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Ether Lipids

Biochemical and Biomedical Aspects

1st Edition - January 28, 1983

Editor: H.K. Mangold

eBook ISBN:

9 7 8 - 0 - 3 2 3 - 1 4 9 7 2 - 3

Ether Lipids: Biochemical and Biomedical Aspects is a 21-chapter text that explores the procedures for the analysis, synthesis, and biomedical application of ether lipids. This… Read more

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Ether Lipids: Biochemical and Biomedical Aspects is a 21-chapter text that explores the procedures for the analysis, synthesis, and biomedical application of ether lipids. This book surveys first the chromatographic analysis of ether lipids and their characterization by mass spectrometry. The following chapter describes the chemical synthesis of lipids containing alkyl or 1-alkenyl chains. Three chapters are devoted to the biosynthesis of ether lipids, and four others cover unusual ether lipids. Significant chapters focus on biologically active ether lipids, including the naturally occurring platelet-activating factor and synthetic alkyl analogs of lysophosphatidylcholines, which exhibit cancerostatic properties. This text further discusses the application of these and related substances in biomedical research as well as in clinical diagnosis and therapy. The remaining chapters highlight the use of ether lipids in studies aimed at elucidating the structure of membranes and their functions. Organic chemists, biochemists, and researchers in the biomedical field will find this book invaluable.

Contributors

Preface

Terminology and Abbreviations

1. Chromatographic Analysis, Isolation, and Characterization of Ether Lipids

I. Introduction

II. Extraction and Purification of Lipids

III. Analysis of Ether Lipids

IV. Summary and Conclusions

References

2. Mass Spectrometry of Ether Lipids

I. Introduction

II. Mass Spectrometry of Alkylglycerolipids

III. Mass Spectrometry of 1-O-(1'-Alkenyl)glycerolipids

References

3. Chemical Synthesis of Ether Lipids

I. Introduction

II. Alkylglycerolipids

III. 1-O-(1'-Alkenyl)glycerolipids

IV. Alkyl Lipids Not Containing Glycerol

V. 1'-Alkenyl Lipids Not Containing Glycerol

References

4. Biosynthesis of O-Alkylglycerol Ether Lipids

I. Introduction

II. Biosynthesis of Glycerol Ether Lipids from Triose Phosphates

III. Biosynthesis of Alkyl-DHAP from Acyl-DHAP

IV. Biosynthesis of Acyl-DHAP

V. Properties of Alkyl-DHAP Synthase

VI. Enzymatic Reduction of Alkyl-DHAP

VII. Enzymatic Acylation of 1-Alkyl-sn-G-3-P to 1-Alkyl-2-acyl-sw-G-3-P

VIII. Conversion of 1-Alkyl-2-acyl-G-3-P to Different Alkylglycerol Ether Lipids

IX. Conclusion

References

5. Biosynthesis of 1-O-(1'Alkenyl)glycerolipids (Plasmalogens)

I. Introduction

II. Biosynthesis of Plasmalogens in Aerobic Organisms

III. Biosynthesis of Plasmalogens in Strictly Anaerobic Microorganisms

References

6. Substrate Specificity of Enzymes Catalyzing the Biosynthesis of Ether Lipids

I. Introduction

II. Formation of Long-Chain Alcohols

III. Formation of the Ether Bond

IV. Enzymatic Acylation of Alkylglycerolipids

V. Ethanolaminephosphotransferase and Cholinephosphotransferase

VI. Dehydrogenation of Alkylglycerolipids to Plasmalogens

VII. Conclusion

References

7. Ether Glycolipids

I. Introduction

II. Bacterial Ether Glycolipids

III. Mammalian Ether Glycolipids

IV. Conclusion

References

8. Dialkyidiglycerol Tetraethers

I. Introduction

II. Occurrence

III. Chemistry of Dialkyidiglycerol Tetraethers

IV. Conclusion

References

9. Ether Lipids Containing Steryl Moieties

I. Occurrence

II. Chemical Synthesis

III. Application in Biochemical Studies

References

10. Divinyl Ether Fatty Acids

I. Introduction

II. Occurrence

III. Isolation and Purification

IV. Structure Elucidation

V. Biosynthesis

VI. Degradation

VII. Function of Vinyl Ether Fatty Acids

References

11. Autoxidation of Ether Lipids

I. Introduction

II. Autoxidation Kinetics

III. Autoxidation Products and the Mechanism of Their Formation

IV. Conclusions

References

12. Ether Lipids as Substrates for Lipolytic Enzymes

I. Introduction

II. Lipolytic Enzymes Involved in the Catabolism of Ether Lipids

III. Ether Lipids as Model Compounds in Studies on Lipolytic Processes

IV. Application of Lipolytic Enzymes for the Preparation of Ether Lipids

V. Application of Diether Phospholipids in the Preparation and Affinity Labeling of Phospholipase A2

References

13. Ether Lipids in the Diet of Humans and Animals

I. Introduction

II. Ether Lipids in Human Food and Animal Feed

III. Metabolism of Ether Lipids in the Alimentary Canal

IV. Ether Lipids as Nonfattening Fats

V. Prospectus

References

14. Ether Lipids in Clinical Diagnosis and Medical Research

I. Introduction

II. Trialkylglycerols (Triethers) in Fat Absorption Studies

III. Ether Lipids as Chemical Indicators in Neoplasms

IV. Ether Lipids as Chemical Mediators

V. Conclusions

References

15. Therapeutic Effects of Ether Lipids

I. Introduction

II. Alkylglycerols and Their Esters

III. Methoxy-Substituted Alkylglycerols

IV. Acetal Analogs of Phosphatidic Acids

V. Alkyl Ethers of Halogenopropanediols

References

16. Synthetic Alkyl Analogs of Lysophosphatidylcholme: Membrane Activity, Metabolic Stability, and Effects on Immune Response and Tumor Growth

I. Introduction

II. Interactions of LLAs with Cell Surfaces

III. Effect of LLAs on Immune Response

IV. Effects of LLAs on the Growth of Experimental Tumors

V. Metabolic Stability of LLAs

VI. Conclusions

References

17. Ether Lipids in Biological and Model Membranes

I. Introduction

II. Ether Lipids in Biological Membranes

III. Ether Lipids in Model Membranes

References

18. Platelet-Activating Factor: An Ether Lipid with Biological Activity

I. Introduction

II. Historical Background and Definition

III. Cellular Origin of PAF-Acether

IV. Interactions of PAF-Acether with Platelets

V. Molecular Assembly of PAF-Acether

VI. Biological Activities of PAF-Acether Analogs: Structure-Activity Relationships

VII. PAF-Acether in Physiology and Pathology

VIII. Other Effects of PAF-Acether

IX. The End Result of Leukocyte-Platelet Interaction: Enhancement of Vascular Permeability-Its Role in Physiology and Pathology

X. Conclusions

References

19. Procedures for the Analysis of Ether Lipids

I. General Methods

II. Specific Procedures

References

20. Procedures for the Synthesis of Ether Lipids

I. General Methods

II. Procedures

References

21. Procedures for Biomédical Investigations

I. Preparation of Small Unilamellar Vesicles

II. Preparation of Large Unilamellar Vesicles

III. Assay of the Stereospecificity of Triacylglycerol Hydrolases

IV. Assay of the Effect of Lipids on Neutrophil Migration

V. Assay of 1-O-Alkyl-2-O-acetyl-sn-glycero-3-phosphocholines (Platelet-Activating Factor) with Radiolabeled Serotonin

References

Index