Antioxidant activity of chalcones: The chemiluminescence determination of the reactivity and the quantum chemical calculation of the energies and structures of reagents and intermediates |
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Authors: | R F Vasil’ev V D Kancheva G F Fedorova D I Batovska A V Trofimov |
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Institution: | 1.Emanuel Institute of Biochemical Physics,Russian Academy of Sciences,Moscow,Russia;2.Institute of Organic Chemistry with Centre of Phytochemistry,Bulgarian Academy of Sciences,Sofia,Bulgaria |
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Abstract: | Six antioxidants from the class of chalcones (ArOH), compounds from which flavonoids are obtained in nature, were studied.
The antiradical activity of chalcones and a number of related compounds was determined by a chemiluminescence method using
the scavenging of peroxide radicals ROO· + ArOH → ROOH + OAr· (with the rate constant k
7) in a model reaction of diphenylmethane (RH) oxidation. The structures and energies of the reagents and intermediates were
determined by semiempirical quantum chemical (PM3, PM6) calculations. 3,4-Dihydroxychalcone and caffeic acid, which have a
catechol structure, that is, two neighboring OH groups in phenyl ring B, exhibited high antioxidant activity (k
7 ≈ 107 l mol−1 s−1); this is consistent with the lowest bond strengths D(ArO-H) of 79.2 and 76.6 kcal/mol, respectively. The abstraction of a hydrogen atom by the ROO· radical is the main reaction path of these compounds; however, the low stoichiometric coefficients of inhibition (f = 0.3–0.7) suggest a contribution of secondary and/or side reactions of ArOH and OAr·. In the other chalcones, the ArO-H bond is stronger (D(ArO-H) = 83–88 kcal/mol) and the antioxidant activity is lower (k
7 = 104–105 l mol−1 s−1). |
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