Triterpenoid saponins from Anagallis monelli ssp. linifolia (L.) Maire and their chemotaxonomic significance

Abstract

Thirteen undescribed triterpenoid saponins named monellosides A-M, were isolated from the aerial parts of Anagallis monelli ssp. linifolia (L.) Maire, together with ten known oleanane-type glycosides. Their structures were elucidated by 1D and 2D-NMR spectroscopy (COSY, TOCSY, HSQC, HMBC and ROESY) as well as high resolution mass spectrometry (HR-ESI-MS) and acid hydrolysis. Monellosides A-M have a carbohydrate chain linked on the C-3 of the aglycone with a common β-d-glucopyranosyl-(1 → 4)-α-l-arabinopyranosyl sequence which was further glycosylated by a glucose and/or a xylose. The sequence β-d-xylopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)-]α-l-arabinopyranosyl was common to all the 13,28-epoxy-oleanane core skeleton except one compound. In order to discuss the reclassification of Anagallis in Primulaceae, we compared saponins from species of Myrsinaceae and Primulaceae families and showed that these species were characterized by a pentacyclic triterpenoid saponin with a 13,28-epoxy bridge skeleton. Our phytochemical results increase the knowledge of saponins of the genus Anagallis, their chemotaxonomy and stimulate the evaluation of the biological activities of these saponins.

Keywords: Anagallis monelli; Chemotaxonomy; Primulaceae; Triterpenoid saponins.