~ Pergamon Prog. Lipid Res. Vol. 35, No. 1, pp. 1-51, 1996 Copyright © 1996 ElsevierScienceLtd. All rights reserved Printed in Great Britain 0163-7827(95)00009-7 0163-7827/96/$29.00 BETAINE ETHER-LINKED GLYCEROLIPIDS: CHEMISTRY AND BIOLOGY Valery M. Dembitsky* Natural Products Laboratory, Department of Organic Chemistry, The Hebrew University of Jerusalem, Jerusalem 91904 Israel CONTENTS I. Introduction 2 II. Separation, isolation and structural elucidation of betaine lipids 2 A. Extraction of betaine lipids from plants 2 B. Column chromatography 3 C. Thin-layer Chromatography 4 D. High-performance Liquid Chromatography 4 E. Physico-chemical properties 4 F. Elucidation of betaine lipids 5 I. Diacylglyceryltrimethylhomoserine 5 2. Diacylglycerylhydroxymethyltrimethyl-13-alanine 6 3. Diacylcarboxymethylcholine 6 G. Synthesis of betaine lipid derivatives 6 III. The distribution of betaine lipids in nature 7 A. Lipids of Protozoa 7 B. Algal Lipids 7 1. Lipids of Microalgae 8 Chlorophyta 8 Lipids of Chrysophyceae 14 Lipids of Haptophyceae species 18 Lipids of Chromophyta 18 Lipids of Nannochloropsis (Eustigmaphycaea) 20 Lipids of Raphidophyceae 20 2. Lipids of Macrophytes 21 Rhodophytes (Red algae) 21 Chlorophyta (Green algae) 22 Phaeophytes (Brown algae) 26 C. Lipids of Bryophyta 34 1. Biosynthesis of DGTS 35 D. Lipids of Pteridophytes 35 , 1. The effect of age on the lipid composition 36 E. Lipids of Fungi 37 1. Lipids of Lichens 38 2. Effect of temperature on DGTS composition 38 F. Vascular plants lipids 40 IV. Intracellular localization of betaine lipids 40 V. Resistance of betaine ether-linked lipids to the action of phospholipase D 42 VI. Phylogenetic distribution among major taxonomic groups of betaine and other ether-linked lipids 43 A. Viruses 43 B. Bacteria 44 C. Protozoa 47 D. Chromista 47 E. Fungi 47 F. PiLantae 47 Note added in proof 47 Acknowledgements 47 References 48 *Present address: Department of Biotechnology, Moscow State Academy of Fine Chemical Technology, 86 Vernadsky Avenue, Moscow 117571, Russia.