Table Of ContentSpringer Series in Wood Science
Editor: T. E. Timell
Springer
Berlin
Heidelberg
New York
Barcelona
Budapest
Hong Kong
London
Milan
Paris
Santa Clara
Singapore
Tokyo
Springer Series in Wood Science
Editor: T. E. Timell
M. H. Zimmermann
Xylem Structure and the Ascent of Sap (1983)
J. F. Siau
Transport Processes in Wood (1984)
R. R. Archer
Growth Stresses and Strains in Trees (1986)
w. E. Hillis
Heartwood and Tree Exudates (1987)
S. Carlquist
Comparative Wood Anatomy (1988)
L. W. RobertslP. B. Gahan/R. Aloni
Vascular Differentiation and Plant Growth Regulators (1988)
e. Skaar
Wood-Water Relations (1988)
J. M. Harris
Spiral Grain and Wave Phenomena in Wood Formation (1989)
B. J. Zobel/J. P. van Buijtenen
Wood Variation (1989)
P. Hakkila
Utilization of Residual Forest Biomass (1989)
J. W. Rowe (Ed.)
Natural Products of Woody Plants (1989)
K.-E. L. Eriksson/R. A. Blanchette/P. Ander
Microbial and Enzymatic Degradation of Wood and Wood Components (1990)
R. A. Blanchette/A. R. Biggs (Eds.)
Defense Mechanisms of Woody Plants Against Fungi (1992)
S. Y. Lin/e. W. Dence (Eds.)
Methods in Liguin Chemistry (1992)
G. Torgovnikov
Dielectric Properties of Wood and Wood-Based Materials (1993)
F. H. Schweingruber
Trees and Wood in Dendrochronology (1993)
P. R. Larson
The Vascular Cambium: Development and Structure (1994)
M.-S. Ilvessalo-Pfaffli
Fiber Atlas: Identification of Papermaking Fibers (1995)
B. J. Zobel/J. B. Jett
Genetics of Wood Production (1995)
e. Mattheck/H. Kubler
Wood - The Internal Optimization of Trees (1995)
T. Higuchi
Biochemistry and Molecular Biology of Wood (1997)
T. Higuchi
Biochemistry and
Molecular Biology
of Wood
With 200 Figures and 25 Tables
, Springer
Prof. Dr. TAKAY OSHI HIGUCHI
Wood Research Institute
Kyoto University (retired)
Momoyamacho, Y osai 22-8
Fushimi-ku, Kyoto 612
Japan
Series Editor:
T. E. TIMELL
State University of New York
College of Environmental Science and Forestry
Syracuse, NY 13210, USA
Cover: Transverse section of Pinus lambertiana wood. Courtesy of Dr. Carl de Zeeuw,
SUNY College of Environmental Science and Forestry, Syracuse, New York
ISBN -13: 978-3-642-64419-1 e-ISBN -13: 978-3-642-60469-0
DOl: 10.1007/978-3-642-60469-0
Library of Congress Cataloging-in-Publication Data. Higuchi, Takayoshi, Biochemistry and molecular biology
of wood/To Higuchi, T. Umezawa. p. cm. - (Springer series in wood science) Includes bibliographical refer
ences and index.ISBN-13:978-3-642-64419-1 1. Wood - Anatomy. 2. Wood - Chemistry. 3. Plant molecular
biology. I. Umezawa, T. (Toshiaki), 1957- . II. Title. III. Series. QK647.H53 1997 582'.0495 -
dc20 96-28429
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under the German Copyright Law.
© Springer-Verlag Berlin Heidelberg 1997
Softcover reprint of the hardcover 1st edition 1997
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Preface
Progress in wood chemistry has been related mainly to chemical wood pulping
and bleaching and chemical utilization of wood and wood extractives. Meth
ods of wood analysis were developed by Schorger (proximate analysis in 1917)
and Dore (summative analysis in 1919), and standard methods based on
Schorger's method, e.g., TAPPI standards (Technical Association of the Pulp
and Paper Industry), have been widely used for chemical analysis of woods in
many countries. Thus it is generally known that wood is composed of about
50% cellulose, 20-35% of lignin, 15-25% of hemicelluloses, and variable
amounts of extractives. Chemical characterization and efficient utilization of
these wood components have been studied in laboratories of wood chemistry
and technology in universities and government institutions.
In the last decade, biochemistry and molecular biology of microorganisms,
animals, and plants have greatly progressed. At the same time wood has been
recognized as a unique renewable ecomaterial produced by trees using solar
energy. In addition, many desirable properties of wood and wood components
as biomaterial that affects physiology and psychology in humans have recently
attracted attention.
In order to elucidate the properties of wood and wood components pro
duced by trees, characterization of genes encoding enzymes involved in the
biosynthesis of wood components, differentiation of the cambium into phloem
and xylem, and the mechanisms of the expression of these genes needed to
be investigated. Research on the molecular biology of trees and wood has
just begun in Europe, USA, Canada, New Zealand, and Japan, among other
countries, and rapid progress is being made.
I became interested in wood biochemistry during my stay at Gifu Univer
sity, where the first Wood Biochemistry Laboratory in Japan was founded in
1949, and at the Wood Research Institute, Kyoto University, through research
on the biosynthesis of lignin and formation of heartwood.
I am very much indebted to Dr. Toshiaki Umezawa from the Wood
Research Institute at Kyoto University, who contributed to the section on
"Lignans" (Sect. 4.3.5). Dr. Umezawa was the first to synthesize the lignans,
(-)-secoisolariciresinol, and (-)-matairesinol enzymatically from coniferyl al
cohol. I wish to thank Dr. Stewart A. Brown (Trent University, Canada), Dr.
Fernand Barnoud (Grenoble University, France), Dr. M. Shimada and Dr. F.
Nakatsubo (Kyoto University), Dr. T. Yamasaki (Kagawa University), Dr. H.
Ohashi and Dr. M. Tanahashi (Gifu University), and Dr. Y. Nakamura, Dr. H.
Kuroda, Dr. H. Kutsuki, Dr. S. Kawai, and Dr. H. Fushiki for their assistance
during my studies on lignin biochemistry. I also wish to thank Dr. T. Hoh
VI Preface
(Wood Research Institute, Kyoto University), Dr. D. Shibata and Dr. T.
Hibino (Mitsui Plant Biotechnology Research Institute), Dr. H. Fukuda
(Tokyo University), Dr. H. Ohashi (Gifu University), Dr. K. Fukazawa
(Emeritus Professor at Hokkaido University), Dr. T. Minamikawa (Tokyo
Metropolitan University), Dr. T. Hayashi and Dr. J. Sugiyama (Wood Re
search Institute, Kyoto University), Dr. K. Takabe (Kyoto University), Dr. H.
Kuroda (Wood Research Institute, Kyoto University), Dr. R. Funada (Hok
kaido University), and Dr. K. Fukushima (Nagoya University) for their sup
port and help with this book. I thank the many scientists and publishers who
kindly granted permission for me to use their original illustrations for this
book. Finally, I would like to thank Dr. T. E. Timell, the editor of this series,
and the staff of Springer-Verlag for their help and encouragement during the
preparation of this book.
Kyoto, Japan TAKAYOSHI HIGUCHI
Autumn 1996
Contents
1 Structure and Functions of Wood ....................... . 1
1.1 Microscopic Structure ................................. . 8
1.1.1 Softwoods (Conifers) .................................. . 8
1.1.2 Hardwoods (Dicot Angiosperms) ....................... . 10
1.1.3 Bamboos ............................................ . 11
1.2 Ultrastructure of Wood Cell Walls ...................... . 13
1.2.1 Cellulose Microfibrils ................................. . 14
1.2.2 Orientation of Microfibrils ............................. . 18
1.2.3 Cell Walls of Reaction Woods .......................... . 20
1.3 Ultrastructure and Functions of Wood Cells .............. . 22
1.3.1 Nucleus ............................................. . 22
1.3.2 Ribosomes ........................................... . 25
1.3.3 Endoplasmic Reticulum ............................... . 25
1.3.4 Golgi Apparatus ...................................... . 27
1.3.5 Mitochondria ........................................ . 30
1.3.6 Plastids .............................................. . 32
1.3.6.1 Amyloplasts ......................................... . 33
1.3.6.2 Chloroplasts ......................................... . 34
1.3.7 Vacuoles ............................................ . 35
1.3.8 Cytoskeletons ........................................ . 35
1.3.8.1 Microtubules ......................................... . 35
1.3.8.2 Microfilaments ....................................... . 37
1.3.9 Cell Membrane ....................................... . 38
1.3.10 Cell Wall ............................................ . 40
2 Primary Metabolism in Woody Plants ................... . 43
2.1 Primary and Secondary Metabolism ..................... . 43
2.2 Photosynthesis ....................................... . 44
2.3 Photorespiration ...................................... . 50
2.4 Glycolysis ........................................... . 50
2.5 Tricarboxylic Acid Cycle .............................. . 54
2.6 Pentose Phosphate Cycle .............................. . 57
2.7 Glyoxylate Cycle ..................................... . 60
2.8 Nitrogen Metabolism .................................. . 62
2.8.1 Nitrogen Fixation ..................................... . 62
VIII Contents
2.8.2 Amino Acid Formation 64
2.8.3 Transamination ....................................... . 66
3 Genome Organization, Protein Synthesis,
and Gene Expression ................................. . 68
3.1 Genome Organization ................................. . 68
3.1.1 DNA and Genes ..................................... . 68
3.1.2 Genes and Chromosomes .............................. . 69
3.1.3 Structure and Duplication of DNA ..................... . 71
3.1.4 RNA Synthesis ....................................... . 73
3.1.4.1 Structure and Function of mRNA ...................... . 75
3.1.4.2 Structure and Function of tRNA ........................ . 77
3.1.4.3 rRNA ............................................... . 78
3.1.4.4 Splicing of RNA ...................................... . 79
3.1.4.5 RNA Editing ......................................... . 79
3.1.5 mRNA and the Genetic Code .......................... . 79
3.2 Protein Synthesis ..................................... . 81
3.3 Gene Expression ..................................... . 83
3.3.1 Fundamental Structure of the Gene ..................... . 83
3.3.2 RNA Polymerase and Transcription Apparatus ........... . 84
3.3.3 Base Sequence of Transcription Promoter ............... . 86
3.3.4 The Factor of Transcriptional Control ................... . 86
3.3.5 Regulation of Gene Expression ......................... . 87
3.4 Gene Expression in Plants ............................. . 88
3.4.1 Regulation of Gene Expression by Light ................. . 88
3.4.2 Gene Expression in Chloroplasts ....................... . 89
3.4.3 Gene Expression in Mitochondria ....................... . 92
4 Biosynthesis of Wood Components ..................... . 93
4.1 Chemical Composition of Wood ........................ . 93
4.1.1 Cellulose ............................................ . 93
4.1.2 Hemicelluloses ....................................... . 93
4.1.3 Lignin ............................................... . 94
4.1.4 Aliphatic Compounds ................................. . 95
4.1.5 Sugars ............................................... . 95
4.1.6 Aromatic Compounds ................................. . 95
4.1.7 Terpenes ............................................ . 95
4.1.8 Biosynthetic Pathways ................................. . 95
4.2 Biosynthesis of Cell Wall Polysaccharides ................ . 97
4.2.1 Localization of Polysaccharides in Wood Cell Walls ....... . 97
4.2.2 Metabolism of Sugar Nucleotides ....................... . 99
4.2.2.1 UDP-Glucose Pyrophosphorylase ....................... . 102
4.2.2.2 Sucrose Synthase ..................................... . 102
Contents IX
4.2.2.3 UDP-Glucose Dehydrogenase .......................... . 103
4.2.2.4 UDP-Glucuronate Carboxylase ......................... . 103
4.2.2.5 UDP-Glucose 4-Epimerase ............................ . 104
4.2.2.6 UDP-Glucuronate 4-Epimerase ......................... . 104
4.2.2.7 UDP-Arabinose 4-Epimerase .......................... . 104
4.2.2.8 The myo-Inositol Oxidation Pathway .................... . 105
4.2.3 Biosynthesis of Cellulose .............................. . 106
4.2.3.1 Microorganisms ...................................... . 107
4.2.3.2 Plants ............................................... . 111
4.2.4 Cellulose Microfibrils .................................. . 114
4.2.4.1 Structure of Microfibrils ............................... . 114
4.2.4.2 Formation of Microfibrils .............................. . 117
4.2.4.3 Cell Growth and Microfibril Orientation ................. . 121
4.2.5 Biosynthesis of ~-1,3-Glucan ........................... . 121
4.2.6 Biosynthesis of Xyloglucan ............................. . 123
4.2.7 Biosynthesis of Xylan (Arabinoxylan) ................... . 126
4.2.8 Biosynthesis of Glucomannan .......................... . 127
4.2.9 Biosynthesis of Galactan ............................... . 128
4.2.10 Biosynthesis of Arabinan .............................. . 128
4.2.11 Biosynthesis of Pectin (Polygalacturonic Acid) ............ . 128
4.2.12 Biosynthesis of Sugar Chains of Glycoproteins ............ . 129
4.2.13 Cell Organelles Involved in Polysaccharide Synthesis ...... . 129
4.3 Phenylpropane Derivatives ............................. . 131
4.3.1 The Shikimate Pathway Commonly Involved
in the Biosynthesis of Aromatic Compounds ............. . 134
4.3.1.1 The Enzyme System in Aromatric Biosynthesis ........... . 135
4.3.2 Biosynthesis of Phenylalanine and Tyrosine .............. . 140
4.3.2.1 Phenylalanine and Tyrosine ............................ . 140
4.3.2.2 Diversity of the Shikimate Pathway ..................... . 142
4.3.3 The General Phenylpropanoid Pathway .................. . 144
4.3.3.1 Phenyalanine Ammonia-Lyase ......................... . 145
4.3.3.2 Cinnamate 4-Hydroxylase (C4H) ....................... . 149
4.3.3.3 4-Coumarate: Coenzyme A Ligase (4CL) ................ . 151
4.3.4 Lignin ............................................... . 154
4.3.4.1 Formation of Monolignols ............................. . 156
4.3.4.2 Dehydrogenative Polymerization of Monolignols to Lignins . 168
4.3.4.3 Structural Differences in Dehydrogenation Polymers ...... . 174
4.3.4.4 Differences in Biosynthesis of Lignins Between Tissues
and Plants ........................................... . 177
4.3.5 Lignans .............................................. . 181
4.3.5.1 Introduction ......................................... . 181
4.3.5.2 Structural Features of Lignans .......................... . 182
4.3.5.3 Biosynthetic Pathways of Lignans - In Vivo Experiments .. . 185
4.3.5.4 Enzymatic Lignan Formation ........................... . 188
4.3.6 Flavonoids ........................................... . 194
X Contents
4.3.6.1 Biosynthetic Pathways ................................. . 195
4.3.6.2 Isoftavonoids ......................................... . 206
4.3.7 Stilbenes ............................................ . 214
4.3.7.1 Biosynthesis ......................................... . 214
4.3.7.2 Induction of Stilbene Formation ........................ . 217
4.3.8 Quinones ............................................ . 219
4.3.9 Tannins ............................................. . 226
4.3.9.1 Hydrolyzable Tannins ................................. . 226
4.3.9.2 Condensed Tannins ................................... . 230
4.3.10 Suberin .............................................. . 233
4.4 Lipids ............................................... . 237
4.4.1 Membrane Lipids ..................................... . 237
4.4.2 Acyltriglycerides (Fats) ................................ . 238
4.4.2.1 Saturated Fatty Acids ................................. . 238
4.4.2.2 Unsaturated Fatty Acids ............................... . 240
4.4.2.3 Acyltriglycerides ...................................... . 241
4.4.3 Waxes ............................................... . 242
4.5 Isoprenoids ............................ . . . . . . . . . . . . . . . 243
4.5.1 Structure of Isoprenoids ............................... . 245
4.5.2 Polymerization of Active Isoprene ...................... . 246
4.5.3 Formation of Cyclic Mono- and Sesquiterpenes ........... . 248
4.5.4 Biosynthesis of Carotenoids ............................ . 256
4.5.5 Di- and Triterpenes ................................... . 256
4.5.6 Biosynthesis of Polyterpenes ........................... . 260
4.5.7 Prenylation of Proteins ................................ . 260
4.5.8 Tropolones .......................................... . 261
5 Formation and Development of Wood Tissues ............ . 263
5.1 Development of Phloem and Xylem ..................... . 263
5.1.1 Formation of Phloem and Xylem ....................... . 263
5.1.1.1 Primary Xylem ....................................... . 263
5.1.1.2 Primary Phloem ...................................... . 263
5.1.1.3 Vascular Cambium .................................... . 264
5.1.2 Regulation of Xylem and Phloem Differentiation ......... . 264
5.1.2.1 Plant Hormones ...................................... . 264
5.1.2.2 Other Factors ........................................ . 268
5.1.3 Physiological and Biochemical Processes of Xylem
and Phloem Differentiation ............................ . 269
5.1.3.1 Acquisition of Differentiation Ability .................... . 269
5.1.3.2 Cell Elongation ....................................... . 270
5.1.3.3 Formation of Secondary Walls .......................... . 270
5.1.3.4 Disappearance of Cell Content ......................... . 272
5.1.4 Genes Involved in Tracheary Element Differentiation ..... . 275
5.1.4.1 Genes Expressed Before Vascular Bundle Differentiation .. . 275
