Antioxidant activity and mechanism of the abietane-type diterpene ferruginol
Antioxidant activity and mechanism of the abietane-type diterpene ferruginol
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DOI：
10.1080/14786419.2014.997233
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发表时间：
2015-09-17
影响因子：
2.2
通讯作者：
Ashitani, T.
中科院分区：
文献类型：
--
作者：
Saijo, H.;Kofujita, H.;Ashitani, T.
通过与鼠尾草酸、（+/-）--生育酚和二丁基羟基甲苯的比较，使用2，2-二苯基-1-苦基肼、-胡萝卜素漂白和亚油酸测定，评价了松香烷型二萜类Ferruginol的抗氧化活性。Ferruginol具有最低的抗氧化活性，这组使用的2，2-二苯基-1-苦肼和-胡萝卜素的方法在极性溶剂缓冲液。然而，在非溶剂条件下，ferruginol表现出更强的活性比鼠尾草酸和生育酚的亚油酸氧化。通过对亚油酸甲酯与铁醇反应的GC-MS分析，检测到5个铁醇衍生物峰。经鉴定，三个反应产物分别为脱氢Ferruginol、7-羟基Ferruginol和Sugiol，另外两个峰分别为7-羟基Ferruginol和Ferruginol的醌甲基化物衍生物。反应的时间进程表明，醌甲基化物在反应早期产生，并进一步反应产生脱氢Ferruginol，7-羟基Ferruginol和sugiol。因此，我们推断醌甲基化物的形成是一个关键步骤，在铁红醇的抗氧化反应。
The antioxidant activity of the abietane-type diterpene ferruginol was evaluated by comparison with that of carnosic acid, (+/-)--tocopherol and dibutylhydroxytoluene using 2,2-diphenyl-1-picrylhydrazyl, -carotene bleaching and linoleic acid assays. Ferruginol had the lowest antioxidant activity of this group using the 2,2-diphenyl-1-picrylhydrazyl and -carotene methods in polar solvent buffer. However, ferruginol exhibited stronger activity than carnosic acid and -tocopherol for linoleic acid oxidation under non-solvent conditions. Five peaks corresponding to ferruginol derivatives were detected through GC-MS analysis of the reaction between ferruginol and methyl linoleate. The three reaction products were identified as dehydroferruginol, 7-hydroxyferruginol and sugiol, and the other two peaks were assumed to be 7-hydroxyferruginol and the quinone methide derivative of ferruginol. The time course of the reaction suggests that the quinone methide was produced early in the reaction and reacted further to produce dehydroferruginol, 7-hydroxyferruginol and sugiol. Thus, we inferred that quinone methide formation was a key step in the antioxidant reaction of ferruginol.