Quercetin and related flavonoids conserve their antioxidant properties despite undergoing chemical or enzymatic oxidation

- Chemical/enzymatic oxidation of quercetin does not affect its antioxidant properties.
- ROS-scavenging activity of most flavonoids is largely retained after oxidation.
- Structural features define antioxidant remnant activity of oxidized quercetin.
- Certain structural patterns define susceptibility of quercetin to undergo oxidation.

Oxidation of a phenolic group in quercetin is assumed to compromise its antioxidant properties. To address this assumption, the ROS-scavenging, Folin-Ciocalteau- and Fe-reducing capacities of quercetin and thirteen structurally related flavonoids were assessed and compared with those of mixtures of metabolites resulting from their chemical and enzymatic oxidation. Regardless of the oxidation mode, the metabolites mixtures largely conserved the antioxidant properties of the parent molecules. For quercetin, 95% of its ROS-scavenging and over 77% of its Folin-Ciocalteau- and Fe-reducing capacities were retained. The susceptibility of flavonoids to oxidative disappearance (monitored by HPLC-DAD) and that of the mixtures to retain their antioxidant capacity was favourably influenced by the presence of a catechol (ring-B) and enol (ring C) function. This is the first study to report that mixtures resulting from the oxidation of quercetin and its analogues largely conserve their antioxidant properties.