Hostname: page-component-78c5997874-dh8gc Total loading time: 0 Render date: 2024-11-15T13:22:12.088Z Has data issue: false hasContentIssue false

Bioavailability of α-tocopherol stereoisomers in rats depends on dietary doses of all-rac- or RRR-α-tocopheryl acetate

Published online by Cambridge University Press:  08 March 2007

Søren K. Jensen*
Affiliation:
Department of Animal Health, Welfare and Nutrition, Danish Institute of Agricultural Sciences, Research Centre Foulum, Box 50, DK-8830 TjeleDenmark
Jan V. Nørgaard
Affiliation:
Department of Animal Health, Welfare and Nutrition, Danish Institute of Agricultural Sciences, Research Centre Foulum, Box 50, DK-8830 TjeleDenmark
Charlotte Lauridsen
Affiliation:
Department of Animal Health, Welfare and Nutrition, Danish Institute of Agricultural Sciences, Research Centre Foulum, Box 50, DK-8830 TjeleDenmark
*
*Corresponding author: fax +45 89991166, email [email protected]
Rights & Permissions [Opens in a new window]

Abstract

Core share and HTML view are not available for this content. However, as you have access to this content, a full PDF is available via the ‘Save PDF’ action button.

The biological function of the stereoisomers of α-tocopherol is believed to depend on their bioavailability. Assessment of bioavailability within the body is therefore considered to be a good and easy way to predict biological value. The separation of α-tocopherol methyl ethers by chiral column HPLC is a good and easy tool with which to study the distribution of α-tocopherol stereoisomers. The objective of this investigation was to evaluate the bioavailability and distribution of the stereoisomers of α-tocopherol in the plasma and tissue in growing rats fed 25, 50, 100 or 200mg/kg diet of either RRR- or all-rac-α-tocopheryl acetate for 10d. The ratio between the two vitamin E sources based on their α-tocopherol concentration in plasma and tissues varied in the plasma between 1·04 and 1·74 and in tissues, ratios of 0·84–1·24 for liver, 0·34–1·59 for lung and 0·75–1·50 for spleen were obtained. An increasing dietary level of all-rac-α-tocopheryl acetate decreased the proportion of RRR-α-tocopherol, whereas the other stereoisomers were not affected. RRS-α-Tocopherol was present in the highest proportion, followed by RSR-, RSS- and RRR-α-tocopherol. In contrast to the other tissues and plasma, the liver contained the highest proportion (29–33%) of the four 2S stereoisomers of total α-tocopherol. Rats fed RRR-α-tocopheryl acetate for 10d showed a significant increase in the plasma and tissue content of RRR-α-tocopherol and a simultaneous decrease in the other three 2R isomers, whereas the absolute content of the 2S isomers was unaffected. In adipose tissue, concentrations of the three synthetic 2R isomers remained constant, whereas there was a steep increase in the content of RRR-α-tocopherol.

Type
Research Article
Copyright
Copyright © The Nutrition Society 2006

References

Acuff, RV, Thedford, SS, Hidiroglou, NN, Papas, AM&Odom, TAJA 1994 Relative bioavailability of RRR- and all-rac-alpha-tocopheryl acetates in humans: studies using deuterated compounds. Am J Clin Nutr 60, 397402.CrossRefGoogle ScholarPubMed
Arita, M, Nomura, K, Arai, H & Inoue, K 1997 Alpha-tocopherol transfer protein stimulates the secretion of alpha-tocopherol from a cultured liver cell line through a brefeldin A-insensitive pathway. Proc Natl Acad Sci USA 94, 1243712441.CrossRefGoogle ScholarPubMed
Behrens, WA & Madére, R 1991 Tissue discrimination between dietary RRR-alpha- and all-rac-alpha-tocopherols in rats. J Nutr 121, 454459.CrossRefGoogle ScholarPubMed
Blatt, DH, Pryor, WA, Mata, JE & Rodriguez-Proteau, R 2004 Reevaluation of the relative potency of synthetic and natural a-tocopherol: experimental and clinical observations. J Nutr Biochem 15, 380395.CrossRefGoogle Scholar
Burton, GW & Traber, MGVitamin E: antioxidant activity, biokinetics, and bioavailability. In Annual Review of Nutrition, [Olson, RE, Brier, DM & McCormick, DBeditors ]. Palo Alto, CA: Annual Reviews. 1990 vol.10, pp.357382.Google ScholarPubMed
Burton, GW, Traber, MG, Acuff, RV, Walters, DN, Kayden, H, Hughes, L & Ingold, KU 1998 Human plasma and tissue alpha-tocopherol concentrations in response to supplementation with deuterated natural and synthetic vitamin E. Am J Clin Nutr 67, 669684.CrossRefGoogle ScholarPubMed
Drotleff, AM & Ternes, W 2001 Determination of E/Z-tocotrienols by HPLC. J Chromatogr A 909, 215223.CrossRefGoogle ScholarPubMed
Harris, PL & Ludwig, MI 1949 Relative vitamin E potency of natural and of synthetic alpha-tocopherol. J Biol Chem 179, 11111115.CrossRefGoogle ScholarPubMed
Hosomi, A, Arita, M, Sato, Y, Kiyose, C, Ueda, T, Igarashi, O, Arai, H & Inoue, K 1997 Affinity for alpha-tocopherol transfer protein as a determinant of the biological activities of vitamin E analogs. FEBS Letts 409, 105108.CrossRefGoogle ScholarPubMed
Ingold, KU, Burton, GW, Foster, DOHughes, L, Lindsay, DA & Webb, A 1987 Biokinetics of and discrimination between dietary RRRand SRR-alpha-tocopherols in the male rat. Lipids 22, 163172.CrossRefGoogle ScholarPubMed
Jensen, SK, Engberg, RM & Hedemann, MS 1999 All-rac-alpha-tocopherol acetate is a better vitamin E source than all-rac-alpha-tocopherol succinate for broilers. J Nutr 129, 13551360.CrossRefGoogle ScholarPubMed
Kaneko, K, Kiyose, C, Ueda, T, Ichikawa, H & Igarashi, O 2001 Studies of the metabolism of α-tocopherol stereoisomers in rats using [5-methyl-14C]SRR- and RRR-α-tocopherol. J Lipid Res 41, 357367.CrossRefGoogle Scholar
Kayden, H & Traber, MG 1993 Absorption, lipoprotein transport and regulation of plasma concentrations of vitamin E in humans. Lipid Res 34, 343358.CrossRefGoogle ScholarPubMed
Knarreborg, A, Lauridsen, c, Engberg, RM & Jensen, SK 2004 Dietary antibiotic growth promoters enhance the bioavailability of atocopheryl acetate in broilers through mediations of the lipid absorption processes. J Nutr 134, 14871492.CrossRefGoogle Scholar
Lauridsen, C, Engel, H, Craig, AM & Traber, MG 2002a Relative bioactivity of dietary RRR-alpha-tocopherol- and all-rac-alphatocopheryl acetates in swine assessed with deuterium-labeled vitamin E. J Anim Sci 80, 16.CrossRefGoogle Scholar
Lauridsen, C, Engel, H, Jensen, SK, Craig, AM & Traber, MG 2002b Lactating sows and suckling piglets preferentially incorporate RRR- over all-rac-alpha-tocopherol into milk, plasma and tissues. J Nutr 132, 12581264.CrossRefGoogle ScholarPubMed
Lauridsen, C, Leonard, SW, Griffin, DA, Liebler, DC, McClure, TD & Traber, MG 2001 Quantitative analysis by liquid chromatography-tandem mass spectrometry of deuterium-labeled and unlabeled vitamin E in biological samples. Anal Biochem 289, 8995.CrossRefGoogle ScholarPubMed
Leth, T & Søndergaard, H 1983 Biological activity of all-rac-α-tocopherol and RRR-a-tocopherol determined by three different rat bioassays. Int J Vit Nutr Res 53, 297311.Google Scholar
Liuzzi, JP, Cioccia, AM & Hevia, P 1998 In well-fed young rats, lactose- induced chronic diarrhea reduce the apparent absorption of vitamins A and E and affects preferentially vitamin E status. J Nutr 128, 24672472.CrossRefGoogle Scholar
Meier, R, Tomizaki, T, Schulze-Briese, C, Bauman, U & Stocker, A 2003 The molecular basis of vitamin E retention: structure of human α-tocopherol transfer protein. J Mol Biol 331, 725734.CrossRefGoogle ScholarPubMed
Min, KC, Kovall, RA & Hendrickson, WA 2003 Crystal structure of human a-tocopherol transfer protein bound to its ligand: implications for ataxia with vitamin E deficiency. PNAS 100, 1471314718.CrossRefGoogle Scholar
Moore, ANJ, Dutton, PJ, Zahalka, HA, Burton, GW & Ingold, KU 1995 Bile salt-modulated stereoselection in the cholesterol esterase-catalyzed hydrolysis of alpha-tocopheryl acetates. J Am Chem Soc 117, 56775686.CrossRefGoogle Scholar
Porsgaard, T & Hoy, CE 2000 Absorption by rats of tocopherols present in edible vegetable oils. Lipids 35, 10731078.CrossRefGoogle ScholarPubMed
Scherf, H, Machlin, LJ, Frye, TM, Krautmann, BA & Williams, SN 1996 Vitamin E biopotency: comparison of various ‘naturalderived’ and chemically synthesized alpha-tocopherols. Anim Feed Sci Tech 59, 115126.CrossRefGoogle Scholar
Traber, MG, Burton, GW, Ingold, KU & Kayden, HJ 1990a RRR and SRR-alpha-tocopherols are secreted without discrimination in human chylomicrons, but RRR-alpha-tocopherol is preferentially secreted in very low density lipoproteins. J Lipid Res 31, 675685.CrossRefGoogle ScholarPubMed
Traber, MG, Cohn, W & Muller, DPRAbsorption, transport and delivery to tissues. In Vitamin E in Health and Disease, [Packer, L and Fuchs, J editors]. New York: Marcel Dekker. 1993 3551.Google Scholar
Traber, MG, Kayden, HJ, Green, JB & Green, MH 1986 Absorption of water-miscible forms of vitamin E in a patient with cholestasis and in thoracic duct-cannulated rats. Am J Clin Nutr 44, 914923.CrossRefGoogle Scholar
Traber, MG, Rudel, LL, Burton, GW, Hughes, L, Ingold, KU & Kayden, HJ 1990b Nascent VLDL from liver perfusions of cynomolgus monkeys are preferentially enriched in RRR- compared with SRR-alpha-tocopherol: studies using deuterated tocopherols. J Lipid Res 31, 687694.CrossRefGoogle ScholarPubMed
United States Pharmacopeial Convention (1979) The National Formulary. Rockville, MD: United States Pharmacopeial Convention.Google Scholar
Weiser, H, Riss, G & Kormann, AW 1996 Biodiscrimination of the eight alpha-tocopherol stereoisomers result in preferential accumulation of the four 2R forms in tissues and plasma of rats. J Nutr 126, 25392549.CrossRefGoogle ScholarPubMed
Weiser, H & Vecchi, M 1981 Stereoisomers of a-tocopheryl acetate. II. Characterization of samples by physico-chemical methods and determination of biological activities in the rat resorption-gestation tests. Int J Vitam Nutr Res 51, 100113.Google Scholar
Weiser, H & Vecchi, M 1982 Stereoisomers of a-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, 351370.Google ScholarPubMed
Zahalka, HA, Dutton, PJ, O’Doherty, B, Smart, TAM, Phipps, J, Foster, DO, Burton, GW & Ingold, KU 1991 Bile salt modulated stereoselection in the cholesterol esterase catalyzed hydrolysis of alphatocopheryl acetates. J Am Chem Soc 113, 27972799.CrossRefGoogle Scholar