Xu Jiancong, Nie Xuliang, Hong Yanping, Jiang Yan, Wu Guoqiang, Yin Xiaoli, Wang Chunrong, Wang Xiaoqiang
Jiangxi Key Laboratory of Natural Product and Functional Food, College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China.
Jiangxi Key Laboratory of Natural Product and Functional Food, College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China.
Carbohydr Res. 2016 Apr 7;424:42-53. doi: 10.1016/j.carres.2016.02.009. Epub 2016 Mar 2.
A series of compounds were synthesized by glycosylation of maslinic acid (MA) and corosolic acid (CA) with monosaccharides and disaccharides, and the structures of the derivatives were elucidated by standard spectroscopic methods including (1)H NMR, (13)C NMR and HRMS. The α-glucosidase inhibitory activities of all the novel compounds were evaluated in vitro. The solubility and inhibitory activity of α-glucosidase assays showed that the bis-disaccharide glycosides of triterpene acids possessed higher water solubility and α-glucosidase inhibitory activities than the bis-monosaccharide glycosides. Among these compounds, maslinic acid bis-lactoside (8e, IC50 = 684 µM) and corosolic acid bis-lactoside (9e, IC50 = 428 µM) had the best water solubility, and 9e exhibited a better inhibitory activity than acarbose (IC50 = 478 µM). However, most of glycosylated derivatives possessed lower inhibitory activities than the parent compounds, although their water solubility was enhanced obviously. Moreover, the kinetic inhibition studies indicated that 9e was a non-competitive inhibitor, and structure-activity relationships of the derivatives are also discussed.
通过齐墩果酸（MA）和科罗索酸（CA）与单糖和二糖的糖基化反应合成了一系列化合物，并通过包括（1）H NMR、（13）C NMR和HRMS在内的标准光谱方法阐明了衍生物的结构。对所有新型化合物的α-葡萄糖苷酶抑制活性进行了体外评估。α-葡萄糖苷酶测定的溶解度和抑制活性表明，三萜酸的双二糖糖苷比双单糖糖苷具有更高的水溶性和α-葡萄糖苷酶抑制活性。在这些化合物中，齐墩果酸双乳糖苷（8e，IC50 = 684 µM）和科罗索酸双乳糖苷（9e，IC50 = 428 µM）具有最佳的水溶性，并且9e表现出比阿卡波糖（IC50 = 478 µM）更好的抑制活性。然而，大多数糖基化衍生物虽然水溶性明显提高，但其抑制活性低于母体化合物。此外，动力学抑制研究表明9e是一种非竞争性抑制剂，并且还讨论了衍生物的构效关系。
