Hybrid of Resveratrol and Glucosamine: An Approach To Enhance Antioxidant Effect against DNA Oxidation,Chemical Research in Toxicology

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Hybrid of Resveratrol and Glucosamine: An Approach To Enhance Antioxidant Effect against DNA Oxidation
Chemical Research in Toxicology ( IF 3.7 ) Pub Date : 2018-08-14 00:00:00 , DOI: 10.1021/acs.chemrestox.8b00136
Liang-Liang Bao ₁ , Zai-Qun Liu ₁

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Resveratrol exhibits various pharmacological activities, which are dependent upon phenolic hydroxyl groups. In this work, glucosamine, lipoic acid, or adamantanamine moiety was applied for attaching to ortho-position of hydroxyl group in resorcinol moiety of resveratrol (known as position-2). Antioxidant effects of the obtained hybrids were characterized using DNA oxidative systems mediated by ^•OH, Cu²⁺/glutathione (GSH), and 2,2′-azobis(2-amidinopropanehydrochloride) (AAPH), respectively. The glucosyl-appended imine and amine at position-2 of resveratrol were found to show higher inhibitory effects than other resveratrol derivatives against AAPH-induced DNA oxidation. The antioxidative effect was quantitatively expressed by stoichiometric factor (n, the number of radical-propagation terminated by one molecule of antioxidant). The stoichiometric factors of glucosyl-appended imine and amine of resveratrol increased to 4.74 (for imine) and 4.97 (for amine), respectively, higher than that of resveratrol (3.70) and glucoside of resveratrol (3.49). It was thereby concluded that the combination of resveratrol with glucosamine at position-2 represented a novel pathway for modifying resveratrol structure in the protection of DNA against peroxyl radical-mediated oxidation.

中文翻译：

白藜芦醇和氨基葡萄糖的杂种：增强抗氧化作用抗DNA氧化的一种方法。

白藜芦醇表现出各种药理活性，这取决于酚羟基。在这项工作中，葡糖胺，硫辛酸，或金刚烷胺部分施加用于连接到邻白藜芦醇的部分（被称为位置-2）羟基基团的-位中的间苯二酚。使用分别由^• OH，Cu ²⁺ /谷胱甘肽（GSH）和2,2'-偶氮二（2-ami基丙烷盐酸盐）（AAPH）介导的DNA氧化系统来表征获得的杂种的抗氧化作用。发现在白藜芦醇的2位上的葡萄糖基附加的亚胺和胺显示出比其他白藜芦醇衍生物更高的对AAPH-诱导的DNA氧化的抑制作用。抗氧化作用用化学计量因子（n，是指一分子抗氧化剂终止的自由基繁殖数。白藜芦醇的葡萄糖基附加的亚胺和胺的化学计量因子分别增加到4.74（亚胺）和4.97（对于胺），高于白藜芦醇（3.70）和白藜芦醇的糖苷（3.49）。由此得出结论，在位置2上白藜芦醇与葡糖胺的组合代表了修饰白藜芦醇结构的新途径，以保护DNA免受过氧自由基介导的氧化。

更新日期：2018-08-14

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