Radical scavenging capacity of wine anthocyanins is strongly pH-dependent

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 14, 2005, Pages 5526-5534

  Borkowski, Tomasz ^a   Szymusiak, Henryk ^a   Gliszczyńska Świgło, Anna ^a   Rietjens, Ivonne M C M ^b   Tyrakowska, Bozena ^a  

^a POZNA UNIVERSITY OF ECONOMICS AND BUSINESS   (Poland)

^b WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Anthocyanidins; Anthocyanins; Body fluids; pH; pKa; Radical scavenging capacity; TEAC

Indexed keywords

2,2' AZINO DI (3 ETHYLBENZOTHIAZOLINE) 6 SULFONIC ACID; 2,2'-AZINO-DI-(3-ETHYLBENZOTHIAZOLINE)-6-SULFONIC ACID; ANTHOCYANIN; BENZOTHIAZOLE DERIVATIVE; SCAVENGER; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; METHYLATION; PH; WINE;

ANTHOCYANINS; BENZOTHIAZOLES; FREE RADICAL SCAVENGERS; HYDROGEN-ION CONCENTRATION; METHYLATION; SULFONIC ACIDS; WINE;

EID: 22544447682     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0478556     Document Type: Article

References (24)

1. Kinsella, J. E.; Frankel, E.; German, B.; Kanner, J. Possible mechanisms for the protective role of antioxidants in wine and plant foods. Food Technol. 1993, 85-89.
2. Wang, H.; Cao, G.; Prior, R. L. Oxygen radical absorbing capacity of anthocyanins. J. Agric. Food Chem. 1997, 45, 304-309.
3. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biol. Med. 1996, 20, 933-956.
4. Rice-Evans, C. A.; Miller, N. J.; Bolwell, P. G.; Bramley, P. M.; Pridham, J. B. The relative antioxidant activities of plant-derived polyphenolic flavonoids. Free Radical Res. 1995, 22, 375-383.
5. Lapidot, T.; Harel, S.; Akiri, B.; Granit, R.; Kanner, J. pH-dependent forms of red wine anthocyanins as antioxidants. J. Agric. Food Chem. 1999, 47, 67-70.
6. Stocler, J. C. Bonum vinum laetificat cor hominum. Med. Sci. Monit. 2001, 7, 842-847.
7. Frankel, E. N.; Waterhouse, A. L.; Teissedre, P. L. Principal phenolic phytochemicals in selected California wines and they antioxidant activity in inhibiting oxidation of human low-density lipoproteins. J. Agric. Food Chem. 1995, 43, 890-894.
8. Kahkonen, M. P.; Heinonen, M. Antioxidant activity of anthocyanins and their aglycons. J. Agric. Food Chem. 2003, 51, 628-633.
9. Iacobucci, G. A.; Sweeny, J. G. The chemistry of anthocyanins, anthocyanidins, and related flavylium salts. Tetrahedron 1983, 39, 3005-3038.
10. Grzymislawski, M. Physique of systems related to food bioavailability. In Human Nutrition. Principals of Nutritional Science (in Polish); Gawȩcki, J., Hryniewiecki, L., Eds.; PWN: Warszawa, Poland, 2000; pp 56-72.
11. Tyrakowska, B.; Soffers, A. E.; Szymusiak, H.; Boeren, S.; Boersma, M. G.; Lemanska, K.; Vervoort, J.; Rietjens, I. M. TEAC antioxidant activity of 4-hydroxybenzoates. Free Radical Biol. Med. 1999, 27, 1427-1436.
12. a determination of daphnetin, chlorogenic acid, and quercetin. Z. Naturforsch., B: Chem. Sci. 1998, 53, 315-321.
13. Fukumoto, L. R.; Mazza, G. Assessing antioxidant and prooxidant activities of phenolic compounds. J. Agric. Food Chem. 2000, 48, 3597-3604.
14. Brouillard, R.; Iacobucci, G. A.; G., S. J. Chemistry of anthocyanins pigments. UV-visible spectrophotometric determination of the acidity constants of apigeninidin and three related 3-deoxyflavylium salts. J. Am. Chem. Soc. 1982, 104, 7585-7590.
15. Figueiredo, P.; Elhabiri, M.; Toki, K.; Saito, N.; Dangles, O.; Brouillard, R. New aspects of anthocyanin complexation. Intramolecular copigmentation as a means for colour loss? Phytochemistry 1996, 41, 301-308.
16. Lemanska, K.; Szymusiak, H.; Tyrakowska, B.; Zielinski, R.; Soffers, A. E.; Rietjens, I. M. The influence of pH on antioxidant properties and the mechanism of antioxidant action of hydroxyflavones. Free Radical Biol. Med. 2001, 31, 869-881.
17. Morand, C.; Crespy, V.; Manach, C.; Besson, C.; Demigne, C.; Remesy, C. Plasma metabolites of quercetin and their antioxidant properties. Am. J. Physiol. 1998, 275, R212-R219.
18. Manach, C.; Morand, C.; Crespy, V.; Demigne, C.; Texier, O.; Regerat, F.; Remesy, C. Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett. 1998, 426, 331-336.
19. Cao, G.; Sofic, E.; Prior, R. L. Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships. Free Radical Biol. Med. 1997, 22, 749-760.
20. Lemanska, K.; van der Woude, H.; Boersma, M. G.; Szymusiak, H.; Gliszczyńska-Świglo, A.; Rietjens, I. M. C. M.; Tyrakowska, B. The effect of catechol O-methylation on antioxidant characteristics of quercetin and luteolin-A mechanistic insight. Free Radical Res. 2004, 38, 639-647.
21. 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.
22. Bors, W.; Heller, W.; Michel, C.; Saran, M. Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. Methods Enzymol. 1990, 186, 343-355.
23. Bors, W.; Saran, M. Radical scavenging by flavonoid antioxidants. Free Radical Res. Commun. 1987, 2, 289-294.
24. 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.