Albumin-bound quercetin repairs vitamin E oxidized by apolipoprotein radicals in native HDL3 and LDL

Biochemistry

Volumn 46, Issue 49, 2007, Pages 14305-14315

  Filipe, Paulo ^a,b   Patterson, Larry K ^b,c   Bartels, David M ^c   Hug, Gordon L ^c   Freitas, Joäo P ^a   Mazière, Jean Claude ^b,d,e   Santus, René ^b,f   Morlière, Patrice ^b,d,e  

^a HOSPITAL DE SANTA MARIA   (Portugal)

^b INSERM   (France)

^c UNIVERSITY OF NOTRE DAME   (United States)

^d UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^e AMIENS UNIVERSITY HOSPITAL   (France)

^f MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONS; LIPIDS; OXIDATION; PHYSIOLOGY; SPECTROSCOPIC ANALYSIS; VITAMINS;

APOLIPOPROTEIN RADICALS; HUMAN SERUM ALBUMIN (HSA); QUERCETIN BOUND; SELECTIVE ONE-ELECTRON OXIDATION;

PROTEINS;

ALBUMIN; ALPHA TOCOPHEROL; APOLIPOPROTEIN; APOLIPOPROTEIN A1; APOLIPOPROTEIN A2; HIGH DENSITY LIPOPROTEIN 3; LOW DENSITY LIPOPROTEIN; QUERCETIN;

ARTICLE; FLUOROMETRY; KINETICS; MATHEMATICAL ANALYSIS; PRIORITY JOURNAL; RADIOLYSIS; SPECTROSCOPY;

APOLIPOPROTEIN A-I; APOLIPOPROTEIN A-II; FREE RADICALS; HUMANS; KINETICS; LIPOPROTEINS, HDL3; LIPOPROTEINS, LDL; OXIDATION-REDUCTION; PROTEIN BINDING; QUERCETIN; SERUM ALBUMIN; TRYPTOPHAN; TYROSINE; VITAMIN E;

EID: 37049030246     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi701419d     Document Type: Article

References (44)

1. Steinbrecher, U. P., Zhang, H. F., and Lougheed, M. (1990) Role of oxidatively modified LDL in atherosclerosis, Free Radical Biol. Med. 9, 155-168.
2. Mattson, M. P., Duan, W., Pedersen, W. A., and Culmsee, C. (2001) Neurodegenerative disorders and ischemic brain diseases, Apoptosis 6, 69-81.
3. Davies, K. J. (1987) Protein damage and degradation by oxygen radicals. I. General aspects, J. Biol. Chem. 262, 9895-9901.
4. Hawkins, C. L., Pattison, D. I., and Davies, M. J. (2003) Hypochlorite-induced oxidation of amino acids, peptides and proteins, Amino Acids 25, 259-274.
5. Salmon, S., Mazière, J.-C., Santus, R., Morlière, P., and Bouchemal, N. (1990) UVB-induced photoperoxidation of lipids of human low and high density lipoproteins. A possible role of tryptophan residues, Photochem. Photobiol. 52, 541-545.
6. Goldstein, J. L., and Brown, M. S. (1977) The low-density lipoprotein pathway and its relation to atherosclerosis, Annu. Rev. Biochem. 46, 897-930.
7. Zheng, L., Settle, M., Brubaker, G., Schmitt, D., Hazen, S. L., Smith, J. D., and Kinter, M. (2005) Localization of nitration and chlorination sites on apolipoprotein A-I catalyzed by myeloperoxidase in human atheroma and associated oxidative impairment in ABCA1-dependent cholesterol efflux from macrophages, J. Biol. Chem. 280, 38-47.
8. Parthasarathy, S., Barnett, J., and Fong, L. G. (1990) High-density lipoprotein inhibits the oxidative modification of low-density lipoprotein, Biochim. Biophys. Acta 1044, 275-283.
9. Babior, B. M. (1978) Oxygen-dependent microbial killing by phagocytes (first of two parts), N. Engl. J. Med. 298, 659-668.
10. Ghibaudi, E., and Laurenti, E. (2003) Unraveling the catalytic mechanism of lactoperoxidase and myeloperoxidase, Eur. J. Biochem. 270, 4403-4412.
11. Francis, G. A., Mendez, A. J., Bierman, E. L., and Heinecke, J. W. (1993) Oxidative tyrosylation of high density lipoprotein by peroxidase enhances cholesterol removal from cultured fibroblasts and macrophage foam cells, Proc. Natl. Acad. Sci. U.S.A. 90, 6631-6635.
12. Solar, S., Solar, W., and Getoff, N. (1984) Resolved multisite OH-attack on aqueous tryptophan studied by pulse radiolysis, Radiat. Phys. Chem. 23, 371-376.
13. Peng, D.-Q., Wu, Z., Brubaker, G., Zheng, L., Settle, M., Gross, E., Kinter, M., Hazen, S. L., and Smith, J. D. (2005) Tyrosine modification is not required for myeloperoxidase-induced loss of apolipoprotein A-I functional activities, J. Biol. Chem. 280, 33775-33784.
14. Giessauf, A. B., van Wickern, B., Simat, T., Steinhart, H., and Esterbauer, H. (1996) Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of lipid peroxidation, FEBS Lett. 389, 136-140.
15. Filipe, P., Morlière, P., Patterson, L. K., Hug, G. L., Mazière, J.-C., Mazière, C., Freitas, J. P., Fernandes, A., and Santus, R. (2002) Repair of amino acid radicals of apolipoprotein B100 of low-density lipoproteins by flavonoids. A pulse radiolysis study with quercetin and rutin, Biochemistry 41, 11057-11064.
16. 3. Comparison with LDL. A time-resolved spectroscopic analysis, Biochemistry 46, 5226-5237.
17. de Whalley, C. V., Rankin, S. M., Hoult, J. R., Jessup, W., and Leake, D. S. (1990) Flavonoids inhibit the oxidative modification of low density lipoproteins by macrophages, Biochem. Pharmacol. 39, 1743-1750.
18. Boulton, D. W., Walle, U. K., and Walle, T. (1998) Extensive binding of the bioflavonoid quercetin to human plasma proteins, J. Pharm. Pharmacol. 50, 243-249.
19. Havel, R. J., Eder, H. A., and Bragdon, J. H. (1955) The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum, J. Clin. Invest. 34, 1345-1353.
20. Atmeh, R. F., Shepherd, J., and Packard, C. J. (1983) Subpopulations of apolipoprotein A-I in human high-density lipoproteins their metabolic properties and response to drug therapy, Biochim. Biophys. Acta 751, 175-188.
21. Filipe, P., Haigle, J., Freitas, J. P., Fernandes, A., Mazière, J.-C, Mazière, C., Santus, R., and Morlière, P. (2002) Anti- and prooxidant effects of urate in copper-induced low-density lipoprotein oxidation, Eur. J. Biochem. 269, 5474-5483.
22. Sowell, A. L., Huff, D. L., Yeager, P. R., Caudill, S. P., and Gunter, E. W. (1994) Retinol, α-tocopherol, lutein/zeaxanthin, α- cryptoxanthin, lycopene, α-carotene, trans-β-carotene, and four retinyl esters in serum determined simultaneously by reversed-phase HPLC with multiwavelength detection, Clin. Chem. 40, 411-416.
23. Aksnes, L. (1994) Simultaneous determination of retinol, alpha-tocopherol, and 25-hydroxyvitamin D in human serum by high performance liquid chromatography, J. Pediatr. Gastroenterol. Nutr. 18, 339-343.
24. Thurnham, D. I., Smith, E., and Flora, P. S. (1988) Concurrent liquid-chromatography assay of retinol, α-tocopherol, β-carotene, α-carotene, lycopene and β-cryptoxanthin in plasma, with tocopherol acetate as internal standard, Clin. Chem. 34, 377-381.
25. Dufour, C., and Dangles, O. (2005) Flavonoid-serum albumin complexation: determination of binding constants and binding sites by fluorescence spectroscopy, Biochim. Biophys. Acta 1721, 164-173.
26. Patterson, L. K., and Lilie, J. A. (1974) Computer-controlled pulse radiolysis system, Int. J. Radiat. Phys. Chem. 6, 129-141.
27. Hug, G. L., Wang, Y., Schoneich, C., Jiang, P. Y., and Fessenden, R. W. (1999) Multiple time scale in pulse radiolysis: applications to bromide solutions and dipeptides, Radiat. Phys. Chem. 54, 559-566.
28. 2O-saturated aqueous solutions, J. Phys. Chem. 84, 2088-2089.
29. Filipe, P., Morlière, P., Patterson, L. K., Hug, G. L., Mazière, J.-C., Freitas, J. P., Fernandes, A., and Santus, R. (2004) Oxygen-copper (II) interplay in the repair of semi-oxidized urate by quercetin bound to human serum albumin, Free Radical Res. 38, 295-301.
30. Manach, C., Morand, C., Texier, O., Favier, M. L., Agullo, G., Demigné, C., Régérat, F., and Rémésy, C. (1995) Quercetin metabolites in plasma of rats fed diets containing rutin or quercetin, J. Nutr. 125, 1911-1922.
31. Farhataziz, and Ross, A. B. (1977) Selected specific rates of reactions of transients from water in aqueous solutions. III. Hydroxyl radical and perhydroxyl radical and their radical ions, NSRDS-NBS 59.
32. Davies, M. J., Forni, L. G., and Wilson, R. L. (1988) Vitamin E analogue Trolox C. E.S.R. and pulse-radiolysis studies of free-radical reactions, Biochem. J. 255, 513-522.
33. Jovanovic, S. V., Steenken, S., Simic, M. G., and Hara, Y. (1998) Antioxidant properties of flavonoids: reduction potentials and electronic transfer reactions of flavonoid radicals, in Flavonoids in Health and Disease (Rice-Evans, C., and Packer, L., Eds.), pp 137-161, Marcel Dekker, New York.
34. Filipe, P., Morlière, P., Patterson, L. K., Hug, G. L., Mazière, J.-C., Mazière, C., Freitas, J. P., Fernandes, A., and Santus, R. (2002) Mechanisms of flavonoid repair reactions with amino acid radicals in models of biological systems: a pulse radiolysis study in micelles and human serum albumin, Biochim. Biophys. Acta 1572, 150-162.
35. Jovanovic, S. V., Steenken, S., Tosic, M., Marjanovic, B., and Simic, M. G. (1994) Flavonoids as antioxidants, J. Am. Chem. Soc. 116, 4846-4851.
36. Noguchi, N., and Niki, E. (1998) Dynamics of vitamin E action against LDL oxidation, Free Radical Res. 28, 561-572.
37. Mullen, W., Edwards, C. A., and Crozier, A. (2006) Absorption, excretion and metabolite profiling of methyl-, glucuronyl-, glucosyl and sulpho-conjugates of quercetin in human plasma and urine after ingestion of onions, Br. J. Nutr. 96, 107-116.
38. Manach, C., Morand, C., Crespy, V., Demigné, C., Texier, O., Régérat, F., and Rémésy, C. (1998) Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties, FEBS Lett. 426, 331-336.
39. Janisch, K. M., Williamson, G., Needs, P., and Plumb, G. W. (2004) Properties of quercetin conjugates: modulation of LDL oxidation and binding to human serum albumin, Free Radical Res. 38, 877-884.
40. Cadenas, E., Merényi, G., and Lind, J. (1989) Pulse radiolysis study on the reactivity of Trolox C phenoxyl radical with superoxide anion, FEBS Lett. 253, 235-238.
41. Reyftmann, J.-P., Santus, R., Mazière, J.-C., Morlière, P., Salmon, S., Candide, C., Mazière, C., and Haigle, J. (1990) Sensitivity of tryptophan and related compound to oxidation induced by lipid autoperoxidation. Application to human serum low and high density lipoproteins, Biochim. Biophys. Acta 1042, 159-167.
42. Kalyanaraman, B., Darley-Usmar, V., Struck, A., Hogg, N., and Parthasarathy, S. (1995) Role of apolipoprotein B-derived radical and alpha-tocopheroxyl radical in peroxidase-dependent oxidation of low density lipoprotein, J. Lipid Res. 36, 1037-1045.
43. Rice-Evans, C. A., Miller, N. J., and Paganga, G. (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids, Free Radical Biol. Med. 20, 933-956.
44. Mayer, B., Schumacher, M., Brandstatter, H., Wagner, F. S., and Hermetter, A. (2001) High-throughput fluorescence screening of antioxidative capacity in human serum, Anal. Biochem. 297, 144-153.