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Book Details
Abstract
Vitamin E was discovered in 1922 by Evans and Bishop as an essential micronutrient for reproduction in rats. The active substance was isolated in 1936 by Evans and was named tocopherol, although the tocopherols and tocotrienols are actually a group of eight isomeric molecules that are characterized by a chromanol ring structure and a side chain.
Providing an overview of the state-of-the-art of the chemistry of vitamin E, this book reflects the issues stemming from the complexity of the role and actions in vivo as well as in vitro. It summarizes information on the properties and function of vitamin E, the current understanding of the advantages and limitations of it, and also its application in promotion of health and prevention of diseases. Based on sound, solid scientific evidence, this is a timely addition to the literature as the centennial anniversary of the discovery of this important vitamin approaches.
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Vitamin E: Chemistry and Nutritional Benefits | i | ||
| Preface | v | ||
| Contents | vii | ||
| Chapter 1 - Vitamin E: Structure, Properties and Functions | 1 | ||
| 1.1 Introduction | 1 | ||
| 1.2 Homologues: Nomenclature and Structure | 2 | ||
| 1.3 Physicochemical Properties | 3 | ||
| 1.4 Sources | 4 | ||
| 1.5 Chemical Synthesis | 5 | ||
| 1.6 Analysis | 6 | ||
| 1.7 Functions and Applications | 6 | ||
| 1.8 Stability | 8 | ||
| References | 8 | ||
| Chapter 2 - Tocotrienols: From Bench to Bedside | 12 | ||
| 2.1 Introduction | 12 | ||
| 2.2 Physical and Chemical Properties | 13 | ||
| 2.3 Analysis Method | 15 | ||
| 2.4 Bioavailability | 17 | ||
| 2.4.1 Animals | 17 | ||
| 2.4.2 Humans | 19 | ||
| 2.5 Safety and Tolerance | 20 | ||
| 2.6 Nutritional Benefits | 22 | ||
| 2.6.1 Antioxidant | 22 | ||
| 2.6.2 Anti-aging | 23 | ||
| 2.6.3 Neuroprotection | 24 | ||
| 2.6.4 Anti-inflammation | 24 | ||
| 2.7 Research Gap | 25 | ||
| 2.8 Conclusion | 26 | ||
| References | 26 | ||
| Chapter 3 - The Behaviour of Vitamin E in Membranes | 32 | ||
| 3.1 Introduction | 32 | ||
| 3.2 Membrane Localization, Stabilization, and Fluidity | 33 | ||
| 3.2.1 Transverse Location of Vitamin E | 33 | ||
| 3.2.2 DMPC – The Exception | 34 | ||
| 3.2.3 Vitamin E Diffusion | 35 | ||
| 3.2.3.1 Lateral | 35 | ||
| 3.2.3.2 Transverse Diffusion | 37 | ||
| 3.2.4 Behavior of Non-α-tocopherols in Bilayers | 37 | ||
| 3.3 Tocopherol and Lipid “Rafts” | 38 | ||
| 3.4 The Effect on Membrane-dependent Processes | 41 | ||
| 3.4.1 Tocopherols | 41 | ||
| 3.4.2 Tocotrienols | 42 | ||
| 3.5 Tocol Quinones and Hydroquinones | 43 | ||
| 3.6 Conclusion | 45 | ||
| References | 45 | ||
| Chapter 4 - Chemical Reactivity and Cellular Uptake of Tocopherols and Tocotrienols | 51 | ||
| 4.1 Introduction | 51 | ||
| 4.2 Reactivities Toward Free Radicals | 52 | ||
| 4.3 Antioxidant Activities | 52 | ||
| 4.4 Action of T and T3 as Reductants | 54 | ||
| 4.5 Physical Effects of T and T3 on Membranes | 56 | ||
| 4.6 Incorporation of T3 and T into Membranes | 56 | ||
| 4.7 Cellular Uptake and Distribution of Tocopherols and Tocotrienols | 57 | ||
| 4.8 Cytoprotective Effects of Tocopherols and Tocotrienols | 59 | ||
| 4.9 Different Biological Action of Tocopherol Quinones | 61 | ||
| References | 62 | ||
| Chapter 5 - α-Tocopherol Transfer Protein | 64 | ||
| 5.1 Introduction | 64 | ||
| 5.2 Vitamin E Transport in the Body | 65 | ||
| 5.3 Substrate Specificity of α-TTP | 65 | ||
| 5.4 α-TTP in Vitamin E Homeostasis: Studies of Ataxia with Vitamin E Deficiency and Knockout Mice | 66 | ||
| 5.5 Expression of α-TTP in Extrahepatic Tissues | 67 | ||
| 5.6 Intracellular Vitamin E Transport by α-TTP | 69 | ||
| 5.7 Role of Phosphoinositides in the Vectorial Transport of α-Tocopherol by α-TTP | 69 | ||
| 5.8 Future Prospects | 71 | ||
| References | 72 | ||
| Chapter 6 - Tocopheryl Phosphate | 75 | ||
| 6.1 Introduction | 75 | ||
| 6.2 Synthesis, Extraction and Analysis of TP | 76 | ||
| 6.2.1 Chemical Synthesis of TP | 76 | ||
| 6.2.2 Extraction of TP | 76 | ||
| 6.2.3 Analyses of Samples Containing TP | 77 | ||
| 6.3 TP Hydrolysis | 77 | ||
| 6.4 Biochemical Studies of TP | 77 | ||
| 6.5 TP as Pro-vitamin E | 77 | ||
| 6.6 Biological Synthesis | 78 | ||
| 6.7 Absorption of TP | 78 | ||
| 6.8 Safety of TP | 79 | ||
| 6.9 Effect of TP on Proliferation | 79 | ||
| 6.10 Effect of TP on Gene Expression and Cell Surface Receptor Localization | 80 | ||
| 6.10.1 Effect of TP on CD36 | 80 | ||
| 6.10.2 Effect of TP on THP-1 Monocyte Gene Expression | 80 | ||
| 6.10.3 Effect of TP on NIH3T3-L1 Gene Expression | 81 | ||
| 6.10.4 Comparison Between α-Tocopherol and TP | 81 | ||
| 6.11 Mechanistic Interpretation of TP Action | 82 | ||
| 6.12 Some In Vivo Applications of TP | 83 | ||
| 6.12.1 Effects of TP on Atherosclerosis and Inflammation | 83 | ||
| 6.12.2 Brain Effects of TP | 84 | ||
| 6.12.3 Effect of TP on Tumors | 84 | ||
| 6.12.4 Vehicle for Transdermal Drug Delivery | 84 | ||
| 6.13 Conclusions | 85 | ||
| References | 85 | ||
| Chapter 7 - Novel Functions of Vitamin E Nicotinate | 88 | ||
| 7.1 Introduction | 88 | ||
| 7.2 Evidence for the Occurrence of Vitamin E Nicotinate in the Biological System | 89 | ||
| 7.3 Evidence for the Occurrence of Vitamin E Nicotinate Signaling | 93 | ||
| 7.4 Conclusions | 96 | ||
| References | 96 | ||
| Chapter 8 - Reactive Oxygen Species in Biological Systems | 98 | ||
| 8.1 Introduction | 98 | ||
| 8.2 Vitamin E | 99 | ||
| 8.3 Reactive Oxygen Species and Antioxidants | 100 | ||
| 8.4 Major Biological Oxidants | 102 | ||
| 8.4.1 Superoxide | 102 | ||
| 8.4.2 Hydrogen Peroxide | 105 | ||
| 8.4.3 Nitric Oxide and Peroxynitrite | 106 | ||
| 8.4.4 Hypohalous Acids | 107 | ||
| 8.4.5 Singlet Oxygen | 108 | ||
| 8.4.6 Free Radicals | 109 | ||
| 8.5 Compartmentalisation, Diffusion and Identification of Oxidant Targets | 110 | ||
| 8.6 Conclusions | 113 | ||
| Acknowledgements | 113 | ||
| References | 113 | ||
| Chapter 9 - Lipid Peroxidation: Role of Vitamin E | 118 | ||
| 9.1 Introduction | 118 | ||
| 9.2 Chemical Mechanism of Free Radical Lipid Peroxidation: Initiation, Propagation, Termination, and Inhibition by Antioxidants | 120 | ||
| 9.2.1 Initiation | 120 | ||
| 9.2.2 Propagation | 121 | ||
| 9.2.3 Termination | 122 | ||
| 9.2.4 Inhibition by Antioxidants | 122 | ||
| 9.3 Free Radical Oxidation of PUFAs: Roles of Vitamin E | 123 | ||
| 9.3.1 Free Radical Oxidation of Linoleic Acid | 123 | ||
| 9.3.2 Free Radical Oxidation of Arachidonic Acid | 125 | ||
| 9.4 Antioxidants and LPO: Vitamin E as an Antioxidant for LPO | 127 | ||
| 9.5 Summary and Future Perspectives | 128 | ||
| Acknowledgements | 129 | ||
| References | 129 | ||
| Chapter 10 - Antioxidant Defense Network and Vitamin E | 134 | ||
| 10.1 Introduction: Antioxidant Defense Network | 134 | ||
| 10.2 Role of Vitamin E in the Antioxidant Defense Network | 135 | ||
| 10.3 Factors that Determine the Antioxidant Efficacy of Vitamin E | 137 | ||
| 10.3.1 Chemical Reactivity toward Oxidants | 138 | ||
| 10.3.2 Fate of Antioxidant-derived Radicals | 141 | ||
| 10.3.3 Localization of Antioxidant and Oxidant | 142 | ||
| 10.3.4 Interaction Between Antioxidants | 143 | ||
| 10.3.5 Concentration and Mobility in the Environment | 144 | ||
| 10.3.6 Absorption, Distribution, Retention, Metabolism, and Excretion | 147 | ||
| References | 147 | ||
| Chapter 11 - Vitamin E Inspired Synthetic Antioxidants | 151 | ||
| 11.1 Introduction | 151 | ||
| 11.2 Influence of Simple Structural Modifications on the Antioxidant Activity of Vitamin E | 152 | ||
| 11.2.1 Manipulation of Stereoelectronic Effects to Alter the Reactivity of Tocopherol | 155 | ||
| 11.3 Vitamin-E-inspired Antioxidants Containing Chalcogens | 156 | ||
| 11.3.1 Sulfur-containing Compounds | 156 | ||
| 11.3.2 Selenium-containing Tocopherols | 157 | ||
| 11.3.3 Tellurium-containing Tocopherol Mimics | 158 | ||
| 11.4 Insertion of Nitrogen in the Aromatic Ring: from Phenols to 3-Pyridinols | 158 | ||
| 11.5 Activity in Biological Systems: The Role of the Lipophilic Tail | 160 | ||
| 11.6 Future Perspectives | 162 | ||
| References | 162 | ||
| Chapter 12 - Action of Vitamin E Against Lipid Peroxidation and Cell Death | 165 | ||
| 12.1 Introduction | 165 | ||
| 12.2 Inhibition of Lipid Peroxidation in Homogeneous Solution | 166 | ||
| 12.3 Inhibition of Lipid Peroxidation in Liposomal Membranes | 167 | ||
| 12.4 Inhibition of Lipid Peroxidation in Lipoproteins | 168 | ||
| 12.5 Inhibition of Cell Death by Vitamin E | 169 | ||
| 12.6 Conclusion | 172 | ||
| References | 172 | ||
| Chapter 13 - Oxidation Products of Vitamin E with Lipid-derived Free Radicals | 175 | ||
| 13.1 Introduction | 175 | ||
| 13.2 Oxidation Products of αTH with Lipid-derived Free Radicals | 177 | ||
| 13.2.1 Products of αTH during the Peroxidation of Unsaturated Lipids | 177 | ||
| 13.2.2 Products of αTH on the Secondary Process of Lipid Peroxidation in Micelles and Liposomes | 178 | ||
| 13.3 Oxidation Products of γTH | 179 | ||
| 13.3.1 Products of γTH During the Peroxidation of Unsaturated Lipids | 179 | ||
| 13.3.2 Iron-catalyzed Reaction of Methyl Linoleate Hydroperoxides with γTH in Aprotic and Protic Solvents | 181 | ||
| 13.3.3 Hemin- and Myoglobin-catalyzed Reaction of PLPC-OOH with γTH in Micelles and Liposomes | 183 | ||
| Acknowledgements | 185 | ||
| References | 185 | ||
| Chapter 14 - Metabolism of Vitamin E | 189 | ||
| 14.1 Introduction | 189 | ||
| 14.1.1 Basics | 189 | ||
| 14.1.2 Biosynthesis | 190 | ||
| 14.2 Metabolism | 191 | ||
| 14.2.1 History | 191 | ||
| 14.2.2 Side-chain Degradation | 193 | ||
| 14.2.3 Enzymes Catalyzing the ω-Oxidation for Side-chain Degradation | 195 | ||
| 14.2.3.1 Hints Supporting CYP3A4 as the Key Player Are | 197 | ||
| 14.2.3.2 Regulation of CYP3A4 Expression by Vitamin E Itself | 197 | ||
| 14.2.3.3 Hints Supporting CYP4F2 as the Key Player Are | 198 | ||
| 14.2.3.4 Regulation of CYP4F2 Expression by Vitamin E Itself | 199 | ||
| 14.2.3.5 Other CYPs | 199 | ||
| 14.3 Absorption, Distribution, Excretion | 200 | ||
| 14.3.1 Absorption | 200 | ||
| 14.3.2 Distribution and Retention of α-TOH | 201 | ||
| 14.3.3 Excretion | 202 | ||
| 14.4 Possible Adverse Effects | 202 | ||
| 14.5 Concluding Remarks | 203 | ||
| References | 204 | ||
| Chapter 15 - Analysis of Vitamin E Metabolites | 208 | ||
| 15.1 Vitamin E Metabolism | 208 | ||
| 15.1.1 Non-enzymatic Metabolites | 209 | ||
| 15.1.2 Enzymatic Metabolites | 211 | ||
| 15.2 Analysis of Vitamin E Metabolites | 214 | ||
| 15.2.1 Pre-analytical and Analytical Issues | 215 | ||
| 15.2.2 Deconjugation of Sulfated and Glucuronated Forms | 216 | ||
| 15.2.3 Sample Preparation | 217 | ||
| 15.2.4 Chromatographic Separation and Detection | 218 | ||
| 15.2.5 Levels of Vitamin E Metabolites in Human Blood | 221 | ||
| 15.3 Discussion | 223 | ||
| Acknowledgements | 224 | ||
| References | 224 | ||
| Chapter 16 - Essentiality, Bioavailability, and Health Benefits of α-Tocopherol Stereoisomers | 228 | ||
| 16.1 Introduction | 228 | ||
| 16.2 Structure and Function | 229 | ||
| 16.3 Intestinal and Hepatic Trafficking | 231 | ||
| 16.4 Vitamin E Requirements in Humans | 234 | ||
| 16.5 Cancer and Cardiovascular Health | 236 | ||
| 16.6 Infant and Maternal Health | 237 | ||
| 16.7 Conclusions | 239 | ||
| References | 239 | ||
| Chapter 17 - Vitamin E Deficiency and Inadequacy; Insights Using Zebrafish, Lipidomics and Metabolomics | 242 | ||
| 17.1 Introduction | 242 | ||
| 17.2 Is the Zebrafish Embryo an Appropriate Model for Human Embryogenesis | 243 | ||
| 17.3 Pregnancy, Embryogenesis and Neurodevelopment | 244 | ||
| 17.4 VitE, Polyunsaturated Fatty Acids (PUFAs) and Neurologic Function | 247 | ||
| 17.5 VitE, Anti-ferroptotic Agent | 249 | ||
| 17.6 Conclusion | 251 | ||
| References | 251 | ||
| Chapter 18 - Interference Effect of Vitamin E on Vitamin K Metabolism | 257 | ||
| 18.1 Introduction | 257 | ||
| 18.2 Effect of α-Tocopherol Intake on Vitamin K Concentration | 258 | ||
| 18.2.1 Effect of α-Tocopherol in Rats Fed a Diet Containing Phylloquinone with α-Tocopherol | 258 | ||
| 18.2.2 Effect of α-Tocopherol in Rats Administered Phylloquinone with α-Tocopherol | 259 | ||
| 18.2.3 Effect of α-Tocopherol in Rats Fed a Diet Containing Menaquinone-4 with α-Tocopherol | 259 | ||
| 18.2.4 Effect of α-Tocopherol in Rats Administered Menaquinone-7 with α-Tocopherol | 260 | ||
| 18.3 Effect of γ-Tocopherol Intake on Vitamin K Concentration | 260 | ||
| 18.4 Effect of Vitamin K Intake on Vitamin E Concentration | 261 | ||
| 18.5 Effect of Excess Intake of α-Tocopherol on Physiological Activity of Vitamin K | 262 | ||
| 18.6 Conclusion | 263 | ||
| Acknowledgements | 264 | ||
| References | 264 | ||
| Subject Index | 266 |