The Biosynthesis of mycotoxins: a study in secondary metabolism PDF
Preview The Biosynthesis of mycotoxins: a study in secondary metabolism
The Biosynthesis of Mycotoxins A STUDY IN SECONDARY METABOLISM Contributors John A. Anderson D. J. Robins W. Breitenstein U. Sankawa J. D. Bu'Lock Pieter S. Steyn Heinz G. Floss Ch. Tamm Burchard Franck Robert Vleggaar Cedric W. Holzapfel Philippus L. Wessels G. W. Kirby Mikio Yamazaki ?????? Zamir The Biosynthesis of Mycotoxins A STUDY IN SECONDARY METABOLISM Edited by Pieter S. Steyn National Chemical Research Laboratory Council for Scientific and Industrial Research Pretoria, South Africa 1980 ACADEMIC PRESS A Subsidiary of Harcourt Brace Jovanovich, Publishers New York London Toronto Sydney San Francisco COPYRIGHT © 1980, BY ACADEMIC PRESS, INC. ALL RIGHTS RESERVED. NO PART OF THIS PUBLICATION MAY BE REPRODUCED OR TRANSMITTED IN ANY FORM OR BY ANY MEANS, ELECTRONIC OR MECHANICAL, INCLUDING PHOTOCOPY, RECORDING, OR ANY INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT PERMISSION IN WRITING FROM THE PUBLISHER. ACADEMIC PRESS, INC. Ill Fifth Avenue, New York, New York 10003 United Kingdom Edition published by ACADEMIC PRESS, INC. (LONDON) LTD. 24/28 Oval Road, London NW1 7DX Library of Congress Cataloging in Publication Data Main entry under title: The Biosynthesis of Mycotoxins. Includes bibliographies and index. 1. Mycotoxins—Synthesis. 2. Metabolism, Secondary. 3. Fungi—Physiology. I. Steyn, Pieter S. [DNLM: 1. Mycotoxins—Biosynthesis. QW630 B615] QP632.M9B56 599.02'326 80-12013 ISBN 0-12-670650-6 PRINTED IN THE UNITED STATES OF AMERICA 80 81 82 83 9 8 7 6 5 4 3 2 1 Contents List of Contributors ix Foreword xi Preface xiii / Mycotoxins as Secondary Metabolites J. D. BULOCK I. Introduction 1 II. Diversity 1 III. Occurrence 4 IV. Regulation 7 V. Function 13 References 16 2 Biosynthesis of Ergot Toxins HEINZ G. FLOSS AND JOHN A. ANDERSON I. Introduction 18 II. The Alkaloids of Ergot 19 III. Biosynthesis of the Ergoline System 30 IV. Biosynthesis of Lysergic Acid Derivatives 49 V. Enzymology and Physiology of Ergot Alkaloid Biosynthesis 57 VI. Conclusion 62 References 62 3 The Biosynthesis of Trichothecene Mycotoxins CH. TAMM AND W. BREITENSTEIN I. Introduction 69 II. Biosynthesis of Trichothecenes 79 III. Biosynthesis of the Roridins and Verrucarins 93 References 101 ν VI Contents 4 The Biosynthesis of Aflatoxin and Its Congeners PIETER S. STEYN, ROBERT VLEGGAAR, AND PHILIPPUS L. WESSELS I. Introduction 105 II. Structural Types Biogenetically Related to the Anatoxins 108 III. The Biosynthetic Study of Aflatoxin and Its Congeners 116 IV. The Sequence of the Aflatoxin Biosynthetic Pathway: Elucidation by Using Blocked Mutants, Enzyme Inhibitors, and Conversion of Potential Precursors 140 V. Biosynthetic Scheme 143 References 150 5 The Biosynthesis of the Ergochromes BURCHARD FRANCK I. Introduction 157 II. Hypotheses on Ergochrome Biosynthesis 160 III. Methodology 163 IV. Investigation of Ergochrome Biosynthesis with Labeled Precursors 173 V. Biosynthesis of Related Secoanthraquinones 183 VI. Biomimetic Reactions 186 References 189 6 The Biosynthesis of Neurotropic Mycotoxins MIKIO YAMAZAKI I. Introduction 193 II. Citreoviridin 194 III. Maltoryzine 197 IV. Aspergillic Acid and Related Pyrazine Oxides 199 V. Fumitremorgin, Verruculogen, and Roquefortine 204 VI. Paxilline, Paspaline, and Related Metabolites 210 VII. Tryptoquivalines 213 VIII. Slaframine 218 References 220 7 The Biosynthesis of Patulin and Penicillic Acid LOLITA Ο. Ζ AMIR I. Introduction 224 Contents VU II. Biogenetic Theories 228 III. Methodology Followed during the Study 234 IV. Origin of the Aromatic Precursors 237 V. Secondary Transformations of the Aromatic Precursors 244 VI. Cleavage of the Aromatic Precursors 253 VII. Derailment Metabolites 256 VIII. Metabolic Grids and Concluding Remarks 258 References 266 8 The Biosynthesis of the Cytochalasans CH. TAMM I. Introduction 269 II. Structure 274 III. Biosynthesis 277 IV. Biosynthetic Scheme 290 Addendum 297 References 297 9 The Biosynthesis of Gliotoxin and Related Epipolythiodioxopiperazines G. W. KIRBY AND D. J. ROBINS I. Introduction 301 IL Survey of Structural Types 302 III. The Biosynthesis of Gliotoxin 308 IV. The Biosynthesis of the Aranotins 317 V. The Biosynthesis of Sporidesmin 320 VI. Conclusions 322 Addendum 324 References 325 10 The Biosynthesis of Cyclopiazonic Acid and Related Tetramic Acids CEDRIC W. HOLZAPFEL I. Introduction 327 II. The Structures of Naturally Occurring Tetramic Acids 329 III. The Biosynthesis of Tetramic Acids 330 IV. Enzymes in the Biosynthesis of a-Cyclopiazonic Acid 336 V. The Mechanism of the Oxidative Cyclization of β-Cyclopiazonic Acid 344 viii Contents VI. Metabolic Development of Pénicillium cyclopium during α-Cyclopiazonic Acid Production 346 VII. Links between Primary Metabolism and the Synthesis of α-Cyclopiazonic Acid 350 VIII. Summary 352 References 353 11 The Biosynthesis of Anthraquinonoid Mycotoxins from Pénicillium islandicum Sopp and Related Fungi U. SANKAWA I. Introduction 357 II. Chemical Studies of the Anthraquinonoid Mycotoxins 358 III. Biosynthetic Origin of Anthraquinonoid Mycotoxins 365 IV. Metabolic Relationship of the Anthraquinonoids Produced by Pénicillium islandicum and Related Fungi 372 V. Biomimetic Synthesis of Anthraquinonoids 391 References 393 12 The Biosynthesis of Some Miscellaneous Mycotoxins ROBERT VLEGGAAR AND PIETER S. STEYN I. Introduction 395 II. Ochratoxin and Related Dihydroisocoumarins 397 III. Citrinin 403 IV. Citromycetin 405 V. Zearalenone and Related Metabolites 406 VI. Rubratoxins and Related Metabolites 408 VII. Xanthocillins 410 VIII. Toxic Furanosesquiterpenoids 412 IX. Diplosporin 413 X. Griseofulvin 415 References 419 Index 423 List of Contributors Numbers in parentheses indicate the pages on which the authors' contributions begin. John A. Anderson (17), Department of Chemistry, Texas Tech University, Lubbock, Texas 79409 W. Breitenstein (69), Central Research Laboratories, Ciba-Geigy AG, 4002 Basel, Switzerland J. D. Bu'Lock (1), Weizmann Microbial Chemistry Laboratory, Depart ment of Chemistry, The University, Manchester M13 9PL, England Heinz G. Floss (17), Department of Medicinal Chemistry and Pharmacog nosy, School of Pharmacy and Pharmacal Sciences, Purdue Univer sity, West Lafayette, Indiana 47907 Burchard Franck (157), Institute for Organic Chemistry, University of Munster, D-4400 Munster, West Germany Cedric W. Holzapfel (327), Department of Chemistry, Rand Afrikaans University, Johannesburg 2000, South Africa G. W. Kirby (301), Chemistry Department, The University, Glasgow G12 8QQ, Scotland D. J. Robins (301), Chemistry Department, The University, Glasgow G12 8QQ, Scotland U. Sankawa (357), Faculty of Pharmaceutical Sciences, University of Tokyo, Bunkyo-ku, Tokyo, Japan Pieter S. Steyn (105, 395), National Chemical Research Laboratory, Council for Scientific and Industrial Research, Pretoria 0001, South Africa Ch. Tamm (69, 269), Institute of Organic Chemistry, University of Basel, 4056 Basel, Switzerland Robert VIeggaar (105, 395), National Chemical Research Laboratory, Council for Scientific and Industrial Research, Pretoria 0001, South Africa Philippus L. Wessels (105), National Chemical Research Laboratory, Council for Scientific and Industrial Research, Pretoria 0001, South Africa ix
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