title: 4,4'-Dihydroxy-trans-stilbene, a resveratrol analogue, exhibited enhanced antioxidant activity and cytotoxicity.
abstract: 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.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Gui-Juan
authors.initials: GJ
authors.lastname: Fan
authors.forename: Xiao-Da
authors.initials: XD
authors.lastname: Liu
authors.forename: Yi-Ping
authors.initials: YP
authors.lastname: Qian
authors.forename: Ya-Jing
authors.initials: YJ
authors.lastname: Shang
authors.forename: Xiu-Zhuang
authors.initials: XZ
authors.lastname: Li
authors.forename: Fang
authors.initials: F
authors.lastname: Dai
authors.forename: Jian-Guo
authors.initials: JG
authors.lastname: Fang
authors.forename: Xiao-Ling
authors.initials: XL
authors.lastname: Jin
authors.forename: Bo
authors.initials: B
authors.lastname: Zhou
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D004910:Erythrocyte Membrane / Q000187:drug effects; D006801:Humans; D007700:Kinetics; D015227:Lipid Peroxidation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D000077185:Resveratrol; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D013267:Stilbenes / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000975:Antioxidants; D013267:Stilbenes; C010118:4,4'-dihydroxystilbene; D000077185:Resveratrol