xxi CONTENTS CHAPTER 1: INTRODUCTION TO PHOSPHOLIPIDS 1.1 DEFINITION AND CLASSIFICATION OF LIPIDS Simple lipids

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1 xxi CONTENTS CHAPTER 1: INTRODUCTION TO PHOSPHOLIPIDS 1.1 DEFINITION AND CLASSIFICATION OF LIPIDS Simple lipids Complex lipids NOMENCLATURE OF PHOSPHOLIPIDS SOURCES OF PHOSPHOLIPIDS Phospholipids in Human/Animal Tissues Egg Phospholipids Milk Phospholipids Brain Phospholipids Phospholipids in Liver, Kidney, Muscles and other Tissues Plant Sources of Phospholipids Microbial Sources of Phospholipids APPLICATIONS OF PHOSPHOLIPIDS SEPERATION AND ANALYSIS OF PHOSPHOLIPIDS Separation of Phospholipids Analysis of Phospholipids MAJOR CLASSES OF PHOSPHOLIPIDS Phosphatidyl choline Phosphatidyl ethanolamine Phosphatidyl inositol STRUCTURED PHOSPHOLIPIDS 26

2 xxii Enzymatic and Chemical Methods for the Preparation of Structural Phospholipids REFERENCES 31 CHAPTER 2: CHEMO-ENZYMATIC SYNTHESIS OF PLATELET ACTIVATING FACTOR AND ITS ANALOGUES 2.1 INTRODUCTION Importance of Platelet Activating Factor ISOLATION AND SYNTHESIS OF PLATELET ACTIVATING FACTOR PRESENT INVESTIGATION MATERIALS AND METHODS Materials Methods Preparation of 1-O-tetradecyl-2,3-epoxypropane Preparation of 1-O-hexadecyl-2,3-epoxypropane Preparation of 1-O-octadecyl-2,3-epoxypropane Preparation of 1-O-tetradecyl-2,3-di-Oacetyl glycerol Preparation of 1-O-hexadecyl-2,3-di-Oacetyl glycerol Preparation of 1-O-octadecyl-2,3-di-Oacetyl glycerol Preparation of 1-O-tetradecyl-2-O-acetyl glycerol Preparation of 1-O-hexadecyl-2-O-acetyl glycerol 59

3 xxiii Preparation of 1-O-octadecyl-2-O-acetyl glycerol Preparation of Choline toluene sulfonate Preparation of 1-O-tetradecyl-2-O-acetyl-snglycero-3- phosphor choline Preparation of 1-O-hexadecyl-2-O-acetyl-snglycero-3-phospho choline Preparation of 1-O-octadecyl-2-O-acetyl-snglycero-3-phospho choline Preparation of 1-O-alkyl-2-O-acetylglycerol Preparation of 1-O-tetradecyl-2-O-acetyl-snglycerol-3-Phospho lethanolamine Preparation of 1-O-hexadecyl-2-O-acetyl-snglycero-3-phospho ethanolamine Preparation of 1-O-octadecyl-2-O-acetyl-snglycero-3-phospho ethanolamine RESULTS AND DISCUSSION CONCLUSIONS REFERENCES 88 CHAPTER 3: SYNTHESIS OF N-AMINO ACID PHOSPHATIDYL ETHANOLAMINE DERIVATIVES 3.1 INTRODUCTION Phosphatidyl ethanolamine N-Acylphosphatidyl ethanolamine Mono- and Dimethyl Phosphatidyl ethanolamine 99

4 xxiv 3.2 SYNTHESIS OF DERIVATIVES OF PHOSPHATIDYL ETHANOLAMINE APPLICATIONS OF N-ACYL-PHOSPHATIDYL ETHANOLAMINE Importance of Amino Acids PRESENT INVESTIGATION MATERIALS AND METHODS Materials Methods Preparation of Egg Yolk Lecithin Isolation of PE Preparation of N-Protected Glycine Preparationof N-Protected Valine Preparation of N-Protected Leucine Prepation of N-Protected Isoleucine Prepation of N-Protected Phenylalanine Coupling of Phosphatidyl ethanolamine with N-Protected Glycine Coupling of Phosphatidyl ethanolamine with N-Protected Valine Coupling of Phosphatidyl ethanolamine with N-Protected Leucine Coupling of Phosphatidyl ethanolamine with N-Protected Isoleucine 119

5 xxv Coupling of Phosphatidyl ethanolamine with N-Protected Phenylalanine De-protection of PE-N-Protected Glycine De-protection of PE-N-Protected Valine De-protection of PE-N-Protected Leucine De-protection of PE-N-Protected Isoleucine De-protection of PE-N-Protected Phenylalanine GENERAL PROCEDURE FOR ANTIMICROBIAL ACTIVITY STUDIES General Procedure for Antibacterial Activity General Procedure for Antifungal Activity RESULTS AND DISCUSSION Anti Microbial Activity Evaluation of Phosphatidylethanolamine-N-Amino acids CONCLUSIONS REFERENCES 155 CHAPTER 4: PHOSPHOLIPASE CATALYZED PREPARATION OF HYDROXY FATTY ACID RICH PHOSPHOLIPIDS 4.1 INTRODUCTION LITERATURE SURVEY APPLICATIONS OF PHOSPHOLIPIDS AND HYDROXY FATTY ACID CONTAINING PHOSPHOLIPIDS PRESENT INVESTIGATION MATERIALS AND METHODS Materials 172

6 xxvi Methods Enzyme Immobilization Separation of Methyl Ricinoleate from CME Isolation of Egg Phospholipid mixture and Isolation of PC from Egg Lecithin Isolation of Soya Phospholipid mixture and Isolation of PC From Soybean Lecithin General Procedure for Transesterification of Egg PC with Methyl ricinoleate General Procedure for Transesterification of Soy PC with Methyl ricinoleate Gas Chromatographic Analysis General Procedure for Tranesterification of Egg PL with Methyl ricinoleate General Procedure for Tranesterification of Soy PL with Methyl ricinoleate Enzymatic Hydrolysis of Egg Phosphatidyl choline to Determine Positional Distribution of Fatty Acids Enzymatic Hydrolysis of 1-Ricinoleoyl-2- acyl-sn-glycero-3-phospho choline to Determine Positional Distribution of Fatty Acids Emulsifying Power RESULTS AND DISCUSSION Incorporation of Ricinoleic Acid into Egg PC 181

7 xxvii Effect of Lipase Dosage Effect of Molar Ratio Effect of Reaction Period Incorporation of Ricinoleic Acid into Soy PC Effect of Lipase Dosage Effect of Molar Ratio Effect of Reaction Period Emulsification Power of Phospholipids and Modified Phospholipids Emulsifying Power CONCLUSIONS REFRENCES 193 List of Publications