Chen Jia-Feng, Liu Zai-Qun
Department of Organic Chemistry, College of Chemistry, Jilin University , No. 2519 Jiefang Road, Changchun 130021, China.
Chem Res Toxicol. 2015 Mar 16;28(3):451-9. doi: 10.1021/tx500405b. Epub 2014 Dec 30.
The aim of the present work was to compare the antioxidative effect of the ferrocenyl-appended aurone with that of ferrocenyl-appended flavone; therefore, nine aurones together with the flavone-type analogues were synthesized by using chalcone as the reactant. The radical-scavenging property was evaluated by reacting with the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+·)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. The cytotoxicity was estimated by inhibiting 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that the introduction of the ferrocenyl group remarkably increased the radical-scavenging activities of aurone and flavone. Especially, the ferrocenyl group in flavones can quench radicals even in the absence of the phenolic hydroxyl group, while ferrocenyl-appended aurones can efficiently protect DNA against AAPH-induced oxidation. Therefore, the antioxidative effect was generated by the ferrocenyl group and enhanced by the electron-donating group attaching to the para-position of the ferrocenyl group. Introducing the ferrocenyl group into natural compounds may be a useful strategy for increasing the antioxidative effectiveness.
本研究的目的是比较二茂铁基附加噢哢与二茂铁基附加黄酮的抗氧化效果；因此，以查尔酮为反应物合成了九种噢哢及其黄酮类类似物。通过分别与2,2'-偶氮二(3-乙基苯并噻唑啉-6-磺酸盐)阳离子自由基(ABTS(+·))、2,2'-二苯基-1-苦基肼自由基(DPPH)和加尔文氧基自由基反应来评估自由基清除性能。通过抑制2,2'-偶氮二(2-脒基丙烷盐酸盐)(AAPH)诱导的DNA氧化来估计细胞毒性。发现二茂铁基的引入显著提高了噢哢和黄酮的自由基清除活性。特别是，黄酮中的二茂铁基即使在没有酚羟基的情况下也能淬灭自由基，而二茂铁基附加的噢哢能有效保护DNA免受AAPH诱导的氧化。因此，抗氧化作用是由二茂铁基产生的，并通过连接在二茂铁基对位的供电子基团增强。将二茂铁基引入天然化合物可能是提高抗氧化效果的一种有用策略。
