α-tocopheryl quinone is converted into vitamin E in man

Free Radical Biology and Medicine

Volumn 22, Issue 5, 1997, Pages 931-934

  Moore, Andrew N J ^a   Ingold, K U ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

Tocopherol; Tocopheryl quinone; Free radicals; Vitamin E

Indexed keywords

ALPHA TOCOPHEROL; ALPHA TOCOPHERYLQUINONE; FREE RADICAL;

ANTICOAGULANT THERAPY; ARTICLE; DRUG BLOOD LEVEL; DRUG EFFECT; DRUG TRANSFORMATION; HEART INFARCTION; HUMAN; PRIORITY JOURNAL; STROKE;

ADMINISTRATION, ORAL; AGED; BIOTRANSFORMATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; INTESTINAL ABSORPTION; MALE; VITAMIN E;

EID: 0031016741     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(96)00276-6     Document Type: Article

References (32)

1. Dowd P., Zheng Z. B. On the mechanism of the anticlotting action of vitamin E quinone. Proc. Natl. Acad. Sci. USA. 92:1995;8171-8175.
2. Ingold K. U., Burton G. W., Foster D. O., Hughes L., Lindsay D. A., Webb A. Biokinetics and discrimination between dietary RRR- and SRR- α -tocopherols in the male rat. Lipids. 22:1987;163-172.
3. Traber M. G., Ingold K. U., Burton G. W., Kayden H. J. Absorption and transport of deuterium-substituted 2R,4′R,8′R- α -tocopherol in human lipoproteins. Lipids. 23:1988;791-797.
4. Burton G. W., Ingold K. U., Foster D. O., Cheng S. C., Webb A., Hughes L., Lusztyk E. Comparison of free α -tocopherol and α -tocopheryl acetate as sources of vitamin E in rats and humans. Lipids. 23:1988;834-840.
5. Traber M. G., Burton G. W., Ingold K. U., Kayden H. J. RRR- and SRR- α -tocopherols are secreted without discrimination in human chylomicrons, but RRR- α -tocopherol is preferentially secreted in very low density lipoproteins. J. Lipid Res. 31:1990;675-685.
6. Traber M. G., Rudel L. L., Burton G. W., Hughes L., Ingold K. U., Kayden H. J. Nascent VLDL from liver perfusions of cynomolgus monkeys are preferentially enriched in RRR-compared with SRR- α -tocopherol. J. Lipid Res. 31:1990;687-694.
7. Dutton P. J., Hughes L. A., Foster D. O., Burton G. W., Ingold K. U. Simon metabolites of α -tocopherol are not formed via a rate-controlling scission of the 3′ C-H bond. Free Radic. Biol. Med. 9:1990;435-439.
8. Ingold K. U., Hughes L., Slaby M., Burton G. W. Synthesis of 2R,4′R,8′R- α -tocopherols selectively labelled with deuterium. J. Labelled Compd. Radiopharm. 24:1987;817-831.
9. Cohen N., Lampresti R. J., Neukom C. Studies on the total synthesis of (2R,4′R,8′R)- α -tocopherol (Vitamin E). Stereospecific cyclizations leading to optically active chromans. J. Org. Chem. 46:1981;2445-2450.
10. Burton G. W., Joyce A., Ingold K. U. Is vitamin E the only lipid-soluble, chain-breaking antioxidant in human blood plasma and erythrocyte membranes? Arch. Biochem. Biophys. 221:1983;281-290.
11. Burton G. W., Webb A., Ingold K. U. A mild, rapid and efficient method of lipid extraction for use in determining vitamin E/lipid ratios. Lipids. 20:1985;29-39.
12. Bieri J. G., Tolliver T. J. On the occurrence of α -tocopherolquinone in rat tissue. Lipids. 16:1981;777-779.
13. 14 to tocopheryl-p-quinone in vivo. Arch. Biochem. Biophys. 98:1962;142-145.
14. Simon E. J., Eisengart A., Sundheim L., Milhorat A. T. The metabolism of vitamin E. II. Purification and characterization of urinary metabolites of α -tocopherol. J. Biol. Chem. 221:1956;807-817.
15. Schmandke M., Schmidt G. Zum abbaumechanismus des α -tocopherols im menschlichen organismus. Int. Z. Vitaminforsch. 38:1968;75-78.
16. Schmandke H. Die Bildung von Tocopheronolacton aus α -Tocopherylchinon im menschlichen Organismus. Int. Z. Vitaminforsch. 35:1965;321-327.
17. 13C-NMR study. Leibigs Ann. Chem. 1239-1241; 1994 .
18. Kohar I., Suarna C., Southwell-Keely P. T. Oxidations of α -tocopherol model compound 2,2,5,7,8-pentamethyl-6-chromanol. Formation of 2,2,7,8-tetramethylchroman-5,6-dione. Lipids. 28:1993;1015-1020.
19. Liebler D. C., Kaysen K. L., Kennedy T. A. Redox cycles of vitamin E: Hydrolysis and ascorbic acid dependent reduction of 8a-(alkyldioxy)tocopherones. Biochemistry. 28:1989;9772-9777.
20. Southwell-Keely, P. T. Private communications.
21. 14- α -tocopheryl hydroquinone. Lipids. 2:1967;390-396.
22. Mackenzie J. B., Rosenkrantz H., Ulick S., Milhorat A. T. The biological activity of α -tocopherylhydroquinone and α -tocopherylquinone. J. Biol. Chem. 183:1950;655-662.
23. Mackenzie J. B., Mackenzie C. G. The effect of α -tocopherol, α -tocopherylhydroquinone and their esters on experimental muscular dystrophy in the rat. J. Nutr. 67:1959;223-235.
24. Mackenzie J. B., Mackenzie C. G. The antisterility activity of α -tocohydroquinone in the female rat. J. Nutr. 72:1960;322-324.
25. Green J., Edwin E. E., Diplock A. T., Bunyan J. The effect of a water-soluble metabolite of α -tocopherol on ubiquinone in the rat. Biochim. Biophys. Acta. 49:1961;417-419.
26. Mackenzie J. B., Mackenzie C. G. Vitamin E activity of α -tocopherylhydroquinone and muscular dystrophy. Proc. Soc. Exp. Biol. Med. 84:1953;388-392.
27. Golumbic C., Mattill H. A. The oxidation of vitamin E. J. Biol. Chem. 134:1940;535-541.
28. Issidorides A., Mattill H. A. The biological activity of α -tocopherylhydroquinone in rats. J. Biol. Chem. 188:1951;313-316.
29. Bunyan J., McHale D., Green J. The vitamin E activity of α -tocopherylquinone and α -tocopherylhydroquinone in the rat. Br. J. Nut. 17:1965;391-398.
30. Hughes P. E., Tove S. B. Synthesis of α -tocopherolquinone by the rat and its reduction by mitochondria. J. Biol. Chem. 255:1980;7095-7097.
31. Kohar I., Baca M., Suamo C., Stocker R., Southwell-Keely P. T. Is α -tocopherol a reservoir for α -tocopheryl hydroquinone? Free Radic. Biol. Med. 19:1995;197-207.
32. Traber M. G., Burton G. W., Hughes L., Ingold K. U., Hidaka H., Malloy M., Kane J., Hyams J., Kayden H. J. Discrimination between forms of vitamin E by humans with and without genetic abnormalities of lipoprotein metabolism. J. Lipid Res. 33:1992;1171-1182.