Collect. Czech. Chem. Commun. 2009, 74, 1117-1136
Published online 2009-07-17 23:58:00

Sulfonium-ion glycosidase inhibitors isolated from Salacia species used in traditional medicine, and related compounds

Sankar Mohan and B. Mario Pinto*

Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada, V5A 1S6


A novel class of naturally-occurring glycosidase inhibitors, having sulfonium sulfate structures, has been isolated as bioactive components from Indian plants, belonging to the Salacia genus in the family Celastraceae, and used in Ayurvedic medicine for the treatment of type-2 diabetes. Thus far, five such sulfonium salts, namely, salacinol, kotalanol, salaprinol, ponkoranol and de-O-sulfonated kotalanol, have been isolated from this plant species. These structurally unique zwitterionic glycosidase inhibitors have received much attention due to their therapeutic potential in the treatment of type-2 diabetes. We recently reported a review article which focused mainly on salacinol and related analogues. The present review presents an update on the remaining four compounds from this class of glycosidase inhibitors, with respect to their isolation, glucosidase inhibitory activities, and synthesis. In addition, progress towards the stereochemical structure elucidation of kotalanol, through synthesis of analogues, is described. Review with 42 references.

Keywords: Glycosidase inhibitors; Carbohydrates; Thiasugars; Sulfonium sulfates; Salacinol; Salaprinol; Natural products.

References: 49 live references.