Research Institute for Fundamental Sciences (RIFS), University of Tabriz, Tabriz, Iran.
Food Chem. 2012 Dec 1;135(3):1369-76. doi: 10.1016/j.foodchem.2012.05.070. Epub 2012 May 24.
Antioxidant activity of curcumin has been thoroughly studied to declare the conflicting conclusions about the site of curcumin reactivity and the reaction mechanisms in ROS scavenging. Data confirmed that the antioxidant activity of curcumin's enol isomer (CurE) is not only higher than keto isomer (CurK) but also more than trolox. We found that two phenolic OH play a major role in the antioxidant activity for the both of CurE and CurK tautomers. Interestingly;each one of CurE and CurK isomer is capable to reduce at least two free radicals by two possible labile phenolic O-H sites of reaction. CurK isomer of curcumin reacts by H-atom transfer mechanism but CurE has tendency to react predominantly by electron transfer. Therefore;data proposed that in neutral condition such as inside the cells where;CurK and CurE tautomerism of curcumin equilibrium present;both of H-atom and electron transfer mechanisms engage in reducing free radicals.
姜黄素的抗氧化活性已经得到了深入的研究,以阐明关于姜黄素反应活性部位和 ROS 清除反应机制的相互矛盾的结论。数据证实,姜黄素的烯醇异构体(CurE)的抗氧化活性不仅高于酮式异构体(CurK),而且也高于 Trolox。我们发现,两种酚羟基在 CurE 和 CurK 互变异构体的抗氧化活性中起主要作用。有趣的是,CurE 和 CurK 异构体中的每一种都能够通过两种可能的不稳定酚羟基反应位点还原至少两个自由基。姜黄素的 CurK 异构体通过氢原子转移机制反应,但 CurE 倾向于主要通过电子转移反应。因此,数据表明,在中性条件下,如细胞内,姜黄素的 CurK 和 CurE 互变异构体平衡存在,氢原子和电子转移机制都参与了自由基的还原。