Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA

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• 作者：Chuan Xiao ; Zhi-Guang Song ; Zai-Qun Liu
• 关键词：Xanthotoxol ; Free radical ; Antioxidant ; Oxidation damage of DNA
• 刊名：European Journal of Medicinal Chemistry
• 出版年：2010
• 出版时间：June 2010
• 年：2010
• 卷：45
• 期：6
• 页码：2559-2566
• 全文大小：609 K

文摘

4-Methyl-8-hydroxylpsoralen (MXan) and 4,9-dimethyl-8-hydroxylpsoralen (DMXan) were synthesized in order to clarify the effect of methyl on the antioxidant effectiveness of xanthotoxol (8-hydroxylpsoralen, Xan), which were assessed by bleaching β-carotene in linoleic acid–Triton emulsion, by interacting with 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS⁺), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, and by protecting DNA against the oxidation induced by Cu²⁺/glutathione (GSH) and 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH). Methyl attaching to xanthotoxol did not affect its ability to protect linoleic acid against autoxidation and to inhibit Cu²⁺/GSH-induced oxidation DNA, but decreased its ability to scavenge ABTS⁺ and DPPH, and to protect DNA against AAPH-induced oxidation. Therefore, methyl attenuated the antioxidant effectiveness of xanthotoxol in radical-induced oxidation of DNA.