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

被引：70

作者：

Fan, Gui-Juan ^{[1
]}

Liu, Xiao-Da ^{[1
]}

Qian, Yi-Ping ^{[1
]}

Shang, Ya-Jing ^{[1
]}

Li, Xiu-Zhuang ^{[1
]}

Dai, Fang ^{[1
]}

Fang, Jian-Guo ^{[1
]}

Jin, Xiao-Ling ^{[1
]}

Zhou, Bo ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2009年 / 17卷 / 06期

基金：

中国国家自然科学基金;

关键词：

Resveratrol; Antioxidant; Galvinoxyl; Lipid peroxidation; Copper; Cytotoxicity; TRANS-RESVERATROL; MOLECULAR-STRUCTURE; STRUCTURAL BASIS; CANCER; MECHANISM; CELLS; PICEATANNOL; TOCOPHEROL; OXIDATION; CRYSTAL;

D O I：

10.1016/j.bmc.2009.02.014

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：2360 / 2365

页数：6

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