title: Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities.
abstract: A concise synthesis of (-)-steviamine is reported along with the synthesis of its analogues 10-nor-steviamine, 10-nor-ent-steviamine and 5-epi-ent-steviamine. These compounds were tested against twelve glycosidases (at 143 μg mL(-1) concentrations) and were found to have in general poor inhibitory activity against most enzymes. The 10-nor analogues however, showed 50-54% inhibition of α-L-rhamnosidase from Penicillium decumbens while one of these, 10-nor-steviamine, showed 51% inhibition of N-acetyl-β-D-glucosaminidase (from Jack bean) at the same concentration (760 μM).
authors: School of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia.
authors: Nadechanok
authors: N
authors: Jiangseubchatveera
authors: Marc E
authors: ME
authors: Bouillon
authors: Boonsom
authors: B
authors: Liawruangrath
authors: Saisunee
authors: S
authors: Liawruangrath
authors: Robert J
authors: RJ
authors: Nash
authors: Stephen G
authors: SG
authors: Pyne
mesh_terms: D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001411:Geobacillus stearothermophilus / Q000201:enzymology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D008968:Molecular Conformation; D010407:Penicillium / Q000201:enzymology
chemical_list: D004791:Enzyme Inhibitors; D050111:Imino Sugars; D054836:Indolizidines; C551370:steviamine; D006026:Glycoside Hydrolases