Table Of ContentTakehiko Yokomizo · Makoto Murakami
Editors
Bioactive
Lipid
Mediators
Current Reviews and Protocols
Bioactive Lipid Mediators
Takehiko Y okomizo (cid:129) Makoto Murakami
Editors
Bioactive Lipid Mediators
Current Reviews and Protocols
Editors
Takehiko Yokomizo Makoto Murakami
Department of Biochemistry Lipid Metabolism Project
Juntendo University Graduate School Tokyo Metropolitan Institute
of Medicine of Medical Science
Tokyo , Japan Tokyo , Japan
ISBN 978-4-431-55668-8 ISBN 978-4-431-55669-5 (eBook)
DOI 10.1007/978-4-431-55669-5
Library of Congress Control Number: 2015951082
Springer Tokyo Heidelberg New York Dordrecht London
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Pref ace
A ccording to legend, Hippocrates advocated the use of willow bark, S alix alba , to
ameliorate the pain of childbirth and fever. Salicylates were later isolated as the
active component in willow bark and conjugated with an acetyl group to generate
aspirin. Today, aspirin is the most well-known nonsteroidal antiinfl ammatory drug
and has numerous recognized clinical benefi ts, ranging from reducing the risk of
heart attack and colon polyposis to its frequently exploited antiinfl ammatory and
pain-relief actions, by decreasing the production of prostaglandins and thrombox-
ane from arachidonic acid. The other arachidonate-derived lipid mediators leukotri-
ene B and cysteinyl leukotrienes have also attracted research interest and are now
4
well known, particularly in the immunology fi eld, as a potent leukocyte attractant
and a bronchoconstrictor, respectively.
Recent advances in biochemistry and molecular biology have enabled us to
purify and cDNA-clone multiple biosynthetic enzymes and receptors responsible
for the production and recognition of individual lipid mediators. Numerous lines of
transgenic and knockout mice in relation to lipid mediators have been established
and analyzed to unveil their in vivo roles. Given that some lipid mediators were
shown to cause infl ammatory, immune, or oncogenic disorders, some of these
enzymes and receptors are now recognized as targets for new drugs. Furthermore,
whole sequencing of the human genome led us to discover many orphan receptors,
some of which were later identifi ed as receptors for lysophospholipids or their
derivatives, such as platelet-activating factor, lysophosphatidic acid, and sphingo-
sine 1-phosphate, and their physiological and pathophysiological roles are currently
being extensively analyzed. It has also become evident that omega-3 polyunsatu-
rated fatty acids, which have long been believed to be benefi cial for our health, are
metabolized to another class of lipid mediators (the so-called pro-resolving lipid
mediators), which include resolvins and protectins. The molecular nature of lyso-
phospholipid acyltransferases, which are involved in the remodeling and asymme-
try formation of membrane phospholipids, has fi nally been identifi ed. In addition to
progress in protein chemistry and molecular biology, the development of highly
sensitive mass spectrometry has greatly contributed to the direct identifi cation of
novel lipid mediators that are lowly abundant in tissues. Recently, imaging mass
v
vi Preface
spectrometry successfully elucidated the intra-tissue and intracellular distribution
of a particular class of lipids.
We are proud to say that many Japanese scientists contributed to the recent prog-
ress in lipid mediator research. In 2010, we started to organize a group of Japanese
lipid researchers with the support of the research grant “Lipid machineries” from
the Ministry of Education, Culture, Sports, Science, and Technology in Japan
(MEXT). At the end of this research term, we are pleased to publish this book
entitled B ioactive Lipid Mediators: Current Reviews and Protocols , which contains
22 comprehensive reviews of various lipid mediators and seven up-to-date protocols
to analyze lipid mediators. No such comprehensive book on lipid mediators has
been previously published, and we therefore believe that this book will greatly con-
tribute to the understanding of the roles of lipid mediators in physiology and pathol-
ogy, the determination of research targets for the near future, and the commencement
of drug screening to develop new drugs that target lipid mediators.
We sincerely thank all the authors for their invaluable contributions to this book.
We would like to dedicate this book to two prominent lipid researchers, Professors
Ichiro Kudo and Santosh Nigam, who opened up this fi eld and trained numerous
young researchers over their lifetimes.
Tokyo, Japan Takehiko Yokomizo
Makoto Murakami
Contents
Part I Enzymes and Receptors for Lipid Mediators
1 Lysophospholipid Acyltransferases ....................................................... 3
Hideo Shindou , Takeshi Harayama , and Daisuke Hishikawa
2 Phospholipase A ..................................................................................... 23
2
Makoto Murakami and Yoshitaka Taketomi
3 Prostaglandin Terminal Synthases as Novel Drug Targets ................. 43
Shuntaro Hara
4 Pathophysiological Roles of Prostanoid Receptors
in the Central Nervous System .............................................................. 59
Tomoaki Inazumi and Yukihiko Sugimoto
5 Lipoxygenases: A Chronological Perspective on the Synthesis
of S and R Fatty Acid Hydroperoxides .................................................. 69
Alan R. Brash
6 Leukotriene B Receptors ....................................................................... 85
4
Tomoaki Koga and Takehiko Yokomizo
7 Platelet-Activating Factor (PAF) in Infectious Diseases ...................... 95
Satoshi Ishii
8 Lysophospholipid Mediators: Their Receptors
and Synthetic Pathways .......................................................................... 109
Kuniyuki Kano , Kumiko Makide , Jun Ishiguro , Hiroshi Yukiura ,
Shizu Aikawa , Akiharu Uwamizu , Yuji Shinjo , Kahori Namiki ,
Hiroki Kawana , Saki Nemoto , Hirotaka Matsumoto , Ryoji Kise ,
Asuka Inoue , and Junken Aoki
9 Sphingolipid Metabolism via Sphingosine 1-Phosphate
and Its Role in Physiology, Pathology, and Nutrition .......................... 127
Akio Kihara
vii
viii Contents
10 Fatty Acids Receptors ............................................................................. 139
Akira Hirasawa , Masato Takeuchi , Takafumi Hara ,
Ayako Hirata , Soshi Tanabe , and Naoya Umeda
11 Omega-3 Fatty Acid Metabolism and Regulation
of Inflammation ....................................................................................... 155
Yosuke Isobe and Makoto Arita
Part II Lipid Mediators in Drosophila and Zebrafi sh
12 Membrane Lipid Transporters in Drosophila melanogaster ............... 165
Kohjiro Nagao , Naoto Juni , and Masato Umeda
13 Drosophila: A Model for Studying Prostaglandin Signaling ............... 181
Andrew J. Spracklen and Tina L. Tootle
14 Zebrafish as a Model Animal for Studying Lysophosphatidic
Acid Signaling.......................................................................................... 199
Junken Aoki and Hiroshi Yukiura
15 Sphingosine 1-Phosphate Signaling via Transporters
in Zebrafish and Mice ............................................................................. 207
Yu Hisano , Tsuyoshi Nishi , and Atsuo Kawahara
Part III Lipid Mediators and Diseases
16 Lipid Mediator LPA-Induced Demyelination and
Self-Amplification of LPA Biosynthesis in Chronic
Pain Memory Mechanisms ..................................................................... 223
Hiroshi Ueda and Hitoshi Uchida
17 Vascular Endothelial S1P Receptor Limits Tumor
2
Angiogenesis and Hyperpermeability ................................................... 237
Noriko Takuwa , Yasuo Okamoto , Kazuaki Yoshioka ,
and Yoh Takuwa
18 Roles of Prostaglandins in Regulation of Pathological
Angiogenesis and Lymphangiogenesis .................................................. 253
Masataka Majima
19 Eicosanoids and Aortic Aneurysm ......................................................... 267
Utako Yokoyama , Ryo Ishiwata , and Yoshihiro Ishikawa
20 Cysteinyl Leukotrienes and Disease ...................................................... 279
Laura B. Fanning and Joshua A. Boyce
21 Lipid Mediators and Skin Diseases ....................................................... 303
Tetsuya Honda and Kenji Kabashima
Contents ix
22 Roles and Actions of Arachidonic Acid- Derived Bioactive
Lipids in Stress-Related Behaviors ........................................................ 315
Tomoyuki Furuyashiki and Shiho Kitaoka
Part IV Protocols for Analyzing Lipid Mediators
23 Basic Techniques for Lipid Extraction from Tissues and Cells .......... 331
Toshiaki Okuno and Takehiko Yokomizo
24 Comprehensive Analysis of Eicosanoids ............................................... 337
Yoshihiro Kita and Takao Shimizu
25 Mass Spectrometric Analysis of Phospholipids by Target
Discovery Approach ................................................................................ 349
Kazutaka Ikeda
26 Determination of Sphingolipids by LC-MS/MS ................................... 357
Tomohiro Takahashi , Daisuke Saigusa , Chihiro Takeda ,
Kohei Saito , Naoto Suzuki , Hiroki Tsukamoto ,
and Yoshihisa Tomioka
27 Lipid Machinery Investigation Using MALDI Imaging
Mass Spectrometry ................................................................................. 371
Ikuko Yao , Gustavo A. Romero-Pérez , Dan Nicolaescu ,
and Mitsutoshi Setou
28 Measuring Activation of Lipid G Protein- Coupled
Receptors Using the TGF-α Shedding Assay........................................ 393
Asuka Inoue and Junken Aoki
29 A Novel Anti-FLAG Monoclonal Antibody Is Useful
to Study GPCRs ...................................................................................... 409
Fumiyuki Sasaki and Takehiko Yokomizo
Index ................................................................................................................. 4 19
