Plant Biochemistry This textbook is affectionately dedicated by the editors to the memory of PROFESSOR TOM AP REES 1930-1996 A British plant biochemist internationally recognized for his many contributions to our knowledge of carbohydrate regulation and metabolism in higher plants Plant Biochemistry edited by P.M. Dey Division of Biocliemistry, Scliool of Biological Sciences, Royal Holloway, University of London, Egham Hilh Egtiam, Surrey TW20 OEX, UK. and J.B, Harborne Department of Botany, Plant Sciences Laboratories, University of Reading, Whiteknigtits, Reading RG62AS, UK. ACADEMIC PRESS San Diego London Boston New York Sydney Tokyo Toronto This book is printed on acid-free paper. Copyright © 1997 by ACADEMIC PRESS All Rights Reserved. No part of this pubHcation 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 525 B Street, Suite 1900, San Diego, CaHfomia 92101-4495, USA http://www.apnet.com Academic Press Limited 24-28 Oval Road, London NWl 7DX, UK http://www.hbuk.co.uk/ap/ ISBN 0-12-214674-3 (HB) 0-12-799214-6 (PB) A catalogue record for this book is available from the British Library Typeset by Wyvern Typesetting Ltd, Bristol Printed in Great Britain by Bath Press, Bath. 98 99 00 01 02 BP 9 8 7 6 5 4 3 Contents Contributors ix Preface xi The Plant, the Cell and its Molecular Components P.M. Dey, M.D. Brownleader and J.B. Harborne 1.1 Introduction 1 1.2 Comparative biochemistry ^ 1.3 The eukaryotic plant cell ^ 1.4 Techniques of cell fractionation 24 1.5 Molecular aspects ^1 References 47 Further reading 47 Photosynthesis J.R. Bowyer and R.C. Leegood 2.1 Introduction 49 2.2 Light energy utilization to produce ATP and NADPH 49 2.3 The Benson-Calvin cycle 84 2.4 Photorespiration 90 2.5 C4 photosynthesis 93 2.6 Crassulacean acid metabolism 100 Acknow^ledgements 102 Background reading 102 Further reading 102 Other reference 104 Carbohydrate Metabolism: Primary Metabolism of Monosaccharides M.D. Brownleader, J.B. Harborne and P.M. Dey 3.1 Introduction HI 3.2 Glycolysis HI 3.3 Pentose phosphate pathway H^ 3.4 The citric acid cycle 1^1 3.5 Electron transport and oxidative phosphorylation 126 References and further reading 140 Carbohydrate Metabolism: Storage Carbohydrates G. Avigad and P.M. Dey 4.1 Introduction 143 4.2 Sucrose 143 4.3 Q;,Q;-Trehalose 1-^8 4.4 Other oligosaccharides 1^1 4.5 Fructans 1^9 4.6 Starch 1/^7 4.7 Other reserve polysaccharides 191 References 195 Further reading 203 Carbohydrate Metabolism: Structural Carbohydrates J.S. Grant Reid 5.1 Introduction 205 5.2 The plant cell wall or extracellular matrix 205 5.3 Structures and interactions of plant cell wall polysaccharides 209 5.4 Supramolecular interactions of structural polysaccharides in cell walls 218 VI CONTENTS 5.5 Biosynthesis of structural polysaccharides 223 5.6 Metabolic turnover of structural components 231 5.7 Conclusions 235 References 235 6 Plant Lipid Metabolism John L. Harwood 6.1 The chemistry of plant lipids 237 6.2 Fatty acid biosynthesis 244 6.3 Triacylglycerol synthesis 248 6.4 Membrane lipid biogenesis 250 6.5 Lipid catabolism and turnover 254 6.6 Cutins, suberins and waxes 260 6.7 Plant membranes 263 Further reading 271 7 Primary Nitrogen Metabolism Peter ]. Lea 7.1 Introduction 273 7.2 Nitrogen fixation 273 7.3 Nitrate uptake and reduction 281 7.4 Ammonia assimilation 285 7.5 Asparagine metabolism 290 7.6 Aminotransferases 292 7.7 The aspartate family 293 7.8 The branched chain amino acids 300 7.9 The biosynthesis of proline and arginine 302 7.10 Sulfur amino acids 305 7.11 Histidine 306 Acknowledgements 306 References 306 Nucleic Acids and Proteins Eric Lam 8.1 Introduction 315 8.2 DNA 318 8.3 RNA 324 8.4 Proteins 338 8.5 Summary 349 References 350 9 Regulation of Gene Expression in Plants ].A. Gatehouse 9.1 Introduction 353 9.2 Nuclear genes 353 9.3 Organellar genes 367 9.4 Signaling mechanisms in gene regulation 370 9.5 Gene regulation in plant development 372 9.6 Transgenic plants 376 9.7 Conclusion 381 Further reading 381 10 Phenolic Metabolism D. Strack 10.1 Introduction 387 10.2 Shikimate/arogenate pathway 390 CONTENTS Vll 10.3 Phenylalanine/hydroxycinnamate pathway 393 10.4 Phenylpropanoid pathways 39^ 10.5 Hydroxycinnamate conjugates 397 10.6 Hydroxycoumarins 398 10.7 Hydroxybenzoates 399 10.8 Flavonoids 400 10.9 Lignins 408 10.10 Lignans and NeoHgnans 409 10.11 Tannins 410 10.12 Quinones 413 References 416 11 Isoprenoid Metabohsm ?eter M. Bramley 11.1 Introduction 417 11.2 Nomenclature, classification and occurrence 417 11.3 General pathway of terpenoid biosynthesis 418 11.4 Monoterpenoids 419 11.5 Sesquiterpenoids 421 11.6 Diterpenoids 423 11.7 Triterpenoids 425 11.8 Carotenoids 427 11.9 Polyterpenoids 432 11.10 Minor classes of terpenoids 432 11.11 Control and compartmentation of isoprenoid biosynthesis 433 References 434 12 Special Nitrogen Metabolism Michael Wink 12.1 Introduction 439 12.2 Non-protein amino acids 440 12.3 Amines 443 12.4 Cyanogenic glycosides and glucosinolates 453 12.5 Alkaloids 458 12.6 Auxins, cytokinins and ethylene 471 12.7 Nitrogen bases and cofactors 474 References 485 13 Biochemical Plant Pathology Jonathan D. Walton 13.1 Introduction 487 13.2 Genetics of host/pathogen interactions 489 13.3 Mechanisms of pathogenicity: penetration and spread 491 13.4 Mechanisms of plant resistance 495 References -502 Further reading 502 14 Biochemical Plant Ecology Jeffrey B. Harborne 14.1 Introduction -503 14.2 Plant responses to the environment «503 14.3 Plant response to herbivory: toxin production 506 14.4 Constitutive defense mechanisms -508 14.5 Induced phytochemical response to herbivory 512 14.6 Conclusion 51«5 References ^^^ Vlll CONTENTS 15 Plant Cell Biotechnology M,D. Brownleader and P.M, Dey 15.1 Introduction >517 15.2 Plant cell culture ^18 15.3 Micropropagation 52,2 15.4 Commercial exploitation of plant biotechnology 524 15.5 Definitions 528 Further reading 529 Contributors G. Avigad Department of Biochemistry, University of Medicine and Dentistry of New Jersey, Robert Wood Johnson Medical School, GIS Hoes Lane, Pistacataway, NJ 08854-5635, USA J.R. Bowyer Division of Biochemistry, School of Biological Sciences, Royal Holloway, University of London, Egham, Surrey TW20 OEX, UK Peter M. Bramley Division of Biochemistry, School of Biological Sciences, Royal Hollovs^ay, University of London, Egham, Surrey TW20 OEX, UK M.D. Brownleader Biochemistry Section, School of Applied Science, South Bank University, 103 Borough Road, London SEl OAA, UK P.M. Dey Division of Biochemistry, School of Biological Sciences, Royal Holloway, University of London, Egham Hill, Egham, Surrey TW20 OEX, UK J.A. Gatehouse Department of Biological Sciences, University of Durham, South Road, Durham DHl 3LE, UK J.B. Harborne Plant Science Laboratories, Department of Botany, University of Reading, Whiteknights, Reading RG6 6AS, UK John L. Harwood Department of Biochemistry, University of Wales, Cardiff CFl 1ST, UK Eric Lam AgBiotech Center, Waksman Institute, Rutgers University, Pistcataway, NJ 08855-0759, USA Peter J. Lea Division of Biological Sciences, University of Lancaster, Lancaster LAI 4YQ, UK R.C. Leegood Robert Hill Institute and Department of Animal and Plant Sciences, University of Sheffield, Sheffield SIO 2UQ, UK J.S. Grant Reid Department of Biological and Molecular Sciences, University of Stirling, Stirling FK9 4LA, UK D. Strack Institut fur Pflanzenbiochemie, Weinberg 306120, Halle(Saale), Germany Jonathan D. Walton Department of Energy Plant Research Laboratory, Michigan State University, East Lansing, MI 48824, USA Michael Wink Institut fur Pharmazeutische Biologic, Im Neuenheimer Feld 364, D-6900, Heidelberg, Germany