progress in Inflammation Research Series Editor Prof. Dr. Michael J. Parnham Senior Scientific Advisor PUVA dd Prilaz baruna Filipovica 25 10000 Zagreb Croatia Advisory Board G. Z. Feuerstein (Merck Research Laboratories, West POint, PA, USA) M. Pairet (Boehringer Ingelheim Pharma KG, Biberach a. d. Riss, Germany) W. van Eden (Universiteit Utrecht, Utrecht, The Netherlands) Forthcoming titles: Recent Advances in Pathophysiology of COPO, P.J. Barnes, T.T. Hansel (Editors), 2004 Cancer and Inflammation, D.W. Morgan, U. Forssmann, M. Nakada (Editors), 2004 Antirheumatic Therapy: Adions and Outcomes, R.O. Day, D.E. Furst, P.L. van Riel (Editors), 2003 Cytokines and Joint Iniury, P. Miossec, W.B. van den Berg (Editors), 2004 Antibiotics as Anti-inflammatory and Immunomodulatory Agents, B. Rubin, J. Tamaoki (Editors), 2004 (Already published titles see last page.) Arachidonate Remodeling and Inflammation Alfred N. Fonteh Robert L. Wykle Editors Springer Basel AG Editors Alfred N. Fonteh Robert L. Wykle Huntington Medical Research Institutes Wake Forest University Molecular Neurology Program School of Medicine 99 North EI Molino Avenue Department of Biochemistry Pasadena, CA 91101-1830 Medical Center Boulevard USA Winston-Salem, NC 27157-1016 USA A CIP catalogue record for this book is available from the Library of Congress, Washington D.C., USA Bibliographic information published by Die Deutsche Bibliothek Die Deutsche Bibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data is available in the internet at http://dnb.ddb.de The publisher and editor can give no guarantee for the information on drug dosage and administration contained in this publication. The respective user must check its accuracy by consulting other sources of reference in each individual case. The use of registered names, trademarks etc. in this publication, even if not identified as such, does not imply that theyare exempt from the relevant protective laws and regulations or free for general use. ISBN 978-3-0348-9594-1 ISBN 978-3-0348-7848-7 (eBook) DOI 10.1007/978-3-0348-7848-7 This work is subject to copyright. AII rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, re-use of iIIustrations, recitation, broadcasting, reproduction on micro films or in other ways, and storage in data banks. For any kind of use, permission of the copyright owner must be obtained. © 2004 Springer Basel AG Originally published by Birkhăuser Verlag in 2004 Softcover reprint of the hardcover 1s t Edition 2004 Printed on acid-free paper produced from chlorine-free pulp. TCF 00 Cover design: Markus Etterich, Basel Cover illustration: Arachidonic acid bound to P450BM-3, described in: Graham-Lorence SE et al (1997) J 8iol Chem 272,1127-1135. With the friendly permission of Julian A. Peterson, University of Texas, Southwestern Medical Center at Dallas, USA ISBN 978-3-0348-9594-1 987654321 www.birkhauser-science.com Contents List of contributors vii Preface .. xi Alfred N. Fonteh An outline of arachidonate remodeling and its biological significance . 1 Suzanne E. Barbour, Salma AI-Darmaki and Alex D. Manguikian Phospholipase A2 and remodeling in inflammatory cells . 13 Chad R. Marion and Alfred N. Fonteh Enzymatic and receptor mediated effects of secretory phospholipase A2 on the pathophysiology of inflammatory diseases 37 Jesus Balsinde, Rebeca Perez, Yolanda Saez and Marfa A. Balboa Control of arachidonic acid levels in resting and activated U937 phagocytic cells by Ca2+ -independent phospholipase A2 61 Robert L. Wykle Arachidonate remodeling and PAF synthesis in human neutrophils . 73 Allen M. McAlexander, Brooke 1. Barham, Margaret Johnson and Alfred N. Fonteh Control of long chain polyunsaturated fatty acid levels and the role of inhibitors of incorporation and remodeling on the biosynthesis of lipid mediators. . 89 Massimo Triggiani, Giorgio Giannattasio, Francescopaolo Granata, Stefania Loffredo, Francesca W Rossi, Salvatore Salzano and Gianni Marone Remodeling of arachidonic acid in inflammatory cells of the human lung . 115 Royal D. Saunders and Nicolas G. Bazan Arachidonate remodeling, platelet-activating factor signaling, and the inflammatory response in the central nervous system 131 Alfred N. Fonteh and Michael G. Harrington Remodeling of arachidonate and other polyunsaturated fatty acids in Alzheimer's disease ........................................... 145 Charles N. Serhan and Nan Chiang Lipoxins and resolvins: local mediators in endogenous anti-inflammation and resolution . . . . . . . . . . . . 169 Takayuki Sugiura, Seishi Kishimoto, Saori Oka, Maiko Gokoh and Keizo Waku Metabolism and physiological significance of anandamide and 2-arachidonoylglycerol, endogenous cannabinoid receptor ligands. 211 Index 239 List of contributors Salma AI-Darmaki, Department of Microbiology and Immunology, Virginia Com monwealth University, Box 980678, Richmond, VA 23298-0678, USA Maria A. Balboa, Institute of Molecular Biology and Genetics (IBGM-CSIC), Uni versity of Valladolid School of Medicine, Avenida Ramon y Cajal 7, E-47005 Valla dolid, Spain; e-mail: [email protected] Jesus Balsinde, Institute of Molecular Biology and Genetics (IBGM-CSIC), Univer sity of Valladolid School of Medicine, Avenida Ramon y Cajal 7, E-47005 Valla do lid, Spain; e-mail: [email protected] Suzanne E. Barbour, Department of Biochemistry, Virginia Commonwealth Univer sity, Box 980614, Richmond, VA 23298-0614, USA; e-mail: [email protected] Nicolas G. Bazan, Neuroscience Center of Excellence, Louisiana State University Health Sciences Center, 2020 Gravier Street, Suite D, New Orleans, LA 70112, USA; e-mail: [email protected] Brooke J. Barham, Comprehensive Center for Inflammatory Diseases, Department of Dentistry, University of North Carolina, Chapel Hill, NC 27599, USA; e-mail: [email protected] Nan Chiang, The Center for Experimental Therapeutics and Reperfusion Injury, Department of Anesthesiology, Perioperative and Pain Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, MA 02115, USA; e-mail: [email protected] Alfred N. Fonteh, Molecular Neurology Program, Huntington Medical Research Institutes, 99 North EI Molino Avenue, Pasadena, CA 91101, USA; e-mail: [email protected] vii List of contributors Giorgio Giannattasio, Division of Clinical Immunology and Allergy, University of Naples Federico II, Via Pansini 5, 80131 Naples, Italy; e-mail: [email protected] Maiko Gokoh, Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Tsukui-gun, Kanagawa 199-0195, Japan Francescopaolo Granata, Division of Clinical Immunology and Allergy, University of Naples Federico II, Via Pansini 5, 80131 Naples, Italy; e-mail: [email protected] Michael G. Harrington, Molecular Neurology Program, Huntington Medical Research Institutes, Pasadena, CA 91101-1830, USA; e-mail: [email protected] Margaret Johnson, Department of Medicine, Mayo Clinic, Jacksonville, Florida 32224, USA; e-mail: [email protected] Seishi Kishimoto, Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Tsukui-gun, Kanagawa 199-0195, Japan; e-mail: [email protected] Stefania Loffredo, Division of Clinical Immunology and Allergy, University of Naples Federico II, Via Pansini 5, 80131 Naples, Italy; e-mail: [email protected] Alex D. Manguikian, Department of Biochemistry, Virginia Commonwealth Uni versity, Richmond, VA 23298-0614, USA Chad R. Marion, Infectious Diseases, Department of Internal Medicine, Wake For est University School of Medicine, Winston-Salem, North Carolina, 27157, USA; e-mail: [email protected] Gianni Marone, Division of Clinical Immunology and Allergy, University of Naples Federico II, Via Pansini 5,80131 Naples, Italy: e-mail: [email protected] Allen M. McAlexander, Department of Biology and Health Sciences, Meridith Col lege, Raliegh, NC 27607, USA; e-mail: [email protected] Saori Oka, Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Tsukui-gun, Kanagawa 199-0195, Japan viii List of contributors Rebeca PereZ, Institute of Molecular Biology and Genetics (IBGM-CSIC), Universi ty of Valla do lid School of Medicine, Avenida Ramon y Cajal 7, E-47005 Valladolid, Spain; e-mail: [email protected] Francesca W. Rossi, Division of Clinical Immunology and Allergy, University of Naples Federico II, Via Pansini 5,80131 Naples, Italy Yolanda Saez, Institute of Molecular Biology and Genetics (IBGM-CSIC), Universi ty of Valla do lid School of Medicine, Avenida Ramon y Cajal 7, E-47005 Valladolid, Spain; e-mail: [email protected] Salvatore Salzano, Experimental Endocrinology and Oncology Center, Consiglio Nazionale delle Ricerche (CNR), Italy Royal D. Saunders, Department of Biology, Xavier University of Louisiana, 1 Drex el Drive, Box 85B, New Orleans, LA 70125, USA; e-mail: [email protected] Charles N. Serhan, The Center for Experimental Therapeutics and Reperfusion Injury, Department of Anesthesiology, Perioperative and Pain Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, MA 02115, USA; e-mail: [email protected] Takayuki Sugiura, Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Tsukui-gun, Kanagawa 199-0195, Japan; e-mail: [email protected] Massimo Triggiani, Division of Clinical Immunology and Allergy, University of Naples Federico II, Via Pansini 5, 80131 Naples, Italy, e-mail: [email protected] Keizo Waku, Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Tsukui-gun, Kanagawa 199-0195, Japan; e-mail: [email protected] Robert L. Wykle, Department of Biochemistry, Wake Forest University School of Medicine, Medical Center Boulevard, Winston-Salem, NC 27157, USA; e-mail: [email protected] ix Preface Arachidonic acid (AA) and other 20 or 22-carbon polyunsaturated fatty acids (PUFAs) are precursors of signaling molecules that are critical in disease processes and in regulating normal cell function. Remodeling is critical in homeostatic control and in dictating how PUFAs are converted to mediators. Thus, understanding remodeling will unravel better therapeutic targets for controlling inflammatory dis eases. The review chapters associate AA remodeling and the biosynthesis of mediators of inflammation or pain. By following the movement of AA rather than discussing a single enzyme and its product, the influence of upstream biosynthetic pathways on the formation of lipid mediators and interrelationship between all AA-derived medi ators are examined in a comprehensive fashion. This approach innovates AA metab olism by describing new inhibitors, mode of action of these inhibitors and poten tially efficacious targets not previously examined. This volume is written by experts in the field to serve as a rich resource of knowl edge for scientists and clinicians in academia, and researchers in the pharmaceutical industry involved in inflammation and pain research. Since AA is derived from essential fatty acids, this volume is also of interest to nutritionists. July 2003 A.N. Fonteh R.L. Wykle xi