The 4′-hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol
The 4′-hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol
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DOI：
10.1016/s1383-5718(02)00211-5
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发表时间：
2002-11-26
影响因子：
1.9
通讯作者：
Miyata, N
中科院分区：
文献类型：
--
作者：
Matsuoka, A;Takeshita, K;Miyata, N
3，5，4‘-三羟基-反式二苯乙烯(白藜芦醇)是葡萄中发现的一种多酚植物抗毒素，在体外可诱导较高频率的姐妹染色单体交换(SCES)。为了研究其构效关系，我们合成了6个羟基数目和位置不同的白藜芦醇类似物，并研究了它们在中国仓鼠细胞系(CHL)的染色体畸变率(CA)、微核(MN)和姐妹染色单体交换(SCE)试验中的活性。6个类似物中的2个(3，4‘-二羟基-反式-二苯乙烯和4-羟基-反式-二苯乙烯)在所有三种试验中均表现出明显的阳性反应，且呈浓度依赖性。两者在遗传毒性方面都与白藜芦醇相当或更强。4‘-羟基(OH)类似物具有最简单的化学结构和最强的遗传毒性。其他类似物不含4‘-羟基。这些结果表明，4‘-羟基对二苯乙烯类化合物的遗传毒性是必需的。(C)2002 Elsevier Science B.V.保留所有权利。
We previously reported that 3,5,4'-trihydroxy-trans-stilbene (resveratrol), a polyphenolic phytoalexin found in grapes, induces a high frequency of sister chromatid exchanges (SCEs) in vitro. In this study, to investigate structure activity relationships, we synthesized six analogues of resveratrol differing in number and position of hydroxy groups, and we investigated their activity in chromosomal aberration (CA), micronucleus (MN) and sister chromatid exchange (SCE) tests in a Chinese hamster cell line (CHL). Two of the six analogues (3,4'-dihydroxy-trans-stilbene and 4-hydroxy-trans-stilbene) showed clear positive responses in a concentration-dependent manner in all three tests. Both were equal to or stronger than resveratrol in genotoxicity. The 4'-hydroxy (OH) analogue had the simplest chemical structure and was the most genotoxic. The other analogues did not have a 4'-hydroxy group. These results suggested that a 4'-hydroxy group is essential to the genotoxicity of stilbenes. (C) 2002 Elsevier Science B.V. All rights reserved.