Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand.
Arch Pharm Res. 2016 Oct;39(10):1370-1381. doi: 10.1007/s12272-016-0778-9. Epub 2016 Jun 23.
Furofuran lignans such as sesamin have been recognized as promising antidiabetic agents as they possess curative as well as preventive effects toward diabetes complications. However, to date the structure-activity relationship has not been investigated due to the lack of a practical synthetic route capable of producing diverse furofuran lignans. Herein, we first introduced a single-step synthesis of these compounds starting from samin (4). Reaction of samin with a variety of electron-rich phenolics under acidic conditions afforded a total of 23 diverse furofuran lignans. On examination their inhibitions against α-glucosidase and free radicals, lignans having a free hydroxy group showed considerably enhanced inhibition, compared with their corresponding starter 4 and related lignans sesamin (1) and sesamolin (3). In addition, the mechanism underlying the α-glucosidase inhibition of a particular active lignan (epi -6) was verified to be mixed manner between competitive and noncompetitive inhibition.
呋喃木脂素如芝麻素已被认为是有前途的抗糖尿病药物，因为它们对糖尿病并发症具有治疗和预防作用。然而，由于缺乏能够生产多种呋喃木脂素的实用合成路线，迄今为止尚未研究其构效关系。在此，我们首次从芝麻素（4）出发，通过一步法合成了这些化合物。在酸性条件下，芝麻素与各种富电子酚类化合物反应，总共得到了 23 种不同的呋喃木脂素。在考察它们对α-葡萄糖苷酶和自由基的抑制作用时，具有游离羟基的木脂素与相应的起始原料 4 以及芝麻素（1）和芝麻林素（3）相比，表现出相当强的抑制作用。此外，通过验证特定活性木脂素（表-6）对α-葡萄糖苷酶抑制作用的机制，证实其为竞争和非竞争抑制的混合方式。
