4,4′-Dihydroxy-trans-stilbene, a resveratrol analogue, exhibited enhanced antioxidant activity and cytotoxicity

Resveratrol (3,5,4'-trans-trihydroxystibene) is a natural phytoalexin present in grapes and red wine, which possesses a variety of biological activities including antioxidant activity. In order to find more active antioxidant with resveratrol as the lead compound we synthesized 4,4'-dihydroxy-trans-stilbene (4,4'-DHS). The antioxidant activities of resveratrol and 4,4'-DHS were evaluated by the reaction kinetics with galvinoxyl radical or Cu(II) ions, and the inhibition effects against free-radical-induced peroxidation of human erythrocyte ghosts. It was found that 4,4'-DHS exhibits remarkably higher antioxidant activity than resveratrol. The oxidative products of resveratrol and 4,4'-DHS in the presence of Cu(II) in acetonitrile were identified as the dihydrofuran dimers by spectroscopic method, and the antioxidant mechanism for 4,4'-DHS was proposed. In addition, 4,4'-DHS exhibits remarkably higher cytotoxicity against human promyelocytic leukemia (HL-60) cells than resveratrol. (C) 2009 Elsevier Ltd. All rights reserved.