Echiofruzine, a novel naringenin diglycoside from Echiochilon fruticosum growing in Tunisia

The aerial parts of the Tunisian plant Echiochilon fruticosum yielded a novel flavonol diglycoside: naringenin-5-O-beta-glycopyranoside-3-O-alpha-L-rhamnopyranoside, named Echiofruzine (1), together with the known compounds vomifoliol-9-O-beta-D-glucopyraroside (2), 1-oxo-alpha-ionyl-9-O-beta-D-glucopyranoside (3) and I-O-[beta-D-xylopyranosyl(1 -> 6)-beta-D-glucopyranosyl] eugenol (4), described for the first time in the indicated plant. The structures of the four isolated compounds were established on the basis of chemical and spectroscopic evidence.