title: Modification by ferrocene: An approach to enhance antioxidant ability of ailanthoidol to protect DNA.
abstract: Ailanthoidol is a benzofuran-type neolignan containing an alcoholic and a phenolic hydroxyl groups and can be synthesized following the description in a previous report. In this work, its antioxidant effect was estimated in the experimental system of 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that ailanthoidol can scavenge 1.5 radicals in protecting DNA against AAPH-induced oxidation. Moreover, a benzyl group was used to etherize the phenolic hydroxyl group of ailanthoidol, resulting in the formation of (E)-2-(4'-benzyloxy-3'-methoxyphenyl)-5-(3″-hydroxypropenyl)-7-methoxybenzofuran (BBF). However, BBF cannot protect DNA against AAPH-induced oxidation. This result demonstrated that the alcoholic hydroxyl group cannot play the antioxidative role in protecting DNA. Furthermore, a ferrocenyl group was used to substitute the alcoholic hydroxyl group, leading to the formation of (E)-1-ferrocenyl-3-(2'-(4″-hydroxy-3″-methoxyphenyl)-7'-methoxybenzofuran-5'-yl)prop-2-en-1-one (FBF). FBF can scavenge 2.0 radicals in protecting DNA against AAPH-induced oxidation. This result indicated that the antioxidant ability of FBF was higher than that of ailanthoidol. Finally, FBF and ailanthoidol were applied to trap 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+.)). It was found that FBF can trap 1.92 ABTS(+.), while ailanthoidol can trap 1.58 ABTS(+.). Therefore, the modification of ailanthoidol by ferrocenyl group enhanced radical-scavenging and antioxidative ability of ailanthoidol.
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, No. 2519 Jiefang Road, Changchun 130021, China.
authors.forename: Chao
authors.initials: C
authors.lastname: Zhao
authors.forename: Zai-Qun
authors.initials: ZQ
authors.lastname: Liu
mesh_terms: D000578:Amidines / Q000737:chemistry; D000975:Antioxidants / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D005296:Ferrous Compounds / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry*; D007700:Kinetics; D000075163:Metallocenes; D010084:Oxidation-Reduction
chemical_list: D000578:Amidines; D000975:Antioxidants; D001572:Benzofurans; D005296:Ferrous Compounds; D016166:Free Radical Scavengers; D000075163:Metallocenes; C476933:ailanthoidol; C046728:2,2'-azobis(2-amidinopropane); D004247:DNA; C105430:benzofuran; C004998:ferrocene