Biodiscrimination of the eight α-tocopherol stereoisomers results in preferential accumulation of the four 2R forms in tissues and plasma of rats

Journal of Nutrition

Volumn 126, Issue 10, 1996, Pages 2539-2549

  Weiser, Harald ^a   Riss, Georges ^a   Kormann, Alfred W ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

all rac tocopheryl acetate tocopherol stereoisomers; biodiscrimination activity ratio (biopotency); rats; vitamin E

Indexed keywords

ALPHA TOCOPHEROL; ALPHA TOCOPHEROL DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; CAPILLARY GAS CHROMATOGRAPHY; CONTROLLED STUDY; DRUG DISCRIMINATION; DRUG POTENCY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; ORAL DRUG ADMINISTRATION; RAT; STEREOISOMERISM; VITAMIN METABOLISM;

ANIMALIA;

EID: 0029820501     PISSN: 00223166     EISSN: None     Source Type: Journal    
DOI: 10.1093/jn/126.10.2539     Document Type: Article

References (34)

1. Anonymous (1989) Utilization of deuterated vitamin E compounds in rats and humans. Nutr. Rev. 47: 183-185.
2. Behrens, W. A. & Madère, R. (1991) Tissue discrimination between dietary RRR-α- and all-rac-α-tocopherols in rats. J. Nutr. 121: 454-459.
3. Bernardo, J. M. & Smith, A. F. M. (1994) Bayesian Theory. John Wiley and Sons, New York, NY.
4. Burton, G. W., Ingold, K. U., Foster, D. O., Cheng, S. C., Webb, A., Hughes, L. & Luszty, E. (1988) Comparison of free α-tocopherol and α-tocopheryl acetate as sources of vitamin E in rats and humans. Lipids 23: 834-840.
5. Burton, G. W., Webb, A. & Ingold, K. U. (1985) A mild, rapid, and efficient method of lipid extraction for use in determining vitamin E/lipid ratios. Lipids 20: 29-39.
6. Burton, G. W., Wronska, U., Stone, L., Foster, D. O. &. Ingold, K. U. (1990) Biokinetics of dietary RRR-α-tocopherol in the male guinea pig at three dietary levels of vitamin C and two levels of vitamin E. Evidence that vitamin C does not "spare" vitamin E in vivo. Lipids 25: 199-210.
7. Cohen, N., Scott, C. G., Neukom, C., Lopresti, R. J., Weber, G. & Saucy, G. (1981) Total synthesis of all eight stereoisomers of α-tocopheryl acetate. Determination of their diastereoisomeric and enantiomeric purity by gas chromatography. Helv. Chim. Acta 64: 1158-1173.
8. Cohn, W., Gross, P., Grun, H., Loechleiter, F., Muller, D.P.R. & Zulauf, M. (1992) Tocopherol transport and metabolism. Proc. Nutr. Soc. 51: 179-188.
9. Coursaget, P., Yvonnet, B., Gilks, W. R., Wang, C. C., Day, N. E., Chiron, J.-P. & Diop-Mar, I. (1991) Scheduling of revaccination against hepatitis B virus. Lancet 337: 1180-1183.
10. Dutta-Roy, A. K., Gordon, M. J., Campbell, F. M., Duthie, G. G. & James, W.P.T. (1994) Vitamin E requirements, transport, and metabolism: role of α-tocopherol-binding proteins. J. Nutr. Biochem. 5: 562-570.
11. Fuhrmann, H., Balthazary, S. T. & Sallmann, H.-P. (1994) Bioefficiency of different tocopherols in chicken as assessed by haemolysis test and microsomal pentane production. Br. J. Nutr. 71: 605-614.
12. Ingold, K. U., Burton, G. W., Foster, D. O., Hughes, L., Lindsay, D. A. & Webb, A. (1987) Biokinetics of and discrimination between dietary RRR- and SRR-α-tocopherols in the male rat. Lipids 22: 163-172.
13. Mathias, P. M., Harries, J. T., Peter, T. J. & Muller, D.P.R. (1981) Studies on the in vivo absorption of micellar solutions of tocopherol and tocopheryl acetate in the rat: demonstration and partial characterization of a mucosal esterase localized to the endoplasmic reticulum of the enterocyte. J. Lipid Res. 22: 829-837.
14. Nitta-Kiyose, C., Hayashi, K., Ueda, T. & Igarashi, O. (1994) Distribution of α-toc stereoisomers in rats. Biosci. Biotech. Biochem. 58: 2000-2003.
15. Piironen, V. I., Liljeroos, A. I. & Koivistoinen, P. E. (1991) Transfer of α-tocopherol stereoisomers from feeds to eggs. J. Agric. Food Chem. 39: 99-101.
16. Prasad, K. N. (1993) Author's response. J. Am. Coll. Nutr. 12:317.
17. Riss, G., Kormann, A. W., Glinz E., Walther, W. & Ranalder, U. B. (1994) Separation of the eight stereoisomers of α-tocopherol by chiral phase HPLC and capillary GC after isolation from tissues and plasma. Methods Enzymol. 234: 302-310.
18. Sakamoto, T., Tomita, K., Yanagi, M., Ozawa, T. & Kajiwara, M. (1991) Biological resolution of (2RS)α-tocopherol and (2RS)α-tocopheryl acetate. Chem. Pharm. Bull. 39: 130-132.
19. Thomas, A., Spiegelhalter, D. J. & Gilks, W. R. (1992) BUGS: A program to perform Bayesian inference using Gibbs sampling. In: Bayesian Statistics 4 (Bernardo, J. M., Berger, J. O., Dawid, A. P. & Smith, A.F.M., eds.), pp. 837-842. Clarendon Press, Oxford, U.K.
20. Traber, M. G., Rudel, L. L., Burton, G. W., Hughes, L., Ingold, K. U. & Kayden, H. J. (1991) Nascent VLDL from liver perfusions of cynomolgus monkeys are preferentially enriched in RRR- compared with SRR-α-tocopherol: studies using deuterated tocopherols. J. Lipid Res. 31: 687-694.
21. Ueda, T., Ichikawa, H. & Igarashi, O. (1993) Determination of α-tocopherol stereoisomers in biological specimens using chiral phase high-performance liquid chromatography. J. Nutr. Sci. Vitamin. 39: 207-219.
22. Ueda, T. & Igarashi, O. (1987) New solvent system for extraction of tocopherols from biological specimens for HPLC determination and the evaluation of 2,2,5,7,8-pentamethyl-6-chromanol as an internal standard. J. Micronutr. Anal. 3: 185-198.
23. USP (1985) United States Pharmacopeia, 21st rev. United States Pharmacopeial Convention, Rockville, MD.
24. Vatassery, G. T., Brin, M. F., Fahn, S., Kayden, H. J. & Traber, M. G. (1988) Effect of high doses of dietary vitamin E on the concentrations of vitamin E in several brain regions, plasma, liver, and adipose tissue of rats. J. Neurochem. 51: 621-623.
25. Vecchi, M., Walther, W., Glinz, E., Netscher, T., Schmid, R., Lalonde, M. & Vetter, W. (1990) 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: 782-789.
26. Vuilleumier, J.-P., Keller, H. E., Gysel, D. & Hunziker, F. (1983) Clinical chemical method for the routine assessment of the vitamin status in human populations. Part 1 : The fat-soluble vitamins A and E, and β-carotene. Int. J. Vitam. Nutr. Res. 58: 263-272.
27. Weber, F. & Wiss, O. (1963) Ueber den Stoffwechsel von Stereoisomeren des α-Tokopherols in der Ratte (Metabolism of α-tocopherol stereoisomers in the rat). Helv. Physiol. Acta 21: 341-344.
28. Weiser, H. Brubacher, G. & Wiss, O. (1963) 1-α-Tocopheryl acetate: biological activity. Science 140: 80.
29. Weiser, H. & Kormann, A. W. (1993) Biopotencies of SRR- and all-rac-α-tocopheryl acetate are significantly different. J. Am. Coll. Nutr. 12:316-317.
30. Weiser, H., Riss, G. & Kormann, A. W. (1992) Selective biodiscrimination of α-tocopherol stereoisomers: Similar enrichment of all 2R forms in rat tissues after oral all-rac-α-tocopheryl acetate. Ann. N.Y. Acad. Sci. 669: 393-395.
31. Weiser, H. & Vecchi, M. (1981) Stereoisomers of α-tocopheryl acetate. Characterization of the samples by physico-chemical methods and determination of biological activities in the rat resorption-gestation test. Int. J. Vitam. Nutr. Res. 51: 100-113.
32. Weiser, H. & Vecchi, M. (1982) Stereoisomers of α-tocopheryl acetate. II. Biopotencies of all eight stereoisomers, individually or in mixtures, as determined by rat resorption/gestation tests. Int. J. Vitam. Nutr. Res. 52: 351-370.
33. Weiser, H., Vecchi, M. & Schlachter, M. (1985) Stereoisomers of α-tocopheryl acetate. III. Simultaneous determination of resorption-gestation and myopathy in rats as a means of evaluating biopotency ratios of all-rac- and RRR-α-tocopheryl acetate. Int. J. Vitam. Nutr. Res. 55: 149-158.
34. Weiser, H., Vecchi, M. & Schlachter, M. (1986) Stereoisomers of α-tocopheryl acetate. IV. USP units and α-tocopherol equivalents of all-rac-, 2-ambo- and RRR-α-tocopherol evaluated by simultaneous determination of resorption-gestation, myopathy and liver storage capacity in rats. Int. J. Vitam. Nutr. Res. 56: 45-56.