Regulation of Vitamin E, a Nutritional Antioxidant

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1 The Virtual Free Radical School Regulation of Vitamin E, a Nutritional Antioxidant Maret G. Traber, Ph.D. Department of Nutrition & Food Management Linus Pauling Institute 571 Weniger Hall regon State University Corvallis, regon Fax: maret.traber Vitamin E xygen Society Education Program Traber 1

2 RRR-α-Tocopherol H H 2R 4 R 8 R d-α-tocopherol Vitamin E xygen Society Education Program Traber 2

3 Synthetic vitamin E: all rac-α-tocopherol H H H H RSR RRR H H H RRS H SRR H H SSR H H SRS H H RSS H H Vitamin E xygen Society Education Program Traber 3 SSS

4 Naturally ccurring Tocopherols α-tocopherol H 3 C phytyl tail H H 2R 4 R 8 R β-tocopherol phytyl tail γ-tocopherol H 3 C phytyl tail δ-tocopherol phytyl tail Vitamin E xygen Society Education Program Traber 4

5 Naturally ccurring Naturally ccurring Tocotrienols Tocotrienols unsaturated tail α-tocotrienol H 3 C β-tocotrienol tail γ-tocotrienol H 3 C tail δ-tocotrienol tail Vitamin E xygen Society Education Program Traber 5

6 Vitamin E Functions Specific role in a required metabolic function has not been found Major function appears to be as a fat- soluble, chain-breaking antioxidant Peroxyl radical scavenger Protects polyunsaturated fatty acids (PUFAs) within membranes and lipoproteins Vitamin E xygen Society Education Program Traber 6

7 Lipid Peroxidation R--H Lipid Hydroperoxide Initiating Event R Chain Reaction Carbon-centered Free Radical 2 Initiation Propagation = R-H H H R Peroxyl Radical Polyunsaturated fat Burton & Traber. Annu. Rev. Nutr. 10: ; 1990 Vitamin E xygen Society Education Program Traber 7

8 Vitamin E Chain Breaking Antioxidant R--H Initiating Event R Carbon-centered Free Radical 2 Initiation Lipid Hydroperoxide Chain Reaction Propagation = R-H H H Polyunsaturated fat R Peroxyl Radical R--H α TH α T Lipid Hydroperoxide Termination via Antioxidant Burton & Traber Annu. Rev. Nutr. 10: ; 1990 Vitamin E xygen Society Education Program Traber 8

9 Potential Cellular/Molecular Mechanisms of Vitamin E Endothelial cells Adhesion, N production, superoxide production Smooth muscle cells Proliferation Macrophages Adhesion, invasion, signaling recruitment, RS production Platelets Adhesion, aggregation, clotting Vitamin E xygen Society Education Program Traber 9

10 Vitamin E Biologic Activity in Humans Absorption & Chylomicron Catabolism All forms absorbed and transported to liver Lipoprotein Transport All lipoproteins transport vitamin E Liver Trafficking α-tocopherol specifically secreted into plasma Metabolism Vitamin E metabolites are NT oxidation products Brigelius-Flohe, R. and M.G. Traber. Faseb J. 13: , Vitamin E xygen Society Education Program Traber 10

11 Vitamin E Delivery to Tissues & Lipoproteins During Chylomicron Catabolism CIRCULATING LIPPRTEINS Intestine Vit. E HDL Circulation Vitamin E LPL CHYLMICRNS Fatty acids & vitamin E to tissues CHYLMICRN REMNANTS Tissue Vitamin E Uptake Vitamin E Vit. E Vitamin E Liver Uptake Traber, M.G Vitamin E. In Modern Nutrition in Health and Disease. M. E. Shils, J. A. lson, M. Shike, and A. C. Ross, eds. Williams & Wilkins. Baltimore Vitamin E xygen Society Education Program Traber 11

12 Preferential Secretion of α Tocopherol in VLDL and Its Delivery to Tissues Vitamin E CHYLMICRN REMNANTS Lipolysis LIVER RRRα T Preferential Secretion Vitamin E BILE α T α T VLDL LDL HDL Tissue Uptake Traber, M.G Vitamin E. In Modern Nutrition in Health and Disease. M. E. Shils, J. A. lson, M. Shike, and A. C. Ross, eds. Williams & Wilkins. Baltimore Vitamin E xygen Society Education Program Traber 12

13 Regulation of Liver Vitamin E lipoproteins Vit E Vit E Chylomicron Remnants { α tocopherol other vitamin E α tocopherol transfer protein Bile Plasma α tocopherol Kayden, H.J. and M.G. Traber. J. Lipid Res. 34: , Vitamin E xygen Society Education Program Traber 13

14 Vitamin E Deficiency in Humans Malabsorption Syndromes Abetalipoproteinemia Cholestatic Liver Disease Cystic Fibrosis Short Bowel Syndrome Total Parenteral Nutrition Genetic Abnormalities in α-tocopherol Transfer Protein Familial Isolated Vitamin E Deficiency (FIVE) Friedreich's Ataxia Variants (AVED) Traber, M.G Vitamin E. In Modern Nutrition in Health and Disease. M. E. Shils, J. A. lson, M. Shike, and A. C. Ross, eds. Williams & Wilkins. Baltimore. p Vitamin E xygen Society Education Program Traber 14

15 Clinical Features and Associated Neuromuscular Lesions in Human Vitamin E Deficiency Loss of Position and Vibratory Sensation Peripheral Nerve Posterior Columns Ataxia Cerebellum Spinocerebellar tracts Weakness Skeletal Muscle Traber, M.G Vitamin E. In Modern Nutrition in Health and Disease. M. E. Shils, J. A. lson, M. Shike, and A. C. Ross, eds. Williams & Wilkins. Baltimore. p Vitamin E xygen Society Education Program Traber 15

16 Plasma deuterated α-tocopherol concentrations in controls and subject with ataxia with vitamin E deficiency (AVED) 10 1 nmol/ml 0.1 [d 3 -SRR] [d 6 -RRR] CNTRLS AVED SUBJECT Time (hours) Traber, M.G. et al. J Clin Invest. 85: , Vitamin E xygen Society Education Program Traber 16

17 Vitamin E Definition Recommended intakes limited to the 2R 2 stereoisomer forms of α tocopherol RRR-α-tocopherol Half of the stereoisomers in all rac-α-tocopherol No other forms such as γ tocopherol or tocotrienols meet vitamin E requirement All forms of supplemental α tocopherol used to establish the UL(upper limit) Food and Nutrition Board and Institute of Medicine Dietary Reference Intakes for Vitamin C, Vitamin E, Selenium, and Carotenoids. National Academy Press. Washington, DC. Vitamin E xygen Society Education Program Traber 17

18 Estimated Average Requirement (EAR) and Recommended Daily Allowance (RDAs) for α-tocopherol (mg/day) Life Stage EAR RDA 19+ yrs, M yrs, F Pregnancy Lactation Food and Nutrition Board and Institute of Medicine Dietary Reference Intakes for Vitamin C, Vitamin E, Selenium, and Carotenoids. National Academy Press. Washington, DC. Vitamin E xygen Society Education Program Traber 18

19 Plasma α-tocopherol in Response Plasma 60 α-tocopherol µm 40 to Vitamin E Supplements all rac- RRR α-tocopherol (mg/day) 800 α-tocopherol (α -T) and α- tocopheryl acetate (α -TAC) from supplements: 1 IU RRR-α-TAC divided by 1.36 equals mg RRR-α -TAC 1 IU all rac α -TAc divided by 2 equals mg 2R-α-TAC 400 IU Vitamin E = 294 mg RRR-α-TAc or 268 mg RRR- α -T 200 mg 2R- -α TAc r 182 mg 2R- α -T Devaraj et al. Arterio Thromb Vasc Biol 17:2273, 1997 Vitamin E xygen Society Education Program Traber 19

20 Vitamin E Metabolites α-tocopherol metabolite, αcehc H 3 C CH 2,5,7,8-tetramethyl-2(2 -carboxy-ethyl)-6-hydroxychroman γ-tocopherol metabolite, H 3 C LLUα CH 2,7,8-trimethyl-2(2 -carboxy-ethyl)-6-hydroxychroman Schultz, M. et al. Am J. Clin. Nutr. 62: 1527S-1534S, Wechter, W.J. et al. Proc. Natl. Acad. Sci. USA. 93: , 1996.

21 Summary Vitamin E requirement in humans limited to α tocopherol Liver controls plasma vitamin E concentrations α TTP facilitates α tocopherol secretion into plasma Vitamin E deficiency results from genetic defects in α TTP Vitamin E metabolism may be important in regulating liver vitamin E Vitamin E xygen Society Education Program Traber 21

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