New fatty acid glycosides from the seeds of Cicer arietinum

Abstract

The phytochemical investigation of the seeds of Cicer arietinum Linn (Papilionaceae) afforded eight new fatty acid glycosides identified as n-octadec-9-enoyl-β-D-glucopyranosyl (2→1)-β-D-glucopyranosyl-(2→1) -β-L- arabinofuranosyl-(2→1) -β-L- arabinofuranoside (ciceroleioside) 1, n-docos-11-enoyl-β-D-glucopyranosyl-(2→1)-β-D-glucopyranosyl-(2→1)-β-L-arabino furanosyl-(2→1)-β-L-arabinofuranosyl-(2→1)-β-L-arabinofuranoside (cicercetolioside) 2, n-eicos-11,14-dienoyl-β-D-glucopyranosyl (2→1)-β-D-glucopyranosyl-(2→1) -β-L- arabinofuranosyl -(2→1) -β-L- arabinofuranoside (cicereicosanoside) 4, n-decanoyl-β-D-glucopyranosyl (2→1)-β-D-glucopyranosyl-(2→1)-β-L- arabinofuranosyl -(2→1) -β-L-arabinofuranoside (cicercaprioside) 5, n-octadec-9,12-dienoyl acid-β-D-glucopyranosyl (2→1)- β-D-glucopyranosyl-(2→1) -β-L- arabinofuranosyl -(2→1) -β-L- arabinofuranoside (cicerlinoleioside) 6, n-tetradecanoyl -β-D-glucopyranosyl (2→1)- β-D-glucopyranosyl-(2→1)-β-L- arabinofuranosyl -(2→1) -β-L- arabinofuranosyl-(2→1) -β-L- arabinofuranoside (cicermyristioside) 8, n-octadecanoyl-β-D-glucopyranosyl (2→1)-β-D-glucopyranosyl-(2→1)-β-L- arabinofuranosyl -(2→1) -β-L- arabinofuranoside (cicerstearioside) 9 and n-octadec-9,12-dienoyl- β-D-glucopyranosyl (2→1)- β-D-glucopyranosyl-(2→1)-β-L-arabinofuranosyl-(2→1)-β-L-arabinofuranosyl-(2→1)-β-L-arabino furanoside (ciceroctadecatrieneoside) 10 along with known compounds glyceryl-1-n-octadecanoate-2-n-octadec-9-enoate (glycerostereolein) 3, Stigmasta-5,22-dien-3β-D-glucopyranoside (stigmasterol-β-D-glucopyranoside) 7, Stigmast-5-en-3-O- β-D-glucopyranoside (β-sitosterol glucoside) 11 and α-D-glucopyranosyl- (2→1) α - D-glucopyranosyl(2→1)-β L-arabinofuranoside (triglycoside) 12. Their stereostructures have been elucidated on the basis of spectral data analyses and chemical reactions.