DOI QR코드

DOI QR Code

Vitamin E: α-Tocopherol and the Other Forms of Vitamin E

비타민 E: α-토코페롤 대 그외 비타민 E

  • Cho, Sung-Hee (Department of Food Science and Nutrition, Catholic University of Daegu)
  • 조성희 (대구가톨릭대학교 식품영양학과)
  • Received : 2010.06.07
  • Published : 2010.06.30

Abstract

Vitamin E has been a generic term for all tocopherol and tocotrienol derivatives. The most active form of vitamin E isoforms in vivo is regarded to be $\alpha$-tocopherol which is the only form defined as vitamin E in the US Food and Nutrition Board, causing controversy over setting dietary reference intake (DRI) of vitamin E. However, most of the countries other than the US maintain the original concept that all isoforms are accepted as vitamin E but with different biopotency. The roles of the isoforms of vitamin E other than $\alpha$-tocopherol have received continuous attention. Among them those of $\gamma$-tocopherol and $\alpha$-tocotrienol have been most studied in comparison with $\alpha$-tocopherol, since $\gamma$-tocopherol comprises major form of vitamin E in many plant seeds and those of the both vitamin E have been implicated in unique physiological functions. This review summarizes findings that have led a better understanding of vitamin E absorption, transport, tissue storage and various functions common and specific to vitamin E isoforms focusing $\alpha$- and $\gamma$-tocopherol as well as tocotrienols. It is expected to help redefining vitamin E and setting its DRI for Koreans.

References

  1. Combs GF Jr. Vitamin E. In: The Vitamins, Fundamental Aspects in Nutrition and Health. New York: Academic Press ; 1998. p.189-223
  2. Hu JN, Zhu XM, Adhikari P, Li D, Kim IH, Lee KT. Determination of tocopherol contents in refined edible oils using HPLC method. J Food Sci Nutr 2009; 14(3): 260-264 https://doi.org/10.3746/jfn.2009.14.3.260
  3. Korea Health Industry Development Institute. Development of Nutrient Database -2. Vitamin Composition of Foods - ; 2002
  4. Food and Nutrition Board, Institute of Medicine. Dietary Reference Intakes for Vitamin C, Vitamin E, Selenium, and Carotenoids. Washington, DC: National Academies Press; 2000
  5. Dillard CJ, Gavino VC, Tappel AL. Relative Antioxidant effectiveness of $\alpha$-tocopherol and $\delta$-tocopherol in iron-loaded rats. J Nutr 1983; 113(11): 2266-2273
  6. Jeanes YM, Hall WL, Ellard S, Lee E, Lodge JK. The absorption of vitamin E is influenced by the amount of fat in a meal and the food matrix. Br J Nutr 2004; 92(4): 575-579 https://doi.org/10.1079/BJN20041249
  7. Bruno RS, Leonard SW, Park S, Zhao Y, Traber MG. Human vitamin E requirements assessed with the use of apple fortified with deuterium-labeled $\alpha$-tocopheryl acetate. Am J Clin Nutr 2006; 83 (2): 299-304
  8. Leonard SW, Good CK, Gugger ET, Traber MG. Vitamin E bioavailability from fortified breakfast cereals greater than that from encapsulated supplements. Am J Clin Nutr 2004; 79(1): 86-92
  9. Roxbrough HE, Burton GW, Kelly FJ. Inter- and itra-invdividual variation in plasma and red blood cell vitamin E after supplementation. Free Radic Res 2000; 33: 437-446 https://doi.org/10.1080/10715760000300971
  10. Reboul E, Klein A, Bietrix F, Gleize B, Malezet-Desmooulins C, Schnerider M, Margotat A, Lagrost L, Collet X, Borel P. Scavenger receptor class B type I (SR-BI) is involved in vitamin E transport across the enterocyte. J Biol Chem 2006; 281(8): 4739-4745
  11. Anwar K, Kayden HJ, Hussain MM. Transport of vitamin E by differentiated Caco-2 cells. J Lipid Res 2006; 47: 1261-1273 https://doi.org/10.1194/jlr.M500523-JLR200
  12. Traber MG, Olivecrona T, Kayden HJ. Bovine milk lipoprotein lipase trnasfers tocopherol to human fibroblasts during triglyceride hydrolysis in vitro. J Clin Invest 1985; 75: 1729-1734 https://doi.org/10.1172/JCI111883
  13. Traber MG. vitamin E: In Shils ME, Olson JA, Shike M, Ross AC eds. Modern Nutrition in Health and Disease, 9th edition. Baltimore, MD: Williams & Wilkins; 1999. p.347-362.
  14. Sato Y, Hagiwarsa K, arai H, Inoue K. Purification and characterization of the alpha-tocopherol transfer from the rat liver. FEBS Lett 1991; 288(1): 41-45. https://doi.org/10.1016/0014-5793(91)80999-J
  15. Traber MG, Rudel LL, Burton GW, Hughes L, Ingold KU, Kayden HJ. Nascent VLDL from liver perfusions of cynomolgus monkys are preferentially enriched in RRR-compared with SRR-alpha tocopherol: Studies using deuterated tocopherols. J Lipid Res 1990; 31(4): 687-694
  16. Panagabko C, Morley S, Hernandez M, Cassolato P, Gordon H, Manor D, Atkinson J. Ligand specificity in the CRAL-TRIO protein family. Biochemistry 2003; 42(21): 6467-6474 https://doi.org/10.1021/bi034086v
  17. Dutta-Roy AK. Leishman DJ, Gordon MJ, Campbell FM, Duthie GG. Identification of a low molecular mass (14.2 kDa) alpha-tocopherol- binding protein in the cytosol of rat liver an heart. Biochem Biophy Res Commun 1993; 196(3): 1108-1112 https://doi.org/10.1006/bbrc.1993.2365
  18. Taber MG, Kayden HJ. Vitamin E is delivered to cells via high affinity receptor for low density lipoprotein. Am J Clin Nutr 1984; 40: 747-751
  19. Cohn W, Goss-Sampson MA, Grun H, Muller DP. Plasma clearance and net uptake of alpha-tocopherol an dlow-density lipoprotein by tissues in WHHL and control rabbits. Biochem J 1992; 287: 247-254
  20. Mardones P, Strobel P, Miranda S, Leighton F, Quinones V, Amigo L, Rozowski J, Rigotti A. Alpha-tocopherl metabolism in abnormal in scavenger receptor class B type I (SR-BI)-deficient mice. J Nutr 2002; 132: 443-449
  21. Rigotti A, Miettinen HE, Krieger M. The role of the high-density lipoprotein receptor SR-BI in lipid metabolism of endocrine and other tissues. Endocr Rev 2003; 24: 357-387 https://doi.org/10.1210/er.2001-0037
  22. Handelman GJ, Epstein JP, Spiegelman D, Machlin LJ, Dratz EA Human adipose alpha-tocopherol and gamma-tocopherol kinetics during and after 1 y of alpha-tocopherol supplementation. Am J Clin Nutr 1994; 59(3): 1025-1032
  23. El-Sohemy A. Baylin A, Ascherio A, Kabagambe E, Spiegelman D, Campos H. Population-based study of alpha- and gamma-tocopherol in plasma and adipose tissue as biomarkers of intake in Costa Rican adults. Am J Clin Nutr 2001; 74(3): 356-363
  24. Brigelius-Flohé R, Traber MG. Vitamin E: function and metabolism. FASEB J 1999; 13(10): 1145-1155
  25. Zempleni J, Rucker RB, McCormick DB, Suttie JW. eds Vitamin E (Traber MG) in 'Handbook of Vitamins' 4th ed ; 2007. p.153-174
  26. Yano T, Yajima S, Hagiwara K, Kumadaki I, Yano Y, Otani S, Uchida M, Ichikawa T. Vitamin E inhibits cell proliferation and the activation of extracellular signal-regulated kinase during the promotion phase of lung tumorigenesis irrespective of antioxidative effect. Carcinogenesis 2000; 21(11): 2129-2133. https://doi.org/10.1093/carcin/21.11.2129
  27. Korea Centers for Disease Control and Prevention. The third Korea National Health and Nutrition Examination Survey (KNHANES III); 2005
  28. Hosomi A, Arits M, Sato Y, Kiyose G, Ueda T, Iragashi O, Arai H, Inuoe K. Affinity for alpha-tocopherol transfer protein as a determinant of the biological activities of vitamin E analogs. FEBS Lett 1997; 409(1): 105-108 https://doi.org/10.1016/S0014-5793(97)00499-7
  29. Burton GW, Traber MG, Acuff RV, Walters DN, Kayden H, Hughes L, Ingold KU. Human plasma and tissue $\alpha$-tocopherol concentrations in response to supplementation with deuterated natural and synthetic vitamin E. Am J Clin Nutr 1998; 67: 669-684
  30. Bieri JG, Evarts RP. Gamma tocopherol: metabolism, biological activity and significance in human vitamin E nutrition. Am J Clin Nutr 1974; 27(9): 980-986
  31. Weber C, Podda M, Rallis M, Thiele JJ, Traber MG, Packer L. Efficacy of topically applied tocopherols and tocotrienols in protection of murine skin from oxidative damage induced by UVirradiation. Free Radic Biol Med 1997; 22: 761-769 https://doi.org/10.1016/S0891-5849(96)00346-2
  32. Handelman GJ, Machlin LJ, Fitch K, Weiter JJ, Dratz EA. Oral $\alpha$-tocopherol supplements decrease plasma $\gamma$-tocopherol levels in humans. J Nutr 1985; 115(6): 807-813
  33. Kiyose C, Saito H, Kaneko K, Hamamura K, Tomioka M, Ueda T, Igarashi O.$\alpha$-Tocopherol affects the urinary and biliary excretion of 2,7,8-trimethyl-2(2'-carboxyethly)-6-hydroxychroman, gamma-tocopherol metabolites in rats. Lipids 2001; 36(5): 467- 472 https://doi.org/10.1007/s11745-001-0744-2
  34. Leonard SW, Paterson E, Atkinson JK. Ramakrishnan R, Cross CE, Traber MG. Studies in humans using deuterium-labeled $\alpha$- and $\gamma$-tocopherol demonstrate faster γ-tocopherol disappearance and greater $\gamma$-metabolite production. Free Radic Biol Med 2005; 38(7): 857-866 https://doi.org/10.1016/j.freeradbiomed.2004.12.001
  35. Cooney RV, Franke AA, Harwood PJ, Hatch-Pigott V, Custer LJ, Mordan LJ. $\gamma$-tocopherol detoxification of nitrogen dioxide: superiority to $\alpha$-tocopherol. Proc Natl Acad Sci USA 1993; 90: 1771- 1775 https://doi.org/10.1073/pnas.90.5.1771
  36. Goss SP, Hogg N, Kalyanaraman B. The effect of on nitration of $\gamma$-tocopherol by peroxynitrite. Arch Biochem Biophys 1999; 363: 333-340 https://doi.org/10.1006/abbi.1998.1094
  37. Jiang Q, Elson-Schwab I, Courtemanche C, Ames BN. $\gamma$-tocopherol and its major metabolite, in contrast to $\alpha$-tocopherol, inhibits cyclooxigenase activitiy in macrophages and epithelial cells. Proc Natl Acad Acid USA 2000; 97: 11494-11499 https://doi.org/10.1073/pnas.200357097
  38. Saldeen T, Li D, Mehta JL. Differential effects of$\alpha$- and $\gamma$-tocopherol on low-density lipoprotein oxidation, superoxide activity, pletelet aggregation and arterial thrombogenesis. J Am Coll Cardiol 1999; 34; 1208-1215 https://doi.org/10.1016/S0735-1097(99)00333-2
  39. Liu M, Wallmon A, Olsson-Mortiock C, Wallin R, Sadeen T. Mixed tocopherols inhibit platelet aggregation in humans: potential mechanisms. Am J Clin Nutr 2003; 77: 700-706
  40. Ohrvall M, Sundolf G, Vessby B. Gamma, but not alpha, tocopherol levels in serum are reduced in coronary heart disease patients. J Intern Med 1996; 239: 111-117 https://doi.org/10.1046/j.1365-2796.1996.410753000.x
  41. Kristenson M, Zieden B, Kucinskiene Z. antioxidant status ad mortality from coronary heart disease in Lithuaniann and Swedish men aged 50. BMJ 1997; 314: 629-633
  42. Kushi LH, Folsom AR, Prineas R, Mink PJ, Wu Y, Bostick RM. Dietary antioxidant vitamins and death from coronary heart disease in postmenopausal women. N Eng J Med 1996; 334: 156-162.
  43. Huang HY, Alberg AJ, Norkus E. prospective study of antioxidant micronutrients in the blood and the risk of developing prostate cancer. Am J Epidemiol 2003; 157: 335-344 https://doi.org/10.1093/aje/kwf210
  44. Helzlsouer KJ, Huang HY, Alberg AJ, Hoffman S, Burke A, Norkus EP, Morris JS, Comstock GW. Association between alpha-tocopherol, gamma-tocopherol, selenium, and subsequent prostate cancer. J Natl Cancer Inst 2000; 92(24): 2018-2023. https://doi.org/10.1093/jnci/92.24.2018
  45. Mahabir S, Schendel K, Dong YQ, Barrera SL, Spitz MR, Forman MR. Dietary alpha-, beta-, gamma- and delta-tocopherols in lung cancer risk. Int J Cancer 2008; 123(5): 1173-1180. https://doi.org/10.1002/ijc.23649
  46. Yap SP, Yuen KH, Lim AB. Influence of route of administration on the absorption and disposition of alpha-, gamma- and deltatocotrienols in rats. J Pharm Pharmacol 2003; 55(1): 53-58
  47. Ikeda I, Imasato Y, Sasaki E, Sugano M. Lymphatic transport of alpha-, gamma-, delta-tocotrienols and alpha-tocopherol in rats. Int J Vitam Nutr Res 1996; 66: 217-221
  48. Birringer M, Pfluger P, Kluth D, Lands N, Brigelius-Flohé R. Identities and differences in the metabolism of tocoptrienols and tocopherols in HepG2 cells. J Nutr 2002; 132: 3113-3118
  49. Mustard VK, Smith CA, Ruey PP, Edens NK, DeMichele SJ. Supplementation with 3 compositionally different tocotrienol supplements does not improve dardiovascular disease risk factors in men and women with hypercholesterolemia. Am J Clin Nutr 2002; 76: 1237-1243
  50. Ikeda S, Tohyama T, Yoshimura H, Hanamura K, Abe K, Yamashita K. Dietary α-tocopherol decreases $\alpha$-tocotrienol but not $\gamma$- tocotrienol concentration in rats. J Nutr 2002; 133: 428-434
  51. Roy S, Lado BH, Khanna S, Sen CK. Vitamin E sensitive genes in the developing rat fetal brain: a high-density oligonucleotide microarray analysis. FEBS Lett 2002; 530(1-3): 17-23 https://doi.org/10.1016/S0014-5793(02)03309-4
  52. Quershi AA, Mo H, Packer L, Peterson DM. Isolation and identification of novel tocotrienols from rice bran with hypocholesterolemic, antioxidant, and antitumor properties. J Agric Food Chem 2000; 48: 3130-3140 https://doi.org/10.1021/jf000099t
  53. O'Byrne D, Grundy S, Packer L, Devaraj S, Baldenius K, Hoppe PP, Kraemer K, Jialal I, Traber MG. Studies of LDL oxidation following alpha-, gamma-, or delta-tocotrienyl acetate supplementation of hypercholesterolemic humans. Free Radic Biol Med 2000; 29(9): 834-845. https://doi.org/10.1016/S0891-5849(00)00371-3
  54. Cicero AF, Gaddi A. Rice bran and gama-oryzanol in the treatment of hyperlipoproteinemias and other conditions. Phytother Res 2001; 15: 277-289 https://doi.org/10.1002/ptr.907
  55. Quershi AA, Sami SA, Salser WA, Khan FA. Dose-dependent suppression of serum cholesterol by tocotrienol-rich fraction (TRF- 25) of rice bran in hypercholesterolemic humans. Atherosclerosis 2002; 162: 199-207
  56. Noguchi N, Hanyu R, Nanaka A, Okimoto Y, Kodama T. Inhibition of THP-1 cell adhesion to endothelial cells by alpha-tocopherol and alpha-tocotrienol is dependnent on intracellular concentration of the antioxidants. Free Radic Biol Med 2003; 34: 1614- 1620 https://doi.org/10.1016/S0891-5849(03)00216-8
  57. Newaz MA, Yousefipour Z, Nawal N, Adeeb N. Nitric oxide synthesis activity in blood vessels of spontaneously hypertensive rata: antioxidant protenction by gamma-tocotrienol. J Physiol Phramacol 2003; 54: 319-327
  58. McIntyre BS, Briski KP, Gapor A, Sylvester PW. Antiproliferative and apoptotic effects of tocopherols and tocotrienols on preneoplastic and neoplastic mouse mammaty epithelial cells (445 44). Proc Soc Exp Biol Med 2000; 224(4): 292-301 https://doi.org/10.1046/j.1525-1373.2000.22434.x
  59. Sylvester PW, Nachnani A, Shah S, Briski KP. Role of GTPbinding proteins in reversing the antiproliferative effects of tocotrienols in preheoplastic mammary epithelial cella. Asia Pac J Clin Nutr 2002; 11(suppl 7): S452-S459 https://doi.org/10.1046/j.1440-6047.11.s.7.9.x
  60. Takahashi K, Loo G. Disruption of mitochondria during tocotrienol- induced apoptosis inMDA-MB-231 human breast cancer cells. Biochem Pharmacol 2004; 67: 315-324 https://doi.org/10.1016/j.bcp.2003.07.015
  61. Mo H, Elson CE. Studies of the isoprenoid-mediated inhibition of mevalonate synthesis applied to cancer chemotherapy and chemo prevention. Exp Biol Med 2004; 229: 567-585
  62. Sen CK, Khanna S, Roy S, Packer L. Molecular basis of vitamin E action. Tocotrienol potently inhibits glutamate-induced pp60 (c-Src) kinase activation and death of HT4 neuronal cells. J Biol Chem 2000; 275: 13049-13055 https://doi.org/10.1074/jbc.275.17.13049
  63. Khanna S, Roy S, Ryu U, Bahadduri P, Swaan PW, Ratan RR, Sen CK. Molecular basis of vitamin E action: tocotrienol modulates 12-lipoxygenas, a key mediator of glutamate-induced neurodegeneration. J Biol Chem 2003; 278: 43508-43515 https://doi.org/10.1074/jbc.M307075200

Cited by

  1. Content of Fat-Soluble Nutrients (Cholesterol, Retinol, and α-Tocopherol) in Different Parts of Poultry Meats according to Cooking Method vol.44, pp.2, 2015, https://doi.org/10.3746/jkfn.2015.44.2.234
  2. Analysis of Vitamin E in Agricultural Processed Foods in Korea vol.45, pp.5, 2016, https://doi.org/10.3746/jkfn.2016.45.5.771