Regeneration of lipophilic antioxidants by NAD(P)H:quinone oxidoreductase 1

Protoplasma

Volumn 221, Issue 1-2, 2003, Pages 129-135

  Bello, Rosario I ^a   Kagan, Valerian E ^b   Tyurin, Vladimir ^b   Navarro, Francisco ^c   Alcaín, Francisco J ^a   Villalba, José M ^a  

^a UNIVERSITY OF CÓRDOBA   (Spain)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c UNIVERSITY OF HUELVA   (Spain)

Author keywords

Alpha tocopherol; Alpha tocopherylquinone; Coenzyme Q; Electron paramagnetic resonance; Lipophilic antioxidant; Pig liver

Indexed keywords

ALPHA-TOCOPHEROL; ANIMALS; ANTIOXIDANTS; CATALYSIS; CYTOSOL; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROPHOBICITY; ISOENZYMES; LIVER; NAD(P)H DEHYDROGENASE (QUINONE); NADP; OXIDATION-REDUCTION; SWINE;

SUS SCROFA;

EID: 0038348622     PISSN: 0033183X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00709-002-0068-x     Document Type: Conference Paper

References (30)

1. Beyer RE (1990) The participation of coenzyme Q in free radical production and antioxidation. Free Radic Biol Med 8: 545-565
2. _ Segura-Aguilar J, di Bernardo S, Cavazzoni M, Fato R, fiorentini D, Galli MC, Setti M, Landi L, Lenaz G (1996) The role of DT-Diaphorase in the maintenance of the reduced antioxidant form of coenzyme Q in membrane systems. Proc Natl Acad Sci USA 93: 2528-2532
3. Bindoli A, Valente M, Cavallini L (1985) Inhibition of lipid peroxidation by alpha-tocopherolquinone and alpha-tocopherolhydroquinone. Biochem Int 10: 753-761
4. Burton GW, Ingold KU (1986) Vitamin E: application of principles of physical organic chemistry to the exploration of its structure and function. Acc Chem Res 19: 194-201
5. Cadenas E (1995) Antioxidant and prooxidant functions of DT-Diaphorase in quinone metabolism. Biochem Pharmacol 49: 127-140
6. _ Hochstein P, Ernster L (1992) Pro- and antioxidant functions of quinones and quinone reductases in mammalian cells. Adv Enzymol 65: 97-146
7. Chen S, Clarke PE, Martino PA, Deng PS, Yeh CH, Lee TD, Prochaska HJ, Talalay P (1994) Mouse liver NAD(P)H:quinone acceptor oxidoreductase: protein sequence analysis by tandem mass spectrometry, cDNA cloning, expression in Escherichia coli, and enzyme activity analysis. Protein Sci 3: 1296-1304
8. Ernster L, Navazio F (1958) Soluble diaphorase in animal tissues. Acta Chem Scand 12: 595-602
9. Hayashi T, Kanetoshi A, Nakamura M, Tamura M, Shirahama H (1992) Reduction of alpha-tocopherolquinone to alpha-tocopherolhydroquinone in rat hepatocytes. Biochem Pharmacol 44: 489-493
10. Horie S (1990) Advances in research on DT-Diaphorase-catalytic properties, regulation of activity and significance in the detoxification of foreign compounds. Kitasato Arch Exp Med 63: 11-30
11. Kagan VE, Quinn PJ (1988) The interaction of alpha-tocopherol and homologues with shorter hydrocarbon chains with phospholipid bilayer dispersions: a fluorescence probe study. Eur J Biochem 171: 661-667
12. Kohar I, Baca M, Suarna C, Stocker R, Southwell-Keely PT (1995) Is alpha-tocopherol a reservoir for alpha-tocopheryl hydroquinone? Free Radic Biol Med 19: 197-207
13. Landi L, Fiorentini D, Galli MC, Segura-Aguilar J, Beyer RE (1997) DT-Diaphorase maintains the reduced state of ubiquinones in lipid vesicles thereby promoting their antioxidant function. Free Radic Biol Med 22: 329-335
14. Leray C, Andriamampandry MD, Freund M, Gachet C, Cazenave J-P (1998) Simultaneous determination of homologues of vitamin E and coenzyme Q and products of α-tocopherol oxidation. J Lipid Res 39: 2099-2105
15. Liebler DC, Burr JA (2000) Antioxidant reactions of alpha-tocopherolhydroquinone. Lipids 35: 1045-1047
16. _ Kaysen KL, Kennedy TA (1989) Redox cycles of vitamin E: hydrolysis and ascorbic acid dependent reduction of 8a-(alky-dioxy)tocopherones. Biochemistry 28: 9772-9777
17. Lind C, Hochstein P, Ernster L (1982) DT-Diaphorase as a quinone reductase: a cellular control device against semiquinone and superoxide formation. Arch Biochem Biophys 216: 178-185
18. _ Cadenas E, Hochstein P, Ernster L (1990) DT-Diaphorase: purification, properties and function. Methods Enzymol 186: 287-301
19. Lindsey JA, Zhang HF, Kaseki H, Morisaki N, Sato T, Cornwell DG (1985) Fatty acid metabolism and cell proliferation VII: antioxidant effects of tocopherols and their quinones. Lipids 20: 151-157
20. Neuzil J, Witting PK, Stocker R (1997) α-Tocopheryl hydroquinone is an efficient multifunctional inhibitor of radical-initiated oxidation of low density lipoprotein lipids. Proc Natl Sci USA 94: 7885-7890
21. Niki E, Matsuo M (1992) Rates and products of reaction of vitamin E with oxygen radicals. In: Packer L, Fuchs J (eds) Vitamin E in health and disease. Dekker, New York, pp 235-243
22. Moore ANJ, Ingold KU (1997) α-Tocopheryl quinone is converted into vitamin E in man. Free Radic Biol Med 22: 931-934
23. Morisaki N, Lindsey JA, Stitts JM, Zhang H, Cornwell DG (1984) Fatty acid metabolism and cell proliferation V: evaluation of pathways for the regeneration of lipid peroxides. Lipids 19: 381-394
24. Mukai K, Itoh S, Morimoto H (1992) Stopped-flow kinetic study of vitamin E regeneration reaction with biological hydroquinones (reduced forms of ubiquinone, vitamin K, and tocopherolquinone) in solution. J Biol Chem 267: 22277-22281
25. Prochaska HJ, Talalay P (1986) Purification and characterization of two isofunctional forms of NAD(P)H:quinone reductase from mouse liver. J Biol Chem 261: 1372-1378
26. Shi H, Noguchi N, Niki E (1999) Comparative study on dynamics of antioxidative action of α-tocopheryl hydroquinone, ubiquinol, and α-tocopherol against lipid peroxidation. Free Radic Biol Med 27: 334-346
27. Siegel D, Bolton EM, Burr JA, Liebler DC, Ross D (1997) The reduction of α-tocopherolquinone by human NAD(P)H:quinone oxidoreducatse: the role of α-tocopherolhydroquinone as a cellular antioxidant. Mol Pharmacol 52: 300-305
28. Thornton DE, Jones KH, Jiang Z, Zhang H, Liu G, Cornwell DG (1995) Antioxidant and cytotoxic tocopheryl quinones in normal and cancer cells. Free Radic Biol Med 18: 963-976
29. 13C-NMR study. Liebigs Ann Chem 1239-1241
30. Yamamoto Y, Komuro E, Niki E (1990) Antioxidant activity of ubiquinol in solution and phosphatidylcholine liposome. J Nutr Sci Vitaminol (Tokyo) 36: 505-511