لایب سان

Author(s): Niki, Etsuo

Publisher: Book Network Int'l Limited trading as NBN International (NBNi), Year: 2019

ISBN: 978-1-78801-240-9,1788012402,978-1-78801-621-6,978-1-78801-733-6

viiv i 1v.Introduc2viHmldr mvgm1vemgscorov: Naa Srdgtrmv3Pv.Introducvgm1v:Hdurdr mgsvhnmnydo 31rdn1vpcv3doH v:r4r 5vCInv6 cgsvA lrndcv 7v.IntroducvF8ab RHpsroIn1vpcvdInv6 cgsvA lrndcv 7v.Introduc2vfffNuolN uM Contents Chapter 1 Vitamin E: Structure, Properties and Functions 1 Etsuo Niki and Kouichi Abe 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 Ju-Yen Fu, Geetha Maniam, Fu-Shun Wong, Doryn Meam-Yee Tan, Puvaneswari Meganathan and Lay-Hong Chuah 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 20Published on 04 February 2019 on https://pubs.rsc.org | doi:10.1039/9781788016216-FP007 Contentsviii 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 J. Atkinson, D. Marquardt and T. Harroun 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 3.2.4 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 Yoshiro Saito and Yasukazu Yoshida 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 62Published on 04 February 2019 on https://pubs.rsc.org | doi:10.1039/9781788016216-FP007View Online ixContents Chapter 5 α-Tocopherol Transfer Protein 64 Nozomu Kono and Hiroyuki Arai 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 Angelo Azzi 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 85Published on 04 February 2019 on https://pubs.rsc.org | doi:10.1039/9781788016216-FP007View Online Contentsx Chapter 7 Novel Functions of Vitamin E Nicotinate 88 Y. J. Suzuki, L. Marcocci, K. R. Duncan, D. I. Suzuki and N. V. Shults 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 Christine C. Winterbourn 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 Shanshan Zhong and Huiyong Yin 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 125Published on 04 February 2019 on https://pubs.rsc.org | doi:10.1039/9781788016216-FP007View Online xiContents 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 Etsuo Niki 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 Luca Valgimigli and Riccardo Amorati 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 162Published on 04 February 2019 on https://pubs.rsc.org | doi:10.1039/9781788016216-FP007View Online Contentsxii Chapter 12 Action of Vitamin E Against Lipid Peroxidation and Cell Death 165 Noriko Noguchi 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 Ryo Yamauchi 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 Regina Brigelius-Flohé 14.1 Introduction 189 14.1.1 Basics 189 14.1.2 Biosynthesis 190Published on 04 February 2019 on https://pubs.rsc.org | doi:10.1039/9781788016216-FP007View Online xiiiContents 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 14.3 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 Pierangelo Torquato, Danilo Giusepponi, Roberta Galarini, Desirée Bartolini, Marta Piroddi and Francesco Galli 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 Richard S. Bruno 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 239Published on 04 February 2019 on https://pubs.rsc.org | doi:10.1039/9781788016216-FP007View Online Contentsxiv Chapter 17 Vitamin E Deficiency and Inadequacy; Insights Using Zebrafish, Lipidomics and Metabolomics 242 Maret G. Traber 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 Saiko Ikeda 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

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