The Metabolism, Structure, and Function of Plant Lipids

652 Pages·1987·10.29 MB·English

by  William R. Nes (auth.)

THE METABOLISM,
STRUCTURE,AND
FUNCTION OF
PLANT LIPIDS
THE METABOLISM,
STRUCTURE, AND
FUNCTION OF
PLANT LIPIDS
Edited by
Paul K. Stumpf
University of California, Davis
Davis, California
J. Brian Mudd
ARCO Plant Cell Research Institute
Dublin, California
and
W. DavidNes
u.s. Department of Agriculture
Albany, California
PLENUM PRESS • NEW YORK AND LONDON
Library of Congress Cataloging in Publication Data
International Symposium on Plant Lipids (7th: 1986: University of California, Davis)
The metabolism, structure, and function of plant lipids.
"Proceedings of the Seventh International Symposium on Plant Lipids, held July 27-
August 1,1986, at the University of California, Davis, Davis, California"-T.p. verso.
Includes bibliographies and index.
1. Plant lipids-Congresses. I. Stumpf, Paul K. (Paul Karl), 1919- . II. Mudd, J.
Brian (John Brian), 1929- . III. Nes, W. David. IV. Title. [DNLM: 1. Lipids-metab
olism-congresses. 2. Plants-metabolism-congresses. W3 IN92IBU 7th 1986b / QK
898.L56 161 1986b)
QK898.L56I556 1986 581.19'247 87-1749
ISBN 978-1-4684-5265-5 ISBN 978-1-4684-5263-1 (eBook)
DOI 10.1007/978-1-4684-5263-1
Proceedings of the Seventh International Symposium on Plant Lipids,
held July 27-August 1, 1986, at the University of California, Davis,
Davis, California
© 1987 Plenum Press, New York
Softcover reprint of the hardcover 1s t edition 1987
A Division of Plenum Publishing Corporation
233 Spring Street, New York, N.Y. 10013
All rights reserved
No part of this book may be reproduced, stored in a retrieval system, or transmitted
in any form or by any means, electronic, mechanical, photocopying, microfilming,
recording, or otherwise, without written permission from the Publisher
DEDICATION
Dr. Andrew A. Benson, professor of biology,
Scripps Institution of Oceanography, University
of California, San Diego.
It is customary in the Proceedings of the Symposia on Plant Lipids
to honor one of the major contributors to this field of research.
On this occasion we would like to recognize important discoveries
made by
ANDREW ALM BENSON
who is currently Professor at the Scripps Ins.titute of Oceanography, La
Jolla, California.
Andy Benson obtained his Ph.D. in organic chemistry from the
California Institute of Technology. He subsequently joined the bio
organic chemistry group at the Lawrence Radiation Laboratory of the
University of California at Berkeley at what proved to be a very produc
tive time. Together with Calvin and Bassham he was responsible for the
complete elucidation of the pathway of carbon dioxide assimilation in
photosynthesis.
v
During the research on photosynthesis it is clear that Andy Benson
noticed that in addition to the water soluble compounds labeled after
the supply of radioactive carbon dioxide, lipid soluble compounds were
also synthesized. When he moved to Pennsylvania State University in
1955, he turned his attention to these compounds. During the six years
he spent at Pennsylvania State University Andy and his students made
several important discoveries, including the isolation and characteriza
tion of both phosphatidylglycerol and sulfoquinovosyldiacylglycerol, two
lipids we now know to be of particular significance in the chloroplast.
No account of the chemistry and biochemistry of these compounds is
complete without discussion of the results from Andy Benson's laboratory.
Work on the sulfoquinovosyldiacylglycerol continued in Andy's
laboratories after he moved back to California, but his association with
the Scripps Institute of Oceanography led to new discoveries, particu
larly in the lipids of marine organisms. The finding of arsenic
containing lipids has been particularly interesting and impressive.
Andy Benson has made a deep impression on research in plant lipids
not only by the contributions from his own laboratory but also by
fostering and encouraging the research in other laboratories. We hope
that he will continue to inspire us for years to come.
vi
PREFACE
The Seventh International Symposium on the Structure and Function
of Plant Lipids took place at the University of California, Davis,
California July 27th to August 1st, 1986.
This was the first time the Symposium was held in the United States.
The list of previous host cities reads, Norwich, Karlsruhe, Goteborg,
Paris, Groningen, Neuchatel. The addition of Davis to this distinguished
list was made by the organizers with the doubts of people who give
invitations to parties - will anybody come? In fact 155 participants
registered and there were 21 spouses in attendance.
The scientific program was composed of nine sessions: biochemistry
of isoprenoids and sterols, function of isoprenoids and sterols,
structure and function of lipids, biosynthesis of complex lipids, fatty
acid oxygenases and desaturases, medium and long chain fatty acids,
interaction of university, government and industrial research, algal
lipids, and genetics and biotechnology. In addition to these sessions
of plenary lectures, there were four poster sessions in which about 140
posters were presented. All of this was packed into four days, and
there was some comment about the scarcity of time to ask questions of
the speakers, discuss the posters and even to eat lunch. The compression
of the program was a result of the continued desire of the organizing
committees to avoid concurrent sessions. The congregation of participants
into a single session increases interaction and generates a feeling of
unity at these symposia. This is exemplified by the position of studies
on isopentenoids within the framework of plant lipid biochemists. Only
a few years ago research on isopentenoids was considered distinct from the
work on fatty acids and glycerolipids. These areas become closer as we
emphasize the interaction of lipid components with each other and with
the proteins of biological membranes. The integration of these approaches
is best exemplified by research with chloroplasts, where the biosynthesis
and function of isopentenoid compounds is related to biosynthesis and
function of glycerolipids.
A number of people who were attending the Symposium for the first
time commented on the open and friendly atmosphere. There is a family
feeling since the community of people who work on plant lipids is still
fairly small. At this Symposium however, there were several friends of
the family, people accustomed to reporting their research in other areas
who have much to contribute to the field of plant lipids. We think in
particular of the contribution of Leo Parks on the function of sterols
in yeast, the presentation of Joe Kuc on the importance of lipids in
host-pathogen interactions, and the paper of Rudy Demel on the dynamics
of glycerolipid, sphingolipid and sterol interaction in membranes.
vii
The organization of this Symposium was different from previous
symposia in some aspects. The new sessions in interaction of government,
industrial and university research, and on genetics and biotechnology
are in some respects related. Clearly the field of plant lipids is
entering a phase of research on the molecular biology of lipid biosynthe
tic enzymes. It is equally clear that industrial laboratories have a
stake in the outcome of these investigations. Plant lipid biochemists
recognize that part of their work interfaces with the large and profitable
oleochemical industry. Progress has already been made toward tailoring
oil seed crops for specific purposes. This will be an area for consider
able research in the future. We may expect important results from both
industrial and tax-supported institutions on genetic manipulations and
genetic engineering of the lipid metabolism of higher plants.
Although we continue to understand the biosynthesis of lipids in an
increasingly comprehensive and detailed manner, we still have few
examples of specific functions of lipids in higher plants. Studies on
degradation of specific lipids in thylakoids are making progress in this
area, and the use of Arabidopsis mutants holds further promise in this
area. The proposal by Norio Murata that particular molecular species of
phosphatidylglycerol (PG) are involved in chilling sensitivity has
aroused a great deal of interest because (a) it suggests a specific role
for a chloroplast lipid and (b) it suggests a simple biochemical reason
for the difference between chilling sensitive and chilling resistant
plants. Several papers in these Proceedings bear on this question.
This book presents the material discussed at the Symposium in
Davis. It is a reflection of the state of research in plant lipids in a
comprehensive and up-to-date fashion. It provides an opportunity for
those who were not at the Symposium to review the status of the field,
and for those who were at the Symposium it provides an opportunity to
study details that may have been missed in the actual presentation.
Because of the ad hoc nature of the Plant Lipid Conferences,
financial support waS-essential in order to continue the practice of
having an international meeting with speakers from all corners of the
globe. We therefore wish to acknowledge with considerable gratitude
travel funds donated by the following industrial sources: Arco Plant
Cell Research Institute, DuPont, Calgene, Henkel, Proctor and Gamble,
Monsanto and the Shell Agricultural Chemical Company as well as funds
from state and federal sources: National Science Foundation, University
of California Biotechnology Research and Education Program, Office of
Naval Research (USA), Department of Energy (USA), and Department of
Agriculture (USA).
In addition we wish to thank Mrs. Kathryn Gardner and her colleagues
of the Campus Events and Information Office (UCD) for their great assist
ance in the organization of the conference and Mrs. Billie Gabriel for
her usual excellent secretarial help. One of us is also indebted to Mrs.
Ruth R. Stumpf for her yeoman service during the Conference in smoothing
out ruffled feathers of some of the participants.
P.K. Stumpf
J.B. Mudd
W.D. Nes
viii
CONTENTS
BIOSYNTHESIS AND FUNCTION OF STEROLS AND OTHER ISOPRENOIDS
Multiple Roles for Plant Sterols . 3
W.R. Nes
Stereochemistry of Monoterpene Cyclization . . . . . . . . . . .. 11
R. Croteau
Diterpenes - The Gibberellin Biosynthetic Pathway in Zea mays 19
B.O. Phinney and C.R. Spray
Synthesis of Plastoquinone-9, a-Tocopherol and Phylloquinone
(Vitamin Kl) and Its Integration in Chloroplast Carbon
Metabolism of Higher Plants . . .. ...... 29
D. Schulze-Siebert, U. Homeyer, J. SolI and G. Schultz
Carotenoid Biosynthesis and Carotenogenic Enzymes in Plastids 37
H. Kleinig
Cell Walls and Secondary Products as Obstacles to Plant Enzyme
Isolation: Problems and Solutions, Including a Simple
Liquid Nitrogen Homogenizer for Bulk Tissue Extraction . 45
R.P. Sandstrom and W.D. Loomis
Developmental Regulation of Sterol and Pentacyclic Triterpene
Biosynthesis and Composition: A Correlation with Sorghum
Floral Initiation . . . .. ........... 53
R.C. Heupel, W.D. Nes and J.A. Verbeke
Effect of Intracellular Sterol Concentration on Sterol
Esterification in Yeast ... . . 57
L.W. Parks, T.A. Lewis, C. Low and K. Haeckler
Functional Organization of Carotenoids and Prenylquinones in
the Photosynthetic Membrane . . . . . . . . . 63
H.K. Lichtenthaler
Arachidonic and Eicosapentaenoic Acids, Glucans and Calcium
as Regulators of Resistance to a Plant Disease . . . . 75
M. Zook and J. Kuc
Presence of Unusually High Levels of Cholesterol in the Shoot-
Apices of Flowering Plants . . . . . . . . . . . . 83
V.K. Garg, T.J. Douglas and L.G. Paleg
ix
Changes in Sterol Biosynthesis From [2-14C]Mevalonic Acid
During Development of Cucurbita maxima Seedlings . . 87
V.K. Garg and W.R. Nes
Inhibition of Growth of Celery Cells by Paclobutrazol
and Its Reversal by Added Sterols ..... . 91
P.A. Haughan, J.R. Lenton and L.J. Goad
The Steryl Esters of Higher Plants . .. ..... 95
L.J. Goad, J. Zimowski, R.P. Evershed and V.L. Male
Synthesis and Biological Evaluation of Fungal Bioregulators
of Sterol Biosynthesis ............. . 103
E.J. Parish, P.K. Hanners and W.D. Nes
A Comparison of Sterol and Long Chain Fatty Alcohol
Biosynthesis in Sorghum bicolor . . . .. ..... 107
Y. Sauvaire, B. Tal, R.C. Heupel, R. England, P.K. Hanners,
W.D. Nes and J.B. Mudd
Regulation of Terpenoid Biosynthesis in Tapped Latex . . . . . . .. 111
G.J. Piazza, E.J. Saggese and M.P. Thompson
Triterpenoid Biosynthesis in Euphorbia lathyris .... 115
C.L. Skrukrud, S.E. Taylor, D.R. Hawkins and M. Calvin
Phytosterol Structure and Composition in the Chemosystematics
of the Caryophyllales . . . . .. ........ . 119
J.H. Adler and T.A. Salt
Biosynthesis of Diterpene Phytoalexin Precursors in
Cell-free Extracts of Rice . . . . . . . . 123
K. Wickham and C.A. West
Endogenous Gibberellins in Wheat Shoots 127
J.-T. Lin and A.E. Stafford
Molecular Associations in Lipid-carotenoid Monolayers 131
M. Tomoaia-Cotiqel, J. Zsako, E. Chifu and P.J. Quinn
Separation and Identification of Carotenoid-esters in Red
Pepper /Capsicum annum/ During Ripening 135
P.A. Biacs, J. Bodna~ Hoschke, A. Cs. Pavis, H. Daood,
F. Hajdu and N. Kiss-Kutz
On the Biosynthesis of Fragrance Compounds in Ambrette
(Hibiscus abelmoschus) Seeds . .. ..... 139
M.R. Pollard, S. Jamil-Panah and T.Y. Nee
STRUCTURE AND FUNCTION OF LIPIDS
Structural and Dynamic Aspects of Membrane Lipids 145
R.A. Demel
Lipid Saturation by Catalytic Hydrogenation and Its Effect on
Membrane Structure and Function . . . . . . . . . . 153
L. Vigh
x
Spatial Organization and Functional Roles of Acyl Lipids
in Thylakoid Membranes .. ................ 161
P.A. Siegenthaler, A. Rawyler and C. Giroud
Ultrastructural Studies on Plant Membranes . . . . . . . . . . 169
W.W. Thomson, K.A. Platt-Aloia and R.D. Bliss
Evidences for Different Acyl Lipid Domains in Spinach and Oat
Thylakoid Membranes Supporting Various Photosynthetic
Functions . . . . . . . . . . . . • . . . . . . . . . • . . . 177
P.A. Siegenthaler, C. Giroud and J. Smutny
Phase Transition Behavior of Monogalactosyldiacylglycerol . . . . . 181
P.J. Quinn and L.J. Lis
Is Monogalactosyl Diacylglycerol Involved in the Packaging
of Light-harvesting Chlorophyll Proteins in the
Thylakoid Membrane? . . . . . . . . . . . . . • . . . . 185
P.J. Dominy and W.P. Williams
Mechanisms of Lipid-protein Binding in Photosynthetic Membranes . . 189
D.J. Murphy
Lipid Molecular Species Composition of Granal and Stromal
Lamellae. . . . . . .................. 193
H.A. Norman, J.B. St. John, F.E. Callahan, A.K. Mattoo
and W.P. Wergin
On the Function of Methyl-branched Chain Fatty Acids in
Phospholipids of Cell Membranes of Higher Plants ....... 197
A. Radunz
Freezing Resistance and Lipid Changes in Choline-treated
Wheat Seedlings •. . . . . . . . . . . . . .. ...... 201
W.P. Williams, I. Horvath, P.J. Quinn, P.G. Thomas
and L. Vigh
Drought Stress Effects on Root Cell Membranes . . . . . . . . . 205
H. Svenningsson, M. Andersson and C. Liljenberg
Manipulating Membrane Fatty Acid Compositions of Soybean Plants . . 209
W.B. Terzaghi
Plasma Membrane Lipid Alterations Following Cold Acclimation:
Possible Relevance to Freeze Tolerance . . . . . • . . . . . . 213
D.V. Lynch and P.L. Steponkus
Plasma Membrane and Tonoplast Fractions Isolated from Spinach
Leaves by Preparative Free Flow Electrophoresis:
Effect of Photoinduction ..............•.... 217
C. Penel, G. Auderset, S. Kiefer, A. Sandelius,
A. Brightman, H. Greppin and D.J. Morre
Study of the Intracellular Transfer of Lipids to the
Plasmalemma . • . . . . . 221
P. Moreau, H. Juguelin, R. Lessire and C. Cassagne
Ca2+ and Inter-molecular Bridging of Membranal Phospholipids
and Proteins . . • • 225
Y.Y. Leshem
xi