ENZYMESOF LIPID MET ABOLISM
ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY Editorial Board:
Nathan Back State University 0/ New Y ork at Buf/alo
N. R. Di Luzio Tulane University School 0/ Medicine
Bernard Halpern College de France and Institute o/Immuno·Biology
Ephraim Katehalski The Weizmann Institute 0/ Science
David Kritchevsky Wistar If'stitute
Abel Lajtha New York State Research Institute tor Neurochemistry and Drug Addiction
Rodolfo Paoletti University 0/ Milan
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Volume 100 MYELINATION AND DEMYELINATION
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Volume 101 ENZYMES OF LIPID METABOLlSM
Edited by Shimon Gatt, Louis Freysz, and Paul Mandel
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Edited by H. James Day, Basil A. Molony, Edward E. Nishizawa, and Ronald H. Rynbrandt
ENZYMES OF LIPID METABOLISM
Edited hy
Shimon Gatt Hebrew University - Hadassah Medical School Jerusalern, Israel
Louis Freysz C.N.R.S. Center for Neurochernistry Louis Pasteur University Strasbourg, France
and
Paul Mandel C.N.R.S. Center for Neurochernistry Louis Pasteur University Strasbourg, France
PLENUM PRESS • NEW YORK AND LONDON
Library of Congress Cataloging in Publication Data
Main entry under title:
Enzymes of lipid metabolism.
(Advances in experimental medicine and biology; v. 101) Proceedings. Includes index. 1. Lipid metabolism-Congresses. 2. Enzymes-Congresses. I. Gatt, Shimon. 11. Freysz,
Louis. III. Mandel, Paul. IV. France. Centre national de la recherche scientifique. [DNLM: 1. Lipids-Metabolism-Congresses. 2. Enzymes-Metabolism-Congresses. QU85 E611977] QP751.E59 599'.01'9247 78-886 ISBN 978-1-4615-9073-6 ISBN 978-1-4615-9071-2 (eBook) DOI 10.1007/978-1-4615-9071-2
Proceedings of a Colloquium sponsored by C.N.R.S. held in Strasbourg, France, April 18-22, 1977
Organizers
Shimon Gatt and Paul Mandel
General Secretary
L. Freysz
Organizing Committee
H. Dreyfus A. Farooqui N. Neskovic G. Rebel J. Robert L. Sarlieve G. Vincendon
Scientifie Advisory Committee
P. Desnuelle J. Polonovski K. Suzuki L. Svennerholm G. Tettamanti
© 1978 Plenum Press, New Y ork Softcover reprint of the hardcover 1st edition 1978 A Division of Plenum Publishing Corporation 227 West 17th Street, New York, N.Y.l00n
All rights reserved
No part of this book 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
Preface
This book presents the proceedings of the meeting on "Enzymes of Lipid Metabolism" which took place April 18-22, 1977, at the Mont Ste. Odile convent in Alsace, France. The meeting was convened and co-ehaired by P. Mandel and S. Gatt. L. Freysz was general seeretary. They were assisted by an international advisory committee and a loeal organizing committee.
The purpose of the meeting was to bring together scientists involved in research on a wide variety of aspeets of lipid metabolism and who have a direct interest in the problematies on interacting enzymes with lipid substrates. The aim was to emphasize the latter aspect rather than common enzymologieal aspects such as extraetion, purification, and protein strueture. The rpeoeedings included several symposia and four "round-table" discussions. There was also a presentation of posters, whieh were exhibited during the entire duration of the meeting. All partieipants who presented leetures or posters were requested to summarize their findings, whieh were ineluded in the book. Regretfully, the very fruitful discussions of the "round-tables" were not included, nor were those held in the informal atmosphere of the court yards of the eonvent, the hiking paths in the Vosges mountains, and the bar. For the purpose of coherence, the editors decided not to adhere to the original order of the lectures. The papers in the book are grouped aeeording to the classes of enzymes and the types of reaction which they catalyze.
The very generous assistance of the CNRS, who sponsored the colloquium, is gratefully acknowledged. Without the generous grant of this ageney, the meeting would not have materialized.
We wish to thank members of the scientific advisory committee and loeal organizing committee, as well as Mrs. H. Urban artd M. Sarlieve for excellent secretarial assistance.
v
S. Gatt L. Freysz P. Mandel
Contents
Enzymes Metabolizing Phospholipids: From Infancy to Middle Age (Plenary Lecture) •••••
R.M.C. Dawson
ENZYMES OF THE METABOLISM OF FATTY ACIDS AND NEUTRAL GLYCERIDES
Fatty Acid Biosynthesis during Brain Development J.M. Bourre, S. Pollet, M. Paturneau-Jouas, and N. Baumann
The Role of Soluble Acyl-Thioester Hydrolase in Fatty Acid Chain-Length Termination in Rabbit Mammary Gland and Liver • • • • • • • • • • • • •
J. Knudsen, L. Chivers, and R. Dils
Stereochemical Studies of Hydrogen Incorporation from Nucleotides with Fatty Acid Synthetase from Brevibacterium ammoniagenes • • • • • . • • • •
Y. Seyama, T. Kasama, T. Yamakawa, A. Kawaguchi, and S. Okuda
Cholesterol Oxidase as a Probe for Studying Membrane
1
17
27
37
Composition and Organization • • • • 45 Y. Barenholz, E.J. Patzer, N.F. Moore, and R.R. Wagner
Adsorption and Activation of Pancreatic Lipase at Interfaces • • • • • • • • . • • • •
C. Chapus, M. Semeriva, M. Charles, and P. Desnuelle
Mode of Action of Pancreatic Colipase • • . • B. Borgström
Studies of Lipase and Phospholipase A2 Acting on Lipid Monolayers . • • • • • • • • • • • .
R. Verger, J. Rietsch, F. Pattus, F. Ferrato, G. Pieroni, G.H. de Haas, and P. Desnuelle
vii
57
69
79
viii CONTENTS
Inhibition of Lipase Adsorption at Interfaces Role of Bile Salts MicelIes and Colipase • • • • •• 95
D. Lairon, G. Nalbone, H. Lafont, J. Leonardi, N. Domingo, J.C. Hauton, and R. Verger
Lipases of Rat Brain Microsomes M.C. Cabot and S. Gatt
Identification and Some Characteristics of the Enzyme Protein of the Hormone-Sensitive Lipase from Rat Adipose Tissue
P. Belfrage, B. Jergil, P. Strälfors, and H. Tornqvist
Affinity Chromatography on Heparin-Sepharose of Rat Adipose Tissue Triglyceride Lipase from Cytosol • • • • • • •
A. Vanhove, M. Breton, and J. Polonovski
ENZYMES OF THE METABOLISM OF GLYCEROPHOSPHOLIPIDS
A) Phospholipases
Relationship between Structure and Activity of
101
113
127
Pancreatic Phospholipase A2 •••• • • • •• 137 A.J. Slotboom, M.C.E. van Dam-Mieras, E.H.J.M. Jansen, F. Pattus, H.M. Verheij, and G.H. de Haas
Kinetic Anomalies Associated with Phospholipase A2 Hydrolysis of Micellar Substrates • • • • •• •• 153
T.T. Allgyer and M.A. Wells
Mechanism of Phospholipase A2 Action Towards Mixed MicelIes of Detergent and Phospholipids
E.A. Dennis 165
Chemical Modification of Crotalus atrox Phospholipase A2 by Means of a Photolabile Phosphatidylethano-lamine Analog • • • • • • • • • • • • • • • • • • 177
K.-S. Huang and J.H. Law
Phospholipases A of Krebs 11 Ascites Cells: Release and Subcellular Localization
J. Lloveras, M. Record, G. Ribbes, and L. Douste-Blazy
Specificity, 185
CONTENTS
Phospholipases of Plasmic Membranes of Adipose Tissue. Possible Intermediaries for Insulin Action • • • • • • • •
G. Bereziat, C. Wolf, O. Colard, and J. Polonovski
Calcium-Activated Hydrolysis of Triphosphoinositide in Synaptosomes ••••••••••••••
J.N. Hawthorne and H.D. Griffin
The Activity of Phospholipase D on Aggregates of Phosphatidylcholine, Dodecylsulfate and Ca2+
M. Heller, P. Greenzaid, and D. Lichtenberg
The Preparation of Phospholipids by Phospholipase D S. Kovatchev and H. Eibl
The Effects of Amphiphilic Compounds on Phosphatidate Metabolism • • • • • • • • • • • • • • .
D.N. Brindley, M. Bowley, R.G. Sturton, P.H. Pritchard, J. Cooling, and S.L. Burditt
B) Biosynthesis
Choline and Ethanolamine Kinase Activity in the Cytoplasm of Nerve Endings from Rat Forebrain
S. Spanner and G.B. AnseIl
The Release of Free Ethanolamine in Rat Brain Homogenates Incubated in Krebs Ringer •
S. Spanner and G.B. AnseIl
Ethanolamine and Choline Phosphotransferases of Chicken Brain • • • • • • • • • • • •
L. Freysz, L.A. Horrocks, and P. Mandel
Studies of Rat Brain Choline Ethanolamine Phosphotransferases Using Labeled Alkylacylglycerol as Substrate with Evidence for Reversibility of
191
201
213
221
227
237
247
253
the Reactions • • • •• • • • • • • • • • • • •• 269 G. Goracci, L.A. Horrocks, and G. Porcellati
The Role of Phosphatidylglycerol as a Donor of Phosphatidyl and of ~-Glycerol-l-Phosphate Groups in Biosynthetic Reactions • • • • •
R.A. Pieringer, J.M. Shaw, and M.-C.W. Ganfield 279
ix
x
Membrane-Bound Base-Exchange Reactions in Anima1 Tissues . • . • • • • • • • . • . • • • • •
G. Porce11ati, A. Gaiti, H. Woe1k, G.E. De Medio, M. Brunetti, E. Francescange1i, and G. Trovare11i
The "Base-Exchange" Reaction: The Serine Enzyme T. Taki, T. Miura, and J.N. Kanfer
A Study on the Possib1e Occurrence of Base-Exchange Reactions in Vivo • • • • • • • • • • • • • • ---P. Or1ando, G. Arienti, P. Saracino, L. Corazzi,
P. Massari, and G. Porce11ati
The Biosynthesis and Hormonal Regulation of Surfactant Formation • • • • • •
J.M. Johnston, J.C. Porter, and P.C. MacDona1d
Properties of a Lysophospho1ipase-Transacy1ase from Rat Lung: lts Possib1e Invo1vement in the Synthesis of Lung Surfactant •• • • •
H. van den Bosch and G. W. Brum1ey
A Study on the Turnover of Rat Brain Phosphatidic Acid through the G1ycero1-Phosphate Pathway
L. Binag1ia, R. Roberti, and G. Porce11ati
C) Ether Lipids
Studies on the Biosynthesis of the O-A1ky1 Bond in G1ycero1 Ether Lipids
A.K. Hajra, C.L. Jones, and P.A. Davis
Asymmetrie Loca1ization of A1kyldihydroxyacetone-P Synthase and Acyldihydroxyacetone-P Acyltransferase in Microsoma1 Vesicles
C.O. Rock and F. Snyder
Studies on Soluble Proteins Stimu1ating Plama10gen Biosynthesis • • • • •
F. Paltauf
CONTENTS
287
301
319
327
341
353
369
379
387
Pathway for Hydrolysis of Plasmalogens L.A. Horrocks and S.C. Fu
in Brain . . . . . . . 397
Turnover of Mo1ecular Species of Diacyl and Alkyl Ether Phospho1ipids in Ehrlich Ascites Tumor Ce11s • • • • • • • • • • • • • • • • • 407
K. Waku and Y. Nakazawa
CONTENTS
ENZYMES OF THE METABOL1SM OF SPH1NGOL1P1DS
A) Neuraminidases
Neuraminidase Gang1iosides Interactions • G. Tettamanti, B. Cestaro, B. Venerando, and A. Preti
Action of Rat Brain Sia1idase on Synaptic Membrane Components in situ • • • •
A. Rosenberg
Interaction of Human Brain Neuraminidase with Tritium-Labe11ed Gang1iosides ••••
R.W. Veh and R. Schauer
Studies on Bovine Brain Membrane-Bound
417
439
447
Neuraminidase (Sia1idase) • • • • • • • • • • • • • •• 463 K. Sandhoff, P. Pa11mann, H. Wiegandt, and W. Zieg1er
Intraneuronal Distribution of Cytoso1ub1e Neuraminidase in Pig Brain • • • • • •
B. Venerando, A. Preti, A. Lombardo, B. Cestaro, V. Zambotti, and G. Tettamanti
B) Sphingomye1inases
Effect of Detergents on the Uti1ization of Sphingomye1in by Brain Sphingomye1inases
S. Gatt, T. Dinur, S. Yedgar, and Z. Leibovitz-Ben Gershon
Sphingomye1inase of Human Tissues S. Yamaguchi and K. Suzuki
C) G1yco1ipid Hydro1ases
Purification and Partial Characterization of Human Liver a-Ga1actosidase: 1s a-Ga1actosidase B an a-N-Acety1ga1actosaminidase? . • •
K.J. Dean, S.S.J. Sung, and C.C. Swee1ey
The 1dentity of a-Ga1actosidase B from Liver A.W. Schram, M.N. Hamers, and J.M. Tager
475
487
501
515
525
xii
Effect of Detergents on Ceramide-3 Hydrolysis by a-Ga1actosidase A • • • • • • • • • •
A.W. Schram, M.W. Ho, S. Cordus, M. Samson, M.N. Hamers, J. Brown, D. Robinson, and J.M. Tager
Specificity of Some Exo- and Endo-ß-Ga1actosidases toward G1ycosphingo1ipids • •
Y.-T. Li, C.C. Wan,J.-L. Chien, and S.-C. Li
Studies of Activity and Stabi1ity of Immobi1ized ß-N-Acety1hexosaminidase • • • •
K.-K. Yeung, A.J. Owen, and J.A. Dain
Affinity Methods for the Purification of Ary1su1phatase A • • • • •
G. Dubois and N. Baumann
Existence, Localization and Some Properties of the Activators of Sphingo1ipid Hydro1ases • • • •
H. Jatzkewitz
Studies on the Function of the Activator of Su1phatase A • • • • • • • • • •
G. Fischer and H. Jatzkewitz
G1ucosidase and G1ucocerebrosidase Activity in Subce11u1ar Fractions of Rat Spleen •
Z. Leibovitz-Ben Gershon, J. Rosentha1, and A. Russe11
Inhibitors of ß-G1ucosidases of Anima1 Tissues N.S. Radin
Isolation of Lysosomes from Bovine Brain Tissue. A New Zonal Centrifugation Technique • • • •
B. Overdijk, G.J.M. Hooghwinke1, and J.J.W. Lisman
D) Biosynthesis
UDP-Ga1actose:Ceramide Ga1actosy1transferase. Properties and Effect of Detergents and Phospho1ipids on the Partia11y Purified of Rat Brain •• • • • • • •
N.M. Neskovic, P. Mandel, and S. Gatt
Kinetic
Enzyme
Isolation of an Endogenous Inhibitor of Ceramide G1ycosy1transferases from Rat Brain • • • •
E. Costantino-Ceccarini, A. Cestelli, and K. Suzuki
CONTENTS
531
537
545
555
561
573
583
589
601
613
631
CONTENTS
Ce11u1ar Loca1ization of Na+ ~-Dependent ATPase and of the Enzymes of Su1pho1ipid Metabo1ism in Rabbit Kidney • • • • • • • • • • • • •
J.J. He1wig, J. Pieringer, L.L. Sar1ieve, A.A. Farooqui, G. Rebe1, P. Mandel, and R.A. Pieringer
Contro1 of Gang1ioside Biosynthesis by a Rate Limiting UMP-ase and Product Gang1ioside Inhibition • . • • • • • • • • • • •
J.A. Dain and W.R. Hitchener
Studies on Retina1 Gang1ioside Metabo1ism H. Dreyfus, S. Harth, A. Preti, P.F. Urban, and P. Mandel
Characteristics of the Brain Tissue Disia1ogang1ioside G2a
D. Kostic
Formation of G1ycosy1ated "Proteo1ipid-Like" Materials during Exogenous Protein Ga1actosy1ation
xiii
641
649
655
667
by Human Body Fluids • • • • • • • • • • • • • 679 J.A. Dain and E. Raghupathy
ENZYMATIC ASPECTS OF THE LIPID STORAGE DISEASES
Diagnoses of the Sphingo1ipidoses with Labe11ed Natural Substrates •••••••••••
L. Svennerho1m
Assay of ß-G1ucosidase and Sphingomye1inase for Identification of Patients and Carriers of Gaucher's and Niemann Pick Diseases ••••
D.A. Wenger
Hair Root Analysis in Heterozygotes for Fabry's Disease ••••••••••••••
A. Ejiofor, D. Robinson, D. Wise, M.N. Hamers, and J.M. Tager
Substrate Specificity of Hexosaminidase A Iso1ated from the Liver of a Patient with a Rare Form (AB Variant) of Infantile GM2 Gang1iosidosis and Contro1 Tissues • • • • • • • • • • •
K. Sandhoff, E. Conze1mann, and H. Nehrkorn
Biochemica1 Studies in Sphingomye1in Storage Disorders M.T. Vanier
689
707
719
727
731
xiv
Faetors that Influenee the Uptake and Turnover of Glueoeerebrosidase and a-Galaetosidase in Mammalian Liver • • • • • • • • • • • • • •
P.G. Pentehev, J.W. Kusiak, J.A. Barranger, F.S. Furbish, S.I. Rapoport, J.M. Massey, and R.O. Brady
Enzyme Therapy XI: Immunologie Considerations for Replaeement Therapy with Unentrapped, Erythroeyte-
CONTENTS
745
and Liposome-Entrapped Enzymes •••••• • • • • 753 R.J. Desniek, M.B. Fiddler, S.D. Douglas, and L.D.S. Hudson
List of Partieipants 765
Contributor Index • 773
Subjeet Index 777