Multiple free radical scavenging reactions of aurones

Abstract

A series of naturally occurring 3',4'-dihydroxy aurones have been studied with regard to multiple free radical scavenging reactions in the gas and two liquid phases using density functional theory (DFT). All of the aurones prefer to perform (2 + n)-HAT mechanism to trap 2 + n free radicals, where n is the sum of the numbers of catechol and guaiacyl units in the gas and benzene phases. The second HAT reaction favours occurring in the same catechol moiety of the first HAT mechanism occurring OH group due to the formation of a stable quinone and the highly exothermic step of the final stable product formation. The catechol and guaiacyl moieties show increased potency for the second and fourth H⁺/e^‒ reactions. In the water phase, aurones can perform multiple H⁺/e^‒ reactions through n₁PL-ET-n₂HAT-(n+1-n₂)ET mechanism, where n₁ is the number of OH groups and n₂ is the number of guaiacyl moieties.

Keywords: Antioxidant activity; Aurone; Density functional theory; Multiple H(+)/e(‒) processes.