Osawa T, Sugiyama Y, Inayoshi M, Kawakishi S
Department of Applied Biological Sciences, Nagoya University, Japan.
Biosci Biotechnol Biochem. 1995 Sep;59(9):1609-12. doi: 10.1271/bbb.59.1609.
In order to develop a new type of antioxidative compound which has both the phenolic and beta-diketone moiety in the same molecule, we converted three known curcuminoids, curcumin (diferuloylmethane, U1), (4-hydroxy-3-methoxycinnamoyl)methane (U2), and bis-(4-hydroxycinnamoyl)methane (U3), which are the natural antioxidants of Curcuma longa L. (tumeric), to tetrahydrocurcuminoids (THU1, THU2, and THU3, respectively) by hydrogenation, and evaluated their antioxidative activity by using linoleic acid as the substrate in an ethanol/water system. Further, we used the rabbit erythrocyte membrane ghost and rat liver microsome as in vitro systems and determined the antioxidative activity of these curcuminoids. When we evaluated their antioxidative activity by these assays, it was found that THU1 had the strongest antioxidative activity among all curcuminoids in each assay system. THU1 has been reported to be one of the main metabolites of U1 in vivo [Holder et al., Xenobiotica, 8, 761-768 (1978)]. These results suggest that THU1 must play an important role in the antioxidative mechanism of U1 in vivo by converting U1 into THU1.
为了开发一种在同一分子中同时含有酚羟基和β - 二酮部分的新型抗氧化化合物，我们通过氢化反应将三种已知的姜黄素类化合物，即姜黄素（二阿魏酰甲烷，U1）、（4 - 羟基 - 3 - 甲氧基肉桂酰）甲烷（U2）和双 -（4 - 羟基肉桂酰）甲烷（U3），它们是姜黄（Curcuma longa L.）的天然抗氧化剂，转化为四氢姜黄素类化合物（分别为THU1、THU2和THU3），并以亚油酸为底物，在乙醇/水体系中评估它们的抗氧化活性。此外，我们使用兔红细胞膜微粒体和大鼠肝微粒体作为体外体系，测定这些姜黄素类化合物的抗氧化活性。当我们通过这些测定方法评估它们的抗氧化活性时，发现在每个测定体系中，THU1在所有姜黄素类化合物中具有最强的抗氧化活性。THU1已被报道是U1在体内的主要代谢产物之一[Holder等人，《异生物质》，8，761 - 768（1978）]。这些结果表明，THU1通过将U1转化为THU1，必定在U1体内抗氧化机制中发挥重要作用。
