Anti- and pro-oxidant effects of quercetin in copper-induced low density lipoprotein oxidation: Quercetin as an effective antioxidant against pro-oxidant effects of urate

European Journal of Biochemistry

Volumn 271, Issue 10, 2004, Pages 1991-1999

  Filipe, Paulo ^a   Haigle, Josiane ^b   Silva, João Nuno ^a   Freitas, João ^a   Fernandes, Afonso ^a   Mazìère, Jean Claude ^c   Mazière, Cécile ^c   Santus, René ^b,d   Morlière, Patrice ^b,d  

^a HOSPITAL DE SANTA MARIA   (Portugal)

^b MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^c UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^d SAINT LOUIS HOSPITAL   (France)

Author keywords

Antioxidant; Copper; Flavonoid; Low density lipoprotein; Oxidative stress; Pro oxidant; Urate

Indexed keywords

COPPER; LOW DENSITY LIPOPROTEIN; QUERCETIN; URATE;

ANTIOXIDANT ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; ELECTRON TRANSPORT; OXIDATION; OXIDATION REDUCTION POTENTIAL; PRIORITY JOURNAL; PULSE RADIOLYSIS;

ALKENES; ANTIOXIDANTS; CAROTENOIDS; COPPER; HUMANS; KINETICS; LIPID PEROXIDATION; LIPOPROTEINS, LDL; MALONDIALDEHYDE; OXIDANTS; OXIDATION-REDUCTION; QUERCETIN; URIC ACID;

EID: 2442710045     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.2004.04111.x     Document Type: Article

References (69)

1. Hertog, M.G., Feskens, E.J., Hollman, P.C., Katan, M.B. & Kromhout, D. (1993) Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study. Lancet 342, 1007-1011.
2. Knekt, P., Jarvinen, R., Reunanen, A. & Maatela, J. (1996) Flavonoid intake and coronary mortality in Finland: a cohort study. Br. Med. J. 312, 478-481.
3. Kuo, S.-M. (1997) Dietary flavonoid and cancer prevention: evisence and potential mechanism. Crit. Rev. Oncog. 8, 47-69.
4. Manach, C., Morand, C., Crespy, V., Demigné, C., Texier, Régérat, F. & Rémésy, C. (1998) Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett. 426, 331-336.
5. Hollman, P.C.H., Gaag, M.V.D., Mengelers, M.J.B., van Trijp, J.M.P., de Vries, J.H.M. & Katan, M.B. (1996) Absorption and disposition kinetics of the dietary antioxidant quercetin in man. Free Radic. Biol. Med. 21, 703-707.
6. Parthasarathy, S., Printz, D.J., Bloyd, D., Joy, L. & Steinberg, D. (1986) Macrophage oxidation of low density lipoprotein generates a modified form recognized by the scavenger receptor. Arteriosclerosis 6, 505-510.
7. Steinbrecher, U.P., Lougheed, M., Kwan, W.C. & Dirks, M. (1989) Recognition of oxidized low density lipoprotein by the scavenger receptor of macrophages results from derivatization of apolipoprotein B by products of fatty acid peroxidation. J. Biol. Chem. 264, 15216-15223.
8. Steinberg, D., Parthasarathy, S., Caew, T.E., Khoo, J.C. & Witzum, J.L. (1989) Beyond cholesterol: modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320, 915-924.
9. Witzum, J.L. (1994) The oxidation hypothesis of atherosclerosis. Lancet 344, 793-795.
10. Bors, W., Michel, C. & Saran, M. (1994) Flavonoid antioxidants: rate constants for reactions with oxygen radicals. In Methods in Enzymology: Oxygen Radicals in Biological Systems (Packer, L., ed.), Part D, pp. 420-429. Academic Press, San Diego, CA.
11. Jovanovic, S., Steenken, S., Rosic, M., Marjanovic, B. & Simic, M. (1994) Flavonoids as antioxidants. J. Am. Chem. Soc. 116, 4846-4851.
12. Jovanovic, S., Steenken, S., Simic, M. & 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. & Packer, L., eds), pp. 137-161. Marcel Dekker, New York.
13. Morel, G., Lescoat, P., Cogrel, O., Sergent, O., Pasdeloup, N., Brissot, P. & Cillard, J. (1993) Antioxidant and iron-chelating activities of the flavonoids catechin, quercetin and diosmetin on iron-loaded rat hepatocyte cultures. Biochem. Pharmacol. 45, 13-19.
14. Moran, J., Klucas, R., Grayer, R., Abian, R.J. & Becana, M. (1997) Complexes of iron with phenolic compounds from soybean nodules and other legume tissues: prooxidant and antioxidant properties. Free Radic. Biol. Med. 22, 861-870.
15. 2+ ions: implications for their antioxidant properties. Biochem. J. 330, 1173-1178.
16. Yoshino, M. & Murakami, K. (1998) Interaction of iron with polyphenolic compounds: application to antioxidant characterization. Anal. Biochem. 257, 40-44.
17. Chimi, R., Cillard, J., Cillard, P. & Rahmani, M. (1991) Peroxyl and hydroxyl radical scavenging activity of some natural phenolic antioxidants. J. Am. Oil Chemists Soc. 68, 307-312.
18. Salah, N., Miller, N., Paganga, G., Tijburg, L., Bolwell, G. & Rice-Evans, C. (1995) Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants. Arch. Biochem. Biophys. 332, 339-346.
19. Tikkanen, M., Wähälä, K., Ojala, S., Vihma, V. & Adlercreutz, H. (1998) Effect of soybean phytoestrogen intake on LDL oxidation resistance. Proc. Natl Acad. Sci. USA 95, 3106-3110.
20. Boulton, D., Walle, U.K. & Walle, T. (1998) Extensive biding of the bioflavonoid quercetin to human plasma proteins. J. Pharm. Pharmacol. 50, 243-249.
21. Clemetson, C. & Andersen, L. (1966) Plant polyphenols as antioxidants for ascorbic acid. Ann. NY Acad. Sci. 136, 339-378.
22. Harper, K.A., Morton, A.D. & Rolfe, E.J. (1969) The phenolic compounds of black currant juice and their protective effect on ascorbic acid. III. The mechanism of ascorbic acid oxidation and its inhibition by flavonoids. J. Food Technol. 4, 255-267.
23. Sorata, Y., Takahama, U. & Kimura, M. (1988) Cooperation of quercetin with ascorbate in the protection of photosensitized lysis of human erythrocytes in the presence of hematoporphyrin. Photochem. Photobiol. 48, 195-199.
24. Hodnick, W.F., Milosavlievic, E.B., Nelson, J. & Pardini, R. (1988) Electrochemistry of flavonoids: relationships between redox potential, inhibition of mitochondrial respiration, and production of oxygen radicals by flavonoids. Biochem. Pharmacol. 37, 2607-2611.
25. Negre-Salvayre, A., Affany, A., Hariton, C. & Salvayre, R. (1991) Additional antilipoperoxidant activities of alpha-tocopherol and ascorbic acid on membrane like systems are potentiated by rutin. Pharmacology 42, 262-272.
26. Kandaswami, C., Perkins, E., Soloniuk, D.S., Drzewiecki, G. & Middleton, E. (1993) Ascorbic acid-enhanced antiproliferative effect of flavonoids on squamous cell carcinoma in vitro. Anti-Cancer Drug 4, 91-96.
27. Laranjinha, J., Vieira, O., Madeira, V. & Almeida, L. (1995) Two related phenolic antioxidants with opposite effects on vitamin E content in low density lipoproteins oxidized by ferrylmyoglobin: consumption vs regeneration. Arch. Biochem. Biophys. 323, 373-381.
28. Lotito, S. & Fraga, C. (1998) (+)-Catechin prevents human plasma oxidation. Free Radic. Biol. Med. 24, 435-441.
29. Rusznyak, S. & Szent-Györgyi, A. (1936) Vitamin P: flavonols as vitamins. Nature 138, 27.
30. Bentsath, A., Rusznyak, S. & Szent-Györgyi, A. (1936) Vitamin nature of flavones. Nature 138, 798.
31. Esterbauer, H., Gebicki, J., Puhl, H. & Jürgens, G. (1992) The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radic. Biol. Med. 13, 341-390.
32. Davies, K.J.A., Sevanian, A., Muakkassah-Kelly, S.F. & Hochstein, P. (1986) Uric acid iron ion complexes: a new aspect of the antioxidant functions of uric acid. Biochem. J. 235, 747-754.
33. -) in aqueous solution. J. Phys. Chem. Ref. Data 17, 513-886.
34. Simic, M.G. & Jovanovic, S.V. (1989) Antioxidation mechanisms of uric acid. J. Am. Chem. Soc. 111, 5778-5782.
35. Becker, B.F. (1993) Towards the physiological function of uric acid. Free Radic. Biol. Med. 14, 615-631.
36. Filipe, P., Haigle, J., Freitas, J.P., Fernandes, A., Mazière, J.-C., Mazière, C., Santus, R. & Morlière, P. (2002) Anti- and pro-oxidant effects of urate in copper-induced low-density lipoprotein oxidation. Eur. J. Biochem. 269, 5474-5483.
37. Filipe, P., Lança, V., Silva, J.N., Morlière, P., Santus, R. & Fernandes, A. (2001) Flavonoids and urate antioxidant interplay in plasma oxidative stress. Mol. Cell. Biochem. 221, 79-87.
38. Havel, R.J., Eder, H.A. & Bragdon, J.H. (1955) The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum. J. Clin. Invest. 34, 1345-1353.
39. Peterson, G.L. (1977) Simplification of the protein assay method of Lowry et al. which is more generally applicable. Anal. Biochem. 83, 346-356.
40. Corongiu, F.P., Banni, S. & Dessi, M.A. (1989) Conjugated dienes detected in tissue lipid extracts by second derivative spectrophotometry. Free Radic. Biol. Med. 1, 183-186.
41. Esterbauer, H., Lang, J., Zadravec, S. & Slater, T.F. (1984) Detection of malonaldehyde by high performance liquid chromatography. In Methods in Enzymology: Oxygen Radicals in Biological Systems (Packer, L., ed.), pp. 319-328. Academic Press, Orlando, FL.
42. Behrens, W.A., Thompson, J.N. & Madère, R. (1982) Distribution of alpha-tocopherol in human plasma lipoproteins. Am. J. Clin. Nutr. 35, 691-696.
43. Thurnham, D.I., Smith, E. & 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.
44. Windholz, M. (1976) The Merck Index. An Encyclopedia of Chemicals and Drugs, 9 edn. Merck. Inc, Rahway, NJ.
45. Patel, R.P. & Darley-Usmar, V.M. (1999) Molecular mechanisms of the copper dependent oxidation of low-density lipoprotein. Free Rad. Res. 30, 1-9.
46. Berliner, J.A., Territo, M.C., Sevanian, A., Ramin, S., Kim, J.A., Bamshad, B., Esterson, M. & Fogelman, A.M. (1990) Minimally modified low density lipoproteins stimulates monocyte endothelial interactions. J. Clin. Invest. 85, 1260-1266.
47. Carrero, P., Ortega, H., Martínez-Botas, J., Gómez- Coronado, D. & Larusción, M.A. (1998) Flavonoid-induced ability of minimally modified low-density lipoproteins to support lymphocyte proliferation. Biochem. Pharmacol. 55, 1125-1129.
48. Rice-Evans, C., Leake, D., Bruckdorfer, R. & Diplock, A.T. (1996) Practical approaches to low density lipoprotein oxidation: whys, wherefores and pittfalls. Free Radic. Res. 25, 285-311.
49. Halliwell, B. (1995) Oxidation of low density lipoproteins: questions of initiation, propagation and the effect of antioxidants. Am. J. Clin. Nutr. 61, 670S-677S.
50. Esterbauer, H. & Jurgens, G. (1993) Mechanistic and genetic aspects of susceptibility of LDL to oxidation. Curr. Opin. Lipid. 4, 114-124.
51. Proudfoot, J.M., Croft, K.D., Puddey, I.B. & Belli, L.J. (1997) The role of copper reduction by α-tocopherol in low-density lipoprotein oxidation. Free Radic. Biol. Med. 23, 720-728.
52. Perugini, C., Seccia, M., Albano, E. & Bellomo, G. (1997) The dynamic reduction of Cu (II) to Cu (I) and not Cu (I) availability is a sufficient trigger for low density liporpotein oxidation. Biochim. Biophys. Acta 1347, 191-198.
53. Giessauf, A., Steiner, E. & Esterbauer, H. (1995) Early destruction of tryptophan residues of apolipoprotein B is a vitamin E-independent process during copper-mediated oxidation of LDL. Biochim. Biophys. Acta 1256, 221-232.
54. Maiorino, M., Zamburlini, A., Roveri, A. & Ursini, F. (1995) Copper-induced lipid peroxidation in liposomes, micelles and LDL: which is the role of vitamin E? Free Radic. Biol. Med. 18, 67-74.
55. Yoshida, Y., Tsuchida, J. & Niki, E. (1995) Interaction of α-tocopherol with copper and its effects on lipid peroxidation. Biochim. Biophys. Acta 1200, 85-92.
56. Kontush, A., Meyer, S., Finck, B., Kohlschutter, A. & Beisiegel, U. (1996) α-Tocopherol as a reductant for Cu (II) in human lipoproteins. Triggering role of in the initiation of lipid peroxidation. J. Biol Chem. 271, 11106-11112.
57. Perugini, C., Seccia, M., Bagnati, M., Cau, C., Albano, E. & Bellomo, G. (1998) Different mechanisms are progressively recruited to promote Cu (II) reduction by isolated human low density lipoprotein undergoing oxidation. Free Radic. Biol. Med. 25, 519-528.
58. Lynch, S.M. & Frei, B. (1995) Reduction of copper not iron, by human low density lipoprotein. J. Biol. Chem. 270, 5158-5163.
59. Patel, R., Svistunenko, D., Wilson, M.T. & Darley-Usmar, V. (1997) Reduction of Cu (II) by lipid hydroperoxides: implications for the copper-induced oxidation of low-density lipoprotein. Biochem. J. 322, 425-433.
60. Pecci, L., Montefoschi, G. & Cavallini, D. (1997) Some new details on the copper-hydrogen peroxide interaction. Biochem. Biophys. Res. Commun. 235, 264-267.
61. McAnlis, G.T., McEneny, J., Pearce, J. & Young, I.S. (1999) Absorption and antioxidant effects of quercetin from onions, in man. Eur. J. Clin. Nutrit. 53, 92-96.
62. 2+-induced low density lipoprotein in propagation phase. FEBS Lett. 401, 230-234.
63. Otero, P., Viana, M., Herrera, E. & Bonet, B. (1997) Antioxidant and prooxidant effects of ascorbic acid, dehydroascorbic acid and flavonoids on LDL submitted to different degrees of oxidation. Free Radic. Res. 27, 619-626.
64. 2+-induced low density lipoprotein oxidation. FEBS Lett. 405, 186-190.
65. Abuja, P.M. (1999) Ascorbate prevents prooxidant effects of urate in oxidation of human low density lipoprotein. FEBS Lett. 446, 305-308.
66. Bagnati, M., Perugini, C., Cau, C., Bordone, R., Albano, E. & Bellomo, G. (1999) When and why a water-soluble antioxidant becomes pro-oxidant during copper-induced low-density lipoprotein oxidation: a study using uric acid. Biochem. J. 340, 143-152.
67. Jovanovic, S.V., Steenken, S., Hara, Y. & Simic, M.G. (1996) Reduction potentials of flavonoid and model phenoxy radicals: which ring in flavonoids is responsible for antioxidant activity? J. Chem. Soc. Perkin Trans. 2, 2797-2504.
68. Santus, R., Patterson, L.K., Filipe, P., Morlière, P., Hug, G.L., Fernandes, A. & Mazière, J.-C. (2001) Redox reactions of the urate radical/urate couple with the superoxide radical anion, the tryptophan neutral radical and selected flavonoids in neutral aqueous solutions. Free Radic. Res. 35, 129-136.
69. Filipe, P., Morlière, P., Patterson, L.K., Hug, G.L., Mazière, J.-C., Freitas, J.P., Fernandes, A. & Santus, R. (2004) Oxygen-copper (II) interplay in the repair of semi-oxidized urate by quercetin bound to human serum albumin. Free Rad. Res. 38, 295-301.