Cyclopentenoid cyanohydrin glycosides with unusual sugar residues.

Abstract

The cyclopentenoid cyanohydrin glycosides passicapsin and passibiflorin have been identified as (1S, 4R)-1-(beta-D-glucopyranosyloxy)-4-(2,6-dideoxy-beta-D-xylo-hex o pyranosyloxy)-2-cyclopentene-1-carbonitrile and (1S, 4R)-1-(beta-D-glucopyranosyloxy)-4-(6-deoxy-beta-D-gulopyranosy loxy)-2- cyclopentene-1-carbonitrile, respectively, using one- and two-dimensional NMR spectroscopy, selective acid-catalysed cleavage of the glycosidic linkages of the deoxy sugars, and optical rotation data.