title: Gabosines P and Q, new carbasugars from Streptomyces sp. and their α-glucosidase inhibitory activity.
abstract: Two new polyoxygenated cyclohexenone 'ketocarbasugars', named gabosines P and Q (1 and 2), were isolated from the culture of the actinomycete Streptomycetes strain no. 8, along with two known cyclic dipeptides. The structures and absolute configurations of the new metabolites were determined by spectroscopic data (1D- and 2D-NMR, HR-ESI-MS, and IR), chemical transformation, and electronic circular dichroism (ECD). These compounds were evaluated for α-glucosidase inhibitory activity in vitro. Only compound 1 exhibited IC50values of 9.07μM, with potency higher than that of the control acarbose. Molecular docking studies revealed the existence of hydrogen bonding and hydrophobic interaction between the enzyme and gabosine P. The results will be useful in designing new anti-diabetes control agents.
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Jing
authors.initials: J
authors.lastname: Wei
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Ling-Li
authors.initials: LL
authors.lastname: Liu
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Shuai
authors.initials: S
authors.lastname: Dong
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Hui
authors.initials: H
authors.lastname: Li
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Dan
authors.initials: D
authors.lastname: Tang
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: College of Resource and Environment, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Quan-Hong
authors.initials: QH
authors.lastname: Xue
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China. Electronic address: jinminggao@nwsuaf.edu.cn.
authors.forename: Jin-Ming
authors.initials: JM
authors.lastname: Gao
mesh_terms: D003512:Cyclohexanones / Q000302:isolation & purification / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors / Q000302:isolation & purification / Q000494:pharmacology*; D062105:Molecular Docking Simulation; D013057:Spectrum Analysis / Q000379:methods; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D003512:Cyclohexanones; D065089:Glycoside Hydrolase Inhibitors
keywords: Absolute configuration; Carbasugars; Electronic circular dichroism; Gabosines; Streptomyces sp.; α-Glucosidase