Influence of B-ring hydroxylation on interactions of flavonols with bovine serum albumin

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 7, 2008, Pages 2350-2356

  Xiao, Jianbo ^a,b   Suzuki, Makiko ^b   Jiang, Xinyu ^a   Chen, Xiaoqing ^a   Yamamoto, Koichiro ^b   Ren, Fenglian ^a   Xu, Ming ^a  

^a CENTRAL SOUTH UNIVERSITY   (China)

^b Department of Nutrition   (China)

Author keywords

Antioxidant activity; Bovine serum albumin; Chromatographic retention factor; Flavonol; Fluorescence quenching; Free radical scavenger activity; Partition coefficient

Indexed keywords

BOVINE SERUM ALBUMIN; FLAVONOL DERIVATIVE;

ARTICLE; BINDING SITE; CHEMISTRY; HYDROGEN BOND; HYDROXYLATION; METABOLISM; PHYSICAL CHEMISTRY; SPECTROFLUOROMETRY; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET SPECTROPHOTOMETRY;

BINDING SITES; CHEMISTRY, PHYSICAL; FLAVONOLS; HYDROGEN BONDING; HYDROXYLATION; SERUM ALBUMIN, BOVINE; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; STRUCTURE-ACTIVITY RELATIONSHIP;

BOVINAE;

EID: 42449128003     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf7037295     Document Type: Article

References (34)

1. Bravo, M. N.; Silva, S.; Coelho, A. V.; Boas, L. V.; Bronze, M. R. Analysis of phenolic compounds in Muscatel wines produced in Portugal. Anal. Chim. Acta 2006, 563, 84-92.
2. Volpi, N.; Bergonzini, G. Analysis of flavonoids from propolis by on-line HPLC-electrospray mass spectrometry. J. Pharm. Biomed. 2006, 42, 354-361.
3. Woodman, O. L.; Meeker, W. F.; Boujaoude, M. Vasorelaxant and antioxidant activity of flavonols and flavones: Structure-activity relationships. J. Cardiovasc. Pharm. 2005, 46, 302-309.
4. Heijnen, C. G. M.; Haenen, G.R.M.M.; van Acker, F. A. A.; van der Vijgh, W. J. F.; Bast, A. Flavonoids as peroxynitrite scavengers: the role of the hydroxyl groups. Toxicol. in Vitro 2001, 15, 3-6.
5. Chen, J. W.; Zhu, Z. Q.; Hu, T. X.; Zhu, D. Y. Structure-activity relationship of natural flavonoids in hydroxyl radical-scavenging effects. Acta Pharmacol. Sin. 2002, 23, 667-672.
6. Miyake, T.; Shibamoto, T. Antioxidative activities of natural compounds found in plants. J. Agric. Food Chem. 1997, 45, 1819-1822.
7. Cushnie, T. P. T.; Hamilton, V. E. S.; Chapman, D. G.; Taylor, P. W.; Lamb, A. J. Aggregation of Staphylococcus aureus following treatment with the antibacterial flavonol galangin. J. Appl. Microbiol. 2007, 103, 1562-1567.
8. Bestwick, C. S.; Milne, L. Influence of galangin on HL-60 cell proliferation and survival. Cancer Lett. 2006, 243, 80-89.
9. Park, J. S.; Rho, H. S.; Kim, D. H.; Chang, I. S. Enzymatic preparation of kaempferol from green tea seed and its antioxidant activity. J. Agric. Food Chem. 2006, 54, 2951-2956.
10. Tu, Y.; Lian, T.; Yen, J.; Chen, Z.; Wu, M. Antiatherogenic effects of kaempferol and rhamnocitrin. J. Agric. Food Chem. 2007, 55, 9969-9976.
11. Hu, Y.; Cheng, Z.; Heller, L. I.; Krasnoff, S. B.; Glahn, R. P.; Welch, R. M. Kaempferol in red and pinto bean seed (Phaseolus vulgaris L.) coats inhibits iron bioavailability using an in vitro digestion/human Caco-2 cell model. J. Agric. Food Chem. 2006, 54, 9254-9261.
12. Ramos, F. A.; Takaishi, Y.; Shirotori, M.; Kawaguchi, Y.; Tsuchiya, K.; Shibata, H.; Higuti, T.; Tadokoro, T.; Takeuchi, M. Antibacterial and antioxidant activities of quercetin oxidation products from yellow onion (Allium cepa) skin. J. Agric. Food Chem. 2006, 54, 3551-3557.
13. Chimenti, F.; Cottiglia, F.; Bonsignore, L.; Casu, L.; Casu, M.; Floris, C.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaro, S.; Ortuso, F.; Trombetta, G.; Loizzo, A.; Guarino, I. Quercetin as the active principle of Hypericum hircinum exerts a selective inhibitory activity against MAO-A: Extraction, biological analysis, and computational study. J. Nat. Prod. 2006, 69, 945-949.
14. Belinha, I.; Amorim, M. A.; Rodrigues, P.; de Freitas, V.; Moradas-Ferreira, P.; Mateus, N.; Costa, V. Quercetin increases oxidative stress resistance and longevity in Saccharomyces cerevisiae. J. Agric. Food Chem. 2007, 55, 2446-2451.
15. McPhail, D. B.; Hartley, R. C.; Gardner, P. T.; Duthie, G. G. Kinetic and stoichiometric assessment of the antioxidant activity of flavonoids by electron spin resonance spectroscopy. J. Agric. Food Chem. 2003, 51, 1684-1690.
16. Butkovic, V.; Klasinc, L.; Bors, W. Kinetic study of flavonoid reactions with stable radicals. J. Agric. Food Chem. 2004, 52, 2816-2820.
17. Crespy, V.; Morand, C.; Besson, C.; Manach, C.; Demigne, C.; Remesy, C. Quercetin, but not its glycosides, is absorbed from the rat stomach. J. Agric. Food Chem. 2002, 50, 618-621.
18. Papadopoulou, A; Green, R. J.; Frazier, R. A. Interaction of flavonoids with bovine serum albumin: A fluorescence quenching study. J. Agric. Food Chem. 2005, 53, 158-163.
19. Rawel, H. A.; Meidtner, K.; Kroll, J. Binding of selected phenolic compounds to proteins. J. Agric. Food Chem. 2005, 53, 4228-4235.
20. Kim, D.; Park, J.; Kim, J.; Han, C.; Yoon, J.; Kim, N.; Seo, J.; Lee, C. Flavonoids as mushroom tyrosinase inhibitors: A fluorescence quenching study. J. Agric. Food Chem. 2006, 54, 935-941.
21. Soares, S.; Mateus, N.; Freitas, V. Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary α-amylase (HSA) by fluorescence quenching. J. Agric. Food Chem. 2007, 55, 6726-6735.
22. Xiao, J. B.; Chen, J. W.; Cao, H.; Ren, F. L.; Yang, C. S.; Chen, Y.; Xu, M. Study of the interaction between baicalin and bovine serum albumin by multi-spectroscopic method. J. Photochem. Photobiol. A 2007, 191, 222-227.
23. Rawel, H. M.; Frey, S. K.; Meidtner, K; Kroll, J; Schweigert, F. J. Determining the binding affinities of phenolic compounds to proteins by quenching of the intrinsic tryptophan fluorescence. Mol. Nutr. Food Res. 2006, 50, 705-713.
24. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed.; Kluwer Academic/Plenum Publishers: New York, 1999.
25. Xiao, J. B.; Shi, J.; Cao, H.; Wu, S. D.; Ren, F. L.; Xu, M. Analysis of binding interaction between puerarin and bovine serum albumin by multi-spectroscopic method. J. Pharm. Biomed. 2007, 45, 609-615.
26. Fang, F.; Li, J. M.; Pan, Q. H.; Huang, W. D. Determination of red wine flavonoids by HPLC and effect of aging. Food Chem. 2007, 101, 428-433.
27. Dangles, O.; Dufour, C.; Bret, S. Flavonol-serum albumin complexation. Two-electron oxidation of flavonols and their complexes with serum albumin. J. Chem. Soc., Perkin Trans. 1999, 2, 737-744.
28. Moreira, M. R.; Kanashiro, A.; Kabeya, L. M.; Polizello, A. C. M.; Azzolini, A. E. C. S.; Curti, C.; Oliveira, C. A.; Amaral, A. T.-d.; Lucisano-Valim, Y. M. Neutrophil effector functions triggered by Fc-gamma and/or complement receptors are dependent on B-ring hydroxylation pattern and physicochemical properties of flavonols. Life Sci. 2007, 81, 317-326.
29. Burda, S.; Oleszek, W. Antioxidant and antiradical activities of flavonoids. J. Agric. Food Chem. 2001, 49, 2774-2779.
30. Pietta, P. G. Flavonoids as antioxidants. J. Nat. Prod. 2000, 63, 1035-1042.
31. William, R. J.; Spencer, J. P.; Rice-Evans, C. Flavonoids: Antioxidants or signaling molecular. Free Radical Biol. Med. 2004, 36, 838-894.
32. Kang, H. M.; Kim, J. H.; Lee, M. Y.; Son, K. H.; Yang, D. C.; Baek, N. I. Relationship between flavonoid structure and inhibition of farnesyl protein transferase. Nat. Prod. Res. 2004, 18, 349-356.
33. Yang, B.; Kotani, A.; Arai, K.; Kusu, F. Estimation of the antioxidant activities of flavonoids from their antioxidant potentials. Anal. Sci. 2001, 17, 599-604.
34. Pannala, A. S.; Chan, T. S.; O'brien, P. J.; Rice-Evans, C. A. Flavonoid B-ring chemistry and antioxidant activity: Fast reaction kinetics. Biochem. Biophys. Res. Commun. 2001, 282, 1161-1168.