Table Of ContentPlant-derived Natural Products
Anne E. Osbourn (cid:129) Virginia Lanzotti
Plant-derived
Natural Products
Synthesis, Function, and Application
Editors
Anne E. Osbourn Virginia Lanzotti
Head, Department of Metabolic Biology University of Molise
John Innes Centre DISTAAM
Colney Lane Via F. De Sanctis
Norwich NR4 7UH, UK 86100 Campobasso
[email protected] Italy
[email protected]
[email protected]
ISBN 978-0-387-85497-7 e-ISBN 978-0-387-85498-4
DOI 10.1007/978-0-387-85498-4
Springer Dordrecht Heidelberg London New York
Library of Congress Control Number: 2009926301
© Springer Science+Business Media, LLC 2009
All rights reserved. This work may not be translated or copied in whole or in part without the written permission
of the publisher (Springer Science+Business Media, LLC, 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.
While the advice and information in this book are believed to be true and accurate at the date of going to press,
neither the authors nor the editors nor the publisher can accept any legal responsibility for any errors or omissions
that may be made. The publisher makes no warranty, express or implied, with respect to the material contained
herein.
Printed on acid-free paper
Springer is part of Springer Science+Business Media (www.springer.com)
Preface
Plants produce a huge array of natural products (secondary metabolites). These compounds have
important ecological functions, providing protection against attack by herbivores and microbes
and serving as attractants for pollinators and seed-dispersing agents. They may also contribute to
competition and invasiveness by suppressing the growth of neighbouring plant species (a phenom-
enon known as allelopathy). Humans exploit natural products as sources of drugs, flavouring
agents, fragrances and for a wide range of other applications. Rapid progress has been made in
recent years in understanding natural product synthesis, regulation and function and the evolution
of metabolic diversity. It is timely to bring this information together with contemporary advances
in chemistry, plant biology, ecology, agronomy and human health to provide a comprehensive
guide to plant-derived natural products.
Plant-derived natural products: synthesis, function and application provides an informative
and accessible overview of the different facets of the field, ranging from an introduction to the
different classes of natural products through developments in natural product chemistry and biol-
ogy to ecological interactions and the significance of plant-derived natural products for humans.
In the final section of the book a series of chapters on new trends covers metabolic engineering,
genome-wide approaches, the metabolic consequences of genetic modification, developments in
traditional medicines and nutraceuticals, natural products as leads for drug discovery and novel
non-food crops.
Anne E. Osbourn
Virginia Lanzotti
v
Contents
Part I The Chemical Composition of Plants
1 Introduction to the Different Classes of Natural Products ......................................... 3
Karin Springob and Toni M. Kutchan
2 Natural Products from Seaweeds ................................................................................. 51
Efstathia Ioannou and Vassilios Roussis
3 Use of Secondary Metabolite Variation in Crop Improvement ................................. 83
Daniel J. Kliebenstein
4 Approaches to the Analysis of Plant-Derived Natural Products ............................... 97
Lionel Hill and Trevor L. Wang
5 Opportunities and Challenges for Ethnobotany at the Start
of the Twenty-First Century .......................................................................................... 127
Monique S.J. Simmonds
Part II Secondary Metabolite Biosynthesis
6 Introduction to the Different Classes of Biosynthetic Enzymes ................................ 143
Luzia V. Modolo, Angelika I. Reichert, and Richard A. Dixon
7 Methods for Molecular Identification of Biosynthetic Enzymes in Plants ............... 165
Sarah O’ Connor
8 Regulation of Secondary Metabolism by Jasmonate Hormones ............................... 181
Hongtao Zhang and Johan Memelink
9 Metabolite Channeling and Multi-enzyme Complexes .............................................. 195
Brenda S.J. Winkel
vii
viii Contents
10 Glycosylation of Secondary Metabolites and Xenobiotics ....................................... 209
Fabián E. Vaistij, Eng-Kiat Lim, Robert Edwards, and Dianna J. Bowles
11 Handling Dangerous Molecules: Transport and Compartmentation
of Plant Natural Products ........................................................................................... 229
Markus Klein and Werner Roos
12 Participation of Phytochemicals in Plant Development and Growth...................... 269
Lucille Pourcel and Erich Grotewold
Part III Biological Activity
13 Biological Activity of Defence-Related Plant Secondary Metabolites ..................... 283
John P. Morrissey
14 The Role of Natural Products in Plant-Microbe Interactions ................................. 301
Giuliano Bonanomi, Francesco Vinale, and Felice Scala
15 Role of Natural Products in Nature: Plant–Insect Interactions .............................. 321
Ruth Gordon-Weeks and John A. Pickett
16 Oligosaccharide Signalling Molecules ........................................................................ 349
Robert A. Field
17 Biological Activity of Allelochemicals ........................................................................ 361
Franck E. Dayan and Stephen O. Duke
18 Health Benefits of Dietary Plant Natural Products .................................................. 385
Maria Traka and Richard F. Mithen
19 Floral Scents and Fruit Aromas Inspired by Nature ................................................ 405
Florence Negre-Zakharov, Michael C. Long, and Natalia Dudareva
Part IV New Trends
20 Bioengineering .............................................................................................................. 435
Maxim Itkin and Asaph Aharoni
21 Genome Wide Approaches in Natural Product Research ........................................ 475
Jürgen Ehlting, Björn Hamberger, Jean-François Ginglinger,
and Danièle Werck-Reichhart
22 Metabolomics and the Detection of Unintended Effects
in Genetically Modified Crops ................................................................................... 505
Laetitia Shintu, Gwénaëlle Le Gall, and Ian J. Colquhoun
Contents ix
23 Recent Advances in Traditional Medicines and Dietary Supplements ................... 533
Jeevan Prasain and Stephen Barnes
24 Plant-Derived Natural Products as Leads for Drug Discovery ............................... 547
Li Pan, Esperanza J. Carcache de Blanco, and A. Douglas Kinghorn
25 Speciality Non-food Crops........................................................................................... 569
Adrian P. Higson and Alison Hamer
Index ...................................................................................................................................... 585
Contributors
Asaph Aharoni Ian J. Colquhoun
Department of Plant Sciences, Weizmann Institute Institute of Food Research, Norwich Research
of Science, Israel Park, Norwich NR4 7UA, UK
[email protected] [email protected]
Stephen Barnes Franck E. Dayan
Department of Pharmacology and Toxicology, Natural Products Utilization Research Unit,
Room 452 McCallum Research Building, Agricultural Research Service, United States
University of Alabama at Birmingham, 1918 Department of Agriculture, P.O. Box 8048,
University Boulevard, University, MS 38677, USA
Birmingham, AL 35294 [email protected]
Center for Nutrient-Gene Interaction,
Birmingham, AL 35294
Richard A. Dixon
University of Alabama at Birmingham,
Plant Biology Division, Samuel Roberts
and Purdue University-University of Alabama
Noble Foundation, Ardmore, OK 73401,
Botanicals Center for Age-Related Disease,
USA
Birmingham, AL 35294
[email protected]
[email protected]
Natalia Dudareva
Giuliano Bonanomi
Department of Horticulture and Land
Dipartimento di Arboricoltura, Botanica e
scape Architecture, Purdue University,
Patologia vegetale,
West Lafayette, IN 47907, USA
University of Naples Federico II, Via Università
[email protected]
100, 80055 Portici, Napoli, Italy
[email protected]
Stephen O. Duke
Dianna J. Bowles Natural Products Utilization Research Unit,
Centre for Novel Agricultural Products, Agricultural Research Service, United States
Department of Biology, Department of Agriculture, P.O. Box 8048,
University of York, University, MS 38677, USA
York YO10 5DD, UK [email protected]
[email protected]
Robert Edwards
Esperanza J. Carcache de Blanco School of Biological & Biomedical
Division of Medicinal Chemistry and Sciences, Durham University,
Pharmacognosy, College of Pharmacy, The Ohio South Road, Durham, DH1 3LE,
State University, Columbus, OH 43210, USA UK
[email protected] [email protected]
xi
xii Contributors
Jürgen Ehlting Adrian P. Higson
Department of Plant Metabolic Responses, The National Non-Food Crops Centre, Biocentre,
Institute for Plant Molecular Biology (IBMP), York Science Park, Innovation Way,
C.N.R.S., 28 rue Goethe, 67000 Strasbourg, Heslington, York, YO10 5DG, UK
France [email protected]
Current address: Centre for Forest Biology,
University of Victoria,
P.O. Box 3020 STN CSC, Lionel Hill
Victoria BC V8W 3N5, Canada Department of Metabolic Biology,
[email protected] John Innes Centre, Norwich Research Park,
Colney, Norwich NR4 7UH, UK
[email protected]
Robert A. Field
Department of Biological Chemistry,
John Innes Centre, Colney Lane, Norwich NR4
Efstathia Ioannou
7UH, UK
Department of Pharmacognosy
rob.fi [email protected]
and Chemistry of Natural Products, School of
Pharmacy, University of Athens, Panepistimiopolis
Jean-François Ginglinger Zografou, Athens 15771, Greece
Department of Plant Metabolic Responses, [email protected]
Institute for Plant Molecular Biology (IBMP),
C.N.R.S., 28 rue Goethe, 67000 Strasbourg,
France Maxim Itkin
[email protected] Department of Plant Sciences, Weizmann
Institute of Science, Israel
[email protected]
Ruth Gordon-Weeks
Department of Biological Chemistry, Centre for
Pest and Disease Management,
A. Douglas Kinghorn
Rothamsted Research, West Common, Harpenden,
Division of Medicinal Chemistry and
Hertfordshire, AL5 2JQ,
Pharmacognosy, College of Pharmacy,
UK
The Ohio State University, Columbus,
[email protected]
OH 43210, USA
[email protected]
Erich Grotewold
Department of Plant Cellular and Molecular
Biology, The Ohio State University, Columbus, Markus Klein
Ohio, USA Zurich Basel Plant Science Center,
[email protected] University of Zurich, Plant Biology,
Zollikerstrasse 107,
CH-8008 Zurich, Switzerland
Björn Hamberger
Martin-Luther University Halle-Wittenberg,
Michael Smith Laboratories, University of British
Pharmaceutical Biology, Molecular Cell Biology,
Columbia, 2185 East Mall, Vancouver
Kurt-Mothes-Str. 3, D-06120 Halle, Germany
BC V6T 1Z4, Canada
[email protected]
[email protected]
Alison Harner Daniel J. Kliebenstein
The National Non-Food Crops Centre, Biocentre, Department of Plant Sciences,
York Science Park, Innovation Way, University of California, Davis,
Heslington, York, YO10 5DG, UK One Shields Avenue, Davis, CA 95616, USA
[email protected] [email protected]
Contributors xiii
Toni M. Kutchan Florence Negre-Zakharov
Donald Danforth Plant Science Center, Department of Plant Sciences,
975 North Warson Road, University of California, Davis,
St. Louis, MO 63132, CA 95616, USA
USA [email protected]
[email protected]
Sarah O’Connor
Gwénaëlle Le Gall Massachusetts Institute of Technology,
Institute of Food Research, Department of Chemistry, 18-592, 77
Norwich Research Park, Massachusetts Ave, Cambridge,
Norwich NR4 7UA, MA 02139, USA
UK [email protected]
[email protected]
Li Pan
Eng-Kiat Lim Division of Medicinal Chemistry and
Centre for Novel Agricultural Products, Pharmacognosy, College of Pharmacy, The Ohio
Department of Biology, University of York, State University, Columbus, OH 43210, USA
York YO10 5DD, UK [email protected]
[email protected]
John A. Pickett
Michael C. Long Department of Biological Chemistry,
Department of Horticulture and Landscape Centre for Pest and Disease Management,
Architecture, Purdue University, West Lafayette, Rothamsted Research, West Common, Harpenden,
IN 47907, USA Hertfordshire, AL5 2JQ, UK
[email protected] [email protected]
Johan Memelink Lucille Pourcel
Institute of Biology, Leiden University, Clusius Department of Plant Cellular and Molecular
Laboratory, Wassenaarseweg 64, 2333 AL Leiden, Biology, The Ohio State University,
The Netherlands Columbus, Ohio, USA
[email protected] [email protected]
Richard F. Mithen Jeevan Prasain
Institute of Food Research, Colney Lane, Department of Pharmacology and Toxicology,
Norwich, NR4 7UA, UK Birmingham,
[email protected] AL 35294 University of Alabama at Birmingham,
and Purdue University-University of Alabama
Luzia V. Modolo Botanicals Center for Age-Related Disease,
Plant Biology Division, Samuel Roberts Noble Birmingham, AL 35294
Foundation, Ardmore, OK 73401, USA [email protected]
[email protected]
Angelika I. Reichert
John P. Morrissey Plant Biology Division, Samuel Roberts Noble
Microbiology Department, University College Foundation, Ardmore, OK 73401, USA
Cork, Ireland [email protected]
[email protected]
