Novel Cyclopentenoid Cyanohydrin Rhamnoglucosides from Flacourtiaceae¹

Abstract

Two novel cyclopentenoid cyanohydrin glycosides, (1 S,4 R)-and (1 R,4 S)-1-[6- O-(alpha- L-rhamnopyranosyl)-beta- D-glucopyranosyloxy]-4-hydroxy-2-cyclopentene-1-carbonitrile, were isolated from seeds of the Indian medicinal plant HYDNOCARPUS PENTANDRA (F. Ham.) Oken (Flacourtiaceae) and characterized by optical rotations as well as (1)H-and (13)C-NMR spectra. The structural assignment is founded on these data and on degradation with alpha- L-rhamnosidase to the corresponding beta- D-glucopyranosides, epivolkenin and taraktophyllin, also present in the seeds in small amounts. Earlier reports of cyclopentenoid rhamnoglucosides from Passifloraceae are rejected.