Secondary metabolites from the aerial parts of Centaurea pannonica (Heuff.) Simonk. from Serbia and their chemotaxonomic importance

Abstract

The non polar extract of Centaurea pannonica (Heuff.) Simonk., growing wild in Serbia, was studied and twenty-five compounds including 14 sesquiterpene lactones, 7 flavonoids, 3 lignans and 1 phenylpropanoid glycoside were isolated. All compounds were isolated for the first time from this species. Among them, one germacranolide 2α-hydroxy, 8-dehydroxy 15-O-methacrylate salonitenolide (1) and two guaianolides 2α,8α-dihydroxy-dehydrocostus lactone (2) and pannonin (3) are new natural compounds. The structures of the compounds were established on the basis of spectroscopic analyses (UV, IR, HREIMS and 1D & 2D NMR). The chemical profile of C. pannonica, which belongs to the "Centaurea jacea" group, was compared to previously studied taxa of the same group and used to assess the phylogenetic relationships in the group.

Keywords: C. pannonica (Heuff.) Simonk.; Centaurea L.; Centaurea jacea group; Chemotaxonomy; Flavonoids; Guaianolides; Lignans; NMR.