BIOCHEMISTRY OF LIPIDS, LIPOPROTEINS AND MEMBRANES New Comprehensive Biochemistry Volume 31 General Editor G BERNARD1 Paris Amsterdam - Lausanne - ELSEVIER NewYork - Oxford - Shannon - Tokyo Biochemistry of Lipids, Lipoproteins and Membranes Editors DENNIS E VANCE and JEAN E VANCE Lipid and Lipoprotein Research Group, Faculty of Medicine, 328 Heritage Medical Research Centre, Edmonton, Alberta, Canada T6G 2S2 1996 Amsterdam - Lausanne - ELSEVIER NewYork - Oxford - Shannon - Tokyo Elsevier Science B.V Sara Burgerhartstraat 25 P.O Box 21 1, 1000 AE Amsterdam, The Netherlands L i b r a r y of Congress C a t a l o g i n g - i n - P u b l i c a t i o n Data B i o c h e m i s t r y o f l i p i d s , l i p o p r o t e i n s , and membranes / e d i t o r s , Dennis E Vance and J e a n E Vance cm (New c o m p r e h e n s l v e b i o c h e m i s t r y v 31) p I n c l u d e s b i b l i o g r a p h i c a l r e f e r e n c e s and i n d e x a l k p a p e r ) ISBN 0-444-82364-6 I S B N 0-444-82359-X ( h b k (pbk a l k paper) Lipids Metabolism L i p o p r o t e ~ n s - - M e t a b o l i s m Membrane lipids Metabolism I V a n c e Dennis E 11 Vance, J e a n E 111 S e r i e s OD415.N48 v o l 31 OP75 I 574.19'2 s dc20 [574.19'2471 96-22129 CIP The cover illustration, which originally uppeured in the Journul is reproduced with the kind permission of Dr E.A Dennis ofBiological Chemistrv, ISBN 444 82359 X (hardbound) ISBN 444 82364 (paperback) ISBN 444 80303 (series) 1996 Elsevier Science B.V All rights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, without the prior written permission of the publisher, Elsevier Science B.V., Copyright and Permissions Department, P.O.Box 521, 1000 AM Amsterdam, The Netherlands Special regulations for readers in the USA - This publication has been registered with the Copyright Clearance Center Inc (CCC), 222 Rosewood Drive, Danvers, MA 01923 Information can be obtained from the CCC about conditions under which photocopies of parts of this publication may be made in the USA All other copyright questions, including photocopying outside the USA, should be referred to the copyright owner, Elsevier Science B.V unless otherwise specified No responsibility is assumed by the publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein This book is printed on acid-free paper Printed in The Netherlands V Preface This is the third edition of this advanced textbook which has been written with two major objectives in mind One is to provide an advanced textbook covering the major areas in the fields of lipid, lipoprotein and membrane biochemistry and molecular biology The chapters within this volume are written for students who have already taken an introductory course in biochemistry, who are familiar with basic concepts and principles of biochemistry and have a general background knowledge in the area of lipid metabolism This book should therefore provide the basis for an advanced course for students in the biochemistry of lipids, lipoproteins and membranes The second objective of this book is to provide a clear summary of these research areas for scientists presently working in, or about to enter, these and related fields This book should satisfy the need for a general reference and review book for scientists studying lipids, lipoproteins and membranes Excellent up-to-date reviews are available on the various topics covered by this book, and many of these reviews are cited in the individual chapters However, this book remains unique in that it is not a series of exhaustive reviews of the various topics, but rather is a current, readable and critical summary of these areas of research This book should allow scientists to become familiar with recent developments related to their own research interests, and should also help clinical researchers and medical students keep abreast of developments in basic science that are important for subsequent clinical advances All the chapters have been extensively revised since the last edition and up-to-date information is included Three new chapters have been included to take into account substantial new insights into the roles of glycerolipids in signal transduction, lipid metabolism in adipose tissue, and lipid metabolism in plants We have not attempted to cover in detail the structure and function of biological membranes since that subject is covered already in a number of excellent books However, the first chapter does contain a summary of the principles of membrane structure as a basis for the subsequent chapters We have limited the number of references cited and emphasized review articles However, some readers may wish access to the primary literature in some instances Thus, we have introduced a novel approach to literature citation suggested by Charles Sweeley In some of the chapters reference has been made to published work by citing the name of the senior author and the year in which the work was published This should allow the reader to find the original citation via a computer search The editors and contributors assume full responsibility for the content of the various chapters and we would be pleased to receive comments and suggestions for future editions of this book We are indebted to many other people who have made this book possible In particular we extend our thanks to Brad Hillgartner, Deborah Hodge, Laura Petrosky, Ten-ching Lee and Shirley Poston Dennis and Jean Vance Edmonton, Alberta, Canada March 1996 This Page Intentionally Left Blank VII List of contributors D.A Bernlohr, 257 Department of Biochemistry, University of Minnesota, S140 Gortner Lab, 1479 Gortner Avenue, St Paul, MN 55108-1022, USA H.W Cook, 129 Atlantic Research Centre, Dalhousie University, Halifm, Nova Scotia, Canada, B3H 4H7 J.E Cronan Jr., 35 Departments of Microbiology and Biochemistry, University of Illinois, Urbana, IL 61801, USA P.R Cullis, I Department of Biochemistry and Molecular Biology, Faculty of Medicine, University of British Columbia, Vancouver, B C., Canada, V6T 123 R.A Davis, 341,473 Department of Biology, San Diego State University, San Diego, CA 92182-0057, USA P.A Edwards, 341 Department of Biological Chemistry, UCLA School of Medicine, 33-257 CHS, P.O Box 951 737, LQS Angeles, CA 90095-1737, USA D.B Fenske, Department of Biochemistry and Molecular Biology, Faculty of Medicine, University of British Columbia, Vancouver, B C., Canada, V6T 123 P.E Fielding, 495 Cardiovascular Research lnstitute, University of California Medical Center, San Francisco, CA 94143-0130, USA C.J Fielding, 495 Cardiovascular Research Institute, University of California Medical Center, San Francisco, CA 94143-0130, USA F.A Fitzpatrick, 283 Cell Biology and Inflammation Research, Upjohn Company, 301 Henrietta Street, Kalamazoo, MI 49001, USA A.G Goodridge, 101 Department of Biochemistry, University of Iowa, Iowa City, IA 52242, USA M.J Hope, Division of Dermatology, Faculty of Medicine, University of British Columbia, Vancouver, B.C., Canada, V5Z l L S Jackowski, 35 Department of Biochemistry, St Jude Children’s Research Hospital, Memphis, TN 38101, USA J.D Lambeth, 237 1510 Clifton Road NE, Rollins Research Center #4001, Department of Biochemistry, Emory University Medical School, Atlanta, GA 30322, USA A.H Merrill, Jr., 309 Department of Biochemistry, 41 13 Rollins Research Center, Emory University, Atlanta, GA 30322-3050 USA VIII J.B Ohlrogge, 363 Department of Botany and Plant Pathology, Michigan State University, East Lansing, MI 48824-1312, USA R.A.F Reithmeier, 425 MRC Group in Membrane Biology, Department of Medicine, Room 7344, Medical Sciences Building, University of Toronto, Toronto, Ontario, Canada, M5S IA8 C.O Rock, 35 Department of Biochemistry, St Jude Children’s Research Hospital, Memphis, TN 38101, USA S.H Ryu, 237 Signal Transduction Laboratory, Department of Life Sciences, Pohang University of Science and Technology, Pohang, 790-600, South Korea L.M Salati, 101 Department of Biochemistry, West Virginia University, Morgantown, WV 26506, USA K.M Schmid, 363 Department of Biological Sciences, Butler University, 460 Sunset Avenue, Indianapolis, IN 46208-3485, USA W.J Schneider, 517 Department of Molecular Genetics, University and Biocenter Vienna, Dr Bohr - Game 912, A-1030 Vienna, Austria H Schulz, 75 City College of CUNY, Department of Chemistry, New York, NY 10031, USA M.A Simpson, 257 Department of Biochemistry, University of Minnesota, S140 Gortner Lab, 1479 Gortner Avenue, St Paul, MN 55108-1022, USA W.L Smith, 283 Department of Biochemistry, Michigan State University, East Lansing, MI 48824, USA F Snyder, 183 Medical Sciences Division, Oak Ridge Associated Universities, Post Ofice Box I 17, Oak Ridge, TN 37831-0117, USA C.C Sweeley, 309 Department of Biochemistry, Michigan State University, East Lansing, MI 48824, USA J.E Vance, 473 Lipid and Lipoprotein Research Group, University of Alberta, Edmonton, Alberta, Canada, T6G 2S2 D.E Vance, 153 Lipid and Lipoprotein Research Group and Department of Biochemistry, University of Alberta Edmonton, Alberta, Canada, T6G 2S2 D.R Voelker, 391 Department of Medicine, The National Jewish Center for Immunology and Respiratory Medicine, 1400 Jackson Street, Denver, CO 80206, USA M Waite, 21 Department of Biochemistry, Bowman Gray School of Medicine, Wake Forest University, Winston-Salem, NC 27157, USA IX Contents Preface V List of contributors VII Chapter Physical properties and functional roles of lipids in membranes P R Cullis D B Fenske and M J Hope Introduction and overview Lipid diversity and distribution 2.1 Chemical diversity of lipids 2.2 Membrane lipid composi 2.3 Transbilayer lipid asymmetry Model membrane systems 3.1 Lipid isolation and purifi 3.2 Techniques for making model membrane vesicles 3.3 Techniques for making planar bilayers and monolayers 3.4 Reconstitution of integral membrane proteins into vesicles Physical properties of lipids 4.1 Gel-liquid-crystalline phase behavior 4.2 Lipid polymorphism 4.3 Factors which modulate lipid polymorphism 4.4 The physical basis of lipid polymorphism Lipids and the permeability properties of membranes 5.1 Theoretical considerations 5.2 Permeability of water and non-electrolytes 5.3 Permeability of ions Lipid-protein interactions 6.1 Extrinsic proteins 6.2 Intrinsic proteins Lipids and membrane fusion 7.1 Fusion of model systems 7.2 Fusion of biological membranes Model membranes and drug delivery Future directions References 3 8 9 11 13 13 17 20 21 22 22 23 24 25 25 26 27 27 28 30 32 32 Chapter Lipid metabolism in prokaiyotes C.O Rock S Jackowski and J.E Cronan Jr 35 The study of bacterial lipid metabolism Historical introduction An overview of lipid metabolism in E coli Genetic analysis of lipid metabolism Membrane systems of E coli Lipid biosynthetic pathways in E coli 35 35 36 36 40 41 540 scribed by the LDL receptor system; subsequently, research has pointed to different modes of lipoprotein catabolism The discovery of the VLDL receptors, a result of molecular biological studies, has raised more questions than answers; first, its physiological role(s) in mammals is at present completely unknown In oviparous animals, the picture is much clearer, but questions remain: what mechanisms orchestrate the correct tissue distribution of ligands which are recognized by receptors in oocytes and somatic cells? We have gained some insights into, but must learn more about, the regulation of the individual receptor genes in order to be able to understand exactly why several similar proteins are expressed in a single organism Redundancy in gene products which provides back-up systems, such as the LDL receptor and LRP for chylomicron remnant removal, is one of the biological means to protect from genetic disease The studies in the laying hen have revealed the roles of multiple and possibly redundant genes in oocyte growth, the key to reproduction in oviparous species Along other lines, future research will undoubtedly continue to focus on the nature of the mechanism of HDL-cell surface interactions, HDL’s role in signal transduction, and the mode of transporting intracellular cholesterol to the cell surface and onto HDL Also, despite significant advancements, the mechanism for chylomicron remnant removal needs further attention Is the LRP only one of a group of such large receptors? What is the exact role of proteoglycans in the removal of triacylglycerol-rich lipoproteins? Furthermore, are scavenger receptors indeed involved in foam cell formation, and which is (are) the most significant (i.e detrimental) in vivo modification(s) of LDL? Finally, efforts to develop preventive and/or curative gene therapy currently concentrate on extensive studies in transgenic animals The real value of these approaches in non-human systems should be defined in the next decade References Goldstein, J.L., Brown, M.S., Anderson, R.G.W Russell, D.W and Schneider, W.J (1985) Receptormediated endocytosis: concepts emerging from the LDL receptor system Annu Rev Cell Biol 1, 139 Schneider, W.J (1989) The low density lipoprotein receptor Biochim Biophys Acta 988, 303-317 Tolleshaug, H., Goldstein, J.L., Schneider, W.J and Brown, M.S (1982) Posttranslational processing of the LDL receptor and its genetic disruption in familial hypercholesterolemia Cell 30, 715-724 Yamamoto, T., Davis, C.G., Brown, M.S., Schneider, W.J., Casey, M.L., Goldstein, J.L and Russell, D.W (1984) The human LDL receptor: a cysteine-rich protein with multiple Alu sequences in its mRNA Cell 39,27-38 Esser, V., Limbird, L.E., Brown, M.S., Goldstein, J.L and Russell, D.W (1988) Mutational analysis of the ligand binding domain of the low density lipoprotein receptor J Biol Chem 263, 13282-13290 Davis, C.G., van Driel, I.R., Russell, D.W., Brown, M.S and Goldstein, J.L (1987) The low density lipoprotein receptor Identification of amino acids in cytoplasmic domain required for rapid endocytosis J Biol Chem 262, 407554082 Yang, J., Brown, M.S., Ho, Y.K and Goldstein, J.L (1995) Three different rearrangements in a single intron truncate sterol regulatory element binding protein-2 and produce sterol-resistant phenotype in three cell lines J Biol Chem 270, 12152-12161 Lehrman, M.A., Russell, D.W., Goldstein, J.L and Brown, M.S (1986) Exon-Alu recombination deletes kilobases from the low density lipoprotein receptor gene, producing a null phenotype in familial hypercholesterolemia Proc Natl Acad Sci USA 83, 3679-3683 54 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 Lehrman, M.A., Schneider, W.J., Brown, M.S., Davis, C.G., Elhammer, A,, Russell, D.W and Goldstein, J.L (1987) The Lebanese allele at the LDL receptor locus: nonsense mutation produces truncated receptor that is retained in endoplasmic reticulum J Biol Chem 262,401410 Yamamoto, T., Bishop, R.W., Brown, M.S., Goldstein, J.L and Russell, D.W (1986) Deletion in cysteine-rich region of LDL receptor impedes transport to cell surface in WHHL rabbit Science 232, 12301237 Van Driel, I.R., Goldstein, J.L., Siidhof, T.C and Brown, M.S (1987) First cysteine-rich repeat in ligand-binding domain of low density lipoprotein receptor binds Ca2+ and monoclonal antibodies, but not lipoproteins J Biol Chem 262, 17443-17449 Brown, M.S and Goldstein, J.L (1976) Analysis of a mutant strain of human fibroblasts with a defect in the internalization of receptor-bound low density lipoprotein Cell 9, 663-674 Pearse, B.M.F and Robinson, M.S (1990) Clathrin, adaptors and sorting Annu Rev Cell Biol 6, 151-171 Herz, J., Hamann, U., Rogne, S., Myklebost, Gausepohl, H and Stanley, K.K (1988) Surface location and high affinity for calcium of a 500 Kd liver membrane protein closely related to the LDLreceptor suggest a physiological role as lipoprotein receptor EMBO J 7.41 194127 Strickland, D.K., Ashcom, J.D., Williams, S., Burgess, W.H., Migliorini, M and Argraves, W.S (1990) Sequence identity between the a2-macroglobulin receptor and low density lipoprotein receptor-related protein suggests that this molecule is a multifunctional receptor J Biol Chem 265, 17401-17404 Kneger, M and Herz, J (1994) Structures and functions of multiligand lipoprotein receptors: macrophage scavenger receptors and LDL receptor-related protein (LRP) Annu Rev Biochem 63,601437 Herz, J and Willnow, T.E (1995) Lipoprotein and receptor interactions in viva Curr Opin Lipidol 6, 97- 103 Takahashi, S., Kawarabayasi, Y., Nakai, T., S a k i , J and Yamamoto, T (1992) Rabbit very low density lipoprotein receptor: a low density lipoprotein receptor-like protein with distinct ligand specificity Proc Natl Acad Sci USA 89,9252-9256 Jingami, H and Yamamoto, T (1995) The VLDL receptor: wayward brother of the LDL receptor Curr Opin Lipidol 6, 104-108 Schneider, W.J and Nimpf, J (1993) Lipoprotein receptors: old relatives and new arrivals Curr Opin Lipidol 4, 205-209 Bujo, H., Hermann, M., Kaderli, M.O., Jacobsen, L., Sugawara, S., Nimpf, J., Yamamoto, T and Schneider, W.J (1994) Chicken oocyte growth is mediated by an eight ligand binding repeat member of the LDLreceptor family EMBO J 13, 5165-5175 Schneider, W.J (1995) Yolk precursor transport in the laying hen Curr Opin Lipidol 6, 92-96 Steyrer, E., Barber, D.L and Schneider, W.J (1990) Evolution of lipoprotein receptors: the chicken oocyte receptor for VLDL and vitellogenin binds the mammalian ligand, apolipoprotein E J Biol Chem 265, 19575-19581 Schneider, W.J., Carroll, R., Severson, D.L and Nimpf, J (1990) Apolipoprotein VLDL-I1 inhibits lipolysis of triglyceride-rich lipoproteins in the laying hen J Lipid Res 31, 507-513 MacLachlan, I., Nimpf, J and Schneider, W.J (1994) Avian riboflavin binding protein binds to lipoprotein receptors in association with vitellogenin J Biol Chem 269,24127-24132 Jacobsen, L., Vieira, P.M., Schneider, W.J and Nimpf, J (1995) The chicken oocyte receptor for lipoprotein deposition recognizes alpha2-macroglobulin.J Biol Chem 270,64684475 Nimpf, J., Stifani, S., Bilous, P.T and Schneider, W.J (1994) The somatic cell-specific LDL receptorrelated protein of the chicken: close kinship to mammalian LDL receptor gene family members J Biol Chem 269,212-219 Kovanen, P.T (1995) Role of mast cells in atherosclerosis, in: Chemical Immunology, Vol 62 Human Basophils and Mast Cells Clinical Aspects, Karger, Basel, pp 132-170 Yochem, J , Greenwald, I (1993) A gene for a low density lipoprotein receptor-related protein in the nematode Cuenorhabditis eleguns Proc Natl Acad Sci USA 90,45724576, Saito, A,, Pietromonaco, S., Kwor-chieh Loo, A and Farquhar, M (1994) Complete cloning and sequencing of rat gp330/’megalin’, a distinctive member of the low density lipoprotein receptor gene family Proc Natl Acad Sci USA 91,9725-9729 This Page Intentionally Left Blank 543 Subject Index A23 187,301,303-304 ACAT, 341-342,347,354-356 Acetoacetyl-CoA thiolase, 84,96 Acetyl and malonyl transferases, 116-1 17 Acetyl-CoA carboxylase, 42,68, 103-1 13, 119,121-123,125,266,270-271,274, 278,366,370-371 Acetyl-CoA, 43,68 - dependent acetyltransferase,201 Acetylcholine, 157 N-Acetyl glucosamine, 178 p-N-Acetylhexosminidase,329 Acholeplasma Laidlawii, 172 Acyl analogs, 190, 194,201 Acyl carrier protein, 35,37,41,4546, 50, 70,364,366,368-371,374,380,383-386 - synthetase, 60 Acyl hydrolases, 21 1, 217-218,221 Acyl modification, 234 Acyl-acyl carrier protein, 41,45-50, 58-60, 62,67-70,74 Acyl-CoA - dehydrogenases, 80-82,90,95 - oxidase, 91-92 - reductase, 191 - synthetases, 77-78, 80 Acyl-CoA:cholesterol acyltransferase,354 Acyldihydroxyacetone-P, 193, 203 1-Acylglycerol-3-Pacyltransferase, 154 2-Acy lglycerolphosphoethanolamine acyltransferase,59 Acyltransferase, 37,42,49-50, 56-57, 60, 62,69,371-372 Adipocyte cultures, I22 Adipocyte lipid binding protein, 259, 264 ADP-ribosylation factor, 250 Al-Alkyl desaturase system, 195 0-Alkyl - analog of phosphatidic acid and alkylacylglycerols, 194 - bond: mechanism of formation, 192 - cleavage enzyme, 203 - lipids, 184 Alkylacetylglycerols, 190 Alkyldihydroxyacetone-Psynthase, 192193 ALLN, 484-485 Alu sequence, 526-527 Alzheimer’s disease, 491492 Aminophospholipidtransporter, 406,409 AMP-activated protein kinase, 110-1 12 Amphipathic a helices, 159,477 Amphipathicj3-sheets, 477 Anaerobic bacteria, 188 Anti-inflammatory steroids, 292 Anticancer agents, 30-3 Apo A 1,490 - gene,490 Apo A2,490 Apolipoprotein B, 474489,491492 - acylation, 481 - degradation, 484485,491 - gene, 474,477480,486 - mRNA editing, 480 - mRNA, 478,480,482,487,491 - translocation, 483,485-486,491 Apo C, 49 Apo E, 491 Apo E-deficient mice, 491 Apo E4,49 1,492 Apo(a), 486 APO-VLDL-11,532-533 Arabidopsis thaliana, 372, 374, 379, 382 Arachidonate, 283-285, 287, 289,291-292, 294,300,302,308,310 Arachidonate cascade, 230 Arachidonic acid, 283-284, 287, 289, 299300,303,306-308,310 Archaebacteria, 72 Asialoglycoproteinreceptor, 449 Aspirin, 292,294 Asthma, 306 Ataxia telangiectasia, 253 Atherosclerosis, 536 ATP dependent transbilayer movement of aminophospholipids,405 ATP-citrate lyase, 19 Autooxidation, 284 544 B megaterium, 392,402 Bacilli, 70 Bacillus, 66,70-7 Bacterial permeability-increasingprotein, 229 Bacteroides, 72 Band 3,426,454,459-460 Base-exchange, 233 Betaine, 157 - aldehyde dehydrogenase, 157 Bidirectionality of this transport process, 408 Bilayer, 1-3,6-7,9-11, 13-14, 16-23,2529,3 1-33 - Hn transitions, 20 Bile acids, 341-346,353-357 Biological activities, 189 Biological membranes, 1, 19 Bip, 460462,466 Bis(monoacylglycerol)phosphate, 172 Bound polysomes, 432,437 Bradykinin, 285,289 Brain A9 desaturase, 139 Brefeldin A, 412,415416,484 CIEBP, 260-262,270,279 C2-ceramide,202 Ca2+-ATPase,454 Ca2+-dependentphospholipid binding (CaLB) region, 230 CaCo-2 cells, 479 Calcium, 238-241,246248,250 Calmodulin-dependentprotein kinase, 110 Calnexin, 460-461 Calsequestrin, 454-455 20-Carboxy-LTB4,304 Cardiolipin, 37, 53, 57, 366-368, 374 Carnithe palmitoyltransferase,79, 81, 88-90, 96 Carnitine:acylcarnitinetranslocase, 79 Casein kinase, 2, 110, 112 Catabolic enzymes, 203 Catabolism of chylomicrons, 528 Catalytic triad, 230 CCAAT/enhancer-bindingproteins, 260 CDP-choline:1,2-diacylglycerol cholinephosphotransferase, 160 CDP-DG, 155,171,173-174,176-177 CDP-DG synthase, 171 CDP-diacylglycerol,37,50-53,57, 169, 171, 176 CDP-ethanolamine, 155, 160, 166-168, 176 CDP-ethanolamine:1,2-diacylglycerol ethanolaminephosphotransferase,168 Cell cycle, 323, 334, 336 Cell mediators, 208 Cell surface proteins, 177 Centrioles, 414-415 Cerarnidase, 322, 329-330, 334, 337 Ceramide, 309-315,317-320,322-324,327332,334,336,338 - synthase, 19,322 - synthesis, 318 Cerebroside, 309-3 10 Cerebrosulfatide, 309 Cerebrotendinous xanthomatosis, 357 Cerulenin, 61 CETP, 504,506,513-515 Chain elongation, 129, 131-135, 141-142, 144-146,149-151 Chaperones, 460 Chicken oocytes, 530 Chimaerin, 245 Chloroplasts, 363-365,371-374, 381 CHO mutant, 159, 170 Cholesterol, 4,5, 11, 14, 16, 19, 20, 23, 28, 31,33,400,416-417,473,475,481,483, 486,488-491 - efflux, 535 - esterification,483 - oxidase, 397,400,416 Cholesteryl ester, 473,475 Cholesteryl ester transfer protein (CEPT), 14 Choline, 156-158,160-162,166-167, 170, 175-1 77,485 - deficiency, 482 - deficient, 163 - dehydrogenase, 157 - ethanolamine kinase, 166 - kinase, 157 - phosphotransferase, 160 - plasmalogens, 197 - transport, 157 Chromosome, 36, 39,42,58,61 Chylomicron, 263,274,473,495-496, 504 - retention disease (Anderson's disease), 487 - secretion, 487 545 cis-acting elements, 121,123-124 cis geometric configuration, 130,136,143 Citrate, 105 Clinical defects, 149 Clostridium, 72 cmc, 211-212,214-215,217,222 CoA-dependent transacylase, 200,201,205 CoA-independent transacylase/phospholipase A,, 200 Coated vesicle, 520-521 Covalent modification, 105,109-1 10,113, I25 cPLA~,287,289 CT, 155, 158-168,171,176,179-180 CTP, 156,159,163,176 CTP:phosphocholine cytidylyltransferase, 155-156,158,419 CTP:phosphoethanolamine cytidylyltransferase, 167-168 CTX, 357 Cyanide inhibition, 139 Cyclic AMP-independent protein kinase, 10 Cyclooxygenase, 283,289,291-292,294, 308-3 10 Cyclopropane fatty acid, 37,54 Cyclopropenoid fatty acids, 139 Cytidine deaminase, 480 Cytochrome b,, 133,138,141,144,426,452 Cytochrome P450,296,304, 306,308,451 Cytokines, 310,337 Cytoplasmic membrane of Bacillus megaterium, 392 A5 desaturase, 142,144,147,149,151 A6 desaturase, 139,143-147,149,151 Deacylation-reacylation, 176 - cycle, 222 3-Decenoyl-N-acetylcysteamine, 61 Dehydrase, I1 6-118 Dendrology of phospholipases, 224 Desaturase, 131,135,137-140,144,149, 15 1,364,366,369-370,373-374,380, 382-385,387 Desaturation, 129,131,135,137,139,141151,363,367,369-370,374,378,381, 385 Dexamethasone, 336,337 DG, 400,402,404,406,408,410-41 Diacylglycerol, 237-240,244-248,250-251, 391,400 - kinase, 37,59-60,66,239 - lipase, 239 Dialkylglycerophosphocholines, 188 Diazoborines, 61 A3~5,A2,4-Dienoyl-CoA isomerase, 86 2,4-Dienoyl-CoA reductase, 84,86-87,96 Diet, 129,131,134-135,138,140,143-151 Dietary, 132,139,142-143,145,147-148, 152 - sphingolipids, 332 Differential scanning calorimetry, 13 Differentiation, 257-259,261-262,280 Dihydroxyacetone-P, 192,203 Dihydroxyacetone-P acyltransferase, 154, 192 Diphosphatidylglycerol, 155, 171 Disulfide bonds, 224,228 Di thiothrei tol-insensitive cholinephosphotransferase, 201 Docosahexaenoic, 482 Dolichol-mannose, 178 Double bonds, 130-131,133,135-136,141- 143,145,147 DPG, 155, 171-175,180 DPG synthase, 174 Drosophila, 166,168,171 Drug delivery via liposomal systems, 30 Escherichia coli, 35-59,61-64,66-67,69- 71,73 EETs, 307 EGF precursor homology domain, 524-525, 529 5,8,11,14,17-Eicosapentaenoate,283 Eicosapentaenoic, 482 Electron-transferring flavoprotein, 82,95-96 Embryogenesis, 331 Endoplasmic reticulum, 131-135,137-138, 144,151,367 - localization, 460,466 Endosomal compartments, 415 Enoyl-ACP reductase, 37,47 Enoyl-CoA hydratases, 82 A3,A2-trans-Enoy I-CoA isomerase, 84 Enterohepatic circulation, 354 EpETrEs, 308-309,310 546 Epoxide hydrolase, 303,308-309 5,6-Epoxy prostaglandins, 309 Epoxygenase, 283-284,306310 Erucic acid, 377 Essential fatty acid, 129, 131, 139-140, 142144, 146147, 149-150 ETF, 82,96 Ethanolarnine - lysoplasmalogens,200 - phosphate, 33 - plasmalogen, 185, 187-188, 195-196, 198,209 Ether linkages in phospholipids, 183 Ether lipid synthesis, 191, 203 Evolution, 235 Evolutionary relatedness, 224 Extrinsic proteins, 25 FABPs, 76-77 FadR, 63-65 Familial hypercholesterolemia,522 Families of fatty acids, 143 Farnesyl, 341,343-345,347-348,350-352, 357-3 60 Fasting, 134, 148 Fatty acid - binding proteins, 76 - in animal cells, 76 - oxidation in E coli, 93 - oxidation in mitochondria, 78 - synthase, 103-104, 106, 113-121, 123125,366,368-370,383 - synthesis, 101-105, 107-109, 117, 119, 122,124-125 Fatty acylation, 459,476 Fatty alcohols, 203 Feedback inhibition, 66-67,69,71 Female germ cell, 531 Fish oil, 145-147 FLAP, 304 Fluorescent phospholipid analogs, 394 Fluorimetric assays, 213 Follicles, 531 Fumonisins, 322, 337 Fused LDL particles, 538 G-X-S-X-G active-site motif, 23 y-Glutamyl transpeptidase, 305 G-proteins, 241-242 G-protein coupled receptors, 191,426,455 Galactolipids, 363,365, 367, 371-372, 374 Galactosylceramide,3 10,315 Gangliosides, 309,312,316317,323-324, 332-335,338 - G~I,334 - G~3,334 Gel state, 13 Gene expression, 140 - in yeast, 176 Gene therapy, Gene transfer, 481 Genetic engineering, 363,377, 383-384,386 Geranylgeranyl, 343,357-359 GlcNAc, 178-179 Glucocorticoids, 270 Glucose transporter, 259-260,265,279 Glucose-6-phosphatedehydrogenase, 104105,119 Glucosylcerarnide,3 15 GLUTl, 265-266 GLUT4,265-266,271 Glutathione, 296,301-303, 309 Glycerol-3-P acyltransferase, 153 Glycerolipids, 237 Glycolipids, , Glycosyl phosphatidylinositols, 177 Glycosylation, 476,481 N-Glycosylation,448,456 0-Glycosylation, 459 Glycosyltransferases,323-324, 327, 333 Glyoxylate cycle, 364, 367-368, 377 Glyoxysomes, 368,377 Golgi, 476477,482,484,488490 - localization, 466467 Granules, 538-539 GTP-binding proteins, 464-465 Guanosine 5'-diphosphate-3'-diphosphate, 69 Halophilic bacteria, 188 Heart disease, 145 Hemagglutinin, 448,460-461,464,468 Hematopoietic cells, 327, 333 Hemolytic activity, 223 Hepatic lipase, 220 Hepatoma cell lines, 124 Hepatoma, 163, 165 547 HepG2 cells, 479,481-482,485 12(R)-HETE,307 Heterologous desensitization, 270 Hexagonal H, structure, 17 Hibernoma, 259 High density lipoprotein (HDL), 473-475, 477,490-491,495-497,504,506-513, 515,519,535-540 HMG-COA - reductase, 341, 344,347-348,350-354, 356-357,359-360,520-522 - synthase, 520-521,525 Hormonal regulation, 139 Hormone-sensitive lipase, 266-271, 274,278 55’-HpETE, 299-300 HpETEs, 299 Hydrophobic amines, 417-418 Hydroxy-fatty acids, 324, 332 3-Hydroxyacyl-ACP dehydrase, 47 L-3-Hydroxyacyl-CoAdehydrogenases, 83 7a-Hydroxylase, 342,346347,353,355357,360 27-Hydroxylase, 345-346, 357 15-Hydroxyprostaglandindehydrogenases, 297 4-~-Hydroxysphinganine,31 Hyperglycemia, 27 Hyperplasia, 258 Hypobetalipoproteinemia, 477 Hypoglycin, 89-90 IAA, 396,400-401 Ibuprofen, 294 IgM, , 4 , Inherited diseases of fatty acid oxidation, 96 Inhibitors of - fatty acid oxidation, 90 - sphingolipid metabolism, 19 INOl, 176-177 Ino2p-Ino4p heterodimer, 177 IN04, 177 myo-Inositol, 317 Inositol, 153, 155, 171, 176-178 - phosphate-glycan, 113 - phosphates, 239 - phospholipids, 171-172 Inositol-1-P synthase, 177 Insects, 138-139, 141-143 Insulin receptor tyrosine kinase, 271, 279 Interfacial activation, 214 Interferons, 278 Interlamellar attachment sites, 28 Interleukin, 278 Interleukin-1j3,295 Intermembrane lipid movement in Gramnegative bacteria, 408 Intermembrane lipid transport, 406 Internal elastic lamina, 536-537 Intestine, 7 , 81,485487,49049 Intramembrane lipid translocation and model membranes, 399 Intrinsic or integral membrane proteins, 26 Inverted micellar intermediates, 28-29 Ionizing radiation, 336 Isethionylacetimidate,396-397,401 Isoprenoids, 341, 343, 374 Isoprostanes, 284 6-Keto-PGFl,, 284 j3-Ketoacyl synthase, 116-1 17 Ketoacyl synthases, 369 3-Ketoacyl- ACP reductase, 46 3-Ketoacyl-ACP synthase, 4345,48,61-62, 64,68 3-Ketoacyl-CoA thiolase, 81-82, 84,89-90, 93.95 Lactosylceramide, 310, 315 Large unilamellar vesicle (LUV), Lauric acid, 377,383,386 Low density lipoprotein - metabolism, 416 - receptor, 518-534,536-538,540 - receptor gene, 525,528,532 - receptor supergene family, 525, 530 - receptor-related protein, 18, 528-529 Lean body mass, 276 Lecithin:cholesterolacyltransferase, 509 Leucine-zipper proteins, 260 Leukotrienes, 299-301,303,305-306,308, 309-3 10 Ligand binding domain, 523, 525-526,528 Lipases, 186,204-206, 377 Lipid - asymmetry, , , 13,32, 392 548 - bodies, 367, 376377,379 diversity, 391 - isolation and purification, - kinases, 237,238,253 - polymorphism, 17,20-22, 25-26 - transfer proteins, 486 - transfer, 485486,490 - transporters, 263-264 Lipid-binding proteins, 264, 267 Lipidic particle structure, 28 Lipolysis, 266, 269-270 Lipoproteins, 314, 320,327, 337 - assembly, 474 - lipase, 220, 274,497 - metabolic pathways, 517 - metabolism, 219-220 - receptor dichotomy, 533 Lipoprotein(a), 486 Liposomes, 9, 31, 33 Lipovitellogenin, 478 Lipoxygenase, 299-300,302,387 5-Lipoxygenase, 299-304,306 12-Lipoxygenase,300, 302 15-Lipoxygenase,300,302 Liquid-crystalline lipid bilayers, 23 Liquid-crystalline state, 2, 13-14 Liver acetyl-CoA carboxylase-associated kinase, 1I0 Liver tumor suppression, 165 Long-chain fatty acyl-CoA, 103, 108-1 I , 113 Loop models, 452 Low density membrane, 416 LTA3,303 LTA4 hydrolase, 301, 303 LTA,, 300-303 LTAs, 303 LTB4,3011303-306 LTC4 synthase, 301, 303 LTC4,301,303,305-306 LTE4,305-306 Lysolipid, 221-222 Lysosomal targeting, 467 Lysosphingolipids, 18 - a2-Macroglobulin, 529,533, 534 Macrophage, 159, 164, 169, 172,490491, 536-538 Malic enzyme, 104-105,119-121, 124 Malonyl-CoA, 80,87-89,98, 105-107, 113, 116 MAM (for mitochondria-associated membrane), 13 Mast cells, 536, 538-539 MDO, 41,59-60,66 mdr2 and PC transport, 405 Mechanism-based inhibitor, 23 Membrane, 35-38,40-41,49-50,52-57,5960,62-64,66-67,70-71,73-74 - binding domains, 291 - components, 208 - fusion, 20, 22,27-29,3 1, 33 - permeability, 16,22, 32 - potential (AV), 3, 23-24 - proteins, 425-43 1,433436,439,441443,446447,449457,459465466, 468-469 Membrane-derived oligosaccharides, 59 Metabolic poisons, 406,409,416 Metabolic regulation, 206 Mevinolin, 351-352, 356-357, 359 Microelectrophoresis,217 Microsomal - phospholipid transporter, 403 - triacylglycerol transfer protein, 485, 488 Microsomes, 43 1,434,436-437,439,441, 443,447448,456 Mitochondria associated membrane (MAM), 412 Mitochondria, 131-132, 366, 368 Mitochondria1 - elongation, 132, 134-135 - uptake of fatty acids, 78 Mixed micelles, 216,219-220 Molecular - cloning, 206 - genetics, 419,421 - packing, 218 - sequencing, 191,206 Monomethylethanolamine,483 Monomolecular film, 214,224 Monounsaturated fatty acid, 368, 382 MTP, 485487,490,492 Multi-span membrane proteins, 426,428, 450,452453,455,460 549 Multienzyme complex of fatty acid oxidation, 95 Multilamellar vesicles (MLVs), Mutant alleles at the LDL receptor, 522 Mycobacterium, 71 Myelination, 134, 135 Myeloperoxidase, 304 Na+/K+ATPase, 309-3 10 NADH, 133-135, 137-138 NADH-cytochromeb5 reductase, 137-1 38 NADPH, 133-135, 137 Nature of the aggregated lipid, 217 NBD-PC, 405,409 NBD-Cer, 41 NBD GlcCer, 413,415 NBD-SM, 413,415 Neonatal adrenoleukodystrophy,96 Neural - development, 331 - growth, 135 Neurons, 49 Neutral ether-linked glycerolipids, 195 NF-IL6/C/EBP, 296 Niemann-Pick disease, 309, 328 Niemann-Pick type C (NPC) disease, 416 Non-bilayer structures, 2, 25,27-28,32 Non-specific lipid transfer protein, 398,406 NSF, 463,465 Nuclear envelope, 287, 291-292, 295 Nuclear magnetic resonance (NMR), 13 - 2H-NMR, 16-17, 19,26 - 31P-NMR,17-20,26,28 Nuclear matrix, 159 Obesity, 258,276-279 Odd-chain fatty acids, 84 Oleic acid, 482 Oleosins, 377 Oocyte receptor for VLDL and VTG (OVR), 532 Oocyte-specific LRP, 534 OPIl gene, 177 Organelle specific lipid metabolism, 399 OVR, 529,532,534 B-Oxidation, 75,78-87, 89-98, 364, 366368,377 /?-Oxidationin peroxisomes, 91 #-Oxidation, 304, 308-309 Oxidative damage, 536 Oxygenase, 137, 140 Paramagnetic analogs of phospholipids, 394 Pause-transfer sequences, 484 Penicillium notatum, 22 Pentose phosphate pathway, 105 Peptidoleukotrienes, 304-305 Perilipins, 267 Permeability coefficient, 22-23 Permeabilized cells, 412413,419 Peroxidase, 289,291-292 Peroxisomes, 132, 135, 143, 151-152, 368 - proliferators, 261 Petroselinic acid, 383, 385 PGD synthase, 296 PGD2,296 PGE synthase, 296 PGE2,283,296-298 PGF,, 296 PGF, synthase, 296 PGH synthase, 287,289,291-292, 294,309310 PGHS-1,289,291-292,294-295 PGHS-2,289,291-296 PGI synthase, 296 PGI,, 284, 287, 296, 298 PGP, 37 Phase transition, 218 Phorbol esters, 323,331,333,337 Phosphatidic acid, 153-156, 160, 169, 171174, 176-177,248,250,364,366,371373,378-379 - phosphohydrolase, 154 Phosphatidylcholine (PC), 156,237-238, 246-248,251,365-366,373-374,378379,482,485 - hydrolysis, 247 - transfer protein, 400 Phosphatidylethanolamine (PE), 50, 57,70, 166,366-367,373-374,378 - methylation, 165 - N-methyltransferase, 160 Phosphatidylglycerol (PG), 50-53, 56, 59, 66, 155, 171-174,365 Phosphatidylinosjtol (PI), 337,460 - (bis)phosphate, 232 550 anchored proteins, 233 cycle, 238 -glycan-linkage, 318 3-kinase, 252 4-kinase, 172 - 5-kinase, 252 - 4P 5-kinase, 172 - phosphates, 387 - synthase, 172, 176 - transport, 41 - 3,4,5-trisphosphate, 237, 252-253 Phosphatidylrnonomethylethanolamine, 483, 485 Phosphatidylserine (PS), , s 1-52 - biosynthesis, 169 - decarboxylase, 1,2, 37, 52, 167-168, 176,399,408,411-412 - synthase, 167, 169-170, 176 Phosphocholine, 158, 161-163,176 Phosphodiesterases,212 Phosphodimethylethanolarnine, 161 Phosphoethanolamine, 155, 161, 168, 178 6-Phosphogluconate dehydrogenase, 104105, 119 Phosphohydrolase, 194-196, 198,201-202, 205-206 Phospholipases, 55,204, 211,213, 219, 228, 23 1-232,233,397 - A2, 186,198-201,206-208,403 - C6,337 - C isoforrns, 241 - C, 177 - D, 247-254,335,337 Phospholipid, 3, 5-9, 11, 15-18, 20,25-27, 363,367,371,377,473,475,482-483, 488,489-490 Phospholipid transfer protein (PLTP), 397398,418,421,506,513 4’-Phosphopantetheine prosthetic, 17 Phosphorylation, 102, 105-107, 109-1 13, 117, 157, 159, 164,166,231 - of cytidylyltransferase, 164 PIP2,237-238,240-241,243,247,250,252253 PIT gene, 419,420 Plasma - cholesterol, 150 - lipoproteins, 495 - Plasmalogen, 183, 185-188, 195,204,208209 - analogs, 190, 195 Plasmalogenase, 204 Plasmalopsychosines,3 18 Plasmanylcholines, 183, 195, 207 Plasmanylethanolamines, 195-196,207 Plastids, 364, 372,374 Platelet activating factor (PAF), 183, 185, 188-1 90, 195, 199-203,205-210,231, 233,234 - acetylhydrolase, 205-206,209 - biosynthesis via the de novo pathway, 201 - transacetylase, 201-202 Platelet-derived growth factor, 337 Pleckstrin homology (PH) domains, 241 PLTP, 506,5 13-5 14 Polyglycerophospholipids, 172 Polymorphic states, 218 Polysaturated fatty acid, 382 Polyunsaturated fatty acids, 129, 141-142, 367,379-382,384 PPGPP,69-70 Prep-HDL, 490,496,506,508,511-512 Prenylation, 357 Preprolactin, 439,44142,444,453 Primary cultures of hepatocytes, 124 Promoter, 295,296 Prostaglandin, 131, 143-144, 146, 150, 387 - E2.337 - synthesis, 228,234 Protein disulfide isomerase, 481,485 Protein kinases, 336-337 - A, 110 - C, 110, 159, 163, 169,244 Protein phosphatase, 336 Protein phosphatase 2A, 112 Protein sorting in epithelial cells, 468 Proton-relay mechanism, 227 Psoriatic lesions, 307 Psychosines, 18 PUFA metabolism, 142, 147, 150 ras, 358-359 Receptors, 285,298-299,306,310 - precursors, 526 - tyrosine kinase, 244,248, 252 - mediated endocytosis, 520 - and antagonists, 190 Reconstitution techniques, 11, 13 Recycling of exogenous cholesterol, 41 Red blood cell membrane, 392 Refeeding, 134, 138-140, 144, 147 Refsum’s disease, 97 Regulation - CDP-ethanolamine pathway, 168 - fatty acid oxidation, 87 - phosphatidylcholine biosynthesis, 161, 163 - sphingolipid metabolism, 331 Remodeling route, 199 Restricted ovulator, 532 9-cis Retinoic acid, 261-262 Retroconversion, 145 Reverse cholesterol transport, 490, 19,535536 RhoA, 250 Rhodobacter sphaeroides, 161 Rhodopseudomonas, 70-7 Riboflavin binding protein, 534 Ribophorins, 442,456 Satiety, 257, 276-278 Saturated fatty acid, 368, 370, 372, 382-383, 385 Scavenger receptors, 536-538,540 SCD, 138-140 Scooting and hopping model, 216-217 SECI4 gene, 419 SEC14p, 163 SecGlp, 431,441-444 Serine palmitoyltransferase,3 19-321 Shape property of lipids, 21 Sialic acid (N-acetylneuraminicacid, 12 Signal - anchor, 433,442,449455,466 - anchor sequences, 449,45 1,453454 - hypothesis, 431433 - peptidase, 443 - peptides, 291 - recognition particle (SRP), 431,439 - sequences, 433,436,438441,448-449, 451455,462,469,483 - transduction, 129, 131, 237-238, 252253 Small unilamellar vesicles (SUVs), Smith-Lemli-Opitz syndrome, 346 SNF1, 111 Space fitting model, 225 Sphinganine, 310,317,319, 322, 331, 333, 336 Sphingolipid, 375 - activator proteins (SAPS),329 - and signal transduction, 334 Sphingomyelin, 3, 5-6, 16,29, 309-310, 312, 314,322-323,327-328,331-332,336338 Sphingomyelinase, 319, 328, 336-337, 397 SphingomyelinaseD, 328 Sphingosine, 201-202,309-311, 314, 319, 322,328,330-331,333-335,337 - 1-phosphate, 19,331, 337 - kinase, 330, 337 Spin labeled analogs - phosphatidylcholine,400,404 - phospholipids, 395 sPLA,, 287 Sprecher pathway, 143, 145 src homology (SH2 and SH3) domains, 241 SRE-1,349-351 SREBP-l,348-349 SRP, 431,433,439441,444,449,451-455, 462,467 SRP receptor, 440-441,444 Stalk structures, 28 Stearoyl-CoA desaturase, 138 Sterols, 341, 343, 347-353, 356, 360, 366367,374-375 - regulatory element binding protein 1, 348-349 Stop transfer sequences, 433,436,438,448450,452454,469 Stringent response, 69-70 Sucrase-isomaltase,45 Suicide inactivation, 291, 296,302 Sulfatide, 327 Sulfolipid, 365-366,373-374, 387 Super-induction, 139 Sympathetic nervous system, 267-268, 272, 274,277 tli-2 - PE transport, 405 PS transport, 405 552 TATA box, 296,302 Thermal regulation, 46, 62-63 Thermal stability, 272 Thermoneutrality, 274 Thioesterase, 58, 67-68, 116, 118,369-370, 383-386 Thiolactomycin, 61 Thyroid hormone, 490 TM segment, 425,428,441-442,446,449, 451456,459,461,466 TNBS, 396,401402,409,411 TRAM, 431,441442,444,453 trans double bonds, 147 trans fatty acids, 385 trans-2-hexadecena1, 33 trans-3-hexadecenoic acid, 367 Transacylation, 219, 222 Transbilayer movement - of lipid at the endoplasmic reticulum, 402 - of PC in erythrocytes, 403 -of plasma membrane PC in nucleated cells, 404 Transcription run-on assay, 119 Transcriptional and post-trmscriptiona! regulation, 119 Transcriptional regulation, 63,478 Translation or elongation arrest, 440 Translocation hypothesis, 162 Translocon, 431,441444,451453,456 Transmembrane pH gradients, 7, 31-32 Transphosphatidylation, 212, 233, 248-249 Transport - in prokaryotes, 407 - of cholesterol to the plasma membrane, 41 - of exogenous PC analogs from the cell surface to intracellular organelles, 409 - of newly synthesized PC from the ER to the mitochondria, 409 - of newly synthesized PE to the plasma membrane, 409 - of newly synthesized PS to the mitochondria, 412 - of newly synthesized sphingolipids from the Golgi to the plasma membrane, 413 Triacylglycerol (TG), 257-260,262, 264267,269-272,274,276,278,363,367, 370-371,373-374,376-379,383,474475,485,488-489 - biosynthesis, 169 - synthesis, 482 Trifunctional/Loxidation complex, 82, 84 Trifunctional enzyme, 92-93 Trinitrobenzenesulfonate, 396397,401 Triton X-100,216-217,219,221,232 Truncated apo B, 483 Trypanosoma brucei, 177 Tumor - necrosis factor-a, 278, 336 - promotion, 244 - suppressor, 165-166, 179 TxA synthase, 296 T x A ~284,296,298 , T x B ~284 , Type I membrane proteins, 425-426,436, 443,445,449-450,452 Type II membrane proteins, 426,441,449, 45 1452,457,466 Tyrosine kinases, 241, 243,253 Tyrosyl radical, 291,294 U18666A, Uncoupling protein, 258-259, 273-274, 275 Uptake, 76 Van der Waals forces, 130 Vascularization, 257, 272 Very low density lipoprotein (VLDL), 473, 495-498,500,502-505,511,513,515 - assembly, 477-478,485-488,490492 - receptor, 523,529-530,532,540 Vesicle-mediated drug delivery, 31 Vesicular transport, 462 Vimentin, 417-418 Vitellogenin, 477,486 vps34p, 253 VSV glycoprotein, 447449,459,462463, 468 Watanabe Heritable Hyperlipidemic rabbits, 526 X-linked adrenoleukodystrophy, 97 X-ray crystallographic analysis, 224 553 Yolk sac, 478 Yolk, 530-534 Zellweger syndrome, 96 Zileuton, 306 Zinc deficiency, 150 Zn2+-rnetallohydrolase,303 Zyrnogens, 224 This Page Intentionally Left Blank .. .BIOCHEMISTRY OF LIPIDS, LIPOPROTEINS AND MEMBRANES New Comprehensive Biochemistry Volume 31 General Editor G BERNARD1 Paris Amsterdam - Lausanne - ELSEVIER NewYork - Oxford -... Sphingoid bases 2.2 Ceramides 2.3 Phosphosphingolipids 313 313 314 314 315 315 316 318 318 318 318 319 322 322 3.3 Neutral glycosphingolipids ._ 323 3.4 Gangliosides ... Vance and J.E Vance (Eds.), Biochemistry of Lipids, Lipoproteins and Membranes 1996 Elsevier Science B.V All rights reserved CHAPTER Physical properties and functional roles of lipids in membranes