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Synthesis of water soluble glycosides of pentacyclic dihydroxytriterpene carboxylic acids as inhibitors of α-glucosidase

Xu, Jiancong, Nie, Xuliang, Hong, Yanping, Jiang, Yan, Wu, Guoqiang, Yin, Xiaoli, Wang, Chunrong, Wang, Xiaoqiang
Carbohydrate research 2016 v.424 pp. 42-53
acarbose, alpha-glucosidase, disaccharides, glycosides, glycosylation, in vitro studies, inhibitory concentration 50, monosaccharides, nuclear magnetic resonance spectroscopy, structure-activity relationships, triterpene acids, water solubility
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 1H NMR, 13C 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.