Flavonol glycosides and iridoids from asperula lilaciflora

A new flavonol glycoside, quercetin 3-O-[6″′-O-3,5-dihydroxycinnamoyl-β-glucopyranosyl-(1→2)]-β-galactopyranoside (named lilacifloroside; 1) and a new iridoid 2 (named asperulogenin), were isolated from the aerial parts of Asperula lilaciflora in addition to eight known secondary metabolites, i.e., quercetin, kaempferol, quercetin 3-O-β-glucopyranosyl-(1→2)-β-galactopyranoside, quercetin 3-O-bglucopyranosyl-(1→2)-arabinopyranoside, asperuloside, deacetylasperulosidic acid, asperulosidic acid methyl ester, and chlorogenic acid. The structures were elucidated on the basis of extensive 1D- and 2DNMR experiments as well as MS data. Compound 1 contains the rare 3,5-dihydroxycinnamoyl moiety in its structure. This work constitutes the first phytochemical study of the title plant.