Genistein- and daidzein 7-O-β-D-glucuronic acid retain the ability to inhibit copper-mediated lipid oxidation of low density lipoprotein

Molecular Nutrition and Food Research

Volumn 52, Issue 12, 2008, Pages 1457-1466

  Kgomotso, Tiny ^a   Chiu, Francis ^b   Ng, Ken ^a  

^a MONASH UNIVERSITY   (Australia)

^b MONASH UNIVERSITY   (Australia)

Author keywords

Antioxidant activity; Daidzein glucuronide; Genistein glucuronide; Isoflavones metabolites; Lipid oxidation

Indexed keywords

ANTIOXIDANT; DAIDZEIN; GENISTEIN; GLUCURONIC ACID; ISOFLAVONE DERIVATIVE; LOW DENSITY LIPOPROTEIN; OXIDIZED LOW DENSITY LIPOPROTEIN;

ARTICLE; CHEMISTRY; DRUG EFFECT; HUMAN; LIPID PEROXIDATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ANTIOXIDANTS; GENISTEIN; GLUCURONIC ACIDS; HUMANS; ISOFLAVONES; LIPID PEROXIDATION; LIPOPROTEINS, LDL; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION;

EID: 57549101902     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.200800010     Document Type: Article

References (60)

1. Scalbert, A., Manach, C., Morand, C., Remesy, C., Dietary polyphenols and the prevention of diseases, Crit. Rev. Food Sci. Nutr. 2005, 45, 287-305.
2. Ho, H. M., Chen, R. Y., Leung, L. K., Chan, F. L., et al., Difference in flavonoid and isoflavone profile between soybean and soy leaf, Biomed. Pharmacother. 2002, 56, 289-295.
3. Kroon, P. A., Clifford, M. N., Crozier, A., Day, A. J., et al., How should we assess the effects of exposure to dietary polyphenols in vitro?, Am. J. Clin. Nutr. 2004, 80, 15-21.
4. Paganga, G., Rice-Evans, C. A., The identification of flavonoids as glycosides in human plasma, FEBS Lett. 1997, 401, 78-82.
5. Andlauer, W., Kolb, J., Frust, P., Absorption and metabolism of genistein in isolated rat small intestine, FEBS Lett. 2000, 475, 127-130.
6. Sfakianos, J., Coward, L., Kirk, M., Barnes, S., Intestinal uptake and biliary excretion of the isoflavone genistein in rats, J. Nutr. 1997, 127, 1260-1268.
7. Piskula, M. K., Yamakoshi, J., Iwai, Y., Daidzein and genistein but not their glucosides are absorbed from the rat stomach, FEBS Lett. 1999, 447, 287-291.
8. Aldercreutz, H., van der Wildt, J., Kinzel, J., Attalla, H., et al., Lignan and isoflavonoid conjugates in human urine, J. Steroid Biochem. Mol. Biol. 1995, 52, 97-103.
9. Hendrich, S., Bioavailability of isoflavones, J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2002, 777, 203-210.
10. Zhang, Y., Hendrich, S., Murphy, A., Glucuronides are the main isoflavone metabolites in women, Am. Soc. Nutr. Sci. J. Nutr. 2003, 133, 399-404.
11. Friedman, M., Brandon, D. L., Nutritional and health benefits of soy proteins, J. Agric. Food Chem. 2001, 49, 1069-1086.
12. Shelnutt, S. R., Cimino, C. O., Wiggings, P. A., Ronis, M. J. J., Badger, T. M., Pharmacokinetics of the glucuronide and sulphate conjugates of genistein and daidzein in men and women after consumption of a soy beverage, Am. J. Clin. Nutr. 2002, 76, 588-594.
13. Soucy, N. V., Parkinson, H. D., Sochaski, M. A., Borghoff, S. J., Kinetics of genistein and its conjugated metabolites in pregnant Sprague-Dawley rats following single and repeated genistein administration, Toxicol. Sci. 2005, 90, 230-240.
14. Pratt, D. E., Birac, P. M., Source of antioxidant activity of soybeans and soy products, J. Food Sci. 1979, 44, 1720-1722.
15. Wei, H., Wei, L., Frenkel, K., Bowen, R., Barnes, S., Inhibition of tumor promoter-induced hydrogen peroxide formation in vitro and in vivo by genistein, Nutr. Cancer 1993, 20, 1-12.
16. Record, I. R., Dreosti, I. E., McInerney, J. K., The antioxidant activity of genistein in vitro, J. Nutr. Biochem. 1995, 6, 481-485.
17. Lee, C. H., Yang, L., Xu, J. Z., Yeung, S. Y. V., et al., Relative antioxidant activity of soybean isoflavones and their glycosides, Food Chem. 2005, 90, 735-741.
18. Rufer, C. E., Kulling, S. E., Antioxidant activity of isoflavones and their major metabolites using different in vitro assays, J. Agric. Food Chem. 2006, 54, 2926-2931.
19. Jha, H. C., Von Recklinghausen, G., Zilliken, F., Inhibition of in vitro microsomal lipid peroxidation by isoflavonoids, Biochem. Pharmacol. 1985, 34, 1367-1369.
20. Arora, A., Nair, M. G., Strasburg, G. M., Antioxidant activities of isoflavones and their biological metabolites in a liposomal system, Arch. Biochem. Biophys. 1998, 356, 133-141.
21. Mitchell, J. H., Gardner, P. T., McPhail, D. B., Morrice, P. C., et al., Antioxidant efficacy of phytoestrogens in chemical and biological model systems, Arch. Biochem. Biophys. 1998, 360, 142-148.
22. Patel, R. P., Boersma, B. J., Crawford, J. H., Hogg, N., et al., Antioxidant mechanisms of isoflavones in lipid systems: Paradoxical effects of peroxyl radical scavenging, Free Radic. Biol. Med. 2001, 31, 1570-1581.
23. Wilson, T., March, H., William, B. J., Hou, Y., et al., Antioxidant effects of phyto-and synthetic-estrogens on cupric ion-induced oxidation of human low-density lipoproteins in vitro, Life Sci. 2002, 70, 2287-2297.
24. Turner, R., Baron, T., Wolffram, S., Minihane, A. M., et al., Effect of circulating forms of soy isoflavones on the oxidation of low density lipoprotein, Free Radic. Res. 2004, 38, 209-216.
25. Tikkanen, M. J., Wahala, K., Ojala, S., Vihma, V., Adlercreutz, H., Effect of soybean phytoestrogen intake on low density lipoprotein oxidation resistance, Proc. Natl. Acad. Sci. USA 1998, 95, 3106-3110.
26. Wiseman, H., O'Reilly, J. D., Aldercreutz, H., Mallet, A. I., et al., Isoflavone phytoestrogens consumed in soy decrease F2-isoprostane concentrations and increase resistance of low-density lipoprotein to oxidation in humans, Am. J. Clin. Nutr. 2000, 72, 395-400.
27. Hodgson, J. M., Croft, K. D., Puddey, I. B., Mori, T. A., Beilin, L. J., Soybean isoflavonoids and their metabolic products inhibit in vitro lipoprotein oxidation in serum, J. Nutr. Biochem. 1996, 7, 664-669.
28. Steiberg, D., Witztum, J. L., Is oxidative modification hypothesis relevant to human atherosclerosis? Do the antioxidant trails conducted to date refute the evidence?, Circulation 2002, 105, 2107-2111.
29. Chacko, B. K., Chandler, R. T., Mundhekar, A., Khoo, N., et al., Revealing anti-inflammatory mechanisms of soy isoflavones by flow: Modulation of leukocyte-endothelial cell interactions. Am. J. Physiol. Heart Circ. Physiol. 2005, 289, H908-H915.
30. Fang, Y. C., Chen, B. H., Huang, R. F. S., Lu, Y. F., Effect of genistein supplementation on tissue genistein and lipid peroxidation of serum, liver and low-density lipoprotein in hamsters, J. Nutr. Biochem. 2004, 15, 142-148.
31. Kerry, B., Abbey, M., The isoflavone genistein inhibits copper and peroxyl radical mediated low density lipoprotein oxidation, Atherosclerosis 1998, 140, 341-347.
32. Meng, Q. H., Lewis, P., Wahala, K., Aldercreutz, H., Tikkamen, M. J., Incorporation of esterified soya bean isoflavones with antioxidant activity into low-density lipoprotein, Biochem. Biophys. Acta 1999, 1438, 369-376.
33. Moon, J.-H., Tsushida, T., Nakahara, K., Terao, J., Identification of quercetin 3-O-[beta]-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin, Free Radic. Biol. Med. 2001, 30, 1274-1285.
34. Akhtar, M. H. A., Abdel-Aal, E. S. M., Recent advances in the analyses of phytoestrogens and their role in human health, Curr. Pharm. Anal. 2006, 2, 183-193.
35. Arts, M. J. T. J., Sebastiaan, D. J., Voss, H.-P., Haenen, G. R. M. M., Bast, A., A new approach to assess the total antioxidant capacity using the TEAC assay, Food Chem. 2004, 88, 567-570.
36. Benzie, I. F. F., Strain, J. J., The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power", Anal. Biochem. 1996, 239, 70-76.
37. Puhl, H. G., Waeg, G., Esterbauer, H., Methods to determine oxidation of low-density lipoproteins, Methods Enzymol. 1994, 233, 425-441.
38. Cren-Olive, C., Teissier, E., Duriez, P., Rolando, C., Effect of catechin O-methylated metabolites and analogues on human LDL oxidation, Free Radic. Biol. Med. 2003, 34, 850-855.
39. Wright, J. S., Johnson, E. R., Dilabio, G. A., Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants, J. Am. Chem. Soc. 2001, 123, 1173-1183.
40. Rice-Evans, C. A., Miller, N. J., Paganga, G., Structure-antioxidant activity relationships of flavonoids and phenolic acids, Free Radic. Biol. Med. 1996, 20, 933-956.
41. Soobrattee, M. A., Neergheen, V. S., Luximon-Ramma, A., Aruoma, O., Bahrorun, T., Phenolics as potential antioxidant therapeutic agents: Mechanism and actions, Mutat. Res. 2005, 579, 200-213.
42. Kao, T. H., Chen, B. H., Functional components in soybean cake and their effects on antioxidant activity, J. Agric. Food Chem. 2006, 54, 7544-7555.
43. Roginsky, V., Lissi, E. A., Review of methods to determine chain-breaking antioxidant activity in food, Food Chem. 2005, 92, 235-254.
44. Osakabe, N., Polyphenols and atherosclerosis, Bitamin 2006, 80, 275-280.
45. Lamb, D. J., Mitchinson, M. J., Learke, D. S., Transition metal ions within atherosclerotic lesions can catalyse the oxidation of low density lipoprotein by macrophages, FEBS Lett. 1995, 374, 12-16.
46. Abuja, P. M., Esterbaurer, H., Simulation of lipid peroxidation in low-density lipoprotein by a basic "skeleton" of reactions, Chem. Res. Toxicol. 1995, 8, 753-763.
47. Brukitt, M. J., A critical overview of the chemistry of copper-dependent low density lipoprotein oxidation: Roles of lipid hydroperoxide, a-tocopherol, thiols and ceruloplasmin, Arch. Biochem. Biophics. 2001, 394, 117-135.
48. Vedavanam, K., Srijayanta, S. O., Reilly, J., Raman, A., Wiseman, H., Antioxidant action and potential antidiabetic properties of an isoflavonoid-containing soyabean phytochemical extract (SPE), Phytother. Res. 1999, 13, 601-608.
49. Zhou, B., Miao, Q., Yang, L., Liu, Z. L., Antioxidative effects of flavonols and their glycosides against the free-radical-induced peroxidation of linoleic acid in solution and in micelles, Chemistry 2005, 11, 680-691.
50. Hou, L., Zhou, B., Yang, L., Liu, Z. L., Inhibition of human low density lipoprotein oxidation by flavonols and their glycosides, Chem. Phys. Lipids 2004, 129, 209-219.
51. Hou, L., Zhou, B., Yang, L., Liu, Z. L., Inhibition of free radical initiated peroxidation of human erythrocyte ghosts by flavonols and their glycosides, Org. Biomol. Chem. 2004, 2, 1419-1423.
52. Dai, F., Miao, Q., Zhou, B., Yang, L., Lia, Z. L., Protective effects of flavonols and their glycosides against free radical-induced oxidative haemolysis of red blood cells, Life Sci. 2006, 78, 2488-2493.
53. Shirail, M., Kawai1, Y., Yamanishi, R., Kinoshita, T., et al., Effect of a conjugated quercetin metabolite, quercetin 3-glucuronide, on lipid hydroperoxide-dependent formation of reactive oxygen species in differentiated PC-12 cells, Free Radic. Res. 2006, 40, 1047-1053.
54. Cao, G., Sofic, E., Prior, R. L., Antioxidant and prooxidant behaviour of flavonoids: Structure-activity relationship, Free Radic. Biol. Med. 1997, 22, 749-760.
55. Jain, A., Martin, M. C., Parveen, N., Khan, N. U., et al., Reactivities of flavonoids with different hydroxyl substituents for the cleavage of DNA in the presence of Cu(II), Phytother. Res. 1999, 13, 609-612.
56. Mira, L., Fernandez, M. T., Santos, M., Rocha, R., et al., Interactions of flavonoids with iron and copper ions: A mechanism for their antioxidant activity, Health Sci. 2002, 36, 1199-1208.
57. Zheng, L. F., Wei, Q. Y., Cai, Y. J., Fang, J. G., et al., DNA damage induced by resveratrol and its synthetic analogues in the presence of Cu(II) ions: Mechanism and structure-activity relationship, Free Radic. Biol. Med. 2006, 41, 1807-1816.
58. Win, W., Caoa, Z. X., Peng, X. X., Trush, M. A., Li, Y. B., Different effects of genistein and resveratrol on oxidative DNA damage in vitro, Mutat. Res. 2002, 513, 113-120.
59. Cheng, Z. Y., Ren, J., Li, Y. Z., Chang, W. B., Chen, Z. D., Establishment of a quantitative structure-activity relationship model for evaluating and predicting the protective potentials of phenolic antioxidants on lipid peroxidation, J. Pharm. Sci. 2003, 92, 475-484.
60. Abuja, P. M., Liebmann, P., Hayn, M., Schauenstein, K., Esterbauer, H., Antioxidant role of melatonin in lipid oxidation of human LDL, FEBS Lett. 1997, 413, 289-293.