Novel Flavonol Glycosides from the Aerial Parts of Lentil (Lens culinaris)

While the phytochemical composition of lentil (Lens culinaris) seeds is well described in scientific literature, there is very little available data about secondary metabolites from lentil leaves and stems. Our research reveals that the aerial parts of lentil are a rich source of flavonoids. Six kaempferol and twelve quercetin glycosides were isolated, their structures were elucidated using NMR spectroscopy and chemical methods. This group includes 16 compounds which have not been previously described in the scientific literature: quercetin 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-galactopyranoside-7-O-beta-D-glucuropyranoside (1), kaempferol 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-galactopyranoside-7-O-beta-D-glucuropyranoside (3), their derivatives 4-10,12-15,17,18 acylated with caffeic, p-coumaric, ferulic, or 3,4,5-trihydroxycinnamic acid and kaempferol 3-O-{[(6-O-E-p-coumaroyl)-beta-D-glucopyranosyl(1-->2)]-alpha-L-rhamnopyranosyl(1-->6)}-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (11). Their DPPH scavenging activity was also evaluated. This is probably the first detailed description of flavonoids from the aerial parts of lentil.