New glycosides from Herniaria fontanesii

Abstract Herniaria fontanesii Gay (caryophyllaceae) is widespread in the Mediterranean area. In the traditional pharmacopoeia of Morocco, the aerial parts of this plant are used for the treatment of lithiasis. We have studied the title plant and now we report the isolation and identification of tree flavonoids and four oleanane saponins. The mixture of glycosides was isolated from the methanol extract of the aerial parts of H.fontanesii and separated by multiple chromatographic steps. The structure of the pure glycosids was elucidated by means of mass spectrometry (FAB-MS), NMR technics ( 1 H, 13 C, 2D homo and heteronuclear COSY) and chemical analysis (methanolysis, methylation, alkaline hydrolysis). The flavonoids isolated are: (−) catechine : 1 ; 3-O-robinobioside Isorhamnetine: 2 ; and a new one : 3'" feruloyl-3-O-robinobioside Isorhamnetine: 3. The four saponins are new oleanane saponins. Their structures were established as: Herniaria saponin A: 28-o-{[ a-L-rhamnopyranosyl (1−>2) [α-L-rhamnopyranosyl (1−>3)]-β-D-xylopyranosyl (1−>2)-β-D-fucopyranosyl} ester of 3-O-β-D-glucopyranosyl uronic (1−>4) α-L- rhamnopyranosyl] 2 β, 3 β-dihydroxy olean 12-en 23, 28-dioic Herniaria saponin B : 28-o-[α-L-rhamnopyranosyl (1−>2)[α-L-rhamnopyranosyl(1−>3)]-β-D-xylopyranosyl (1−>2)-β-D-fucopyranosyl] ester of 3-O-[β3-D-glucopyranosyl uronic (1−>4) α-L- rhamnopyranosyl] 2 β, 3 β, 16-α-trihydroxy olean-12-en 23, 28-dioic Herniaria saponin C : 28-o-[α-L-rhamnopyranosyl (1−>2) [α-L-rhamnopyranosyl (1−>3)]-β-D-4-acetoxyfucopyranosyl] ester of 3-O-[α-L-rhamnopyranosyl (1−>2)-β-D-glucopyranosyl uronic] 2 β, 3 β, 16- α-trihydroxy olean12-en 23, 28-dioic acid. Herniaria saponin D : 28-o-{a-L-rhamnopyranosyl (1−>2)-[α-L-rhamnopyranosyl (1−>3] 13-D-fucopyranosyl} ester of 3-O-[α-L-rhamnopyranosyl (1−>2)-β-D-glucopyranosyl uronic] 2 β, 3 β, 16- α-trihydroxy olean12-en 23, 28-dioic acid