title: α-Glucosidase inhibitors and phytotoxins from Streptomyces xanthophaeus.
abstract: Twenty-four metabolites 1-24 were isolated from the fermentation broth of Streptomyces xanthophaeus. Their structures were elucidated on the basis of spectroscopic analysis and by comparison of their NMR data with literature data reported. Daidzein (1), genistein (2) and gliricidin (3) inhibited α-glucosidase in vitro with IC50values of 174.2, 36.1 and 47.4 μM, respectively, more potent than the positive control, acarbose. Docking study revealed that the amino acid residue Thr 215 is the essential binding site for active ligands 2. In addition, the phytotoxic effects of all compounds were assayed on radish seedlings, five of which, 3, 8, 13, 15 and 18, inhibited the growth of radish (Raphanus sativus) seedlings with inhibitory rates of >60% at a concentration of 100 ppm, which was comparable or superior to the positive control glyphosate. This is the first report of the phytotoxicity of the compounds.
authors.affiliation: a Shaanxi Key Laboratory of Natural Products & Chemical Biology, School of Chemistry and Pharmacy , Northwest A&F University , Yangling , P.R. China.
authors.forename: Jing
authors.initials: J
authors.lastname: Wei
authors.affiliation: a Shaanxi Key Laboratory of Natural Products & Chemical Biology, School of Chemistry and Pharmacy , Northwest A&F University , Yangling , P.R. China.
authors.forename: Xiu-Yun
authors.initials: XY
authors.lastname: Zhang
authors.affiliation: a Shaanxi Key Laboratory of Natural Products & Chemical Biology, School of Chemistry and Pharmacy , Northwest A&F University , Yangling , P.R. China.
authors.forename: Shan
authors.initials: S
authors.lastname: Deng
authors.affiliation: a Shaanxi Key Laboratory of Natural Products & Chemical Biology, School of Chemistry and Pharmacy , Northwest A&F University , Yangling , P.R. China.
authors.forename: Lin
authors.initials: L
authors.lastname: Cao
authors.affiliation: a Shaanxi Key Laboratory of Natural Products & Chemical Biology, School of Chemistry and Pharmacy , Northwest A&F University , Yangling , P.R. China.
authors.forename: Quan-Hong
authors.initials: QH
authors.lastname: Xue
authors.affiliation: a Shaanxi Key Laboratory of Natural Products & Chemical Biology, School of Chemistry and Pharmacy , Northwest A&F University , Yangling , P.R. China.
authors.forename: Jin-Ming
authors.initials: JM
authors.lastname: Gao
mesh_terms: D020909:Acarbose / Q000494:pharmacology; D001665:Binding Sites; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical / Q000379:methods; D065089:Glycoside Hydrolase Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D031224:Raphanus / Q000187:drug effects / Q000254:growth & development; D036226:Seedlings / Q000187:drug effects; D013302:Streptomyces / Q000737:chemistry*; D018675:Toxicity Tests / Q000379:methods; D000520:alpha-Glucosidases / Q000378:metabolism
chemical_list: D065089:Glycoside Hydrolase Inhibitors; D000520:alpha-Glucosidases; D020909:Acarbose
keywords: 2,5-diketopiperazine; Streptomyces xanthophaeus; cyclodipeptide; herbicide; phytotoxins; α-glucosidase inhibitors