title: Synthesis of water soluble glycosides of pentacyclic dihydroxytriterpene carboxylic acids as inhibitors of α-glucosidase.
abstract: 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.
authors.affiliation: Jiangxi Key Laboratory of Natural Product and Functional Food, College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China.
authors.forename: Jiancong
authors.initials: J
authors.lastname: Xu
authors.affiliation: Jiangxi Key Laboratory of Natural Product and Functional Food, College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China.
authors.forename: Xuliang
authors.initials: X
authors.lastname: Nie
authors.affiliation: Jiangxi Key Laboratory of Natural Product and Functional Food, College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China. Electronic address: xyqcjx@163.com.
authors.forename: Yanping
authors.initials: Y
authors.lastname: Hong
authors.affiliation: Jiangxi Key Laboratory of Natural Product and Functional Food, College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Jiang
authors.affiliation: Jiangxi Key Laboratory of Natural Product and Functional Food, College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China.
authors.forename: Guoqiang
authors.initials: G
authors.lastname: Wu
authors.affiliation: Library of Jiangxi Agricultural University, Nanchang 330045, China.
authors.forename: Xiaoli
authors.initials: X
authors.lastname: Yin
authors.affiliation: Jiangxi Key Laboratory of Natural Product and Functional Food, College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China.
authors.forename: Chunrong
authors.initials: C
authors.lastname: Wang
authors.affiliation: Jiangxi Key Laboratory of Natural Product and Functional Food, College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China; Department of Biological Sciences, University of North Texas, Denton, TX 76203, United States.
authors.forename: Xiaoqiang
authors.initials: X
authors.lastname: Wang
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D053978:Pentacyclic Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility; D013329:Structure-Activity Relationship; D014867:Water / Q000737:chemistry; D000520:alpha-Glucosidases / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D065089:Glycoside Hydrolase Inhibitors; D006027:Glycosides; D053978:Pentacyclic Triterpenes; D014867:Water; D000520:alpha-Glucosidases
keywords: Glycosylation; Pentacyclic dihydroxytriterpene acids; Water solubility; α-Glucosidase inhibitor