Department of Organic Chemistry, College of Chemistry, Jilin University, No. 2519 Jiefang Road, Changchun 130021, China.
Biochimie. 2012 Aug;94(8):1805-11. doi: 10.1016/j.biochi.2012.04.017. Epub 2012 Apr 21.
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.
杨芽醇是一种苯并呋喃型新木脂素，含有一个醇羟基和一个酚羟基，可以按照以前的报道进行合成。在这项工作中，它的抗氧化作用在 2,2'-偶氮二(2-脒基丙烷)盐酸盐 (AAPH)诱导的 DNA 氧化实验系统中进行了评估。结果发现，杨芽醇可以清除 1.5 个自由基，保护 DNA 免受 AAPH 诱导的氧化。此外，用苄基醚化杨芽醇的酚羟基，得到(E)-2-(4'-苄氧基-3'-甲氧基苯基)-5-(3″-羟丙基)-7-甲氧基苯并呋喃(BBF)。然而，BBF 不能保护 DNA 免受 AAPH 诱导的氧化。这一结果表明，醇羟基在保护 DNA 方面不能发挥抗氧化作用。此外，用二茂铁基取代醇羟基，得到(E)-1-二茂铁基-3-(2'-(4″-羟基-3″-甲氧基苯基)-7'-甲氧基苯并呋喃-5'-基)丙-2-烯-1-酮(FBF)。FBF 可以清除 2.0 个自由基，保护 DNA 免受 AAPH 诱导的氧化。这一结果表明，FBF 的抗氧化能力高于杨芽醇。最后，FBF 和杨芽醇被用于捕获 2,2'-偶氮双(3-乙基苯并噻唑啉-6-磺酸)阳离子自由基(ABTS(+.)。结果发现，FBF 可以捕获 1.92 ABTS(+.)，而杨芽醇可以捕获 1.58 ABTS(+.)。因此，二茂铁基对杨芽醇的修饰增强了杨芽醇的清除自由基和抗氧化能力。
