Platelet-activating factor and structurally related alkyl ether lipids

498 Pages·1991·36.351 MB·English

by  Wolfgang J Baumann

Platelet-Activating Factor
and Structurally Related
Alkyl Ether Lipids
EDITOR
Wolfgang J. Baumann
Co-edited by
Shoshichi Nojima
Keizo Inoue
Masaji Ohno
Ichiro Kudo
Shohei Makino
Kunihiko Saito
Morio Setaka
Keizo Waku
Index Editor
Barbara Malewicz
Published by the American Oil Chemists’Society
iii
Copyright © 1991 AOCS Press
AOCS Mission Statement
To be a forum for the exchange of ideas, information and experience among those with a
professional interest in the science and technology of fats, oils and related substances in
ways that promote personal excellence and provide for a high standard of quality.
Declaration by the Governing Board
The American Oil Chemists’Society is organized for charitable, educational and scientific
purposes. It does not have as its purpose the promotion of any product, manufacturers, lab-
oratory or business. Members of the Society, and employees of the Society, do not and
may not speak for or on behalf of the Society without the expressed permission of the
Governing Board. This prohibition includes the use of the American Oil Chemists’Society
logo or letterhead when making a statement of a technical or economic nature. Members
of the Society, or employees of the Society, speak only for themselves when giving opin-
ion or making statements concerning technical matters and economic matters.
Copyright ©1991 by the American Oil Chemists’Society. All rights reserved. No part of
this book may be reproduced or transmitted in any form or by any means without written
permission of the publisher.
Printed in the United States of America
iv
Copyright © 1991 AOCS Press
PREFACE
This special Lipids issue represents a thorough, state-of-the-art therapy. This timely collection is the most comprehensive
account on platelet activating factor (PAF) and structurally compendium of peer-reviewed papers published in the PAF
related alkyl lysophospholipids (ALP). The present collection field to date.
contains some hundred peer-reviewed research articles and I wish to express my sincere thanks to Professor Shoshichi
reviews by the world’s leading authorities in this field. The Nojima, Chairman of the Conference, and to the Members of
contributions are based on papers and posters which were orig- the Organizing Committee for their commitment and for mak-
inally presented at the Third International Conference on ing the Conference a most memorable experience. Thanks are
Platelet-Activating Factor and Structurally Related Alkyl Ether also due to the colleagues who have co-edited the papers. I am
Lipids held in Tokyo, Japan, in May 1989. Most of the origi- deeply indebted to the many referees for their enormous efforts
nal research papers and focused in-depth review articles have and their expert advice; without them peer-review would not
since been updated and provide a detailed overview of the state have been possible. My cordial thanks also to Dr. Barbara
of current research on ether lipid mediators covering biochem- Malewicz, Kerry McParland and Kerry Ruck at the Hormel
ical, cell biological, physiological and pathological aspects of Institute for their tireless efforts and encouragement, and to
PAF function as well as the role of ether lipids (ALP) in Annette Wall and the entire Lipids Production Staff for their
cancer therapy. extraordinary dedication and care. Last but not least, I would
The present volume covers a wide range of specialized like to thank each of the authors for their contributions and for
topics including PAF metabolism and its regulation; PAF and their cooperation and patience in revising and updating their
PAF analogs and their metabolic effects; PAF analysis by papers. This special issue is the result of a special team effort.
spectrometric and immunological assay; PAF receptor and All involved can be proud of it.
PAF antagonists; cell biology of PAF; PAF and the cerebral This special issue of Lipids should become a key reference
system; PAF, the cardiovascular system, and hypotension; source for researchers in a broad range of biochemical, biolog-
PAF, the respiratory system, allergy, and asthma; PAF and the ical and biomedical disciplines concerned with the role of PAF,
renal system; PAF and the gastrointestinal system; the patho- ALP, and related ether lipid mediators and their respective
physiology of PAF; and alkyl lysophospholipids in cancer modes of action.
Wolfgang J. Baumann
Editor
Copyright © 1991 AOCS Press
Third International Conference
on Platelet-Activating Factor
and Structurally Related
Alkyl Ether Lipids
held in Tokyo, Japan, May 8-12, 1989
Organizing Committee
Chairman Shoshichi Nojima (Teikyo University)
Secretary Keizo Inoue (University of Tokyo)
Treasurer Masaji Ohno (University of Tokyo)
Members
Takeshi Abe (Teikyo University) Terumasa Miyamoto (University of Tokyo)
Kazuo Imamura (Foundation for Advancement Toshio Muramatsu (Tokyo Medical and Dental University)
of International Science) Sachiko Oh-ishi (Kitasato University)
Yutaka Kasuya (Hoshi University) Kunihiko Saito (Kansai Medical School)
Makoto Katori (Kitasato University) Morio Setaka (Teikyo University)
Ichiro Kudo (University of Tokyo) Yousuke Seyama (University of Tokyo)
Yuichi Kumahara (Osaka University) Hiroaki Tsukatani (University of Tokushima)
Shohei Makino (Dokkyo University) Tamio Yamakawa (The Tokyo Metropolitan Institute
Makoto Matsumoto (Shizuoka College of Pharmacy) of Medical Science)
Haruki Mikawa (Kyoto University) Keizo Waku (Teikyo University)
The Symposium was sponsored by The Pharmaceutical Society of Japan and
the Foundation for Advancement of International Science, in cooperation with the
Japanese Society of Allergology, The Japanese Inflammation Society, The
Japanese Biochemical Society, The Japanese Pharmacological Society, and the
Japanese Conference on the Biochemistry of Lipids.
vii
Copyright © 1991 AOCS Press
OPENING REMARKS
Distinguished Guests, Ladies and Gentlemen,
I regard it a great honor to have been asked to deliver the —the multiple forms and the diverse range of biological activ
opening remarks to the Third International Conference on ities of PAF
Platelet-Activating Factor and Structurally Related Alkyl —PAF receptor and signal transduction
Ether Lipids. —the development of specific antagonists for use in receptor
Dear friends, it is my privilege to extend a hearty welcome studies and as potential anti-PAF drugs
to all of you who have come to the Third International —the implications of the involvement of PAF in health and
Conference on PAF from all over the world. As you know very disease.
well, the First Conference was held in Paris in 1983, and the We will also have a session on alkyl ether lipids which
Second Conference in Gatlinburg in 1986. Both conferences have selective antitumor activities, as we had at the Second
were very successful. We are now about to open our Third Conference.
Conference. The present Conference will cover a wide range of topics
We here in Japan are happy that our country was chosen to ranging from organic synthesis to clinical relevance.
host this important Conference. As soon as it had been decided Reflecting the rapid expansion and the progress that has been
by the International Steering Committee in 1986 that Japan made in this fascinating field, we received 235 abstracts of
should host the next Conference, we formed a Japanese papers; so, we will have a very tight day-by-day schedule. We
Organizing Committee. This Committee worked diligently to have brought together, from nineteen countries from all parts of
make this Conference a success. All the people gathering here the world, scientists working in universities, industry and public
share a keen interest in PAF. I know you will enjoy a week of institutions. As new methodologies are being developed and
fruitful discussions beginning today. new lines of investigation are being followed, this Conference
We have received more than 400 pre-registrations of will certainly serve as a catalyst to foster the exchange of ideas.
which about 150 were from abroad. We are expecting that the At this point, allow me to take this opportunity to express
final number of registrants will be close to 450. This clearly my sincere gratitude to Teikyo University, the various founda-
speaks for the great expansion in this fascinating field of tions, and the drug and chemical companies of Japan who have
research. The program of this Conference also reflects the provided such generous support, thereby enabling us to hold
remarkable growth and the advances that have been made in this Conference.
recent years. I hereby declare this Conference open. I hope that all par-
We will have sessions on ticipants will spend a successful week together to bring the
—the molecular and structural requirements for expression of Conference to a really fruitful conclusion.
biological activity in PAF antagonists and agonists Thank you very much.
—new analytical methods for PAF
—regulatory and enzymatic mechanisms of PAF biosynthesis Shoshichi Nojima
and catabolism Chairman
Copyright © 1991 AOCS Press
Contents
Volume 26, Number 12
December 1991
APUBLICATION OF THE AMERICAN OILCHEMISTS’SOCIETY
P.O. Box 3489, Champaign, IL61826–3489 USA (217) 359–2344 Telex 4938651 AOCS Ul
965 Platelet-Activating Factor (PAF): An Introduction
Shoshichi Nojima
PAF Metabolism and Its Regulation
967 Studies on the Selectivity of Enzymes Involved in Platelet-Activating Factor
Formation in Stimulated Cells
H. van den Bosch, A. Sturk, J.W. ten Cate and A.J. Aarsman
974 Regulation of the Biosynthesis of Platelet-Activating Factor in Alveolar
Macrophages
Takayuki Sugiura, Ayako Ojima-Uchiyama, Yasuo Masuzawa, Masamichi
Fujita, Yasuhito Nakagawa and Keizo Waku
979 Platelet-Activating Factor Acetylhydrolase Activity in Human Tissues
and Blood Cells
Diana M. Stafforini, Stephen M. Prescott, Guy A. Zimmerman and
Thomas M. McIntyre
986 Properties of PAF-Synthesizing Phosphocholinetransferase and Evidence
for LysoPAF Acetyltransferase Activity in Rat Brain
Gianfrancesco Goracci and Ermelinda Francescangeli
992 The Metabolism of 1-Acyl-PAF in Rabbit Platelets And Its Possible Interaction
With PAF
Lhousseine Touqui, Clystenes Soares Silva and Bernardo Boris Vargaftig
997 Platelet-Activating Factor (PAF) Stimulates the LysoPAF Acetyltransferase
in Leukocyte-Rich Plasma: Use in PAF Antagonist Studies
Thomas W. Doebber, Margaret S. Wu, Anthony Mauriello and Alfred Alberts
1004 Kinetic Studies of Human and Rat Neutrophil LysoPAF Acetyltransferase
Using LysoPAF and DansyllysoPAF as Substrates
Peter W. Schindler and Ewa Ninio
1011 The Effect of Inhibitors of Platelet Aggregation on the Metabolism of Platelet-
Activating Factor (PAF) in Washed Rabbit Platelets
C. O’Neill, A.J. Ammit, R. Korth, S. Fleming and X. Wells
1015 The Hormonal Regulation of Platelet-Activating Factor Acetylhydrolase Activity
in Plasma
Shuichi Miyaura, Noriei Maki, William Byrd and John M. Johnston
PAF and Signal Transduction
1021 Recent Advances in Our Understanding of the Biochemical Interactions
Between Platelet-Activating Factor and Arachidonic Acid—A Review
Floyd H. Chilton, Marc Cluzel and Massimo Triggiani
1028 Inositol Phospholipid Turnover in PAF Transmembrane Signalling—AR eview
Shivendra D. Shukla
1034 Transmembrane Signalling and Paf-Acether Biosynthesis—A Review
Ewa Ninio and Francine Joly
1038 PAF Effects on Transmembrane Signaling Pathways in Rat Kupffer Cells
Chandrashekhar R. Gandhi and Merle S. Olson
1044 Platelet-Activating Factor May Participate in Signal Transduction Processes
in Rabbit Leukocytes
Alastair G. Stewart and Trudi Harris
(continued on next page)
xi
Copyright © 1991 AOCS Press
Contents
Volume 26, Number 12
December 1991
1050 Inhibition by the PAF Antagonist WEB 2086 of PAF Induced
lnositol-1,4,5-trisphosphate Production in Human Platelets
F.W. Birke and H.A. Ensinger
1054 Phorbol Ester Stimulates PAF Synthesis via the Activation of Protein Kinase C
in Rat Leukocytes
Masahiko Hayashi, Yohsuke Imai and Sachiko Oh-ishi
1060 Tumor Necrosis Factor Release by Human Monocytes Stimulated with
Platelet-Activating Factor
N.M. Ruis, J.K. Rose and F.H. Valone
1065 Guinea Pig Bone Marrow Cells Treated with Platelet-Activating Factor Generate
Factor(s) Which Affects Their DNA Synthesis and Microbicidal Activity
Ichiro Kudo, Toshiyuki Kato, Hidetoshi Hayashi, Ryohei Yanoshita, Koichi
Ikizawa, Hiroko Uda and Keizo Inoue
1071 Effect of Platelet-Activating Factor on Tumor Necrosis Factor-Induced
Superoxide Generation from Human Neutrophils. Possible Involvement
of G Proteins
Pierre Braquet, David Hosford, Philipe Koltz, Jean Guilbaud and Monique
Paubert-Braquet
1076 Protein Kinase C is not Involved in the Desensitization of Platelet Activating
Factor Receptor in Rabbit Platelets
Lee-Young Chau
1080 A Unique Pool of Free Arachidonate Serves as Substrate for both
Cyclooxygenase and Lipoxygenase in Platelets
Françoise Chevy, Claude Wolf and Odile Colard
PAF and PAF Analogs and Their Metabolic Effects
1086 Biotransformation of Alkylglycerols in Plant Cell Cultures: Production
of Platelet Activating Factor and Other Biologically Active Ether Lipids
—A Review
Helmut K. Mangold, Shashank S. Apte and Nikolaus Weber
1093 Paf-Acether in Human Skin—A Review
Yves Denizot, Laurence Michel, Jacques Benveniste, Alain Meybeck,
Yolène Thomas and Louis Dubertret
1095 Chemical Synthesis and Physiological Activity of Sulfonium Analogues
of Platelet Activating Factor
Morris Kates, George A. Adams, Merle L. Blank and Fred Snyder
1102 Effect of Platelet-Activating Factor on Lipoprotein Lipase and Blood Lipids
Keiji Mimura, Susumu Yukawa, Yoshio Mori, Kazuya Okada, Masatoshi Mune,
Osamu Nishikawa, Akira Hibino, Miyahiko Sonobe, Tetuya Goto and Hiroshi
Nomoto
1108 Effect of Platelet-Activating Factor on Cortisol and Corticosterone Secretion
by Perfused Dog Adrenal
Tadaomi Aikawa, Taeko Hirose, Itsuro Matsumoto, Toshiko Morikawa, Toshio
Shimada, Yumi Mine, Yoshiki Tsujimoto and Yoshiro Tsuji
(continued on next page)
xii
Copyright © 1991 AOCS Press
Contents
Volume 26, Number 12
December 1991
PAF Analysis by Spectrometric and Immunological Assay
1112 Tandem Mass Spectrometry of Negative Ions from Choline Phospholipid
Molecular Species Related to Platelet Activating Factor
J.A. Zirrolli, K.L. Clay, R.C. Murphy
1117 Determination of Platelet-Activating Factor by a Chemiluminescence Method
and Its Application to Stimulated Guinea Pig Neutrophils
Yukio Hasegawa, Eiko Kunow, Junko Shindou and Hidetaka Yuki
1122 Specific Binding of Antibodies to Platelet-Activating Factor (PAF) as
Demonstrated by Thin-Layer Chromatography/lmmunostaining
Ken Karasawa, Noriko Satoh, Toshio Hongo, Yasuhito Nakagawa,
Morio Setaka and Shoshichi Nojima
1126 Radioimmunoassay for Platelet-Activating Factor
Ken Karasawa, Noriko Satoh, Toshio Hongo, Yasuhito Nakagawa,
Morio Setaka and Shoshichi Nojima
1130 Synthesis of a PAF Immunogen and Production of PAF-Specific Antibodies
Mary A. Smal, Brian A. Baldo and John W. Redmond
1136 A Specific, Sensitive and High-Capacity Immunoassay for PAF
Brian A. Baldo, Mary A. Smal and Alistair C. McCaskill
1140 Quantitation by Radioimmunoassay of PAF in Human Saliva
Sue J. Cooney, Mary A. Smal and Brian A. Baldo
1144 Inhibitor(s) of Platelet-Activating Factor (PAF) in Human Saliva
Mary A. Smal and Brian A. Baldo
PAF Receptor and Antagonists
1148 L-659,989: A Useful Probe in the Detection of Multiple Conformational States
of PAF Receptors—A Review
San-Bao Hwang and My-Hanh Lam
1154 Chemical and Biochemical Characterization of Lignan Analogs as Novel PAF
Receptor Antagonists—A Review
T.Y. Shen
1157 Thieno-triazolo-1,4-diazepines as Antagonists of Platelet-Activating Factor:
Present Status—A Review
Jorge Casals-Stenzel
1162 PAF Receptor Structure: A Hypothesis—A Review
J.-J. Godfroid, G. Dive, J. Lamotte-Brasseur, J.-P. Batt and F. Heymans
1167 PAF Receptor And “Cache-Oreilles” Effect. Simple PAF Antagonists
J. Lamotte-Brasseur, F. Heymans, G. Dive, A. Lamouri, J.-P. Batt, C. Redeuilh,
D. Hosford, P. Braquet and J.-J. Godfroid
1172 Discovery and Preliminary Pharmacology of Sch 37370, a Dual Antagonist
of PAF and Histamine
M. Motasim Billah, Robert W. Egan, Ashit K. Ganguly, Michael J. Green,
William Kreutner, John J. Piwinski, Marvin I. Siegel, Frank J. Villani and Jesse K.
Wong
1175 PAF Inhibitory Activity of Diketopiperazines: Structure-Activity Relationships
Norihiko Shimazaki, Ichiro Shima, Masanori Okamoto, Keizo Yoshida, Keiji
Hemmi and Masashi Hashimoto
(continued on next page)
viii
Copyright © 1991 AOCS Press
Contents
Volume 26, Number 12
December 1991
1179 Pharmacological Properties of YM461, a New Orally Active Platelet-Activating
Factor Antagonist
Toshimitsu Yamada, Munetoshi Saito, Toshiyasu Mase, Hiromu Hara, Hitoshi
Nagaoka, Kiyoshi Murase and Kenichi Tomioka
Cell Biology of PAF
1184 Bioactions of 5-Hydroxyicosatetraenoate and its Interaction with Platelet-
Activating Factor—A Review
Adriano G. Rossi and Joseph T. O’Flaherty
1189 Platelet-Activating Factor (PAF) Receptor Antagonists Inhibit Arachidonic
Acid-Induced Platelet Aggregation in Rabbit Whole Blood
Alaina Jean Ammit and Chris O’Neill
1193 Biological Response of Guinea Pig Peritoneal Macrophages to Platelet-
Activating Factor
Hidetoshi Hayashi, Ichiro Kudo, Shoshichi Nojima and Keizo Inoue
1200 Production of Platelet-Activating Factor by Human Normodense and
Hypodense Eosinophils
Ayako Ojima-Uchiyama, Yasuo Masuzawa, Takayuki Sugiura, Keizo Waku,
Takeshi Fukuda and Sohei Makino
1204 Immunoregulatory Functions of Paf-Acether. VI. Dual Effect on Human B Cell
Proliferation
Corinne Leprince, Eric Vivier, Dominique Treton, Pierre Galanaud, Jacques
Benveniste, Yolande Richard and Yolène Thomas
1209 Intracellular Ca2+ Concentration and H O Production in Mouse Peritoneal
2 2
Macrophages Are Stimulated by Platelet Activating Factor
Masayuki Sasaki, Kazutaka Maeyama and Takehiko Watanabe
1214 Platelet-Activating Factor Stimulates Receptor-Mediated Formation of Reactive
Oxygen Intermediates in Human Monocytes
M.G. Pustynnikov, N.V. Porodenko, O.V. Makarova, A.V. Kozyukov, E.Yu.
Moskaleva, A.A. Sokolovsky and E.S. Severin
1218 Calcium Channel Blockade Inhibits Platelet Activating Factor Production
by Human Umbilical Vein Endothelial Cells
J.P. Tolins, A. Melemed, D. Sulciner, K.S. Gustafson and G.M. Vercellotti
1223 The Effect of Eicosapentaenoic Acid Consumption on Human Neutrophil
Chemiluminescence
Philip J. Thompson, Neil L.A. Misso, Marion Passarelli and Martin J. Phillips
1227 Role of Platelet-Activating Factor (PAF) in Superoxide Production by Human
Polymorphonuclear Leukocytes
Shuji Takahashi, Toshikazu Yoshikawa, Yuji Naito, Toru Tanigawa, Norimasa
Yoshida and Motoharu Kondo
1231 IgA Immune Aggregates Stimulate Platelet-Activating Factor and Superoxide
Anion Production by Human Neutrophils. A Comparison with IgG Aggregates
Paloma Hernando, Jesús Edigo, Rosario de Nicolás and Eva González
(continued on next page)
Copyright © 1991 AOCS Press
Contents
Volume 26, Number 12
December 1991
PAF and the Cerebral System
1236 Platelet-Activating Factor and Polyunsaturated Fatty Acids in Cerebral
Ischemia or Convulsions: Intracellular PAF-Binding Sites and Activation
of a Fos/Jun/AP-1 Transcriptional Signaling System—A Review
Nicolas G. Bazan, Stephen P. Squinto, Pierre Braquet, Thomas Panetta
and Victor L. Marcheselli
1243 Calcium Ion Mobilization in Neuronal Cells Induced by PAF
Elizabeth Kornecki and Yigal H. Ehrlich
1247 Role of Platelet-Activating Factor in Aggregation of Leukocytes and Platelets
in Cerebral Ischemia
S. Uchiyama, M. Yamazaki and S. Maruyama
PAF, the Cardiovascular System, and Hypotension
1250 Cardiovascular Effects of Platelet-Activating Factor—A Review
Robert E. Goldstein, Giora Z. Feuerstein, Linda M. Bradley, Joseph J.
Stambouly, Francisco R.M. Laurindo and Nancy J. Davenport
1257 Platelet-Activating Factor in Cardiovascular Stress Situations—A Review
Reuven Rabinovici, Tian-Li Yue and Giora Feuerstein
1264 Studies on the Role of Platelet-Activating Factor in Blood Pressure Regulation
Katsuhiko Sakaguchi, Shigeto Morimoto, Fuminori Masugi, Shuichi Saeki,
Toshio Ogihara, Kouji Yamada and Isao Yamatsu
1269 Intravascular Release of a Platelet-Activating Factor-Like Lipid (PAF-LL)
Induced by Cigarette Smoking
Tada-atsu Imaizumi
1274 Platelet-Activating Factor (PAF) Induces Contraction of Saponin-Skinned
Smooth Muscle of Coronary Artery
A.I. Soloviev and P. Braquet
PAF, the Respiratory System, Allergy, and Asthma
1277 Role for Platelet-Activating Factor in Asthma —A Review
K.F. Chung and P.J. Barnes
1280 The Contribution of Platelet-Activating Factor to Allergen-Induced Eosinophil
Infiltration and Bronchial Hyperresponsiveness—A Review
C.P. Page
1283 Platelet Activating Factor-Induced Pulmonary Accumulation of 111lndium-Oxine
Labelled Neutrophils in Anesthetized Guinea Pigs
Ursula Hultkvist-Bengtsson, Gary P. Anderson, Madeleine Kings and John Morley
1287 Platelet Activating Factor Induced Respiratory Mucosal Damage
Ken-ichi Hisamatsu, Tetsuya Ganbo, Tsutomu Nakazawa and Yoshihiko Murakami
1292 Platelet-Activating Factor Detected in Bronchoalveolar Lavage Fluids from an
Asthmatic Patient
Tsugio Horii, Hitoshi Okazaki, Minoru Kino, Yohnosuke Kobayashi, Kiyoshi
Satouchi and Kunihiko Saito
1297 Platelet-Activating Factor (PAF) in Allergic Diseases: Inhibitory Effects of Anti-
Allergic Drugs, Ketotifen and Three Kampo Medicines on PAF Production
Tsuneyoshi Nakamura, Motoaki Kuriyama, Keiko Ishihara, Yukio Matsumura
and Terumasa Miyamoto
(continued on next page)
Copyright © 1991 AOCS Press