Department of Organic Chemistry, College of Chemistry, Jilin University, No. 2519 Jiefang Road, Changchun 130021, China.
Eur J Med Chem. 2011 May;46(5):1821-6. doi: 10.1016/j.ejmech.2011.02.041. Epub 2011 Feb 23.
The antioxidant capacities of ferrocenyl-substituted curcumin derivatives including 1,7-bis(p-hydroxy-m-methoxyphenyl)-4-ferrocenylidene-hepta-1,6-diene-3,5-dione (FCU), 1-(p-hydroxy-m-methoxyphenyl)-3-hydroxy-7-ferrocenyl-hepta-1,4,6-trien-5-one (FFT), and 1-(p-hydroxy-m-methoxyphenyl)-5-ferrocenyl-penta-1,4-dien-3-one (FDZ) were evaluated in 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH), Cu2+/glutathione (GSH), and hydroxyl radical (.OH)-induced oxidation of DNA, and in trapping 2,2'-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+), and galvinoxyl radicals. FCU, FFT, and FDZ protected DNA against Cu2+/GSH-induced oxidation, but promoted .OH-induced oxidation of DNA. FCU, FFT, and FDZ scavenged 9.5, 5.7, and 4.7 radicals in protecting DNA against AAPH-induced oxidation. FCU can trap more DPPH and ABTS+ than FDZ and FFT, whereas FCU, FFT, and FDZ cannot react with galvinoxyl radical. Both phenolic hydroxyl groups and iron atom in ferrocenylidene curcumin derivatives play antioxidant role in this case.
研究了取代二茂铁基姜黄素衍生物包括 1,7-双（对-羟基-间甲氧基苯基）-4-二茂铁亚基庚-1,6-二烯-3,5-二酮（FCU）、1-（对-羟基-间甲氧基苯基）-3-羟基-7-二茂铁庚-1,4,6-三烯-5-酮（FFT）和 1-（对-羟基-间甲氧基苯基）-5-二茂铁基戊-1,4-二烯-3-酮（FDZ）在 2,2'-偶氮双（2-脒基丙烷）盐酸盐（AAPH）、Cu2+/谷胱甘肽（GSH）和羟基自由基（.OH）诱导的 DNA 氧化以及捕获 2,2'-二苯基-1-苦基肼基（DPPH）、2,2'-偶氮双（3-乙基苯并噻唑啉-6-磺酸）阳离子自由基（ABTS+）和半醌自由基中的抗氧化能力。FCU、FFT 和 FDZ 可保护 DNA 免受 Cu2+/GSH 诱导的氧化，但促进了 DNA 的.OH 诱导氧化。FCU、FFT 和 FDZ 在保护 DNA 免受 AAPH 诱导氧化时，可分别清除 9.5、5.7 和 4.7 个自由基。FCU 可捕获比 FDZ 和 FFT 更多的 DPPH 和 ABTS+，而 FCU、FFT 和 FDZ 不能与半醌自由基反应。在这种情况下，酚羟基和二茂铁亚基中的铁原子在取代二茂铁基姜黄素衍生物中均发挥抗氧化作用。
