Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan.
Bioorg Med Chem Lett. 2010 Sep 15;20(18):5398-401. doi: 10.1016/j.bmcl.2010.07.110. Epub 2010 Aug 1.
Two new 2-arylbenzofurans, glycybenzofuran (1) and cyclolicocoumarone (2), together with 10 known flavonoids including licocoumarone (3), glycyrrhisoflavone (4), glisoflavone (5), cycloglycyrrhisoflavone (6), isoliquiritigenin (7), licoflavone A (8), apigenin (9), isokaempferide (10), glycycoumarin (11), and isoglycycoumarin (12), were isolated from the roots of Glycyrrhiza uralensis and their structures were determined by extensive spectroscopic analyses. Compounds 1 and 5 showed significant protein tyrosine phosphatase-1B (PTP1B) inhibitory activity in vitro with the IC50 values of 25.5 and 27.9 microM, respectively. The structure-activity relationship indicated that the presence of prenyl group and ortho-hydroxy group is important for exhibiting the activity. Kinetic analysis indicated that compound 1 inhibits PTP1B by a competitive mode, whereas compound 5 by a mixed mode.
两种新的 2-芳基苯并呋喃，glycybenzofuran（1）和环木脂素酮（2），以及 10 种已知的类黄酮，包括 licocoumarone（3），glycyrrhisoflavone（4），glisoflavone（5），cycloglycyrrhisoflavone（6），isoliquiritigenin（7），licoflavone A（8），apigenin（9），isokaempferide（10），glycycoumarin（11）和 isoglycycoumarin（12），从甘草的根部分离出来，通过广泛的光谱分析确定了它们的结构。化合物 1 和 5 在体外显示出显著的蛋白酪氨酸磷酸酶-1B（PTP1B）抑制活性，其 IC50 值分别为 25.5 和 27.9 microM。构效关系表明，prenyl 基团和邻位羟基的存在对于表现出活性是重要的。动力学分析表明，化合物 1 通过竞争性模式抑制 PTP1B，而化合物 5 通过混合模式抑制 PTP1B。
