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Ether Lipids
Biochemical and Biomedical Aspects
1st Edition - January 28, 1983
Editor: H.K. Mangold
eBook ISBN:9780323149723
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