New Triterpenoid Saponins from the Roots of Saponaria officinalis

Three new triterpenoid saponins (1–3), along with nine known saponins, were isolated from the roots of Saponaria officinalis L. Two of them: vaccaroside D (4) and dianchinenoside B (5) are known, but not previously reported for S. officinalis, and seven others: saponarioside C (6), D (7), F (8), G (9), I (10), K (11), and L (12) have been previously isolated from this plant. The structures of the new saponins were established as 3- O-β-D-xylopyranosyl-16α-hydroxygypsogenic acid-28- O-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (1), 3- O-β-D-xylopyranosyl-16α-hydroxygypsogenic acid-28- O-[β-D-glucopyranosyl-(1→3)]-[α-D-galactopyranosyl-(1→6)-α-D-galactopyranosyl-(1→6)-β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (2) and 3- O-β-D-xylopyranosyl-gypsogenic acid-28- O-[β-D-glucopyranosyl-(1→3)]-[6- O-(3-hydroxy-3-methylglutaryl)-β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (3). Their structures were elucidated by extensive spectroscopic methods, including 1D- (1H, 13C) and 2D-NMR (D QF-COSY, TOCSY, ROESY, HSQC and HMBC) experiments, as well as high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), ESI-MS/MS and acid hydrolysis.