UUnnttiittlleedd--22 11 1100//2288//22001133 1122::4455::0055 PPMM Plant ChemiCal Biology Plant ChemiCal Biology edited by Dominique auDenaert Paul overvoorDe Copyright © 2014 by John Wiley & Sons, Inc. All rights reserved Published by John Wiley & Sons, Inc., Hoboken, New Jersey Published simultaneously in Canada No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750–8400, fax (978) 750–4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748–6011, fax (201) 748–6008, or online at http://www.wiley.com/go/permission. Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762–2974, outside the United States at (317) 572–3993 or fax (317) 572–4002. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our web site at www.wiley.com. Library of Congress Cataloging-in-Publication Data: Plant chemical biology / edited by Dominique Audenaert, Paul Overvoorde. p. cm. Includes bibliographical references and index. ISBN 978-0-470-94669-5 (hardback) 1. Botanical chemistry. I. Audenaert, Dominique, 1976– editor of compilation. II. Overvoorde, Paul, 1968– editor of compilation. [DNLM: 1. Plants–chemistry. 2. Biochemical Phenomena. 3. Plant Physiological Phenomena. QK 861] QK861.P525 2014 572′.2–dc23 2013035521 ISBN: 9780470946695 10 9 8 7 6 5 4 3 2 1 Contents PrefaCe vii ContriButors ix Part one introDuCtion 1 1.1 from herbal remedies to Cutting-edge science: a historical Perspective of Plant Chemical Biology 3 Michelle Q. Brown, Abel Rosado, and Natasha V. Raikhel Part two sourCes of small moleCules 19 2.1 Compound Collections 21 Reg Richardson 2.2 Combinatorial Chemistry library Design 40 Robert Klein and Stephen D. Lindell 2.3 natural Product-Based libraries 64 Alan L. Harvey Part three iDentifiCation of new ChemiCal tools By high-throughPut sCreening 73 3.1 assay Design for high-throughput screening 75 Frank W. An and Jose R. Perez v vi CONTeNTS Part four use of ChemiCal Biology to stuDy Plant Physiology 93 4.1 use of Chemical Biology to understand auxin metabolism, signaling, and Polar transport 95 Ken-ichiro Hayashi and Paul Overvoorde 4.2 Brassinosteroids signaling and Biosynthesis 128 Takeshi Nakano and Tadao Asami 4.3 Chemical genetic approaches on aBa signal transduction 145 Eunjoo Park and Tae-Houn Kim 4.4 Jasmonic acid 160 Christian Meesters and Erich Kombrink 4.5 Chemical genetics as a tool to study ethylene Biology in Plants 184 Yuming Hu, Filip Vandenbussche, and Dominique Van Der Straeten Part five use of ChemiCal Biology to stuDy Plant Cellular ProCesses 203 5.1 the use of small molecules to Dissect Cell wall Biosynthesis and manipulate the Cortical Cytoskeleton 205 Darby Harris and Seth DeBolt 5.2 the use of Chemical Biology to study Plant Cellular Processes: subcellular trafficking 218 Ash Haeger, Malgorzata Łangowska, and Stéphanie Robert Part six target iDentifiCation 233 6.1 target identification of Biologically active small molecules 235 Paul Overvoorde and Dominique Audenaert Part seven translation of Plant ChemiCal Biology from the laB to the fielD 247 7.1 Prospects and Challenges for translating emerging insights in Plant Chemical Biology into new agrochemicals 249 Terence A. Walsh 7.2 In Vitro Propagation 263 Hans Motte, Stefaan Werbrouck, and Danny Geelen inDex 289 PrefaCe Plant biologists have a long history of using small molecules (e.g., MW < 500 Da) to explore developmental, physiological, and metabolic pathways. Compared to molecular genetic approaches used to study biological processes in plants, the roots of plant chemical biology became well established in the first decades of the twentieth century with the discovery of plant growth regulators or plant hormones. Since this time, the capacity of organic synthetic chemists to create and characterize the effect of small molecules provided the basis for understanding processes such as cell elongation through the action of auxins, the stimulation of cell division via the activity of cytokinins, the control of fruit senescence by gibberellins, and the influence of abscisic acid on seed dormancy. In addition, naturally occurring molecules as well as synthetic analogues formed the basis for genetic screens that looked for resistant or hypersensitive mutant plants. During the past 30 years, this approach led to the discovery of cellular components and pathways that inte- grate environmental and developmental information into regulated phenotypic outcomes. Plant Chemical Biology provides tools that overcome the pleiotropic effects of plant hormones. A single hormone makes defining the role of specific components or signaling pathways a challenge. The capacity to identify novel compounds that stimulate or inhibit a subset of a signaling cascade holds tremendous promise for refining our understanding of these pathways. The coupling of this potential with advances in combinatorial chemistry offers exciting opportunities to develop new tools for basic and applied applications. In recent years, the querying of large collec- tions of diverse compounds through the use of robust assays has led to an impressive array of new discoveries in the field of plant biology. vii viii PReFACe This book intends to provide advanced students and professionals in plant biology—molecular biologists, physiologists, biochemists, or those active in agriculture, horticulture, or agronomy—a summary of key aspects of plant chemical biology. even as the pace of progress in this subfield accelerates, we hope that you will discover in the following chapters a summary of key findings to date, as well as an overview of the available compound collections, principles of assay design, and the translatability of these new tools to applied settings. In this day and age, no volume provides an encyclopedic review. We hope that our selection of topics reveals one of the ways that the quest for understanding biological processes drives the innovation of new technologies, which in turn propel our understanding of the biology. We thank the authors of this collection. Their expertise and experience allows each topic to be handled with insight and depth. Without their contributions and patience, this book would not have been possible. We thank our institutions, Macalester College and VIB, for their support during the preparation of this book. Finally, we acknowledge the steadfast encouragement of our spouses, Lynn Overvoorde and eva Vermeulen, and our children, Mia, Anika, Vigdis, Sigun, and eldrid, during this process. Dominique Audenaert Paul Overvoorde
Description: