title: Ferrocenyl-appended aurone and flavone: which possesses higher inhibitory effects on DNA oxidation and radicals?
abstract: 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.
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University , No. 2519 Jiefang Road, Changchun 130021, China.
authors.forename: Jia-Feng
authors.initials: JF
authors.lastname: Chen
authors.forename: Zai-Qun
authors.initials: ZQ
authors.lastname: Liu
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D001572:Benzofurans / Q000737:chemistry / Q000494:pharmacology*; D004247:DNA / Q000378:metabolism*; D005296:Ferrous Compounds / Q000737:chemistry / Q000494:pharmacology*; D047309:Flavones / Q000737:chemistry / Q000494:pharmacology*; D005609:Free Radicals / Q000378:metabolism; D010084:Oxidation-Reduction
chemical_list: D000975:Antioxidants; D001572:Benzofurans; D005296:Ferrous Compounds; D047309:Flavones; D005609:Free Radicals; C486837:aurone; D004247:DNA