title: Synthesis and glycosidase inhibition of the enantiomer of (-)-steviamine, the first example of a new class of indolizidine alkaloid.
abstract: (+)-Steviamine, the enantiomer of the natural (-)-steviamine, and its corresponding C5 epimer have been synthesized from the D-ribose-derived cyclic nitrone. (-)-Steviamine was found to be the first naturally occurring iminosugar that causes any inhibition of alpha-galactosaminidases.
authors.affiliation: Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Xiang-Guo
authors.initials: XG
authors.lastname: Hu
authors.forename: Barbara
authors.initials: B
authors.lastname: Bartholomew
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Nash
authors.forename: Francis X
authors.initials: FX
authors.lastname: Wilson
authors.forename: George W J
authors.initials: GW
authors.lastname: Fleet
authors.forename: Shinpei
authors.initials: S
authors.lastname: Nakagawa
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: Yue-Mei
authors.initials: YM
authors.lastname: Jia
authors.forename: Renate
authors.initials: R
authors.lastname: van Well
authors.forename: Chu-Yi
authors.initials: CY
authors.lastname: Yu
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006596:Hexosaminidases / Q000037:antagonists & inhibitors*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism; D036625:Stevia / Q000737:chemistry
chemical_list: D000470:Alkaloids; D050111:Imino Sugars; D054836:Indolizidines; C551370:steviamine; D006596:Hexosaminidases