Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China.
J Agric Food Chem. 2010 Apr 14;58(7):4126-31. doi: 10.1021/jf904089q.
3-(2'-, 3'-, and 4'-Hydroxybenzylidene)-7-methoxychroman-4-one (o-, m-, and p-HBMC) was synthesized for the clarification of the influence of the hydroxyl group at the B ring on the antioxidant activity of homoisoflavonoid. The three homoisoflavonoids used herein can reduce peroxynitrite. p-HBMC exhibited high activity to reduce singlet oxygen. Furthermore, o-, m-, and p-HBMC can scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+)) and 2,2'-diphenyl-1-picrylhydrazyl (DPPH) and galvinoxyl radicals. The rates of o-HBMC trapping of DPPH and galvinoxyl radicals were higher than those of m- and p-HBMC, whereas m-HBMC can trap ABTS(+) rapidly. o-HBMC was found to possess high activity in the beta-carotene-linoleic acid bleaching test and to protect methyl linoleate against 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation efficiently. Finally, o-HBMC served as a prooxidant in Cu(2+)/glutathione (GSH)- and hydroxyl radical-mediated oxidations of DNA. m- and p-HBMC protected DNA against hydroxyl radical-mediated oxidation of DNA effectively, and o- and p-HBMC behaved as antioxidants to protect DNA against AAPH-induced oxidation. Thus, the hydroxyl group attaching to the ortho- and para-positions in the B ring was of importance for the homoisoflavonoid's enhancement of antioxidant activity.
3-(2'-, 3'-, 和 4'-羟基苯亚甲基)-7-甲氧基色满-4-酮（o-, m-, 和 p-HBMC）被合成，以阐明 B 环上的羟基对异黄酮类抗氧化活性的影响。本文中使用的三种异黄酮类化合物都可以还原过氧亚硝酸盐。p-HBMC 表现出高的还原单线态氧的活性。此外，o-, m-, 和 p-HBMC 可以清除 2,2'-联氮双（3-乙基苯并噻唑啉-6-磺酸）阳离子自由基（ABTS(+)) 和 2,2'-二苯基-1-苦基肼自由基（DPPH）和半醌自由基。o-HBMC 捕获 DPPH 和半醌自由基的速率高于 m-和 p-HBMC，而 m-HBMC 可以快速捕获 ABTS(+)。o-HBMC 在β-胡萝卜素-亚油酸漂白试验中表现出高活性，并有效地保护甲基亚油酸免受 2,2'-偶氮双（2-脒基丙烷）盐酸盐（AAPH）诱导的氧化。最后，o-HBMC 作为铜（2+）/谷胱甘肽（GSH）和羟基自由基介导的 DNA 氧化的促氧化剂。m-和 p-HBMC 有效地保护 DNA 免受羟基自由基介导的氧化，而 o-和 p-HBMC 作为抗氧化剂保护 DNA 免受 AAPH 诱导的氧化。因此，B 环上的邻位和对位上的羟基对于异黄酮类化合物增强抗氧化活性是重要的。
