhas broughttogethercontributionsfrom friends andcolleaguesfrom many
parts ofthe world. Aseditors, wewould like tothankall those who have taken part inthe
writing and preparation of this book.
M. F.ROBERTS
M. WINK
vii
Contents
Chapter 1
Introduction
MargaretF. Roberts and Michael Wink
1. Introduction......... ..... .... ..... .. ... .... .. .... ...... ........ .. 1
2. HistoricalImportanceof Alkaloids................................... 1
3. Biochemistry... ........ ... .... .. .... ..... .. ....... ....... ..... ... 2
3.1. Classificationof Alkaloids..................................... 2
3.2. BiogeneticGroupingof Alkaloids. .............................. 3
3.3. OccurrenceandDistribution ....................... 3
4. Ecology.. ... .. .... .. .. ...... .. ..... .. .... .... ... .... .. ... ... ... . 4
5. Pharmacological Activities.......................................... 5
References....................................................... 6
Part I. Historical and Cultural Perspectives
Chapter2
AShort History of Alkaloids
Michael Wink
1. Introduction...... ..... .... ... ..... ........ ............ ...... .. .. . 11
2. AlkaloidsandAlkaloid-Producing Plantsin Antiquity.................... 12
2.1. Useof Alkaloid-Producing Plantsin EarlyMedicine................ 12
2.2. Roleof AlkaloidsandAlkaloidalPlantsfor"Murder" and"Magic" ... 14
3. AlkaloidalPlantsandFungiPlayingan ImportantRole
in theHistoryofMankind. ......................................... 17
3.1. Aconitum napellus (FamilyRanunculacaea) ....................... 17
3.2. Amanita muscaria (FamilyAmanitaceae)......................... 18
3.3. Areca catechu (FamilyArecaceae) .. ............................ 19
3.4. Aristolochia clematitis (FamilyAristolochiaceae) 19
3.5. Atropa belladonna (FamilySolanaceae) .......................... 20
ix
x Contents
3.6. Banisteriopsis caapa, B. inebrians (Family Malpighiaceae) ... ....... 22
3.7. Buxus sempervirens (Family Buxaceae) .......................... 22
3.8. Camellia sinensis (FamilyTheaceae) ............................ 23
3.9. Chelidonium majus (FamilyPapaveraceae)........................ 24
3.10. Clavicepspurpurea (Family Hypocreaceae)....................... 25
3.11. Colchicum autumnale (Family Liliaceae) ......................... 26
3.12. Conium maculatum (Family Umbelliferae)..... .. ........... ..... . 27
3.13. Datura metel (Family Solanaceae) 28
3.14. Delphinium consolida (Family Ranunculaceae) .................... 28
3.15. Dictamnus albus (Family Rutaceae) ............................. 29
3.16. Ephedrafragilis (Family Ephedraceae). .. . . .. 29
3.17. Erythroxylum coca (Family Erythroxylaceae).. .................... 30
3.18. Hyoscyamus niger,H. albus, H. muticus (Family Solanaceae) ........ 31
3.19. Lophophora williamsii (Family Cactaceae).. ..... . 32
3.20. Lupinus albus (Family Leguminosae) ............................ 32
3.21. Lycopodium clavatum, L annotinum (Family Lycopodiaceae) ........ 33
3.22. Mandragora officinarum, M. autumnalis (Family Solanaceae) ........ 34
3.23. Nicotiana tabacum (Family Solanaceae). ......................... 35
3.24. Papaver somniferum (Family Papaveraceae) 35
3.25. Peganum harmala (Family Zygophyllaceae) 37
3.26. Physostigma venenosum (FamilyLeguminosae). ................... 38
3.27. Psilocybe mexicana (Family Agaricaceae) ........................ 38
3.28. Punica granatum (Family Punicaceae) ........................... 39
3.29. Ruta graveolens (Family Rutaceae). ............................. 40
3.30. Solanum dulcamara (Family Solanaceae)......................... 40
3.31. Taxusbaccata (Family Taxaceae) ............................... 41
3.32. Turbinacorymbosa (FamilyConvolvulaceae). ..................... 42
3.33. Veratrumalbum (Family Liliaceae). ............................. 42
References....................................................... 44
Major Reviews .............................................. 44
Key References.............................................. 44
Chapter 3
Alkaloids in Arrow Poisons
H. D. Neuwinger
1. Introduction........... .. .. ......... .... .. .. ....... ..... .. ..... .. . 45
2. African Arrow Poisons............................................. 46
2.1. Poisoned Weapons ........................................... 47
2.2. Poison Preparation ........................................... 49
2.3. Plant Sources and Their Active Principles ........................ 50
3. South American Arrow Poisons. ..................................... 71
3.1. Classification and Composition. ................................ 72
3.2. Chemistry. .. .. ..... .. ..... .. ..... ............. .. ........... 73
3.3. Pharmacology, Toxicology. .................................... 74
3.4. Medicinal Use............................................... 75
Contents xi
3.5. Other Plant Arrow Poisons 76
4. Asian Arrow Poisons .............................................. 77
4.1. Indonesia, Borneo, Philippines, Hainan, Vietnam,Cambodia ......... 78
4.2. Burma. Thailand, Malaysia .................................... 79
Appendix: Composition of African Arrow Poisons ...................... 81
References....................................................... 82
General References. .......................................... 82
Specific References 83
Part II. Biochemistry
Chapter 4
Chemical Taxonomy of Alkaloids
Peter G. Waterman
1. Introduction... ...... .... .. ... ..... ..... ..... .. ..... ......... ..... 87
2. What Is an Alkaloid?.............................................. 87
2.1. A UnifyingTheme in the Biosynthesis of True Alkaloids............ 88
3. The Impact of Alkaloids on Taxonomy. ............................... 88
3.1. Alkaloids Originating from Tyrosine (and Phenylalanine),
UsualIy through Dopa 90
3.2. Indole-seco-Loganin-Derived Alkaloids :........ 96
3.3. Anthranilic Acid as an Alkaloid Substrate ........................ 98
3.4. Alkaloids from Ornithine and Lysine ............................ 100
3.5. Pseudoalkaloids. .. .. ... .... ... ... .. .. .......... .... .... .... .. 104
4. Concluding Comments. ............................................ 105
References....................................................... 105
General Reviews. ............................................ 105
Key References............................................... 106
Chapter 5
Enzymology of Alkaloid Biosynthesis
Margaret F. Roberts
I. Introduction........... ..... .... ... ... .. .......... .... ... .. ..... .. 109
2. Biosynthesis of Acetate-Derived Simple Piperidine Alkaloids. ............ 110
3. Biosynthesis of Quinolizidine Alkaloids. .............................. 112
4. Biosynthesis of Benzylisoquinoline Alkaloids. ......................... 114
4.1. The Formation of (S)-Norcoclaurine............................. 114
4.2. Biosynthesis of the Tetrahydroberberine Alkaloids.................. 116
4.3. The Route to the Protopine and Benzophenanthridine Alkaloids 118
4.4. Biosynthesis of the Morphinan Alkaloids :............ 120
5. Indole Alkaloid Biosynthesis. ....................................... 121
5.1. Formation of (S)-Strictosidine.................................. 123