Naslov
Kinetic study of flavonoid reactions with stable radicals

Autori
Butković, Vjera ; Klasinc, Leo ; Bors, Wolf

Izvornik
Journal of agricultural and food chemistry (0021-8561) 52 (2004), 10; 2816-2820

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
flavonoids; antiradical activity; reaction rate constants; DPPH and BDPA radicals; correlation with reduction potential; structure-activity relationship (SAR)

Sažetak
The antiradical activities of some flavonols (kaempferol, quercetin, robinetin, quercetagetin, and myricetin), flavones (apigenin, baicalein, and luteolin), flavanones (naringenin and dihydroquercetin), and flavanols [(+)-catechin and (-)-epicatechin] were determined by measuring the reaction kinetics with 2, 2-diphenyl-1-picrylhydrazyl (DPPH) and alpha, gamma-bisdiphenylene-beta-phenylallyl (BDPA) radicals. The reactions, which follow the mixed second-order rate law, were investigated under pseudo-first-order conditions by use of a large excess of flavonoids, and their stoichiometry was determined by spectrophotometric titration. The results confirm stoichiometric factors of 1, 2, and 3 for flavonoids with one, two, and three hydroxyl groups in the B-ring, respectively, excluding kaempferol, which, despite a single OH group in the B-ring, has a factor of 2, which is explained by the 3-OH group supporting the reaction with free radicals. Structure- activity considerations indicate for the present series of flavonoids the importance of multiple OH substitutions and conjugation. The logarithms of reaction rate constants with the OH, DPPH, and BDPA radicals correlate well with the reduction potential of the flavonoids.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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