Synthesis and activity of a potent alpha-glucosidase inhibitor, (1R, 6R, 8S)-cis-1,6-dihydroxypyrrolizidine, and its isomer

Abstract

The synthesis of cis- and trans-1,6-dihydroxypyrrolizidine starting from trans-4-hydroxy-L-proline and their evaluation as glycosidase inhibitors are reported. The cis-isomer was found to be a potent inhibitor against alpha-glucosidase and showed weak inhibitory effect against other glycosidases. The trans-isomer exhibited weak inhibitions of b-glucosidase and amyloglucosidase and poor inhibition of other glycosidases.