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The Science of Flavonoids
The Science of Flavonoids
Edited by
Erich Grotewold
The Ohio State University
Columbus, Ohio, USA
348809185.001.png
Erich Grotewold
Department of Cellular and Molecular Biology
The Ohio State University
Columbus, Ohio 43210
USA
grotewold.1@osu.edu
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 Science Business 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 Science Business 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. These compounds and their derived pigments have
contributed to shaping our knowledge of modern genetics, providing colorful tools
to investigate a number of central plant problems, including the biology of
transposons, the regulation of gene expression, gene silencing, and the organization
of metabolic pathways. The legacy left by several outstanding chemists who have
devoted their lives to the understanding of the chemistry of flavonoids is being
carried by a growing number of scientists who take interdisciplinary approaches to
continue to advance our knowledge of the pathway and develop new means to
manipulate the synthesis of these compounds, which have significant potential in
providing solutions to plant and animal illnesses alike.
The interdisciplinary nature of the research currently being carried out in the area
of flavonoids is part of the spirit that this book has tried to capture. Chemistry,
biochemistry, genetics, and cellular and molecular biology are all parts of the
toolbox that the investigator has at hand in addressing fundamental biological
questions regarding the biosynthesis, storage, regulation, evolution, and biological
activities of flavonoids. These tools are combined in each of the nine chapters that
form this book to address what I have perceived to be some of the most significant
challenges currently being pursued in the area of the biology of flavonoids. If
specific topics have been left out, such as, for example, the metabolic engineering of
flavonoids, it is only because in my opinion the number of reviews in this subject
exceeds the quantity of novel relevant primary research publications.
Chapter 1 provides a novel look at flavonoids from the perspective of
stereochemistry. Chapter 2 provides an overview of the state of the art in flavonoid
isolation and characterization. Historic and up-to-date perspectives on the
biosynthesis of flavonoids are provided in Chapter 3. Chapter 4 integrates the
studies in several plants to provide models on how the multiple branches of
flavonoid biosynthesis might be regulated. Chapter 5 explores the poorly
understood mechanisms that underlie the trafficking of flavonoids within cells. A
review of the contributions that flavonoids and derived pigments have and continue
to provide to geneticists and molecular biologists is provided in Chapter 6. Chapter
7 illustrates models that may help to explain the evolution of flavonoids and the
corresponding regulatory and biosynthetic genes. Chapter 8 delves into the
expanding field of the role that flavonoids play in health, and Chapter 9 provides a
review on the role of flavonoids as plant-signaling molecules.
I want to finish by thanking the authors who contributed to this book and for
their patience in bearing with the multiple revisions of their submissions. I also
want to acknowledge the several reviewers who provided me with comments on the
chapters. Most wholeheartedly I want to thank Sarat Subramaniam for his help with
the formatting and editing of the book.
v
CONTENTS
CHAPTER 1
1
The Stereochemistry of Flavonoids
J.P.J. Marais, B. Deavours, R.A Dixon, and D. Ferreira
CHAPTER 2
47
Isolation and Identification of Flavonoids
M. Stobiecki and P. Kachlicki
CHAPTER 3
71
The Biosynthesis of Flavonoids
B.S.J. Winkel
The Regulation of Flavonoid Biosynthesis
97
F. Quattrocchio, A. Baudry, L. Lepiniec, and E. Grotewold
CHAPTER 5
123
Transport of Flavonoids: From Cytosolic Synthesis to Vacuolar Accumulation
S. Kitamura
CHAPTER 6
147
Flavonoid Pigments as Tools in Molecular Genetics
S. Chopra, A. Hoshino, J. Boddu, and S. Iida
CHAPTER 7
175
The Evolution of Flavonoids and Their Genes
M.D. Rausher
CHAPTER 8
213
Flavonoids as Nutraceuticals
J-K. Lin and M-S. Weng
CHAPTER 9
239
Flavonoids as Signal Molecules: Targets of Flavonoid Action
W.A. Peer and A.S. Murphy
Index
269
vii
CHAPTER 4

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