Antioxidant effects of alpha- and gamma-carboxyethyl-6-hydroxychromans

Carboxyethyl-6-hydroxychromans (CEHC), the major metabolites of both tocopherols (Toc) and tocotrienols (Toc-3), have been found in human plasma. In the present study, the antioxidant properties of alpha- and gamma-CEHC were measured and compared with alpha- and gamma- tocopherols. Following results were obtained: (1)alpha- and gamma-CEHC have the same reactivities toward radicals and exert the same antioxidant activities against lipid peroxidation in organic solution as the corresponding parent tocopherols respectively; (2) the partition coefficient decreased in the order alpha-Toc (3.36) > gamma-Toc (3.14) > alpha-CEHC (2.26) > pentamethyl-6-chromanol (1.92) > gamma-CEHC (1.83) > 0 > Trolox (-0.97); (3) alpha- and gamma-CEHC scavenge aqueous radicals more efficiently but they inhibit the lipid peroxidation within the membranes less efficiently than the corresponding alpha- and gamma-Toc, respectively; (4) alpha-CEHC inhibits the oxidation synergistically with ascorbate; and (5) alpha- and gamma-CEHC reduce Cu(II) to give Cu(I) and corresponding quinones as major product, but the prooxidant effect of CEHC in the presence of cupric ion was small. These results imply that CEHC may act as an antioxidant in vivo especially for those who take tocopherol supplement.