Skip to main content
SpringerLink
Log in

Simultaneous determination of RRR- and SRR-α-tocopherols and their quinones in rat plasma and tissues by using chiral high-performance liquid chromatography

  • Published:
Lipids

Abstract

We established a method to simultaneously determine RRR- and SRR-α-tocopherol (α-Toc) and their quinones in biological samples by chiral-phase high-performance liquid chromatography (HPLC). α-Toc had a shorter retention time than α-tocopherylquinones (α-TQ), and 2-ambo-α-Toc was completely separated into two peaks; the first peak was RRR-α-Toc and the second SRR-isomer by chiral HPLC connected Chiralcel OD-H column and Sumichiral OA4100 column. In contrast, of the two peaks of α-TQ, the first was the SRR-isomer. We also investigated differences in the distribution of RRR- and SRR-α-TQ in rat tissues after oral administration of 2-ambo-α-Toc by the above HPLC method. Rats deficient in vitamin E were divided into two groups, control and experimental, and tissues were collected at 3, 6, and 24 h after oral 2-ambo-α-Toc administration. The concentrations of RRR- and SRR-α-Toc and their quinones in plasma and each tissue were determined. The concentration of SRR-α-TQ in plasma and adrenal glands was not significantly different from RRR-α-TQ. However, the concentration of SRR-α-TQ in liver up to 6 h after oral administration was higher than that of RRR-α-TQ, and SRR- and RRR-α-TQ levels were similar at 24 h after oral administration. Therefore, we may assume that the formation of α-TQ in vivo was not different between RRR- and SRR-isomer and that it was not affected by the presence of α-Toc stereoisomers.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

HPLC:

high-performance liquid chromatography

PMC:

2,2,5,7,8-pentamethyl-6-hydroxychroman

TLC:

thin-layer chromatography

α-Toc or γ-Toc:

α- or γ-tocopherol

α-TQ:

α-tocopherylquinone

α-TTP:

α-tocopherol transfer protein

VLDL:

very low density lipoprotein

References

  1. Traber, M.G. (1994) Determinants of Plasma Vitamin E Concentrations, Free Radical Biol. Med. 16, 229–239.

    Article  CAS  Google Scholar 

  2. Weiser, H., and Vecchi, M. (1982) Stereoisomers of α-Tocopheryl Acetate II. Biopotencies of All Eight Stereoisomers, Individually or in Mixtures, as Determined by Rat Resorption-Gestation Test, Int. J. Vitam. Nutr. Res. 52, 351–370.

    PubMed  CAS  Google Scholar 

  3. Ingold, K.U., Burton, G.W., Foster, D.O., Hughes, L., Lindsay, D.A., and Webb, A. (1987) Biokinetics of and Discrimination Between Dietary RRR- and SRR-α-Tocopherols in the Male Rat, Lipids 22, 163–172.

    PubMed  CAS  Google Scholar 

  4. Traber, M.G., Ingold, K.U., Burton, G.W., and Kayden, H.J. (1988) Absorption and Transport of Deuterium-Substituted 2′R,4′R,8′R-α-Tocopherol in Human Lipoproteins, Lipids 23, 791–797.

    PubMed  CAS  Google Scholar 

  5. Nitta, C., Hayashi, K., Ueda, T., and Igarashi, O. (1993) Distribution of α-Tocopherol Stereoisomers in Rats, Biosci. Biotechnol. Biochem. 57, 1406–1407.

    CAS  Google Scholar 

  6. Nitta-Kiyose, C., Hayashi, K., Ueda, T., and Igarashi, O. (1994) Distribution of α-Toc Stereoisomers in Rats, Biosci. Biotechnol. Biochem. 58, 2000–2003.

    CAS  Google Scholar 

  7. Kiyose, C., Muramatsu, R., Ueda, T., and Igarashi, O. (1995) Change in the Distribution of α-Tocopherol Stereoisomers in Rats After Intravenous Administration, Biosci. Biotechnol. Biochem. 59, 791–795.

    Article  PubMed  CAS  Google Scholar 

  8. Kiyose, C., Muramatsu, R., Fujiyama-Fujiwara, Y., Ueda, T., and Igarashi, O. (1995) Biodiscrimination of α-Tocopherol Stereo-isomers During Intestinal Absorption, Lipids 30, 1015–1018.

    PubMed  CAS  Google Scholar 

  9. Kiyose, C., Muramatsu, R., Kameyama, Y., Ueda, T., and Igarashi, O. (1997) Biodiscrimination of α-Tocopherol Stereoisomers in Humans After Oral Administration, Am. J. Clin. Nutr. 65, 785–789.

    PubMed  CAS  Google Scholar 

  10. Hosomi, A., Arita, M., Sato, Y., Kiyose, C., Ueda, T., Igarashi, O., Arai, H., and Inoue, K. (1997) Affinity for α-Tocopherol Transfer Protein as a Determinant of the Biological Activities of Vitamin E Analogs, FEBS Lett. 409, 105–108.

    Article  PubMed  CAS  Google Scholar 

  11. Ueda, T., Ichikawa, H., and Igarashi, O. (1993) Determination of α-Tocopherol Stereoisomers in Biological Specimens Using Chiral Phase High-Performance Liquid Chromatography, J. Nutr. Sci. Vitaminol. 39, 207–219.

    PubMed  CAS  Google Scholar 

  12. Weiser, H., Riss, G., and Kormann, A.W. (1996) Biodiscrimination of the Eight α-Tocopherol Stereoisomers Results in Preferential Accumulation of the Four 2R Forms in Tissues and Plasma of Rats, J. Nutr. 126, 2539–2549.

    PubMed  CAS  Google Scholar 

  13. Kayden, H.J., and Traber, M.G. (1993) Absorption, Lipoprotein Transport, and Regulation of Plasma Concentration of Vitamin E in Humans, J. Lipid Res. 34, 343–358.

    PubMed  CAS  Google Scholar 

  14. Hughes, P.E., and Tove, S.B. (1980) Synthesis of α-Tocopherol quinone by the Rat and Its Reduction by Mitochondria, J. Biol. Chem. 255, 7095–7097.

    PubMed  CAS  Google Scholar 

  15. Bieri, J.G., and Tolliver, T.J. (1981) On the Occurrence of α-Tocopherolquinone in Rat Tissue, Lipids 16, 777–779.

    PubMed  CAS  Google Scholar 

  16. Koskas, J.P., Cillard, J., and Cillard, P. (1984) Separation of α-Tocopherol, α-Tocopherolquinone and α-Tocopherol Dimer by Reversed-Phase High-Performance Liquid Chromatography, J. Chromatogr. 287, 442–446.

    Article  CAS  Google Scholar 

  17. Vatassery, G.T., and Smith, W.E. (1987) Determination of α-Tocopherolquinone (vitamin quinone) in Human Serum, Platelets, and Red Cell Membrane Samples, Anal. Biochem. 167, 411–417.

    Article  PubMed  CAS  Google Scholar 

  18. Moore, N.J., and Ingold, K.U. (1997) α-Tocopheryl Quinone Is Converted into Vitamin E in Man, Free Radical Biol. Med. 22, 931–934.

    Article  CAS  Google Scholar 

  19. Howell, S.K., and Wang, Y.-H. (1982) Quantitation of Physiological α-Tocopherol, Metabolites, and Related Compounds by Reversed-Phase High-Performance Liquid Chromatography, J. Chromatogr. 227, 174–180.

    PubMed  CAS  Google Scholar 

  20. Simon, E.J., Gross, C.S., and Milhorat, A.T. (1956) The Metabolism of Vitamin E. I. The Absorption and Excretion of d-α-Tocopheryl-5-methyl-C14-succinate, J. Biol. Chem. 221, 797–805.

    PubMed  CAS  Google Scholar 

  21. Dutton, P.J., Hughes, L.A., Foster, D.O., Burton, G.W., and Ingold, K.U. (1990) Simon Metabolites of α-Tocopherol Are Not Formed via a Rate-Controlling Scission of the 3′C-H Bond, Free Radical Biol. Med. 9, 435–439.

    Article  CAS  Google Scholar 

  22. Schultz, M., Leist, M., Petrzika, M., Gassmann, B., and Brigelius-Flohe, R. (1995) Novel Urinary Metabolite of α-Tocopherol, 2,5,7,8-Tetramethyl-2(2′-carboxyethyl)-6-hydroxychroman, as an Indicator of an Adequate Vitamin E Supply? Am. J. Clin. Nutr. 62, 1527S-1534S.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Tokyo Metropolitan Research Institute for Environmental Protection, 136-0075, Tokyo, Japan

    Tadahiko Ueda

  2. Institute of Environmental Science for Human Life, Ochanomizu University, 2-1-1, Ohtsuka, Bunkyo-ku, 112-8610, Tokyo, Japan

    Chikako Kiyose, Kazuyo Kaneko, Riho Muramatsu & Osamu Igarashi

Authors
  1. Chikako Kiyose
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kazuyo Kaneko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Riho Muramatsu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tadahiko Ueda
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Osamu Igarashi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chikako Kiyose.

About this article

Cite this article

Kiyose, C., Kaneko, K., Muramatsu, R. et al. Simultaneous determination of RRR- and SRR-α-tocopherols and their quinones in rat plasma and tissues by using chiral high-performance liquid chromatography. Lipids 34, 415–422 (1999). https://doi.org/10.1007/s11745-999-0380-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-999-0380-x

Keywords

Search

Navigation