Lipids in health and disease

Lipids in Health and Disease SUBCELLULAR BIOCHEMISTRY SERIES EDITOR J. ROBIN HARRIS, University of Mainz, Mainz, Germany ASSISTANT EDITORS P.J. QUINN, King’s College London, London, U.K. Recent Volumes in this Series Volume 33 Bacterial Invasion into Eukaryotic Cells Tobias A. Oelschlaeger and Jorg Hacker Volume 34 Fusion of Biological Membranes and Related Problems Edited by Herwig Hilderson and Stefan Fuller Volume 35 Enzyme-Catalyzed Electron and Radical Transfer Andreas Holzenburg and Nigel S. Scrutton Volume 36 Phospholipid Metabolism in Apoptosis Edited by Peter J. Quinn and Valerian E. Kagan Volume 37 Membrane Dynamics and Domains Edited by P.J. Quinn Volume 38 Alzheimer’s Disease: Cellular and Molecular Aspects of Amyloid beta Edited by R. Harris and F. Fahrenholz Volume 39 Biology of Inositols and Phosphoinositides Edited by A. Lahiri Majumder and B.B. Biswas Volume 40 Reviews and Protocols in DT40 Research Edited by Jean-Marie Buerstedde and Shunichi Takeda Volume 41 Chromatin and Disease Edited by Tapas K. Kundu and Dipak Dasgupta Volume 42 Inflammation in the Pathogenesis of Chronic Diseases Edited by Randall E. Harris Volume 43 Subcellular Proteomics Edited by Eric Bertrand and Michel Faupel Volume 44 Peroxiredoxin Systems Edited by Leopold Flohé and J. Robin Harris Volume 45 Calcium Signalling and Disease Edited by Ernesto Carafoli and Marisa Brini Volume 46 Creatine and Creatine Kinase in Health and Disease Edited by Gajja S. Salomons and Markus Wyss Volume 47 Molecular Mechanisms of Parasite Invasion Edited by Barbara A. Burleigh and Dominique Soldati-Favre Volume 48 The Coronin Family of Proteins Edited by Christoph S. Clemen, Ludwig Eichinger and Vasily Rybakin Peter J. Quinn  Xiaoyuan Wang Editors Lipids in Health and Disease 13 Editors Peter J. Quinn King’s College London Biochemistry Department 150 Stamford Street London SE1 9NH United Kingdom [email protected] ISBN: 978-1-4020-8830-8 Xiaoyuan Wang Jiangnan University State Key Laboratory of Food Science and Technology 1800 Lihu Avenue Wuxi 214122 China [email protected] e-ISBN: 978-1-4020-8831-5 Library of Congress Control Number: 2008931355 # 2008 Springer ScienceþBusiness Media B.V. No part of this work 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, with the exception of any material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work. Printed on acid-free paper 9 8 7 6 5 4 3 2 1 springer.com INTERNATIONAL ADVISORY EDITORIAL BOARD R. BITTMAN, Queens College, City University of New York, New York, USA D. DASGUPTA, Saha Institute of Nuclear Physics, Calcutta, India L. FLOHE, MOLISA GmbH, Magdeburg, Germany H. HERRMANN, German Cancer Research Center, Heidelberg, Germany A. HOLZENBURG, Texas A&M University, Texas, USA H-P. NASHEUER, National University of Ireland, Galway, Ireland S. ROTTEM, The Hebrew University, Jerusalem, Israel M. WYSS, DSM Nutritional Products Ltd., Basel, Switzerland Preface Lipids are functionally versatile molecules. They have evolved from relatively simple hydrocarbons that serve as depot storages of metabolites and barriers to the permeation of solutes into complex compounds that perform a variety of signalling functions in higher organisms. This volume is devoted to the polar lipids and their constituents. We have omitted the neutral lipids like fats and oils because their function is generally to act as deposits of metabolizable substrates. The sterols are also outside the scope of the present volume and the reader is referred to volume 28 of this series which is the subject of cholesterol. The polar lipids are comprised of fatty acids attached to either glycerol or sphingosine. The fatty acids themselves constitute an important reservoir of substrates for conversion into families of signalling and modulating molecules including the eicosanoids amongst which are the prostaglandins, thromboxanes and leucotrienes. The way fatty acid metabolism is regulated in the liver and how fatty acids are desaturated are subjects considered in the first part of this volume. This section also deals with the modulation of protein function and inflammation by unsaturated fatty acids and their derivatives. New insights into the role of fatty acid synthesis and eicosenoid function in tumour progression and metastasis are presented. The phospholipids form the principal constituents of the lipid bilayer matrix of cell membranes. They constitute a range of lipid classes characterised by the substituents attached to the phosphate group. Each lipid class, in turn, consists of a range of molecular species characterised by the length, degree of unsaturation and position and type of attachment to the glycerol backbone. Cell membranes can be comprised of upwards of hundreds of individual molecular species of lipid. The proportion of each molecular species present in particular cell membranes of homeothermic organisms is preserved within relatively narrow limits by biochemical homeostatic mechanisms. The lipids found in the membranes of poikilothermic organisms are seen to change in response to environmental factors like temperature and salinity which infers that the biochemical changes in membrane lipids result in adaptive changes in the physical properties of the lipid matrix. One particular role of polar lipids in membranes is the integration and organization of intrinsic proteins into the matrix. This feature is examined by exploring how membrane lipids that form vii viii Preface non-bilayer structures can influence the function of integral membrane proteins. Dysfunction in membranes has been associated with deficiencies of phospholipids that tend to form non-bilayer structures and the role of these lipids in protein folding and formation of oligomeric protein complexes is explored. Disorders of lipid metabolism are believed to underlie a variety of organ pathologies and risk factors associated with circulatory diseases. Phospholipase hydrolysis of cardiac sarcolemmal membrane phospholipids generates products involved in the pathophysiology of heart disease. Signalling pathways augmented by these products are evaluated in the context of their potential for therapeutic intervention. One of the products of phospholipase A2 hydrolysis, lysophospholipid, is known to be involved in activation of G-protein coupled receptors and one chapter is devoted to an overview of the role of lysophospholipids in normal and pathological conditions. A summary of recent findings in human and animal models is provided. Oxidation of phospholipids may represent a general mechanism underlying a range of chronic inflammatory and autoimmune diseases. Oxidised phospholipids are also associated with many other conditions involving generation of reactive oxygen species. Deacylation and transacylation with lysophosphatide intermediates is an important process in membrane lipid homeostasis and the role of these lysolipids as cell modulators is now recognized. Free radical oxidation of membrane phospholipids results in release and activation of pro-apoptotic factors and the generation of ‘‘eat me’’ signals culminating in phagocytosis of the target cell. Sphingolipids are also constituents of the lipid bilayer matrix. Some members form a group of complex glycosphingolipids many of which are surface antigens and are known to be involved in the social organization of cells in tissues. Sphingolipids and their metabolites act in a variety of regulatory roles including the metabolism of lipids in general and in the biosynthesis of sterols in particular. Although the precise mechanisms of how sphingolipids regulate lipid metabolism are not known, this relationship has important implications with regard to cellular lipid homeostasis, composition of lipoproteins and development of atherosclerosis. These functions have been examined together with how these lipids alter endothelial barrier functions and cellular immune responses. Sphingolipids are implicated in many disease states including metastatic conditions and apoptosis. The way sphingolipids act via membrane signalling platforms like rafts is discussed as well as how such actions may be targeted in the development of therapeutic strategies. Finally, a complete understanding of the role of lipids in health and disease can only be achieved by detailed knowledge of the changes in molecular species of lipid in response to physiological or pathological states. This aspect of lipidology has received considerable impetus in the recent past by the combination of powerful separation and analytical techniques. An appreciation of the analytical power of current lipidomic techniques can be given by the fact that 100 nmoles of lipid, an amount that can be extracted from a conventional tissue culture flask containing one million cells, is sufficient for a Preface ix complete lipidomic analysis. The application of such lipidomic analyses in discerning intracellular lipid traffic and monitoring disease is presented. It is anticipated that deployment of lipidomic methodology in wider fields will lead to a greater understanding of the role of lipids in health and disease. This volume is aimed to generate the necessary enthusiasm and curiosity to realize these ambitions. London Wuxi Peter J. Quinn Xiaoyuan Wang About the Editors Peter J Quinn has been a Professor of Biochemistry at King’s College London since 1989 and has held visiting Professorships at Pittsburgh, Nagoya and Tsinghua Universities. His primary research interest is biological membranes and their constituents. The approach in this research has been to apply a range of biophysical methods including real-time synchroron X-ray diffraction, neutron scattering, differential scanning calorimetry, freeze-fracture electron microscopy, nuclear magnetic resonance spectroscopy, laser flash photolysis and Fourier transform infrared spectroscopy to address questions concerned with relationships between biomembrane structure and function. Professor Quinn received his PhD from the University of Sydney and was awarded a DSc from the University of London in 1980. xi xii About the Editors Xiaoyuan Wang is the Cheung Kong Professor for Molecular Biology in the State Key Laboratory of Food Science and Technology at Jiangnan University. He received his PhD from University of London in 2000, and completed postdoctoral training in Dr. William Dowhan’s laboratory at University of Texas Houston Medical School in 2002. Then he worked as a Research Associate in Dr. Christian Raetz’s group at Duke University Medical School until 2007. During the years Dr. Wang has been using a combined molecular genetic and biochemical approach to study the structure, function, and assembly of phospholipids and lipid A in membranes of Gram-negative bacteria. In 2007 Dr. Wang joined Jiangnan University, and was appointed Cheung Kong Chair Professor by the Ministry of Education in the same year. His research interests now include food lipids, food toxins and food safety control. Contents Contributors. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Part I xv Fatty Acids 1 Transcriptional Regulation of Hepatic Fatty Acid Metabolism . . . . . Hervé Guillou, Pascal G.P. Martin and Thierry Pineau 3 2 Modulation of Protein Function by Isoketals and Levuglandins . . . . . Sean S. Davies 49 3 Signalling Pathways Controlling Fatty Acid Desaturation . . . . . . . . . Marı́a Cecilia Mansilla, Claudia E. Banchio and Diego de Mendoza 71 4 Fatty Acid Amide Hydrolase: A Gate-Keeper of the Endocannabinoid System . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 101 Filomena Fezza, Chiara De Simone, Daniele Amadio and Mauro Maccarrone 5 Modulation of Inflammatory Cytokines by Omega-3 Fatty Acids . . . Jing X. Kang and Karsten H. Weylandt 133 6 Eicosanoids in Tumor Progression and Metastasis . . . . . . . . . . . . . . . Sriram Krishnamoorthy and Kenneth V. Honn 145 7 Fatty Acid Synthase Activity in Tumor Cells . . . . . . . . . . . . . . . . . . . Joy L. Little and Steven J. Kridel 169 xiii xiv Contents Part II 8 Phospholipids Lipids in the Assembly of Membrane Proteins and Organization of Protein Supercomplexes: Implications for Lipid-linked Disorders . Mikhail Bogdanov, Eugenia Mileykovskaya and William Dowhan 197 9 Altered Lipid Metabolism in Brain Injury and Disorders . . . . . . . . . . Rao Muralikrishna Adibhatla and J. F. Hatcher 241 10 Lysophospholipid Activation of G Protein-Coupled Receptors . . . . . . Tetsuji Mutoh and Jerold Chun 269 11 Phospholipid-Mediated Signaling and Heart Disease . . . . . . . . . . . . . Paramjit S. Tappia and Tushi Singal 299 12 The Role of Phospholipid Oxidation Products in Inflammatory and Autoimmune Diseases: Evidence from Animal Models and in Humans . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Norbert Leitinger 13 Mediation of Apoptosis by Oxidized Phospholipids . . . . . . . . . . . . . . Gilbert O. Fruhwirth and Albin Hermetter Part III 325 351 Sphingolipids 14 Regulation of Lipid Metabolism by Sphingolipids . . . . . . . . . . . . . . . Tilla S. Worgall 371 15 Multiple Roles for Sphingolipids in Steroid Hormone Biosynthesis . . Natasha C. Lucki and Marion B. Sewer 387 16 Roles of Bioactive Sphingolipids in Cancer Biology and Therapeutics Sahar A. Saddoughi, Pengfei Song and Besim Ogretmen 413 17 Glycosphingolipid Disorders of the Brain . . . . . . . . . . . . . . . . . . . . . . Stephanie D. Boomkamp and Terry D. Butters 441 18 Role of Neutral Sphingomyelinases in Aging and Inflammation . . . . . Mariana Nikolova-Karakashian, Alexander Karakashian and Kristina Rutkute 469 19 Sphingolipid Metabolizing Enzymes as Novel Therapeutic Targets . . Andreas Billich and Thomas Baumruker 487 Contents 20 Ceramide-Enriched Membrane Domains in Infectious Biology and Development . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Katrin Anne Becker, Alexandra Gellhaus, Elke Winterhager and Erich Gulbins Part IV 21 xv 523 Lipidomics MALDI-TOF MS Analysis of Lipids from Cells, Tissues and Body Fluids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Beate Fuchs and Jürgen Schiller 541 Lipidomics in Diagnosis of Lipidoses . . . . . . . . . . . . . . . . . . . . . . . . . C. Wolf and P.J. Quinn 567 Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 589 22 Contributors Rao Muralikrishna Adibhatla Department of Neurological Surgery, H4-330, Clinical Science Center, 600 Highland Avenue, University of Wisconsin School of Medicine and Public Health, Madison, WI 53792-3232, USA Daniele Amadio Department of Experimental Medicine & Biochemical Sciences, University of Rome ‘‘Tor Vergata’’, Rome, Italy Claudia E. Banchio Departamento de Ciencias Biológicas, Facultad de Ciencias Bioquı́micas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (S2002LRK) Rosario, Argentina Thomas Baumruker Novartis Institutes for BioMedical Research, Brunnerstrasse 59, A-1235 Vienna, Austria Katrin Anne Becker Dept. of Molecular Biology, University of Duisburg-Essen, Hufelandstrasse 55, 45122 Essen, Germany Andreas Billich Novartis Institutes for BioMedical Research, Brunnerstrasse 59, A-1235 Vienna, Austria Mikhail Bogdanov Department of Biochemistry and Molecular Biology, University of TexasHouston, Medical School, 6431 Fannin St. Houston, TX 77030, USA Stephanie D. Boomkamp Glycobiology Institute, Department of Biochemistry, University of Oxford, Oxford, OX1 3QU, UK Terry D. Butters Glycobiology Institute, Department of Biochemistry, University of Oxford, Oxford, OX1 3QU, UK xvii xviii Contributors Jerold Chun Department of Molecular Biology, Helen L. Dorris Child and Adolescent Neuropsychiatric Disorder Institute, The Scripps Research Institute, 10550 North Torrey Pines Rd., ICND-118, La Jolla, CA 92037, USA Sean S. Davies Department of Pharmacology, Vanderbilt University, 506A RRB, 2222 Pierce Ave., Nashville, TN 37232, USA Diego de Mendoza Departamento de Microbiologia, Facultad de Ciencias Bioquı́micas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (S2002LRK) Rosario, Argentina Chiara De Simone Department of Experimental Medicine & Biochemical Sciences, University of Rome ‘‘Tor Vergata’’, Rome, Italy William Dowhan Department of Biochemistry and Molecular Biology, University of TexasHouston, Medical School, 6431 Fannin St. Houston, TX 77030, USA Filomena Fezza Department of Experimental Medicine & Biochemical Sciences, University of Rome ‘‘Tor Vergata’’, Rome, Italy Gilbert O. Fruhwirth Institute of Biochemistry, Graz University of Technology, Petersgasse 12/2, A8010 Graz, Austria Beate Fuchs University of Leipzig, Medical Department, Institute of Medical Physics and Biophysics, Härtelstr. 16/18, D-04107 Leipzig, Germany Alexandra Gellhaus Dept. of Molecular Biology, University of Duisburg-Essen, Hufelandstrasse 55, 45122 Essen, Germany Hervé Guillou Laboratoire de Pharmacologie et Toxicologie UR66, INRA, F-31000 Toulouse, France Erich Gulbins Dept. of Molecular Biology, University of Duisburg-Essen, Hufelandstrasse 55, 45122 Essen, Germany J. F. Hatcher Department of Neurological Surgery, H4-330, Clinical Science Center, 600 Highland Avenue, University of Wisconsin School of Medicine and Public Health, Madison, WI 53792-3232, USA Contributors xix Albin Hermetter The Richard Dimbleby Department of Cancer Research, King’s College London, London SE1 1UL, United Kingdom Kenneth V. Honn Departments of Pathology, and Chemistry, Wayne State University School of Medicine, Detroit, MI 4822, USA Jing X. Kang Department of Medicine, Massachusetts General Hospital, Harvard Medical School, Boston, MA 02114, USA Alexander Karakashian University of Kentucky College of Medicine, Department of Physiology, Lexington, KY, USA Steven J. Kridel Department of Cancer Biology and Comprehensive Cancer Center, Wake Forest University School of Medicine, Medical Center Boulevard, WinstonSalem, NC 27157, USA Sriram Krishnamoorthy Departments of Pathology, and Chemistry, Wayne State University School of Medicine, Detroit, MI 4822, USA Norbert Leitinger Robert M. Berne Cardiovascular Research Center, 409 Lane Road, Charlottesville, VA 22908, USA Joy L. Little Department of Cancer Biology and Comprehensive Cancer Center, Wake Forest University School of Medicine, Medical Center Boulevard, WinstonSalem, NC 27157, USA Natasha C. Lucki School of Biology, Georgia Institute of Technology, 310 Ferst Drive, Atlanta, GA 30332-0230, USA Mauro Maccarrone Department of Biomedical Sciences, University of Teramo, Piazza A. Moro 45, 64100 Teramo, Italy Marı́a Cecilia Mansilla Departamento de Microbiologia, Facultad de Ciencias Bioquı́micas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (S2002LRK) Rosario, Argentina Pascal G.P. Martin Laboratoire de Pharmacologie et Toxicologie UR66, INRA, F-31000 Toulouse, France xx Contributors Eugenia Mileykovskaya Department of Biochemistry and Molecular Biology, University of TexasHouston, Medical School, 6431 Fannin St. Houston, TX 77030, USA Tetsuji Mutoh Department of Molecular Biology, Helen L. Dorris Child and Adolescent Neuropsychiatric Disorder Institute, The Scripps Research Institute, 10550 North Torrey Pines Rd., ICND-118, La Jolla, CA 92037, USA Mariana Nikolova-Karakashian University of Kentucky College of Medicine, Department of Physiology, Lexington, KY, USA Besim Ogretmen Department of Biochemistry and Molecular Biology, Hollings Cancer Center, Medical University of South Carolina, Medical University of South Carolina, 173 Ashley Avenue, Charleston, SC 29425, USA Thierry Pineau Laboratoire de Pharmacologie et Toxicologie, Institut National de la Recherche Agronomique (INRA), 180 Chemin de Tournefeuille, BP 3, F 31931 Toulouse, Cedex 9, France Peter J. Quinn Department of Biochemistry, King’s College London, 150 Stamford Street, London SE1 9NH, UK Kristina Rutkute University of Kentucky College of Medicine, Department of Physiology, Lexington, KY, USA Sahar A. Saddoughi Department of Biochemistry and Molecular Biology, Hollings Cancer Center, Medical University of South Carolina, Medical University of South Carolina, 173 Ashley Avenue, Charleston, SC 29425, USA Jürgen Schiller Universität Leipzig, Medizinische Fakultät, Institut für Medizinische Physik und Biophysik, Härtelstr. 16/18, D-04107 Leipzig, Germany Marion B. Sewer School of Biology, Georgia Institute of Technology, 310 Ferst Drive, Atlanta, GA 30332-0230, USA Tushi Singal Institute of Cardiovascular Sciences, St. Boniface General Hospital Research Centre & Department of Physiology, Faculty of Medicine, University of Manitoba, Winnipeg, Canada Contributors xxi Pengfei Song Department of Biochemistry and Molecular Biology, Hollings Cancer Center, Medical University of South Carolina, Medical University of South Carolina, 173 Ashley Avenue, Charleston, SC 29425, USA Paramjit S. Tappia Institute of Cardiovascular Sciences, St. Boniface General Hospital Research Centre & Department of Human Anatomy & Cell Science, Faculty of Medicine, University of Manitoba, Winnipeg, Canada Tilla S. Worgall Dept. of Pathology, Columbia University, 168 W 168 St, BB 457, New York, N.Y. 10032, USA Karsten H. Weylandt Department of Gastroenterology, Rudolf Virchow Hospital, Charité University Medicine, Berlin, 13353, Germany Elke Winterhager Dept. of Molecular Biology, University of Duisburg-Essen, Hufelandstrasse 55, 45122 Essen, Germany Claude Wolf Mass Spectrometry Unit, INSERM U538, Faculte de Medecine P. et M. Curie, University Paris-6, 27 rue de Chaligny, Paris 75012, France