Passibiflorin, epipassibiflorin and passitrifasciatin: cyclopentenoid cyanogenic glycosides from Passiflora

Phytochemistry
1985.0

Abstract

An epimeric mixture of two novel cyclopentenoid cyanogenic glycosides, passibiflorin [1-(6-O-β-D-rhamnopyranosyl-β-D-glucopyranosyloxy)-4-hydroxycyclopent-2-en-1-nitrile] and its C-1 epimer, epipassibiflorin, has been isolated from Passiflora biflora and P. talamancensis. The structures were determined by means of ¹H NMR and ¹³C NMR. Another novel cyclopentenoid cyanogenic glycoside, passitrifasciatin [1-(4-O-β-D-rhamnopyranosyl-β-D-glucopyranosyloxy)hydroxycyclopent-2-en-1-nitrile] is described from Passiflora trifasciata. The structure was determined by means of ¹H NMR. The identification of the sugar moieties was made by HPLC and TLC. The isolation of a β-1→4 and a β-1→6-rhamnoglucoside of cyclopentenoid cyanogens from three species of subgenus Plectostemmo of Passiflora suggests that diglycosides of this type are taxonomically diagnostic for the section.

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