Passibiflorin, α-hydroxy- and α-β-D-glucopyranosyloxy-amides from Passiflora punctata L. leaves

Abstract

A cyanogenic glycoside, passibiflorin (1) and two primary amides, (1S,1R)-1-hydroxy-4-(6-deoxy-β-D-glucopyranosyloxy)-2-cyclopentene-1-carboxamide (2) and (1S,4R)-1-(β-D-glucopyranosyloxy)-4-(6-deoxy- β-D-gulopyranosyloxy)-2-cyclopentene-1-carboxamide (3), were isolated from the leaves of Passiflora punctata L. The carbohydrates D-antiarose (4), glucose (5) and sucrose (6) were also obtained. The structures were established by IR, NMR and MS data and by comparison of these data against values reported in the literature. All the compounds are reported for the first time in P. punctata. In addition, the antimicrobial activities of the amides were evaluated with the diffusion method on agar plates by measuring the zone of inhibition against selected test microorganisms Staphylococcus aureus, Bacillus cereus, Escherichia coli and Pseudomonas aeruginosa, while antifungal activity was assessed against Candida tropicalis. The amides (2 and 3) exhibited activity against all microorganisms and the yeast evaluated. This activity has not been reported prior to this work.