Table Of ContentP. Κ. Stumpf and Ε. Ε. Conn
EDITORS-IN-CHIEF
Department of Biochemistry
and Biophysics
University of California
Davis, California
Volume I The Plant Cell
Ν. E. Tolbert, Editor
Volume 2 Metabolism and Respiration
David D. Davies, Editor
Volume 3 Carbohydrates: Structure and Function
Jack Preiss, Editor
Volume 4 Lipids: Structure and Function
P. K. Stumpf, Editor
Volume 5 Amino Acids and Derivatives
B. J. Miflin, Editor
Volume 6 Proteins and Nucleic Acids
Abraham Marcus, Editor
Volume 7 Secondary Plant Products
Ε. E. Conn, Editor
Volume 8 Photosynthesis
M. D. Hatch and Ν. K. Boardman, Editors
THE
BIOCHEMISTRY
OF PLANTS
A COMPREHENSIVE TREATISE
Volume 7
Secondary Plant Products
Ε. E. Conn, editor
Department of Biochemistry and Biophysics
University of California
Davis, California
1981
ACADEMIC PRESS
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United Kingdom Edition published by
ACADEMIC PRESS, INC. (LONDON) LTD.
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Library of Congress Cataloging in Publication Data
Main entry under title:
The Biochemistry of plants.
Includes bibliographies and indexes.
CONTENTS: v. 1. The plant cell.—v. 2. Metabolism
and respiration.—v. 3. Carbohydrates.—[etc.]—v. 7.
Secondary plant products.
1. Botanical chemistry. I. Stumpf, Paul Karl,
Date. II. Conn, Eric. E.
QK861.B48 581.19'2 80-13168
ISBN 0-12-675407-1 (v. 7) AACR1
PRINTED IN THE UNITED STATES OF AMERICA
81 82 83 84 9 8 7 6 5 4 3 2 1
List of Contributors
Numbers in parentheses indicate the pages on which the authors' contributions begin.
Wolfgang Barz (35), Lehrstuhl fur Biochemie der Pflanzen, Westfalische
Wilhelms-Universitat, D-4400 Munster, Federal Republic of Germany
E. A. Bell (1), Department of Plant Sciences, King's College London, Uni-
versity of London, London SE24, United Kingdom
Stewart A. Brown (269), Department of Chemistry, Trent University, Peter-
borough, Ontario, Canada K9J 7B8
V. S. Butt (627), Botany School, University of Oxford, South Parks Road,
Oxford 0X1 3RA, United Kingdom
Ε. E. Conn (479), Department of Biochemistry and Biophysics, University of
California, Davis, California 95616
Otis C. Dermer (317), Department of Biochemistry, Oklahoma State Univer-
sity, Stillwater, Oklahoma 74074
Donald K. Dougall (21), W. Alton Jones Cell Science Center, Lake Placid,
New York 12946
Heinz G. Floss (177), Department of Medicinal Chemistry, Purdue Univer-
sity, West Lafayette, Indiana 47907
L. Fowden (215), Rothamsted Experimental Station, Harpenden, Herts.,
United Kingdom
Hans Grisebach (457), Lehrstuhl fur Biochemie der Pflanzen, Institut fur
Biologie II der Universitat, D-7800 Freiburg/Br., Federal Republic of
Germany
G. G. Gross (301), Universitat Ulm, Abteilung Allgemeine Botanik, D-7900
Ulm, Federal Republic of Germany
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xiv List of Contributors
Klaus Hahlbrock (425), Biologisches Institut II der Universitat,
D-7800 Freiburg/Br., Federal Republic of Germany
Kenneth R. Hanson (577), Department of Biochemistry and Genetics, The
Connecticut Agricultural Experiment Station, New Haven, Connecticut
06504
Edwin Haslam (527), Department of Chemistry, University of Sheffield,
Sheffield S3 7HF, United Kingdom
Evelyn A. Havir (577), Department of Biochemistry and Genetics, The Con-
necticut Agricultural Experiment Station, New Haven, Connecticut
06504
Wolfgang Hosel (725), Lehrstuhl fur Biochemie der Pflanzen, Westfalische
Wilhelms-Universitat, D-4400 Miinster, Federal Republic of Germany
Johannes Koster (35), Lehrstuhl fur Biochemie der Pflanzen, Westfalische
Wilhelms-Universitat, D-4400 Munster, Federal Republic of Germany
C. J. Lamb (627), Department of Biochemistry, Oxford University, Oxford,
OX1 3RA, United Kingdom
E. Leistner (403), Institut fur Pharmazeutische Biologie und Phytochemie,
Westfalische Wilhelms-Universitat, D-4400 Munster, Federal Re-
public of Germany
Peder Olesen Larsen (501), Chemistry Department, Royal Veterinary and
Agricultural University, DK-1871 Copenhagen, Denmark
Mario Piattelli (557), Department of Chemistry, University of Catania,
Catania, Italy
Jonathan E. Poulton (667), Department of Botany, University of Iowa, Iowa
City, Iowa 52242
David S. Seigler (139), Department of Botany, University of Illinois, Urbana,
Illinois 61801
T. A. Smith (249), Long Ashton Research Station, University of Bristol,
Long Ashton, Bristol BS18 9AF, United Kingdom
Helen A. Stafford (117), Department of Biology, Reed College, Portland,
Oregon 97202
George R. Waller (317), Department of Biochemistry, Oklahoma State Uni-
versity, Stillwater, Oklahoma 74074
Rolf Wiermann (85), Botanisches Institut der Universitat, D-4400 Munster,
Federal Republic of Germany
General Preface
In 1950, James Bonner wrote the following prophetic comments in the
Preface of the first edition of his "Plant Biochemistry" published by Aca-
demic Press:
There is much work to be done in plant biochemistry. Our understanding of many basic
metabolic pathways in the higher plant is lamentably fragmentary. While the emphasis in
this book is on the higher plant, it will frequently be necessary to call attention to conclu-
sions drawn from work with microorganisms or with higher animals. Numerous problems
of plant biochemistry could undoubtedly be illuminated by the closer applications of the
information and the techniques which have been developed by those working with other
organisms . . .
Certain important aspects of biochemistry have been entirely omitted from the
present volume simply because of the lack of pertinent information from the domain
of higher plants.
The volume had 30 chapters and a total of 490 pages. Many of the bio-
chemical examples cited in the text were derived from studies on bacterial,
fungal, and animal systems. Despite these shortcomings, the book had a
profound effect on a number of young biochemists since it challenged them
to enter the field of plant biochemistry and to correct "the lack of pertinent
information from the domain of higher plants."
Since 1950, an explosive expansion of knowledge in biochemistry has
occurred. Unfortunately, the study of plants has had a mixed reception
in the biochemical community. With the exception of photosynthesis,
biochemists have avoided tackling for one reason or another the incredibly
interesting problems associated with plant tissues. Leading biochemical
xv
xvi
General Preface
journals have frequently rejected sound manuscripts for the trivial reason
that the reaction had been well described in£. coli and liver tissue and thus
was of little interest to again describe its presence in germinating pea seeds!
Federal granting agencies, the National Science Foundation excepted, have
also been reluctant to fund applications when it was indicated that the princi-
pal experimental tissue would be of plant origin despite the fact that the most
prevalent illness in the world is starvation.
The second edition of "Plant Biochemistry" had a new format in 1965
when J. Bonner and J. Varner edited a multiauthored volume of 979 pages;
in 1976, the third edition containing 908 pages made its appearance. A few
textbooks of limited size in plant biochemistry have been published. In addi-
tion, two continuing series resulting from the annual meetings and symposia
of photochemical organization in Europe and in North America provided the
biological community with highly specialized articles on many topics of plant
biochemistry. Plant biochemistry was obviously growing.
Although these publications serve a useful purpose, no multivolume series
in plant biochemistry has been available to the biochemist trained and work-
ing in different fields who seeks an authoritative overview of major topics of
plant biochemistry. It therefore seemed to us that the time was ripe to
develop such a series. With encouragement and cooperation of Academic
Press, we invited six colleagues to join us in organizing an eight volume
series to be known as 'The Biochemistry of Plants: A Comprehensive
Treatise." Within a few months, we were able to invite over 160 authors to
write authoritative chapters for these eight volumes.
Our hope is that this Treatise not only will serve as a source of current
information to researchers working on plant biochemistry, but equally im-
portant will provide a mechanism for the molecular biologist who works with
E. coli or the neurobiochemist to become better informed about the interest-
ing and often unique problems which the plant cell provides. It is hoped, too,
the senior graduate student will be inspired by one or more comments in
chapters of this Treatise and will orient his future career to some aspect of
this science.
Despite the fact that many subjects have been covered in this Treatise, we
make no claim to have been complete in our coverage nor to have treated all
subjects in equal depth. Notable is the absence of volumes on phytohor-
mones and on mineral nutrition. These areas, which are more closely asso-
ciated with the discipline of plant physiology, are treated in multi volume
series in the physiology literature and/or have been the subject of specialized
treatises. Other topics (e.g., alkaloids, nitrogen fixation, flavonoids, plant
pigments) have been assigned single chapters even though entire volumes,
sometimes appearing on an annual basis, are available.
Finally, we wish to thank all our colleagues for their enthusiastic coopera-
tion in bringing these eight volumes so rapidly into fruition. We are grateful
General Preface x vu
to Academic Press for their gentle persuasive pressures and we are indebeted
to Ms. Barbara Clover and Ms. BUlie Gabriel for their talented assistance in
this project.
P. K. Stumpf
Ε. E. Conn
Preface to Volume 7
Secondary compounds may be defined as those natural products, usually
of plant origin, which do not function directly in the primary biochemical
activities that support the growth, development, and reproduction of the
organism in which they occur. Such compounds are usually restricted in
their occurrence or distribution in nature. As others have observed, the
choice of the adjective "secondary" to describe such "non-primary" com-
pounds was unfortunate because it suggested that they were unimportant.
That choice may have for a time even hindered progress in studying the
function(s) of secondary compounds in nature. Fortunately, that obstacle, if
it existed, has diminished, and today abundant evidence supports the hy-
pothesis that many secondary (natural) products have played an indispensi-
ble role in maintaining a species during the course of evolution. To the extent
that this volume informs the broader biochemical community of the research
being carried out on these compounds, we shall have achieved one of our
objectives. We also hope that this volume will prove useful to those who are
already working on the biochemistry of secondary compounds.
The treatment of secondary plant products in this volume is divided into
three sections. Chapters 1 through 7 discuss broader aspects of secondary
(natural) products, such as their physiological roles, their metabolic turn-
over, or their relationship to plant taxonomy. The specific examples and
relationships covered in these seven chapters, it is hoped, will find general
application in future investigations carried out on other secondary com-
pounds.
Chapters 8 through 19 deal with 12 classes of secondary compounds. In
some chapters, emphasis is placed on the chemical nature and properties of
the class; in other chapters, various aspects of their metabolism, including
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XX Preface to Volume 7
regulation, are stressed. In Chapter 12, the authors have confined their atten-
tion to the enzymes of alkaloid metabolism, an approach that has permitted
the subject of alkaloids to be restricted to one chapter in the present volume.
Whereas the chapters in this second section discuss 12 different classes of
secondary plant products, other compounds that can properly be described as
secondary plant products are dealt with elsewhere in this treatise (e.g., Chap-
ters 5 and 15 in Volume 3; Chapters 13, 14, 17, 18, and 19 in Volume 4; and
Chapters 8, 9, 10, and 11 in Volume 6). By discussing some secondary
compounds elsewhere in the Treatise, we have maintained Volume 7 at a
reasonable size.
Chapters 20 through 23 in the final section are concerned with enzymes
that are of more than ordinary interest in the metabolism of secondary plant
products. Thus, Chapter 20 discusses phenylalanine ammonia-lyase which
catalyzes the conversion of the primary metabolite phenylalanine to cin-
namic acid, the first reaction in the biosynthesis of phenylpropanoid com-
pounds. Also treated in this section are oxygenases, methyl and glycosyl
transferases, and glycosidases, all of which are intimately involved in the
metabolism of secondary plant products.
I wish to thank the authors who contributed to this volume for their coop-
eration and their patience during its production. I also am grateful for the full
cooperation of the publishers and for the secretarial assistance of Ms. Billie
Gabriel and Ms. Barbara Clover.
Ε. E. Conn
