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Metabolic Engineering of Plant Secondary Metabolism Metabolic Engineering of Plant Secondary Metabolism Edited by R. Verpoorte Division Pharmacognosy, Leiden/Amsterdam Center for Drug Research, Leiden, The Netherlands and A. W. Alfermann Heinrich-Heine- Universitat, Dusseldorf, Institutfiir Entwicklungs- und Molekularbiologie der Pflanzen, Dusseldorf, Germany KLUWER ACADEMIC PUBLISHERS DORDRECHT / BOSTON / LONDON Library of Congress Cataloging-in-Publication Data Metabolic engineering of plant secondary metabolism / editors R. Verpoorte and A. W. Alfermann. p. cm. ISBN 0-7923-6360-4 (alk. paper) 1. Plants-Metabolism. 2. Metabolism, Secondary. I. Verpoorte, R. IL Alfermann, A. W. QK881 .M45 2000 572\42~dc21 00-030654 ISBN 0-7923-6360-4 Published by Kluwer Academic Publishers, RO. Box 17, 3300 AA Dordrecht, The Netherlands. Sold and distributed in North, Central and South America by Kluwer Academic Publishers, 101 Philip Drive, Norwell, MA 02061, U.S.A. In all other countries, sold and distributed by Kluwer Academic Publishers, P.O. Box 322, 3300 AH Dordrecht, The Netherlands. Printed on acid-free paper All Rights Reserved © 2000 Kluwer Academic Publishers No part of the material protected by this copyright notice may be reproduced or utilized in any form or by any means, electronic or mechanical, including photocopying, recording or by any information storage and retrieval system, without written permission from the copyright owner. Printed in the Netherlands. DETAILS OF CONTRIBUTORS Prof. Dr. A.W. Alfermann Heinrich-Heine-Universitat Diisseldorf Institut fur Entwicklungs- und Molekularbiologie der Pflanzen Universitatsstr. 1, Geb. 26.13, 40225 Diisseldorf, Germany Dr. Randolph Arroo Natural Products Research, Department of Pharmaceutical Sciences De Montfort University, Leicester, United Kingdom Dr. Olga Artsaenko Rheinisch-Westfalische Technische Hochschule Institut fur Biologie I, Antibody Engineering Group Worringer Weg 1 52074 Aachen, Germany Dr. Jochen Berlin Gesellschaft fiir Biotechnologische Forschung mbH Mascheroder Weg 1, 38124 Braunschweig, Germany Dr. Daniel Burtin John Innes Centre, Norwich Research Park Norwich NR4 7UH, United Kingdom Dr. Paul Christou John Innes Centre, Norwich Research Park Norwich NR4 7UH, United Kingdom Dr. Kevin M. Davies Crop & Food Research Research, Food Industry Science Centre, Private Bag 11 600, Palmerston North - New Zealand Dr. Vincenzo De Luca Novartis Inc. Seed Biotechnology Research Unit 3054 Cornwallis Road, Research Triangle Park NC 27709, USA Dr. Jiirgen Drossard Rheinisch-Westfalische Technische Hochschule Institut fiir Biologie I, Antibody Engineering Group Worringer Weg 1 52074 Aachen, Germany Dr. Neil J. Emans Rheinisch-Westfalische Technische Hochschule Institut fur Biologie I, Antibody Engineering Group Worringer Weg 1 52074 Aachen, Germany Dr. Lothar F. Fecker Universitatsklinikum Benjamin Franklin, FU Berlin, Hindenburgdamm 30, 12200 Berlin, Germany Dr. Rainer Fischer Rheinisch-Westfalische Technische Hochschule Institut fur Biologie I, Antibody Engineering Group Worringer Weg 1 52074 Aachen, Germany Dr. Bernhard Grimmig Bayer AG Geschaftbereich Pflanzenschutz Landwirtschaftszentrum Monheim 51368 Leverkusen, Germany Prof. Dr. Riidiger Hain Bayer AG Geschaftsbereich Pflanzenschutz Landwirtschaftszentrum Monheim 51368 Leverkusen, Germany Dr. Didier Hallard Division of Pharmacognosy, Leiden/Amsterdam Center for Drug Research Einsteinweg 55, P.O. Box 9502, 2300 RA Leiden,The Netherlands Prof. Dr. Lutz Heide Pharmazeutisches Institut Universitat Tubingen Auf der Morgenstelle 8, 72076 Tubingen, Germany E-mail: [email protected] Dr. Frederique Hilliou John Innes Centre, Norwich Research Park Norwich NR4 7UH, United Kingdom Dr. Paul JJ. Hooykaas Institute of Molecular Plant Sciences, Clusius Laboratory, Leiden University, Wassenaarseweg 64, 2333 AL Leiden, The Netherlands, e-mail: hooykaas @rulbim.leidenuniv.nl Dr. Ben Kemp John Innes Centre, Norwich Research Park Norwich NR4 7UH, United Kingdom Dr. Jan W. Kijne Institute of Molecular Plant Sciences, Clusius Laboratory, Leiden University Wassenaarseweg 64, 2333 AL Leiden, The Netherlands Dr. Mark J. Leech John Innes Centre, Norwich Research Park Norwich NR4 7UH, United Kingdom Dr. Johan Memelink Institute of Molecular Plant Sciences, Clusius Laboratory, Leiden University Wassenaarseweg 64, 2333 AL Leiden, The Netherlands e-mail: memelink @ rulbim. leidenuniv.nl Dr. Frank L.H. Menke Institute of Molecular Plant Sciences, Clusius Laboratory, Leiden University Wassenaarseweg 64, 2333 AL Leiden, The Netherlands Dr. Phillip Morris Cell Manipulation Group, Cell Biology Department, Institute of Grassland and Environmental Research, Plas Gogerddan, Aberystwyth, Ceredigion, SY23 3EB, United Kingdom e-mail: [email protected] Dr. Jorg M. Naehring Rheinisch-Westfalische Technische Hochschule Institut fiir Biologie I, Antibody Engineering Group Worringer Weg 1 52074 Aachen, Germany Dr. Dermot O'Callaghan John Innes Centre, Norwich Research Park Norwich NR4 7UH, United Kingdom Dr. Kirsi-Marja Oksman-Caldentey VTT Biotechnology and Food Research, Technical Research Centre of Finland RO. Box 1501, FIN-02044 VTT, Finland e-mail: [email protected] Dr. Natalia Palacios John Innes Centre, Norwich Research Park Norwich NR4 7UH, United Kingdom Dr. Mark P. Robbins Cell Manipulation Group, Cell Biology Department, Institute of Grassland and Environmental Research, Plas Gogerddan, Aberystwyth, Ceredigion, SY23 3EB, United Kingdom e-mail: [email protected] Dr. Pedro Rocha John Innes Centre, Norwich Research Park Norwich NR4 7UH, United Kingdom Dr. Stephan Schillberg Rheinisch-Westfalische Technische Hochschule Institut fur Biologie I, Antibody Engineering Group Worringer Weg 1 52074 Aachen, Germany Dr. Leslie van der Fits Institute of Molecular Plant Sciences, Clusius Laboratory, Leiden University Wassenaarseweg 64, 2333 AL Leiden, The Netherlands Dr. Rob van der Heijden Division of Pharmacognosy, Leiden/Amstredam Center for Drug Research Einsteinweg 55, RO. Box 9502, 2300 RA Leiden,The Netherlands Dr. Robert Verpoorte Division of Pharmacognosy, Leiden/Amstredam Center for Drug Research Einsteinweg 55, P.O. Box 9502, 2300 RA Leiden,The Netherlands e-mail: VERPOORT©LACDR.Leidenuniv.NL PREFACE In this book we aim at giving a general overview on metabolic engineering of plant secondary metabolism, and show by a series of reviews the progress made in applying molecular biology to alter the production of certain compounds. Several approaches are presently of interest I - improve the production of secondary metabolites used as specialty chemicals, such as drugs, insecticides, dyes, flavours and fragrances. This includes improving the production in plants or plant cells, introducing the production of a compound of interest in another plant species, e.g. more suitable for cultivation, or even the production of complete new compounds. II - altering the quality of a plant, e.g. used as food or an ornamental plant. This includes altering flower colours, changing taste, smell or colour of food, reducing level of toxic or unwanted compounds in food or fodder plants. III - increase resistance against pest and diseases. These different aspects will be the basis of the book. In the two introductory chapters we will first discuss the general background of secondary metabolism and the possibilities to alter secondary metabolite pathways. The next two chapters deal with the state-of-the-art of the transformation technologies: the Agrobacterium system and the particle gun. The next chapter will deal with the possibilities of producing antibodies in plants, this is potentially also applicable for altering secondary metabolite pathways. As secondary metabolite pathways might be under the control of one or just a few genes, Chapter 6 deals with work on transcriptional regulators as possible targets for genetic engireering. The subsequent chapters deal with agricultural applications of metabolic engineering, aiming at improving the quality of plants. The last chapters concern the possibility of altering the production of pharmaceutically interesting compounds in plants or plant cell cultures. Certainly there would have been further examples of the application of metabolic engineering. However, being complete in such a fast moving field would be impossible, rather we preferred to give an overview for some important fields. In principle the strategies can be used for any type of secondary metabolite, taking into account that a number of constraints exist. Anyway we hope that this book will help the reader to have an overview on the posibilities to overproduce compounds, to block the production of unwanted compounds, or produce new compounds in plants or plant cells. Rob Verpoorte and Willi Alfermann Contents Details of Contributors ............................................................. vii Preface .................................................................................... xi 1. Secondary Metabolism ................................................... 1 Introduction .................................................................................... 1 Major Secondary Metabolite Pathways ........................................ 6 Chemodiversity and Pathway Architecture ................................... 15 Regulation ..................................................................................... 19 Conclusions ................................................................................... 23 References ...................................................................................
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