α-Tocopherol Stereoisomers

Vitamins and Hormones

Volumn 76, Issue , 2007, Pages 281-308

  Jensen, Søren Krogh ^a   Lauridsen, Charlotte ^a  

^a DANISH INSTITUTE OF AGRICULTURAL SCIENCES   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT;

ANIMAL; BIOAVAILABILITY; CHEMISTRY; HUMAN; REVIEW; SPECIES DIFFERENCE; STEREOISOMERISM;

ALPHA-TOCOPHEROL; ANIMALS; ANTIOXIDANTS; BIOLOGICAL AVAILABILITY; HUMANS; SPECIES SPECIFICITY; STEREOISOMERISM;

EID: 34347396938     PISSN: 00836729     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0083-6729(07)76010-7     Document Type: Review

References (57)

1. Ames S.R., Ludwig M.I., Nelam D.R., and Robeson C.D. Biological activity of an 1-Epimer of d-α-tocopheryl acetate. Biochem. 2 (1963) 188-190
2. Baker L.R.I., Clark M.L., Fairclough P.D., and Goble H. Identification of two intestinal vitamin D-dependent calcium-binding proteins in the X-linked hypophosphataemic mouse. Biochem. Biophys. Res. Commun. 119 (1984) 850-853
3. Ben Hamida C., Doerflinger N., Belal S., Linder C., Reutenauer L., Dib C., Gypay G., Vignal A., Le Pasilier D., Cohen D., Pandolfo M., Mokini V., et al. Localization of Friedreich ataxia phenotype with selective vitamin E deficiency to chromosome 8q by homozygosity mapping. Nat. Genet. 5 (1993) 195-200
4. Blatt D.H., Pryor W.A., Mata J.E., and Rodriguez-Proteau R. Re-evaluation of the relative potency of synthetic and natural α-tocopherol: Experimental and clinical observations. J. Nutr. Biochem. 15 (2004) 380-395
5. Bramley P.M., Elmadfa I., Kafatos A., Kelly F.J., Manios Y., Roxborough H.E., Schuch W., Sheehy P.J.A., and Wagner K.-H. Review. Vitamin E. J. Sci. Food Agric. 80 (2000) 913-938
6. Brigelius-Flohé R., Kelly F.J., Salonen J.T., Neuzil J., Zingg J.-M., and Azzi A. The European perspective on vitamin E: Current knowledge and future research. Am. J. Clin. Nutr. 76 (2002) 703-716
7. Burton G.W., and Traber M.G. Vitamin E: Antioxidant activity, biokinetics, and bioavailability. In: Olson R.E., Brier D.M., and McCormick D.B. (Eds). "Annual Review of Nutrition" (1990), Annual Reviews Inc., Palo Alto, CA
8. Burton G.W., Traber M.G., Acuff R.V., Walters D.N., Kayden H., Hughes L., and Ingold K.U. Human plasma and tissue alpha-tocopherol concentrations in respons to supplementation with deuterated natural and synthetic vitamin E. Am. J. Clin. Nutr. 67 (1998) 669-684
9. Børsting C.F., Engberg R.M., Jensen S.K., and Damgaard B.M. Effects of high amounts of dietary fish oil of different oxidative quality on performance and health of growing-furring male mink (Mustela vision) and nursing female mink. J. Anim. Physiol. Anim. Nutr. 79 (1998) 210-223
10. Cohen N., Scott C.G., Neukom C., Lopresti R.J., Weber G., and Saucy G. Total synthesis of all eight stereoisomers of α-tocopheryl acetate. Determination of their diastereoisomeric and enantiomeric purity by gas chromatography. Helv. Chim. Acta 64 (1981) 1158-1173
11. Cortinas L., Baroeta A.C., Galobart J., and Jensen S.K. Distribution of α-tocopherol stereoisomers in liver and thigh of chickens. Br. J. Nutr. 92 (2004) 295-301
12. DellaPenna D. A decade of progress in understanding vitamin E synthesis in plants. J. Plant Physiol. 162 (2005) 729-737
13. Derendorf H., Lesko L.J., Chaikin P., Colburn W.A., Lee P., Miller R., Powell R., Rhodes G., Stanski D., and Venitz. Pharmacokinetic/pharmacodynamic modeling in drug research and development. J. Clin. Pharmacol. 40 (1992) 1399-1418
14. Drotleff A.M., and Ternes W. Determination of RS, E/Z-tocotrienols by HPLC. J. Chromatogr. A 909 (2001) 215-223
15. Evans H.M., and Bishop K.S. Existence of a hitherto unknown dietary factor essential for reproduction. J. Am. Med. Assoc. 81 (1923) 889-892
16. Fechner H., Schlame M., Guthmann F., Stevens P.A., and Rüstow B. α- and δ-tocopherol induce expression of hepatic α-tocopherol-tranfer protein mRNA. Biochem. J. 331 (1998) 577-581
17. Harris P.L., and Ludwig M.I. Relative vitamin E potency of natural and of synthetic alpha-tocopherol. J. Biol. Chem. 179 (1949) 1111-1115
18. Hidiroglou N., McDowell L.R., Papas A.M., Antapli M., and Wilkinson N.S. Bioavailability of vitamin E compounds in lambs. J. Anim. Sci. 70 (1992) 2556-2561
19. Hosomi A., Arita M., Sato Y., Kiyose C., Ueda T., Igarashi O., Arai H., and Inoue K. Affinity for α-tocopherol transfer protein as a determinant of the biological activities of vitamin E analogs. FEBS Lett. 409 (1997) 105-108
20. Hosomi A., Goto K., Kondo H., Iwatsubo T., Yokota T., Ogawa M., Arita M., Aoki J., Arai H., and Inoue K. Localization of α-tocopherol transfer protein in rat brain. Neurosci. Lett. 256 (1998) 159-162
21. Ingold K.U., Burton G.W., Foster D.O., Hughes L., Lindsay D.A., and Webb A. Biokinetics of and discrimination between dietary RRR- and SRR-alpha-tocopherols in the male rat. Lipids 22 (1987) 163-172
22. IUPAC-IUB Joint Commission on Biochemical Nomenclature. In: Moss G.P. (Ed). "Nomenclature of Tocopherols and Related Compounds" (1981). http://www.chem.qmul.ac.uk./iupac/misc/toc.html
23. Jensen S.K., Engberg R.M., and Hedemann M.S. All-rac-alpha-tocopherol acetate is a better vitamin E source than all-rac-alpha-tocopherol succinate for broilers. J. Nutr. 129 (1999) 1355-1360
24. Jensen S.K., Kristensen N.B., Lauridsen C., and Sejersen K. Enrichment of cows' milk with natural or synthetic vitamin E. "Proceedings of the 10th Symposium on Vitamins and Additives in Nutrition of Man and Animal." (2005), Jena/Thuringia, Germany 78-83 28-29 September
25. Jensen S.K., Nørgaard J.V., and Lauridsen C. Bioavailability of α-tocopherol stereoisomers in rats depends on dietary doses of all-rac-a-tocopheryl acetate or RRR-a-tocopheryl acetate. Br. J. Nutr. 95 (2006) 477-487
26. Kim H.-S., Arai H., Arita M., Sato Y., Ogihara T., Inoue K., Mino M., and Tamai H. Effect of α-tocopherol status on α-tocopherol transfer protein expression and its messenger RNA level in rat liver. Free Radic. Res. 28 (1998) 87-92
27. Kiyose C., Muramatsu R., Ueda T., and Igarashi O. Rats after intravenous administration. Biosci. Biotech. Biochem. 59 (1998) 791-795
28. Kiyose C., Muramatsu R., Kameyama Y., Ueda T., and Igarashi O. Biodiscriminaion of α-tocopherol stereoisomers in humans after oral administration. Am. J. Clin. Nutr. 65 (1997) 785-789
29. Knarreborg A., Lauridsen C., Engberg R.M., and Jensen S.K. Dietary antibiotic growth promoters enhance the bioavailability of α-tocopheryl acetate in broilers through mediations of the lipid absorption processes. J. Nutr. 134 (2004) 1487-1492
30. Lauridsen C., and Jensen S.K. Influence of supplementation of all-rac-α-tocopheryl acetate preweaning and vitamin C postweaning on α-tocopherol and immune responses of piglets. J. Anim. Sci. 83 (2005) 1274-1286
31. Lauridsen C., and Jensen S.K. Transfer of vitamin E in milk to the newborn. In: Preedy V.R., and Watson R.R. (Eds). "The Encyclopedia of Vitamin E" (2006), CABI International, Wallingford, Oxfordshire, UK 508-516 Chapter 47
32. Lauridsen C., and Jensen S.K. Forms of vitamin E and α-tocopherol status of weaned piglets. In "Proceedings of the 19th International Pig Veterinary Society Congress," (2006), Copenhagen, Denmark 293 16-19 July
33. Lauridsen C., Hedemann M.S., and Jensen S.K. Hydrolysis of tocopheryl and retinyl esters by porcine caboxyl ester hydrolase is affected by their carboxylate moiety and bile acids. J. Nutr. Biochem. 12 (2001) 219-224
34. Lauridsen C., Leonard S.W., Griffin D.A., Liebler D.C., McClure T.D., and Traber M.G. Quantitative analysis by liquied chromatography-tandem mass spectrometry of deuterium-labeled and unlabeled vitamin E in biological samples. Anal. Biochem. 289 (2001) 89-95
35. Lauridsen C., Engel H., Morrie Craig A., and Traber M.G. Relative bioactivity of dietary RRR- over all-rac-α-tocopheryl acetatetes in swine assessed with deuterium-labeled vitamin E. J. Anim. Sci. 80 (2002) 702-707
36. Lauridsen C., Engel H., Jensen S.K., Morrie Craig A., and Traber M.G. Lactating sows and suckling piglets preferentially incorporate RRR- over all-rac-α-tocopherol into milk, plasma and tissues. J. Nutr. 132 (2002) 1258-1264
37. Lodge J.K. Vitamin E bioavailability in humans. J. Plant Physiol. 162 (2005) 790-796
38. Mahan D.C., Kim Y.Y., and Stuart R.L. Effect of vitamin E sources (RRR- or all-rac-α-tocopheryl acetate) and levels on sow reproductive performance, serum, tissue, and milk α-tocopherol contents over a five-parity period, and the effects on the progeny. J. Anim. Sci. 78 (2000) 110-119
39. Meglia G.E., Jensen S.K., Lauridsen C., and Waller K.P. α-Tocopherol concentration and stereoisomer composition in plasma and milk from dairy cows fed natural or synthetic vitamin E around calving. J. Dairy Res. 73 (2006) 227-234
40. Moore A., Burton G.W., and Ingold K.U. Modulation of cholesterol esterase's diastereoselectivity by chiral auxiliaries. The very large effect of a dihydroxy bile acid on the hydrolysis of α-tocoperyl acetates. J. Am. Chem. Soc. 116 (1994) 6945-6946
41. Müller D.P.R., Manning J.A., Mathias P.M., and Harries J.T. Studies of the intestinal hydrolysis of tocopheryl esters. Int. J. Vitam. Nutr. Res. 46 (1976) 207-210
42. Nelis H.J., D'Haese E., and Vermis K. Vitamin E. In: Leenheer A.P., Lambert W.E., and van Bocxlaer J.F. (Eds). "Modern Chromatographic Analysis of Vitamins". 3rd ed. (2000), Marcel Dekker, Inc., New York 143-228
43. Nielsen H.E., Danielsen V., Simesen M.G., Gissel-Nielssen G., Hjarde W., Leth T., and Basse A. Selenium and vitamin E deficiency in pigs. 1. Influence on growth and reproduction. Acta Vet. Scand. 20 (1979) 276-288
44. NRC. "Nutrient Requirements of Swine,". 10th ed. (1998), National Academy Press, Washington, DC
45. Ong D.E. Vitamin A binding proteins. Nutr. Rev. 43 (1985) 225-232
46. Packer L. Vitamin E is nature's master antioxidant. Sci. Am. Sci. Med. 1 (1994) 54-63
47. Scherf H., Machlin L.J., Frye T.M., Krautmann B.A., and Williams S.N. Vitamin E biopotency: Comparison of various 'natural-derived' and chemically synthesized alpha-tocopherols. Anim. Feed Sci. Tech. 59 (1996) 115-126
48. Traber M.G. The bioavailability bugaboo. Am. J. Clin. Nutr. 71 (2000) 1029-1030
49. Traber M.G., Sokol R.J., Burton G.W., Ingold K.U., Papas A.M., Huffaker J.E., and Kayden H.J. Impaired ability of patients with familiar isolated vitamin E deficiency to incorporate α-tocopherol into lipoproteins secreted by the liver. J. Clin. Investi. 85 (1990) 397-407
50. Ueda T., Ichikawa H., and Igarashi O. Determination of α-tocopherol-tocopherol stereoisomers in biological speciments using chiral phase igh-performance liquid chromatography. J. Nutr. Vitaminol. 39 (1993) 207-219
51. Vecchi M., Walther W., Glinz E., Netscher T., Schmid R., Lalonde M., and Wetter W. Chromatographische Trennung und quantitative Bestimmung aller acht Stereoisomeren von α-Tocopherol (Separation and quantitation of all eight stereoisomers of α-tocopherol by chromatography). Helv. Chim. Acta 73 (1990) 782-789
52. VERIS Research summary. A comparison of natural and synthetic vitamin E (1999). http://www.veris-online.org
53. Weiser H., and Vecchi M. Stereoisomers of α-tocopheryl acetate. II. Characterization of samples by physico-chemical methods and determination of biological acitivities in the rat resorption-gestation tests. Int. J. Vitam. Nutr. Res. 51 (1981) 100-113
54. Weiser H., and Vecchi M. Stereoisomers of α-tocopheryl acetate. II. Biopotencies of all eight stereoisomers, induvidually or in mixtures, as dertermined by rat resorption-gestation tests. Int. J. Vitam. Nutr. Res. 52 (1982) 351-370
55. Weiser H., Riss G., and Kormann A.W. Biodiscrimination of the eight alpha-tocopherol stereosismers result in preferential accumulation of the four 2R forms in tissues and plasma of rats. J. Nutr. 126 (1996) 2539-2549
56. Yamauchi J., Iwamoto T., Kida S., Massushige S., Yamada K., and Esashi T. Tocopherol-associated protein is a ligand-dependent transcriptional activator. Biochem. Biophys. Res. Commun. 285 (2001) 295-299
57. Zimmer S., Stocker A., Sarbolouki M.N., Spycher S.E., Sassoon J., and Azzi A. A novel human tocopherol-associated protein: Cloning, in vitro expression, and characterization. J. Biol. Chem. 275 (2000) 25672-25680