FUNCTION AND BIOSYNTHESIS OF LIPIDS

ADV ANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY

Editorial Board:

Nathan Back State University of New York at Buffalo

N. R. Di Luzio Tulane University School of Medicine

Bernard Halpern College de France and Institute of Immuno-Biology

Ephraim Katchalski The Wei:zmann Institute of Science

David Kritchevsky Wistar Institute

Abel Lajtha New York State Research Institute for Neurochemistry and Drug Addiction

RodolEo Paoletti University of Milan

Recent Volumes in this Series

Volume 82 ATHEROSCLEROSIS: Metabolic, Morphologic, and Clinical Aspects

Edited by George W. Manning and M. Daria Haust • 1977

Volume 83 FUNCTION AND BIOSYNTHESIS OF LIPIDS

Edited by Nicolas G. Bazan, Rodolfo R. Brenner, and Norma M. Giusto. 1977

Volume 84 MEMBRANE TOXICITY

Edited by Morton W. Miller and Adil E. Shamoo • 1977

Volume 85A ALCOHOL INTOXICATION AND WITHDRAWAL - IlIa: Biological Aspects of Ethanol

Edited by Milton M. Gross. 1977

Volume l!5B ALCOHOL INTOXICATION AND WITHDRAWAL - I1Ib: Studies in Alcohol Dependence

Edited by Milton M. Gross. 1977

Volume 86A PROTEIN CROSSLINKING: Biochemical and Molecular Aspects

Edited by Mendel Friedman. 1977

Volume 86B PROTEIN CROSSLINKING: Nutritional and Medical Consequences

Edited by Mendel Friedman. 1977

Volume 87 HYPOTHALAMIC PEPTIDE HORMONES AND PITUITARY REGULATION

Edited by John C. Porter. 1977

Volume 88 AVIAN IMMUNOLOGY

Edited by Albert A. Benedict. 1977

Volume 89 MUCUS IN HEALTH AND DISEASE

Edited by Max Elstein and Dennis V. Parke .1977

Volume 90 PARKINSON'S DISEASE: Neurophysiological, Clinical, and Related Aspects

Edited by Fathy S. Messiha and Alexander D. Kenny. 1977

FUNCTION AND BIOSYNTHESIS OF LIPIDS

Edited by

Nicolas G. Bazan Universidad Nacional del Sur - CONICET Bahia Blanca, Argentina

Rodolfo R. Brenner Universidad Nacional de La Plata La Plata, Argentina

and

Norma M. Giusto Universidad Nacional del Sur - CONICET Bahia Blanca, Argentina

PLENUM PRESS • NEW YORK AND LONDON

library of Congress Cataloging in Publication Data

International Symposium on Function and Biosynthesis of Lipids, Sierra de la Ventana, Argentine Republic, 1976. Function and biosynthesis of lipids.

(Advances in experimental medicine and biology; v. 83) Includes index. 1. Lipids-Congresses. I. Bazan, Nicolas. II. Brenner, Rodolfo Roberto, 1922-

III. Giusto, Norma M. IV. Title. V. Series. [DNLM: 1. Lipids-Biosynthesis­Congresses. 2. Lipids-Metabolism-Congresses. WI AD559 v. 83 1976/QU85 I598f 1976J QP751.I637 1975 599'.01'9247 77-6831 ISBN 978-1-4684-3278-7 ISBN 978-1-4684-3276-3 (eBook) DOI 10.1007/978-1-4684-3276-3

Proceedings of the International Symposium on Function and Biosynthesis of Lipids held at Sierra de la Ventana, Tornquist, Province of Buenos Aires, Argentina, November, 1976 (Symposium of the International Union of Biochemistry, No. 79)

© 1977 Plenum Press, New York Softcover reprint of the hardcover 1st edition 1977 A Division of Plenum Publishing Corporation 227 West 17th Street, New York, N. Y. 10011

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 volume contains the proceedings of the International Symposium on Function and Biosynthesis of Lipids held November 1976 at Sierra de la Ventana, Argentina. The conference was organized by the Argentine Biochemical Society and co-sponsored by the International Union of Biochemistry and the Pan American Association of Biochemical Societies.

The Symposium's great success is owed to all the participants, most of whom were actively involved in the interesting and stimu­lating discussions that followed every single lecture and communi­cation delivered. Many thanks also to Drs. R. Anderson, S. Bonting, K. K. Carroll, B. Cecarelli, M. A. Crawford, R. T. Holman, J. Mead, R. H. Michell, G. Porcellati, W. Stoffel, W. Thompson, and H. Wiegandt for chairing Symposium sessions.

The contributions are organized in four sections, preceded by the opening lecture on the role of dolichol phosphate in glyco­protein biosynthesis delivered by Dr. Luis F. Leloir. The first section, on aspects of lipid involvement in the biogenesis of mem­branes, covers the biosynthesis of saturated and unsaturated fatty acids, including enzymology, biosynthetic pathways, and regulation and modifications during development, in the fetus and in tumor~ cells. Papers on the composition and assembly of membrane compo­nents, lipid interactions with proteins and enzymes, developmental changes of lipids, and newer approaches to survey the organization and biogenesis of cellular membranes complete this section.

New information as well as reviews of current concepts about structural specificity, biosynthesis, and function of glycosphingo­lipids are included in the second section.

The third section is devoted to various aspects of biosynthesis, turnover, and function of lipids in the central nervous system, such as metabolism of polyenoic fatty acids, base-exchange reactions, biosynthesis of complex lipids, and the latest progress in phos­phatidylinositol biochemistry. In addition papers on the implica­tions of lipids in transmitter release and in receptors are included.

v

vi PREFACE

The fourth section is composed of several contributions on essential fatty acids in human nutrition, diet, brain, developing retina, and testes, as well as on enzymological studies.

We are grateful to Aerolineas Argentinas; Bodegas y Vinedos Edmundo Norton; Comisi6n de Investigaciones Cientificas of the Province of Buenos Aires; Consejo Nacional de Investigaciones Cient{ficas y Tecnicas, Argentina; the Embassy of the German Federal Republic in Buenos Aires; FIDIA Research Laboratories, Abano Terme, Padua, Italy; Gobernaci6n of the Province of Buenos Aires; Inter­national Union of Biochemistry; Municipalidad of Tornquist; Secre­taria de Estado de Salud Publica; Ministerio de Bienestar Social of Argentina; Secretaria de Estado de Ciencia y Tecnologia; Labora­torios Promeco; Ministerio de Cultura y Educaci6n of Argentina; The British Council; and Universidad Nacional del Sur for their financial support of the Symposium.

We should like to express our gratitude to the staff of the Instituto de Investigaciones Bioquimicas, Universidad Nacional del Sur-Consejo Nacional de Investigaciones Cientificas y Tecnicas, for its valuable help both in the organization of the Symposium and in the preparation of this book. Thanks are also due to Plenum Publishing Corporation for its support.

We hope that this volume will stimulate further productive research on the function of lipids in the cell.

Nicolas G. Bazan

Rodolfo R. Brenner

Norma M. Giusto

Bahia Blanca, January 1977

CONTENTS

In memoriam--Professor Werner Seubert R. R. Brenner

A short history of the biochemistry of lipids in Argentina (Opening address)

R. R. Brenner

OPENING LECTURE

The role of dolichol in protein glycosylation L. F. Leloir

I. LIPID INVOLVEMENT IN THE BIOGENESIS OF MEMBRANES

(A) Biosynthesis of fatty acids

The role of lipid in stearyl CoA desaturation P. W. Holloway, M. Roseman, and M. A. Calabro

Biosynthet~c pathways of polyunsaturated fatty acids

H. Sprecher

The specificity of mammalian desaturases A. T. James

Regulation of the ~9 desaturation O. Mercuri and M. E. De Tomas

Regulatory function of ~6 desaturase--Key enzyme of polyunsaturated fatty acid synthesis

R. R. Brenner

vii

3

9

23

35

51

75

85

viii

Saturated and mono-unsaturated fatty acid biosynthesis in brain: relation to development in normal and dysmyelinating mutant mice

J. M. Bourre, S. Pollet, M. Paturneau-Jouas, and N. Baumann

Protein factor involved in fatty acid desaturation of linoleic acid

A. Catala, A. Leikin, A. M. Nervi, and R. R. Brenner

Biosynthesis of lipids in tumoral cells M. E. De Tomas and O. Mercuri

Specificity of A6 desaturase. Effect of chain length and number of double bonds

J. C. Castuma, R. R. Brenner, and W. Kunau

Fetal accumulation of long-chain polyunsaturated fatty acids

M. A. Crawford, A. G. Hassam, G. Williams, and W. Whitehouse

Materno-fetal transfer of 14C linoleic and arachidonic acids

M. Pascaud, A. Rougier, and N. Delhaye

CONTENTS

103

111

119

127

135

145

(B) Biogenesis and organization of cellular. membranes

OQ the asymmetric composition of plasma membranes E. G. Trams

lnfluence of the lipid environment on the properties of rhodopsin in the photoreceptor membrane

S. L. Bonting, P. J. G. M. van Breugel, and F. J. M. Daemen

Approaches to the biochemistry of regeneration in the central nervous system

B. W. Agranoff

3-D-(-)Hydroxybutyrate dehydrogenase from rat liver mitochondria--Purification and interaction with phospholipids

J. C. Vidal, E. A. Guglielmucci, and A. O. M. Stoppani

153

175

191

203

CONTENTS ix

The role of phospholipids in Na-K ATPase 279 J. J. H. H. M. de Pont and S. L. Bonting

Interactions with phospholipid monolayers of lipids and water-soluble compounds that induce membrane fusion 225

B. Maggio and J. A. Lucy

The lipid composition and Ca transport function of sarcoplasmic reticulum (SR) membranes during development in vivo and in vitro 233

R. L. Boland and A. Martonosi

Lipid metabolism during development in insects 247 A. M. Municio

Composition and metabolism of phospholipids during early stages of vertebrate embryonic development 249

A. M. Pechen de D'Angelo, I. C. Bonini de Romanelli, T. S. Alonso, and N. G. Bazan

1 I. GLYCOSPHINGOLIPIDS--GANGLIOSIDES

Structural specificity of gangliosides H. Wiegandt

The biosynthesis of brain gangliosides--Evidence for a "transient pool" and an "end product pool" of gangliosides

H. J. Maccioni, C. Landa, A. Arce, and R. Caputto

Effects of brain gangliosides on reinnervation of fast-twitch rat skeletal muscle

B. Ceccarelli, F. Aporti, and M. Finesso

Studies on the functions of gangliosides in the central nervous system

R. Caputto, A. H. R. de Maccioni, and B. L. Caputto

The biosynthesis of gangliosides and sialoglycoproteins in bovine retina

J. A. Curtino, H. J. Maccioni, and R. Caputto

Possible presence of psychosine in brain J. M. Pasquini, F. B. Jungalwala, and R. H. McCluer

259

267

283

289

297

303

x CONTENTS

I I I. LIPIDS IN NEURAL TISSUE

(A) Biosynthesis and turnover

Transformations of the polyunsaturated fatty acids in the brain

J. F. Mead, G. A. Dhopeshwarkar, and M. Gan Elepano

The significance of base-exchange reactions in lipid metabolism

G. Porcellati, M. Brunetti, G. E. De Medio, E. Francescangeli, A. Gaiti, and G. Trovarelli

Metabolism of phosphatidylcholine in the central nervous system

E. F. Soto, R. Najle, I. F. de Raveglia, and J. M. Pasquini

Metabolic studies on ethanolamine phosphoglycerides in neuronal and glial cells

H. Woelk, G. Porcellati, L. Binaglia, and G. Goracci

Metabolic relation between phosphatidic acids, CDP-diglycerides, and phosphoinositides

W. Thompson

Neobiosynthesis of phosphatidylinositol and of other glycerolipids in the entire cattle retina

N. G. Bazan, M. G. Ilincheta de Boschero, and N. M. Giusto

~'hosphatidate, phosphatidylinositol, diacylglycerols, and free fatty acids in the brain following electroshock, anoxia, or ischemia

E. B. Rodriguez de Turco, G. D. Cascone, M. F. Pediconi, and N. G. Bazan

Acyl groups, molecular species, and labeling by 14C-glycerol and 3H-arachidonic acid of vertebrate retina glycerolipids

M. I. Aveldano de Caldironi and N. G. Bazan

313

329

345

361

367

377

389

397

CONTENTS xi

(B) Functions

Effect of phospholipid liposomes on the regulation of cerebral metabolism

G. Toffano, A. Leon, G. Savoini, and P. Orlando

Metabolism of phosphatidic acid and phosphatidylinositol in relation to transmitter release from synaptosomes

J. N. Hawthorne and M. R. Pickard

Metabolism and role of phosphatidylinositol in acetylcholine-stimulated membrane function

M. Hokin-Neaverson

The possible involvement of phosphatidylinositol breakdown in the mechanism of stimulus­response coupling at receptors which control cell-surface calcium gates

R. H. Michell, S. S. Jafferji, and L. M. Jones

The biosynthesis of prostaglandins and thromboxanes by nervous tissue

L. S. Wolfe, J. Marion, and K. Rostworowski

The relationship between cholinergic proteolipid and proteodetergent in Torpedo electroplax membranes

E. De Robertis, S. Fiszer de Plazas, and M. C. Llorente de Carlin

Effects of divalent cations, K+, and X-537A on glycerolipid metabolism in the cattle retina

N. M. Giusto and N •. G. Bazan

Effects of temperature, ionic environment, and light flashes on the glycerolipid neosynthesis in the toad retina

H. E. Pascual de Bazan and N. G. Bazan

Muscarinic cholinergic stimulation of phosphatidylinositol turnover in the CNS

O. Canessa de Scarnatti, M. Sato, and E. De Robertis

407

419

429

447

465

469

481

489

497

Selective lipid alterations during experimental allergic encephalomyelitis--An interpretation of the changes

F. A. Cumar, B. Maggio, and G. A. Roth

IV. ESSENTIAL FATTY ACIDS IN NUTRITION

Essential fatty acids in human nutrition R. T. Holman

Essential fatty acids: what level in the diet is most desirable?

K. K. Carroll

The relationship between membrane fatty acids and the development of the rat retina

R. E. Anderson, R. M. Benolken, M. B. Jackson, and M. B. Maude

Dietary essential fatty acids, brain polyunsaturated fatty acids, and prostaglandin biosynthesis

C. Galli, G. Galli, C. Spagnuolo, E. Bosisio, L. Tosi, G. C. Folco, and D. Longiave

Essential fatty acids in testes J. G. Coniglio, A. R. Whorton, and J. K. Beckman

Membrane structure and function with different lipid-supplemented diets

R. N. Farias and R. E. Trucco

Effect of thyroxine on ~6 and ~9 desaturation activity

I. N. T. de Gomez Dumm, M. J. T. de Alaniz, and R. R. Brenner

Biosynthesis of polyunsaturated fatty acids from the linoleic acid family ~n cultured cells

M. J. T. de Alaniz, I. N. T. de Gomez Dumm, and R. R. Brenner

Subject Index

CONTENTS

505

515

535

547

561

575

591

609

617

625