The relative antioxidant activities, against radicals generated in the
aqueous phase, of a range of plant-derived polyphenolic flavonoids, c
onstituents of fruit, vegetables, tea and wine, have been assessed. Th
e results show that compounds such as quercetin and cyanidin, with 3',
4' dihydroxy substituents in the B ring and conjugation between the A
and B rings, have antioxidant potentials four times that of Trolox, th
e vitamin E analogue. Removing the ortho-dihydroxy substitution, as in
kaempferol, or the potential for electron delocalisation by reducing
the 2,3 double bond in the C ring, as in catechin and epicatechin, dec
reases the antioxidant activity by more than 50%, but these structures
are still more effective than a-tocopherol or ascorbate. The relative
significance of the positions and extents of hydroxylation of the A a
nd B rings to the total antioxidant activity of these plant polyphenol
ics is demonstrated.