Molecular structure-affinity relationship of dietary flavonoids for bovine serum albumin

Revista Brasileira de Farmacognosia

Volumn 21, Issue 4, 2011, Pages 594-600

  Shi, Jian ^a   Cao, Hui ^a  

^a NANTONG UNIVERSITY   (China)

Author keywords

BSA; Flavonoids; Protein binding; Structure affinity

Indexed keywords

7 OHFLAVONE; APIGENIN; AURANTIIN; BAICALEIN; BAICALIN; BIOCHANIN A; BOVINE SERUM ALBUMIN; CATECHIN; CHRYSIN; DAIDZEIN; EPIGALLOCATECHIN; FLAVONE; FLAVONOID; GALANGIN; GENISTEIN; GENISTIN; KAEMPFERIDE; KAEMPFEROL; KAEMPFERTRIN; LUTEOLIN; MYRICETIN; NARINGENIN; NOBILETIN; PUERARIN; QUERCETIN; RUTOSIDE; TANGERETIN; TECTORIGENIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; WOGONIN;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CONJUGATION; FLUORESCENCE TITRATION ANALYSIS; GLYCOSYLATION; HYDROGEN BOND; HYDROGENATION; HYDROXYLATION; METHYLATION; NONHUMAN; PARTITION COEFFICIENT;

EID: 80051946994     PISSN: 0102695X     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0102-695X2011005000118     Document Type: Article

References (31)

1. Berezhkovskiy LM 2007. On the calculation of the concentration dependence of drug binding to plasma proteins with multiple binding sites of different affinities: determination of the possible variation of the unbound drug fraction and calculation of the number of binding sites of the protein. J Pharm Sci 96: 249-257.
2. Blade C, Arola L, Salvado MJ 2010. Hypolipidemic effects of proanthocyanidins and their underlying biochemical and molecular mechanisms. Mol Nutr Food Res 54:37-59.
3. Cao H, Wu DH, Wang HX, Xu M 2009. Effect of the glycosylation of flavonoids on interaction with protein. Spectrochim Acta A 73: 972-975.
4. Cao H, Liu Q, Shi J, Xiao JB, Xu M 2008. Comparing the affinities of flavonoid isomers with protein by fluorescence spectroscopy. Anal Lett 41: 521-532.
5. Cheung CWY, Gibbons N, Johnson DW, Nicol DL 2010. Silibinin - A promising new treatment for cancer. Anti-cancer Agents Med Chem 10: 186-195.
6. Cohen SD, Kennedy JA 2010. Plant metabolism and the environment: implications for managing phenolics. Crit Rev Food Sci 50: 620-543.
7. Côté J, Caillet S, Doyon G, Sylvain JF, Lacroix M 2010a. Analyzing cranberry bioactive compounds. Crit Rev Food Sci 50: 872-888.
8. Côté J, Caillet S, Doyon G, Sylvain JF, Lacroix M 2010b. Bioactive compounds in cranberries and their biological properties. Crit Rev Food Sci 50: 666-679.
9. Courts FL, Williamson G 2009. The C-glycosyl flavonoid, aspalathin, is absorbed, methylated and glucuronidated intact in humans. Mol Nutr Food Res 53: 1104-1111.
10. Edenharder R, von Petersdorff I, Rauscher R 1993. Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and other heterocyclic amine mutagens from cooked food. Mutat Res 287: 261-274.
11. Fernandes J, Gattass CR 2009. Topological polar surface area defines substrate transport by multidrug resistance associated protein 1 (MRP1/ABCC1). J Med Chem 52: 1214-1218.
12. Haghi G, Hatami A 2010. Simultaneous quantification of flavonoids and phenolic acids in plant materials by a newly developed isocratic high-performance liquid chromatography approach. J Agric Food Chem 58: 10812-10816.
13. Truchado P, Tourn E, Gallez LM, Moreno DA, Ferreres F, Tomás-Barberán FA 2010. Identification of botanical biomarkers in Argentinean Diplotaxis honeys: flavonoids and glucosinolates. J Agric Food Chem 58: 12678-12685.
14. Morabito G, Trombetta D, Brajendra KS, Ashok KP, Virinder SP, Naccari C, Mancari F, Saija A, Cristani M, Firuzi O, Saso L 2010. Antioxidant properties of 4-methylcoumarins in vitro cell-free systems. Biochimie 92: 1101-1107.
15. Natella F, Lorrain B, Prasad AK, Parmar VS, Saso L, Scaccini C 2010. 4-Methylcoumarins as antioxidants Scavenging of peroxyl radicals and inhibition of human low-density lipoprotein oxidation. Biochimie 92: 1147-1152.
16. Walle T 2009. Methylation of dietary flavones increases their metabolic stability and chemopreventive effects. Int J Mol Sci 10: 5002-5019.
17. Walle T 2007. Methylation of dietary flavones greatly improves their hepatic metabolic stability and intestinal absorption. Mol Pharmaceut 4: 826-832.
18. Wen X, Walle T 2006. Methylated flavonoids have greatly improved intestinal absorption and metabolic stability. Drug Metab Dispos 34: 1786-1792.
19. Xiao JB, Chen JW, Cao H, Ren FL, Yang, CS, Chen Y, Xu M 2007a. Study of the interaction between baicalin and bovine serum albumin by multi-spectroscopic method. J Photochem Photobiol A 191: 222-227.
20. Xiao JB, Shi J, Cao H, Wu SD, Ren FL, Xu M 2007b. Analysis of binding interaction between puerarin and bovine serum albumin by multi-spectroscopic method. J Pharmaceut Biomed Anal 45: 609-615.
21. Xiao J, Chen X, Zhang L, Talbot SG, Li GC, Xu M 2008a. Investigation the mechanism of enhanced effect of EGCG on huperzine A inhibiting acetylcholinesterase activity in rats by multi-spectroscopic method. J Agri. Food Chem 56: 910-915.
22. Xiao, JB, Suzuki M, Jiang XY, Chen XQ, Yamamoto K, Ren FL, Xu M 2008b. Influence of B-ring hydroxylation on interactions of flavonols with bovine serum albumin. J Agric Food Chem 56: 2350-2356.
23. Xiao JB, Chen XQ, Jiang XY, Hilczer M, Tachiya M 2008c. Probing the interaction of trans-resveratrol with bovine serum albumin: a fluorescence quenching study with Tachiya model. J Fluoresc 18: 671-678.
24. Xiao JB, Cao H, Wang YF, Zhao JY, Wei XL 2009. Glycosylation of dietary flavonoids decreases the affinities for plasma protein. J Agric Food Chem 57:6642-6648.
25. Xiao JB, Chen TT, Chen LS, Cao H, Yang F, Bai YL 2010a. CdTe quantum dots (QDs) improve the affinities of baicalein and genistein for human serum albumin in vitro. J Inorg Biochem 104: 1148-1155.
26. Xiao JB, Chen LS, Yang F, Liu CX, Bai YL 2010b. Green, yellow and red emitting CdTe QDs decreased the affinities of apigenin and luteolin for human serum albumin in vitro. J Hazard Mater 82: 696-703.
27. Xiao JB, Cao H, Wang YF, Yamamoto K, Wei XL 2010c. Structure-affinity relationship of flavones on binding to serum albumins: effect of hydroxyl groups on ring A. Mol Nutr Food Res 54: S253-S260.
28. Xiao JB, Cao H, Chen TT, Yang F, Liu CX, Xu XC 2011a. Molecular property-binding affinity relationship of flavonoids for common rat plasma proteins in vitro. Biochimie 93: 134-140.
29. Xiao JB, Chen TT, Cao H, Chen LS, Yang F 2011b. Molecular property-affinity relationship of flavanoids and flavonoids for human serum albumin in vitro. Mol Nutr Food Res 55: 310-317.
30. Yang F, Zhao YR, Kai GY, Xiao JB 2011. Interaction of dietary flavonoids with gamma-globulin: Molecular property-binding affinity relationship aspect. Food Funct 2: 137-141.
31. Zhao JY, Ren FL2009. Influence of hydroxylation and glycosylation in ring A of soybean isoflavones on interaction with BSA. Spectrochim Acta A 72: 682-685.