Vitamin E
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Table of contents
- Contentsvii
- Contributorsxvii
- Prefacexxi
- Chapter 1: Vitamin E1
- I. Introduction2
- II. Vitamin E Structures and Function3
- III. Absorption, Transport, and Distribution to Tissues4
- A. Vitamin E Absorption4
- B. Requirement for Dietary Fat for Absorption4
- C. Requirement for Chylomicron Synthesis5
- D. Role of Exchange Proteins5
- E. Secretion of alpha-Tocopherol by the Liver6
- IV. The alpha-Tocopherol Transfer Protein6
- A. Structure and Localization6
- B. CRAL-TRIO Family7
- V. Regulation of Vitamin E Metabolism and Excretion8
- A. What Is CEHC?8
- B. Metabolism of Vitamin E9
- C. Conjugation of CEHCs12
- D. Biliary Excretion of alpha-Tocopherol13
- E. Implications of Altered Xenobiotic Metabolism13
- VI. Implications for Humans Supplementing with Vitamin E14
- VII. Conclusion16
- Acknowledgments16
- References16
- Chapter 2: Structure and Function of alpha-Tocopherol Transfer Protein: Implications for Vitamin E M23
- I. Introduction24
- II. Structure of alpha-TTP29
- A. Crystallization29
- B. Overall Fold29
- C. Ligand Binding by alpha-TTP30
- D. An Open Conformation of alpha-TTP32
- III. Mutations Associated with AVED34
- A. Structural Considerations34
- B. Biochemical Characterization of AVED-Associated Mutants38
- IV. Summary39
- References40
- Chapter 3: The alpha-Tocopherol Transfer Protein45
- I. Introduction46
- II. Identification of TTP47
- III. TTP and Vitamin E Status: Ataxia with Vitamin E Deficiency48
- IV. TTP and Vitamin E Status: TTP-/- Mice51
- V. Biochemical Activities of TTP51
- A. Specific, High-Affinity Binding of RRR-alpha-TOH52
- B. Facilitation of Ligand Transfer Between Lipid Vesicles53
- VI. Physiological Activities of TTP53
- VII. Three-Dimensional Structure of TTP56
- VIII. Selective Retention of RRR-alpha-TOH and the Evolutionary Origins of TTP58
- IX. Epilogue60
- References60
- Chapter 4: Molecular Associations of Vitamin E67
- I. Introduction68
- II. Physical Properties of Vitamin E70
- III. Interaction of Vitamin E with Lipids in Monolayers70
- IV. Interaction of Vitamin E with Phospholipid Bilayer Membranes73
- V. Distribution and Orientation of Vitamin E in Phospholipid Membranes74
- VI. Motion of Vitamin E in Lipid Assemblies76
- VII. Effect of Vitamin E on Phospholipid Phase Behavior77
- VIII. Effect of Vitamin E on the Structure of Phospholipid Model Membranes79
- IX. Phase Separation of Vitamin E in Phospholipid Mixtures85
- X. Effect of Vitamin E on Membrane Permeability88
- XI. Effect of Vitamin E on Membrane Stability89
- XII. Domains Enriched in Vitamin E in Membranes91
- XIII. Effect of Vitamin E on Membrane Protein Function92
- XIV. Conclusions93
- References93
- Chapter 5: Studies in Vitamin E: Biochemistry and Molecular Biology of Tocopherol Quinones99
- I. Introduction100
- II. Redox Cycling and Arylating Properties of Tocopherol Quinones103
- A. Redox Cycling103
- B. Arylation104
- III. Identification and Analysis of Tocopherols, Quinones, and Adducts108
- A. Tocopherols and Their Quinones108
- B. Thiol Nucleophile Adducts109
- IV. Arylating Tocopherol Quinones and the Unfolded Protein Response111
- V. Tocopherol Quinones and.Mutagenesis112
- VI. Specificity of Phenolic Antioxidant Precursors in Tocopherol Biology113
- A. The alpha-T Story113
- B. The Multifaceted Effects of gamma-T and gamma-CEHC115
- C. Similarities and Differences Between Tocopherols and Tocotrienols118
- VII. Natural Abundance of Tocopherols and Its Effects on Biology118
- A. Plant Sources and the Origins of the Mediterranean and Modern Diets118
- B. The Breast Milk/Infant Formula Conundrum120
- C. Generation of Arylating Tocopherol Quinones in Vegetable Cooking Oils121
- Acknowledgments122
- References122
- Chapter 6: Vitamin E and NF-kappaB Activation: A Review135
- I. Introduction136
- II. Nuclear Factor-kappaB137
- III. In Vitro Studies138
- A. Immune System139
- B. Cardiovascular140
- C. Neural140
- D. Liver141
- E. Epithelial Cells141
- F. Fibroblasts141
- G. Other142
- IV. In Vivo Studies142
- V. Mechanisms by Which Vitamin E May Inhibit NF-kappa B Activation143
- VI. Is the Inhibition of NF-kappaB Activation Necessary for Some of the Activities of Vitamin E?145
- VII. Summary145
- References145
- Chapter 7: Synthesis of Vitamin E155
- I. Introduction156
- II. Synthesis of (All-rac)-alpha-Tocopherol156
- A. Building Blocks for the Aryl Containing Chroman Moiety158
- B. Side Chain Building Blocks158
- C. Synthesis of (all-rac)-alpha-Tocopherol161
- III. Preparation of Optically Active Tocopherols165
- A. Synthesis of Chiral Chroman Compounds167
- B. Synthesis of Chiral Side Chain Components173
- C. Synthesis of (R,R,R)-Tocopherols177
- D. Synthesis of Stereoisomers and Homologues Other Than (R,R,R)-alpha-Tocopherol184
- IV. Synthesis of Tocotrienols188
- References194
- Chapter 8: Tocotrienols: The Emerging Face of Natural Vitamin E203
- I. Historical Developments and the Vitamin E Family204
- II. Biosynthesis of Tocopherols and Tocotrienols206
- III. Changing Trends in Vitamin E Research208
- IV. Unique Biological Functions of Tocotrienols210
- V. Natural Sources of Tocotrienols212
- VI. Bioavailability of Oral Tocotrienols213
- VII. Biological Functions217
- A. Neuroprotection229
- B. Anticancer234
- C. Cholesterol Lowering244
- VIII. Conclusion247
- Acknowledgments248
- References248
- Chapter 9: Vitamin E Biotransformation in Humans263
- I. Introduction264
- II. The Fate of Vitamin E from Ingestion to Excretion264
- III. Biotransformation and Metabolism of Vitamin E as Bioactivation Processes266
- Acknowledgments277
- References277
- Chapter 10: alpha-Tocopherol Stereoisomers281
- I. Introduction283
- II. Sources of Tocopherol, Nomenclature, and Bioactivity284
- A. Presence in Food/Feed Ingredients284
- B. Nomenclature284
- C. Bioactivity and Bioavailability285
- III. Analytical Methods for Separation of alpha-Tocopherol Stereoisomers288
- A. GC and LC Methods289
- B. Deuterium-Labeling and Mass Spectrometry291
- IV. Bioavailability and Secretion into Milk293
- A. Rats293
- B. Pigs296
- C. Humans299
- D. Mink301
- E. Poultry301
- F. Ruminants302
- V. alpha-Tocopherol-Binding Protein (alpha-TTP)303
- VI. Conclusions305
- References305
- Chapter 11: Addition Products of alpha-Tocopherol with Lipid-Derived Free Radicals309
- I. Introduction310
- II. Addition Products of alpha-Tocopherol with Methyl Linoleate-Derived Free Radicals311
- III. Addition Products of alpha-Tocopherol with PC-Peroxyl Radicals in Liposomes314
- IV. Addition Products of alpha-Tocopherol with CE-Peroxyl Radicals317
- V. Detection of the Addition Products of alpha-Tocopherol with Lipid-Peroxyl Radicals in Biological318
- References324
- Chapter 12: Vitamin E and Apoptosis329
- I. Introduction330
- II. Vitamin E and Vitamin E Derivatives331
- A. Natural Isoforms331
- B. Synthetic Dervivatives333
- III. Vitamin E Antioxidant Potency334
- IV. Vitamin E as an Anticancer Agent336
- A. Natural Forms336
- B. Synthetic Derivatives338
- V. Apoptosis339
- VI. Vitamin E Suppression of Apoptosis341
- VII. Vitamin E-Induced Apoptosis342
- A. Natural Forms342
- B. Synthetic Derivatives346
- VIII. Conclusion348
- References348
- Chapter 13: Vitamin E During Pre- and Postnatal Periods357
- I. Introduction358
- II. Prenatal Transfer of Vitamin E359
- A. Biochemical Aspects of the Transfer359
- B. Maternal Vitamin E Levels Increase During Pregnancy361
- C. Vitamin E Reserves of Fetuses and Newborns362
- III. Postnatal Transfer of Vitamin E364
- A. Mammary Gland Uptake364
- B. Milk Vitamin E and the Effect of Suckling on Vitamin E Status of Newborns365
- IV. Vitamin E in Critical Situations366
- A. Preterm Infants: More at Risk for a Vitamin E Deficiency366
- B. Vitamin E and Preeclampsia367
- References368
- Chapter 14: alpha-Tocopherol: A Multifaceted Molecule in Plants375
- I. Introduction376
- II. Occurrence and Antioxidant Function of alpha-Tocopherol in Plants377
- III. Photoprotective Function of alpha-Tocopherol in Plants380
- IV. alpha-Tocopherol and the Stability of Photosynthetic Membranes383
- V. Role of alpha-Tocopherol in Cellular Signaling383
- VI. Have the Functions of Tocopherols Been Evolutionary Conserved?385
- VII. Future Perspectives387
- References387
- Chapter 15: Vitamin E and Mast Cells393
- I. Introduction394
- A. Mast Cells394
- B. Vitamin E395
- II. Cellular Effects of Vitamin E in Mast Cells397
- A. Inhibition of Proliferation and Survival of Mast Cells by Vitamin E397
- B. Possible Molecular Targets for Vitamin E in Mast Cells399
- C. Mast Cell Degranulation and Vitamin E403
- III. Preventive Effects of Vitamin E on Diseases with Mast Cell Involvement406
- A. Vitamin E, Mast Cells, and Asthma406
- B. Vitamin E, Mast Cells, and Skin Diseases407
- C. Vitamin E, Mast Cells, and Atherosclerosis408
- IV. Summary409
- References410
- Chapter 16: Tocotrienols in Cardioprotection419
- I. Introduction420
- II. A Brief History of Vitamin420
- III. Vitamin E, Now and Then421
- IV. Tocotrienols versus Tocopherols423
- V. Sources of Tocotrienols426
- VI. Tocotrienols in Free Radical Scavenging and Antioxidant Activity426
- VII. Tocotrienols and Cardioprotection427
- VIII. Atherosclerosis427
- IX. Tocotrienols in Ischemic Heart Disease429
- X. Summary and Conclusion430
- Acknowledgments430
- References430
- Chapter 17: Vitamin E and Cancer435
- I. Basic Information About Vitamin E436
- A. How Many Vitamin Es Are There?436
- B. Why It Is so Important That the Form of Vitamin E Be Identified Properly?438
- C. Why Is RRR-alpha-Tocopherol the Most Bioavailable Form of Vitamin E?439
- D. Challenges for In Vivo Testing of Vitamin E Forms Other Than RRR-alpha-Tocopherol440
- II. Intervention Trials441
- A. What Have We Learned About Vitamin E and Cancer from Human Intervention Trials?441
- B. Conclusions443
- III. Preclinical Studies443
- A. Lack of Evidence for Anticancer Effects by RRR-alpha-Tocopherol or All-rac-alphaTocopherol443
- B. Evidence for Anticancer Effects of gamma-Tocopherol444
- C. Evidence for Anticancer Effects of Vitamin E Metabolites444
- D. Tocotrienols as Potential Anticancer Agents445
- E. Vitamin E Analogues as Potential Anticancer Agents445
- IV. Anticancer Mechanisms of Action of Vitamin E-Based Compounds446
- V. What About Vitamin E Supplementation and Cancer Survivorship?453
- VI. Conclusions453
- Acknowledgments454
- References454
- Chapter 18: Vitamin E Analogues and Immune Response in Cancer Treatment463
- I. Introduction464
- II. Vitamin E Analogues as Anticancer Agents466
- A. Vitamin E Analogues: Their Structure and Biological Activity466
- B. Initiation of Apoptotic Pathway by Mitochondria Destabilization468
- C. Deregulation of Signaling Pathways by Vitamin E Analogues470
- III. Vitamin E Analogues as Adjuvants in Cancer Chemotherapy473
- IV. Immunological Inducers of Apoptosis: Mechanisms and Clinical Application in Cancer473
- A. Death Receptor Signaling Pathway473
- B. CD95 Activation475
- C. Trail: A Promising Cancer Therapeutic475
- D. Factors Influencing Trail Sensitivity476
- E. Effect of Vitamin E Analogues on the Regulation of Death Receptors: Relevance for Cancer Therapy477
- V. Targeting Immune Surveillance481
- A. Immune Surveillance Against Tumor Development481
- B. Vitamin E Analogues as Adjuvants in Tumor Vaccination482
- VI. Conclusions483
- References483
- Chapter 19: The Roles of alpha-Vitamin E and Its Analogues in Prostate Cancer493
- I. Introduction494
- II. Family Members, Source, and Proper Supplemental Dose of Vitamin E495
- III. General Physiological Function of Vitamin E496
- IV. Vitamin E Absorption and Transport497
- V. alpha-Vitamin E-Binding Proteins498
- A. alpha-Tocopherol Transfer Protein499
- B. alpha-Tocopherol-Associated Protein499
- C. alpha-Tocopherol-Binding Protein500
- D. Other Vitamin E Transport Proteins500
- VI. Vitamin E and Diseases501
- VII. alpha-Vitamin E Function in Prostate Cancer: Clinical Studies501
- VIII. alpha-Vitamin E Function in Prostate Cancer: Animal Studies506
- IX. alpha-Vitamin E in Prostate Cancer: Molecular Mechanism Studies in Cancer Cells507
- A. Cellular Bioavailability of alpha-Vitamin and Ves507
- B. Cell Cycle Arrest and DNA Synthesis Arrest507
- C. Apoptosis508
- D. Signal Pathway509
- E. Invasion, Metastasis, and Angiogenesis510
- X. Summary and Perspectives510
- References512
- Chapter 20: Vitamin E: Inflammation and Atherosclerosis519
- I. Introduction520
- II. Inflammation and Atherosclerosis521
- III. Vitamin E522
- A. Chemical Form and Absorption522
- IV. Animal Studies523
- A. Other Forms of alpha-T and Their Significance524
- B. alpha-T Supplementation in Humans525
- C. Molecular and Cellular Effects of alpha-T529
- V. Intervention Studies530
- VI. Other Forms of Vitamin E531
- A. gamma-Tocopherol531
- B. Absorption and Availability531
- C. gamma-T and Antiinflammatory Effects532
- D. gamma-T and Other Beneficial Effects532
- E. gamma-Tocopherols and Cardiovascular Disease533
- F. gamma-T Supplementation in Humans535
- VII. Tocotrienols536
- VIII. Hypocholesterolemic Effect537
- IX. Antiinflammatory Effects541
- X. Antioxidant Effect541
- XI. Mechanism of Action and Future Direction542
- XII. Conclusion542
- References543
- Chapter 21: Vitamin E in Chronic Liver Diseases and Liver Fibrosis551
- I. Fibrosis in Chronic Liver Diseases552
- II. Oxidative Stress, Chronic Liver Disease, and Liver Fibrosis554
- A. Oxidative Stress in Alcohol-Induced Liver Damage555
- B. Oxidative Stress in Iron-Induced Liver Damage556
- C. Oxidative Stress and Vitamin E in Autoimmune Hepatitis558
- D. Oxidative Stress and Vitamin E in Cholestatic Liver Diseases558
- E. Oxidative Stress in HCV-Related Liver Disease560
- F. Oxidative Stress and Vitamin E in HBV-Related Liver Disease563
- G. Oxidative Stress and Vitamin E in Liver Cirrhosis and Hepatocellular Carcinoma564
- H. Oxidative Stress in Nonalcoholic Fatty Liver Disease565
- References567
- Index575
First published in 1943, Vitamins and Hormones is the longest-running serial published by Academic Press. In the early days of the serial, the subjects of vitamins and hormones were quite distinct. The Editorial Board now reflects expertise in the field of hormone action, vitamin action, X-ray crystal structure, physiology, and enzyme mechanisms. Under the capable and qualified editorial leadership of Dr. Gerald Litwack, Vitamins and Hormones continues to publish cutting-edge reviews of interest to endocrinologists, biochemists, nutritionists, pharmacologists, cell biologists, and molecular biologists. Others interested in the structure and function of biologically active molecules like hormones and vitamins will, as always, turn to this series for comprehensive reviews by leading contributors to this and related disciplines.