Venkatesan P, Rao M N
Department of Pharmaceutical Chemistry, College of Pharmaceutical Sciences, Manipal, India.
J Pharm Pharmacol. 2000 Sep;52(9):1123-8. doi: 10.1211/0022357001774886.
A number of ring substituted analogues of curcumin were synthesized. Their antioxidant properties were studied using three models, inhibition of lipid peroxidation, scavenging of 1,1'-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azinobis(3-ethyl-benzthiazoline-6-sulphonate radical (ABTS+.). In all the models, the phenolic analogues were more active than the non-phenolic analogues, some of which were inactive. The highest antioxidant activity was obtained when the phenolic group was sterically hindered by the introduction of two methyl groups at the ortho position. This and several other compounds were more active than the standard antioxidants alpha-tocopherol and trolox. This study has demonstrated that the phenolic group is important for the antioxidant activity of curcumin and that the structural features that enhance the antioxidant properties of phenols are optimized in curcumin to a significant extent.
合成了多种姜黄素的环取代类似物。使用三种模型研究了它们的抗氧化性能，即抑制脂质过氧化、清除1,1'-二苯基-2-苦基肼（DPPH）和2,2'-偶氮二（3-乙基苯并噻唑啉-6-磺酸盐自由基（ABTS+·）。在所有模型中，酚类类似物比非酚类类似物更具活性，其中一些非酚类类似物无活性。当酚羟基在邻位引入两个甲基而受到空间位阻时，抗氧化活性最高。该化合物以及其他几种化合物比标准抗氧化剂α-生育酚和曲洛昔芬更具活性。这项研究表明，酚羟基对于姜黄素的抗氧化活性很重要，并且在姜黄素中，增强酚类抗氧化性能的结构特征在很大程度上得到了优化。
