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Cell Culture and Somatic Cell Genetics of Plants VOLUME 5 Phytochemicals in Plant Cell Cultures Editorial Advisory Board Indra K. Vasil EDITOR-IN-CHIEF Laboratory of Plant Cell and Molecular Biology University of Florida Gainesville, Florida L. Bogorad F. Constabel D. Dudits P. Maliga R. L. Phillips J. Schell O. Schieder T. A. Thorpe Cell Culture and Somatic Cell Genetics of Plants VOLUME 5 Phytochemicals in Plant Cell Cultures Edited by FRIEDRICH CONSTABEL Plant Biotechnology Institute National Research Council Saskatoon, Saskatchewan, Canada INDRA K. VASIL Department of Botany University of Florida Gainesville, Florida Academic Press, Inc. Harcourt Brace Jovanovich, Publishers San Diego New York Berkeley Boston London Sydney Tokyo Toronto COPYRIGHT © 1988 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. 1250 Sixth Avenue San Diego, California 92101 United Kingdom Edition published by ACADEMIC PRESS INC. (LONDON) LTD. 24-28 Oval Road, London NW1 7DX Library of Congress Cataloging-in-Publication Data (Revised for vol. 5) Cell culture and somatic cell genetics of plants. Includes bibliographies and indexes. Contents: v. 1. Laboratory procedures and their applications — v. 2. Cell growth, nutrition, cyto• differentiation, and cryopreservation — —v. 5. Phytochemicals in plant cell culture. 1. Plant cell culture—Collected works. 2. Plant cytogenetics—Collected works. I. Vasil, I. K. QK725.C37 1984 581'.07'24 83-21538 ISBN 0-12-715005-6 (v. 5 : alk. paper) PRINTED IN THE UNITED STATES OF AMERICA 88 89 90 91 987654321 Contents Contributors xiii General Preface xvii Preface xxi Contents of Previous Volumes xxiii Part I Phenylpropanoids, Naphthoquinones, and Anthraquinones 1 Coumarins and Furanocoumarins 3 ULRICH MATERN, HEINER STRASSER, HILKE WENDORFF, and DARIA HAMERSKI I. Introduction 3 II. Coumarins in Crown Gall Tumors 6 III. Constitutive Coumarins 7 IV. Induced Coumarins 7 V. Biosynthesis 10 VI. Regulation of Biosynthesis 15 VII. Physiological Significance 16 References 16 2 Flavonoids 23 W. HINDERER and H. U. SEITZ I. Introduction 23 II. Major Classes of Flavonoids 24 III. Advantages of Cell Cultures in Studies of Flavonoid Biosynthesis 37 IV. Flavonoids in Tissue and Cell Cultures 38 V. Turnover and Degradation 41 VI. Concluding Remarks 42 References 43 ν vi Contents 3 Anthocyanins H. U. SEITZ and W. HINDERER I. Introduction 49 II. Structure of Anthocyanins 50 III. Occurrence of Anthocyanins in Tissue and Cell Cultures 52 IV. Biosynthesis of Anthocyanins 57 V. Regulation of Anthocyanin Biosynthesis in Tissue and Cell Cultures 62 VI. Accumulation of Anthocyanins in the Central Vacuole 67 References 69 4 Proanthocyanidins and Catechins Μ. N. ZAPROMETOV I. Occurrence 77 II. Influence of Phytohormones 80 III. Nutrients and Precursors 82 IV. Effect of Illumination 83 V. Effect of Polyamines 84 VI. Biosynthesis 85 VII. Conclusions 85 References 86 5 Tannins, Lignans, and Lignins Μ. N. ZAPROMETOV I. Introduction 89 II. Tannins 89 III. Lignans 92 IV. Lignins 93 References 95 6 Naphthoquinones MAMORU TABATA I. Introduction 99 II. Naphthoquinones in Cell Cultures 100 III. Biosynthetic Pathways of Naphthoquinones 104 IV. Intracellular Localization of Naphthoquinones 107 V. Regulation of Naphthoquinone Production 107 References 109 7 Anthraquinones H. KOBLITZ I. Introduction 113 II. Quality of Anthraquinones in Callus and Cell Suspension Cultures 115 III. Quantitative Aspects of Anthraquinone Occurrence 127 IV. Biosynthesis 133 References 136 Contents vii Part II Mevalonates 8 Monoterpenes and Sesquiterpenes DEREK V. BANTHORPE I. General 143 II. Monoterpene Biosynthesis 148 III. Sesquiterpene Biosynthesis 151 IV. Biotransformations 152 V. Special Techniques 152 References 154 9 Diterpenes JAMES P. KUTNEY I. Introduction 159 II. Culture Techniques 161 III. Chemical Analysis 162 IV. Cytotoxic Analysis 162 V. Isolation and Characterization of Secondary Metabolites 170 VI. Biotransformation Experiments 174 VII. Conclusions 174 VIII. Studies in Other Laboratories 175 References 176 10 Bufadienolides SUMITA JHA I. Introduction 179 II. Natural Occurrence of Bufadienolides 180 III. Tissue Culture for Production of Bufadienolides 181 IV. Present Status of Tissue Culture of Plants Yielding Bufadienolides 181 V. Conclusion 189 References 189 11 Cardenolides MARTIN LUCKNER and BEATE DIETTRICH I. Cardenolides: Structure, Biosynthesis, and Significance 193 II. Establishment of Digitalis Tissue Cultures 194 III. Biosynthesis of Cardenolides in Digitalis Shoot Cultures 196 IV. Biosynthesis of Cardenolides in Cultures of Somatic Digitalis Embryos 198 V. Transformation of Cardenolides in Parenchyma-like Digitalis Cells 202 VI. Is There a Future for the Biotechnological Production of Cardenolides by Digitalis Cell and Organ Cultures? 205 References 206 12 Saponins (Ginseng Saponins) TSUTOMU FURUYA I. Introduction 213 II. Callus Induction and Selection 214 viii Contents III. Determination of Growth Ratio 216 IV. Separation of Saponins 216 V. High-Performance Liquid Chromatography of Saponins 217 VI. Determination of Saponins 219 VII. Effects of Plant Growth Regulators and Light on Saponin Production and Growth in Static Cultures 219 VIII. Effect of Various Culture Conditions on Saponin Production and Growth in Suspension Cultures 223 IX. Effect of Inhibitors and Precursors on Saponin Production 225 X. Differentiation and Saponin Production 228 XI. Hairy Root Culture and Saponin Production 228 XII. Conclusion 233 References 233 Part HI Alkaloids 13 Phenylalkylamines (Ephedra Alkaloids) H. C. ARYA and K. G. RAMAWAT I. Introduction 237 II. Distribution 238 III. Tissue Culture 239 IV. Conclusion 242 References 242 14 Pyrrolidines, Piperidines, and Pyridines NOBORU HIRAOKA I. Introduction 245 II. Pyrrolidine and Piperidine Alkaloids 246 III. Pyridine Alkaloids 246 IV. Tobacco Alkaloids 248 V. Conclusions and Perspectives 257 References 258 15 Tropanes GIZELLA PETRI I. Introduction 263 II. Material and Methods 265 III. Results and Discussion 267 IV. Summary 273 References 273 16 Quinolizidines and Pyrrolizidines THOMAS HARTMANN I. Introduction 277 II. Quinolizidine Alkaloids 278 III. Pyrrolizidine Alkaloids 283 IV. Conclusion 285 References 285 Contents ίχ 17 Isoquinolines AKIRA IKUTA I. Introduction 289 II. Production of Isoquinolines 290 III. Chemotaxonomic Approach 296 IV. Biotransformation and Biosynthesis 300 V. Accumulation of Protoberberine Alkaloids 305 VI. Immobilized Cells 307 VII. Redifferentiated Plantlets and Alkaloids 308 VIII. Conclusions 311 References 312 18 Isoquinolines (Papaver Alkaloids) MARGARET F. ROBERTS I. Introduction 315 II. Factors that Promote the Production of Morphinan Alkaloids in Tissue Culture 320 III. Biotransformations 328 IV. Conclusions 330 References 330 19 Quinoline Alkaloids of Cinchona R. WIJNSMA and R. VERPOORTE I. Introduction 337 II. Cell Culture Methods 338 III. Analytical Methods 342 IV. Alkaloid Production in Cinchona Tissue Cultures 348 V. Biosynthetic Studies Using Cinchona Tissue Cultures 349 VI. Prospects and Status 351 References 352 20 β-Carbolines and Indole Alkylamines JOCHEN BERLIN and FLORENZ SASSE I. Introduction 357 II. Cell Culture Systems 358 III. Formation of Harman Alkaloids and Serotonin 359 IV. Studies of Biosynthesis and Regulation 364 V. A Biochemical Selection System 366 VI. Outlook 368 References 368 21 Monoterpene Indole Alkaloids from Apocynaceae Other than Catharanthus roseus J. BALSEVICH I. Introduction 371 II. Structural Types of Alkaloids 373 III. Alkaloids from Cell Cultures 376 IV. Conclusions 381 References 381 X Contents 22 Monoterpene Indole Alkaloids (Catharanthus Alkaloids) VINCENZO DELUCA and WOLFGANG G. W. KURZ I. Introduction 385 II. Production of Indole Alkaloids 386 III. Instability of Cell Lines 390 IV. Enzymology of Indole Alkaloid Biosynthesis 391 V. Enzymatic Synthesis of Vindoline and Dimeric Indole Alkaloids 396 VI. Conclusions 397 References 397 23 Purines THOMAS W. BAUMANN and PETER M. FRISCHKNECHT I. Introduction 403 II. Experimental 405 III. Growth and Productivity 406 IV. Biosynthetic Potential 410 V. Stress-Induced Product Formation 412 VI. Conclusions 414 References 415 24 Acridones (Ruta Alkaloids) U. EILERT I. Introduction 419 II. Acridones in Tissue Cultures 420 III. Acridone Patterns 420 IV. Culture Conditions and Acridone Yield 425 V. Elicitation of Acridone Epoxide Accumulation 427 VI. Biosynthesis of Acridone Alkaloids 428 VII. Acridone Alkaloid Localization 429 References 430 25 Terpenoid and Steroid Alkaloids D. GROGER I. Introduction 435 II. Terpenoid Alkaloids 436 III. Steroid Alkaloids 437 IV. Conclusions 445 References 446 26 Betalains H. BOHM and E. RINK I. Introduction 449 II. Betalain-Synthesizing Cell Cultures 451 III. Factors and Conditions of Betalain Formation 455 IV. Regulation of Betalain Biosynthesis 456 V. Results of General Interest 458 VI. Cell Cultures for Production of Food Dyes? 459 VII. Concluding Remarks 460 References 460 Contents xi Part IV Glucosinolates, Polyacetylenes, and Lipids 27 Glucosinolates G. B. LOCKWOOD I. Introduction 467 II. Plant Cell Cultures 469 III. Analytical Methods 469 IV. Culture Conditions 471 V. Conclusions 471 References 472 28 Allium Compounds H. A. COLLIN and D. MUSKER I. Introduction 475 II. Flavor Production in Intact Plants of Allium Species
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  • The Science of Flavonoids the Science of Flavonoids

    The Science of Flavonoids the Science of Flavonoids

    The Science of Flavonoids The Science of Flavonoids Edited by Erich Grotewold The Ohio State University Columbus, Ohio, USA Erich Grotewold Department of Cellular and Molecular Biology The Ohio State University Columbus, Ohio 43210 USA [email protected] The background of the cover corresponds to the accumulation of flavonols in the plasmodesmata of Arabidopsis root cells, as visualized with DBPA (provided by Dr. Wendy Peer). The structure corresponds to a model of the Arabidopsis F3 'H enzyme (provided by Dr. Brenda Winkel). The chemical structure corresponds to dihydrokaempferol. Library of Congress Control Number: 2005934296 ISBN-10: 0-387-28821-X ISBN-13: 978-0387-28821-5 ᭧2006 Springer ScienceϩBusiness Media, Inc. All rights reserved. This work may not be translated or copied in whole or in part without the written permission of the publisher (Springer ScienceϩBusiness Media, Inc., 233 Spring Street, New York, NY 10013, USA), except for brief excerpts in connection with reviews or scholarly analysis. Use in connection with any form of information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed is forbidden. The use in this publication of trade names, trademarks, service marks and similar terms, even if they are not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. Printed in the United States of America (BS/DH) 987654321 springeronline.com PREFACE There is no doubt that among the large number of natural products of plant origin, debatably called secondary metabolites because their importance to the eco- physiology of the organisms that accumulate them was not initially recognized, flavonoids play a central role.