title: Total synthesis and glycosidase inhibition of broussonetine I and J(2).
abstract: The first total synthesis of both broussonetine I and J2 together with their enantiomers have been accomplished via the same synthetic route through 18 and 16 steps in excellent overall yields (18% and 19%, respectively), starting from R-glyceraldehyde. Broussonetine I was found to be a potent inhibitor of β-glucosidase (IC50 = 2.9 μM), while ent-broussonetine I and ent-broussonetine J2 were found to be potent inhibitors of α-glucosidase (IC50 = 0.33 and 0.53 μM, respectively).
authors.affiliation: Beijing National Laboratory of Molecular Science (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Hui
authors.initials: H
authors.lastname: Zhao
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: Kasumi
authors.initials: K
authors.lastname: Sato
authors.forename: Yue-Mei
authors.initials: YM
authors.lastname: Jia
authors.forename: Chu-Yi
authors.initials: CY
authors.lastname: Yu
mesh_terms: D000818:Animals; D001234:Aspergillus niger / Q000201:enzymology; D002417:Cattle; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006372:Helix, Snails / Q000201:enzymology; D050111:Imino Sugars / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008968:Molecular Conformation; D010944:Plants / Q000201:enzymology; D051381:Rats; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D050111:Imino Sugars; C584909:broussonetine I; C584908:broussonetine J; D006026:Glycoside Hydrolases