Stability of ferric complexes with 3-hydroxyflavone (flavonol), 5,7-dihydroxyflavone (chrysin), and 3′,4′-dihydroxyflavone

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 8, 2005, Pages 2953-2960

  Engelmann, Mark D ^a,b   Hutcheson, Ryan ^a   Cheng, I Francis ^a  

^a UNIVERSITY OF IDAHO   (United States)

^b PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYFLAVONE; 3',4' DIHYDROXYFLAVONE; ACID; ALCOHOL; CHRYSIN; FERRIC ION; FLAVONOID; FLAVONOL; HYDROXYL GROUP; IRON; METAL; UNCLASSIFIED DRUG; WATER;

ANTIOXIDANT ACTIVITY; ARTICLE; BINDING SITE; CALCULATION; CHELATION; CHEMICAL BINDING; COMPETITION; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); CURVE FITTING; DISSOCIATION; METAL BINDING; PH; PH MEASUREMENT; PHYSIOLOGY; POTENTIOMETRY; REGRESSION ANALYSIS; SPECIES DIFFERENTIATION; SPECTROPHOTOMETRY; STOICHIOMETRY; SUBSTITUTION REACTION; TITRIMETRY;

EID: 17244379213     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf048298q     Document Type: Article

References (39)

1. Lin, Y.; Wu, S.; Lin, J. Determination of tea polyphenols and caffeine in tea flowers (Camellia sinensis) and their hydroxyl radical scavenging and nitric oxide supressing effects. J. Agric. Food Chem. 2003, 51, 975-980.
2. Lien, E. J.; Ren, S.; Bui, H.; Wang, R. Quantitative structure activity relationship analysis of phenolic antioxidants. Free Radical Biol. Med. 1999, 26, 285-294.
3. Hanasaki, Y.; Shunjiro, O.; Fukui, S. The correlation between active oxygens scavenging and antioxidant effects of flavonoids. Free Radical Biol. Med. 1994, 16, 845-850.
4. Bors, W.; Heller, W.; Michel, C.; Saran, M. Flavonoids as antioxidants: Determination of radical scavenging efficiencies. Methods Enzymol. 1990, 186, 343-355.
5. Ferrali, M.; Signorini, B.; Caciotti, B.; Sugherini, L.; Ciccoli, L.; Giachetti, D.; Comporti, M. Protection against oxidative damage of erythrocyte membrane by the flavonoid quercetin and its relation to iron chelating activity. FEBS Lett. 1997, 416, 123-129.
6. Kuo, S.; Leavitt, P. S.; Lin, C. Dietary flavonoids interact with trace metals and affect metallothionein level in human intestinal cells. Biol. Trace Elem. Res. 1998, 62, 135-153.
7. Morel, I.; Lescoat, G.; Cillard, P.; Cillard J. Role of flavonoids and iron chelation in antioxidant action. Methods Enzymol. 1994, 234, 437-443.
8. Romanova, D.; Valchalkova, A.; Cipak, L.; Ovesna, Z.; Rauko, P. Study of antioxidant effect of apigenin luteolin and quercetin by DNA protective method. Neoplasma 2001, 48, 104-107.
9. Yoshino, M.; Murakami, K. Interaction of iron with polyphenolic compounds: Application to antioxidant characterization. Anal. Biochem. 1998, 257, 40-44.
10. Sestilli, P.; Diamantini, G.; Bedini, A.; Cerioni, L.; Tommasini, I.; Tarzia, G.; Cantoni, O. Plant derived phenolic compounds prevent the DNA single strand breakage and cytotoxicity induced by tert-butylhydroperoxide via an iron chelating mechanism. Biochem. J. 2002, 364, 121-128.
11. Sugita, O.; Ishizawa, N.; Matsuto, T.; Okada, M.; Kayahara, N. A new method of measuring the antioxidant activity of polyphenols using cumene hydroperoxide. Ann. Clin. Biochem. 2004, 41, 72-77
12. Cheng, I. F.; Breen, K. On the ability of four flavonoids, baicilein, luteolin, naringenin, and quercetin, to suppress the fenton reaction of the iron-ATP complex. Biometals 2000, 13, 77-83.
13. Benninger, C. W.; Hosfield, G. L. Antioxidant activity of extracts, condensed tannin fractions, and pure flavonoids from Phaseolus vulgaris L. seed coat color genotypes. J. Agric. Food Chem. 2003, 51, 7879-7883.
14. Guzy, J.; Kunir, J.; Marekova, M.; Chakova, Z.; Dubayova, K.; Mojiova, G.; Mirossay, L. Effect of quercetin on daunorubicin-induced heart mitochondria changes in rats. Physiol. Res. 2003, 52, 773-780.
15. Chun, O. K.; Kim D.-O.; Moon, H. Y.; Kang, H. G.; Lee, C. Y. Contribution of individual polyphenolics to total antioxidant capacity of plums, J. Agric. Food Chem. 2003, 51, 7240-7245.
16. Peng I.-W.; Kuo, S.-M. Flavonoid structure affects the inhibition of lipid peroxidation in caco-2 intestinal cells at physiological concentrations. J. Nutr. 2003, 133, 2184-2187.
17. Hendricks, J. A.; de Vries, H. E.; van der Pol, S. M..A.; van den Berg, T. K.; van Tol, E. A. P.; Dijkstra, C. D. Flavonoids inhibit myelin phagocytosis by macrophages; a structure-activity relationship study. Biochem. Pharmacol. 2003, 65, 877-885.
18. Matsuda, H.; Morikawa, T.; Toguchida, I.; Yoshikawa, M. Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem. Pharm. Bull. 2002, 50, 788-795.
19. Escandar, G, M,; Sala, L. F. Complexing behavior of rutin and quercetin. Can. J. Chem. 1991, 69, 1994-2001.
20. Cotelle, N. Role of flavonoids in oxidative stress. Curr. Top. Med. Chem. 2001, 1, 569-590.
21. HYPERQUAD, software programs was acquired from Prof. Peter Gans, Department of Inorganic and Structural Chemistry, University of Leeds, Leeds, U.K.
22. Gran, G. Determination of the equivalence point in potentiometric titrations. Part II. Analyst 1952, 77, 661.
23. Johansson, A.; Gran, G. Automatic titration by stepwise addition of equal volumes of titrant. Part V. Extension of the Gran I method for calculation of the equivalence volume in acid-base titrations. Analyst 1980, 105, 802-810.
24. 2 on Gran plots. J. Chem. Educ. 2001, 78, 1132-1135.
25. Clark, N. H.; Martell, A. E. Ferrous chelates of EDTA, HEDTA, and SHBED. Inorg. Chem. 1988, 27, 1297-1298.
26. Stolworthy, J. C. R. Stability of flavonoid complexes of copper-(II) and flavonoid antioxidant activity. Anal. Chim. Acta 1976, 85, 375-381.
27. Chatlas, J.; Jordan, R. B. Complexation of the aqua-iron(III) dimer by tiron: Kinetics of complex formation and dissociation. Inorg. Chem. 1994, 33, 3817-3822.
28. Gans, P.; Vacca, A.; Sabatini, A. Investigation of equilibria in soluiton: Determination of equilibrium constants with the hyperquad suite of programs. Talanta 1996, 43, 1739-1753.
29. Thompson, M.; Williams, C. R., Stability of flavonoid complexes of copper(II) and flavonoid antioxidant activity. Anal. Chim. Acta 1976, 85, 375-381.
30. Mellican, R. I.; Li, J.; Mehansho, H.; Nielsen, S. S. The role of iron and the factors affecting off-color development of polyphenols. J. Agric. Food Chem. 2003, 51, 2304-2316.
31. Smith R. M.; Martell A. E. Critical stability constants. Plenum Press: New York 1975; Vols. 1-4.
32. Konigsberger, L.; Konigsberger, E.; May, P. M.; Hefter, G. T. Complexation of iron(III) by citrate. Implications for iron speciation in blood plasma. J. Inorg. Biochem. 2000, 78, 97-103.
33. Motekaitis, R. J.; Smith, R. M.; Martell, A. E. NIST critically selected stability constants of metal complexes database, version 5.0; NIST Standard Reference Database 46, http://www.nist.gov/srd/webguide/nist46/46_5.htm.
34. Heim, K. E.; Tagliaferro, A. R.; Bobilya, D. J. Flavonoid antioxidants: Chemistry, metabolism, and structure-activity relationships. J. Nutr. Biochem. 2002, 13, 572-584.
35. van Acker, S. A.; van den Berg, D. J.; Tromp, M. N.; Griffioen, D. H.; van Bennekom , W. P.; van der Vijgh, W. J.; Bast, A. Structural aspects of antioxidant activity of flavonoids. Free Radical Biol. Med. 1996, 20, 331-342.
36. Kumamoto, M.; Sonda, T.; Nagayama, K.; Tabata, M. Effects of pH and metal ions on antioxidative activities of catechins. Biosci. Biotechnol. Biochem. 2001, 65, 126-132.
37. Heijnen, C. G.; Haenen, G. R.; Oostveen, R. M.; Stalpers, E. M.; Bast, A. Protection of flavonoids against lipid peroxidation: The structure activity relationship revisited. Free Radical Res. 2002, 36, 575-581.
38. Mira, L.; Fernandez, M. T.; Santos, M.; Rocha, R.; Florencio, M. H.; Jennings, K. R. Interactions of flavonoids with iron and copper ions: A mechanism for their antioxidant activity. Free Radical Res. 2002, 36, 1199-1208.
39. Silva, M. M.; Santos, M. R.; Caroco, G.; Rocha, R.; Justino, G.; Mira, L. Structure-antioxidant activity relationships of flavonoids: A re-examination. Free Radical Res. 2002, 36, 1219-1227.