Ferrocenyl-Appended Aurone
and Flavone: Which Possesses
Higher Inhibitory Effects
on DNA Oxidation and Radicals?
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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<sup><b>+·</b></sup>), 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 <i>para</i>-position of the ferrocenyl
group. Introducing the ferrocenyl group into natural compounds may
be a useful strategy for increasing the antioxidative effectiveness