Uralsaponins M-Y, Antiviral Triterpenoid Saponins from the Roots of Glycyrrhiza uralensis

Thirteen new oleanane-type triterpenoid saponins, uralsaponins M-Y (1-13), and 15 known analogues (14-28) were isolated from the roots of Glycyrrhiza uralensis Fisch. The structures of 1-13 were identified on the basis of extensive NMR and MS data analyses. The sugar residues were identified by gas chromatography and ion chromatography coupled with pulsed amperometric detection after hydrolysis. Saponins containing a galacturonic acid (1-3) or xylose (5) residue are reported from Glycyrrhiza species for the first time. Compounds 1, 7, 8, and 24 exhibited good inhibitory activities against the influenza virus A/WSN/33 (H1N1) in MDCK cells with IC50 values of 48.0, 42.7, 39.6, and 49.1 mu M, respectively, versus 45.6 mu M of the positive control oseltamivir phosphate. In addition, compounds 24 and 28 showed anti-HIV activities with IC50 values of 29.5 and 41.7 mu M, respectively.