New Triterpenoid Saponins from. Green Vegetable Soya Beans and Their Anti-Inflammatory Activities

Ten compounds were isolated and identified from green vegetable soya beans, of which five are new triterpenoid, saponins (1-5) and five are known compounds (6-10). The chemical structures of the five triterpenoid saponins (1-5) were elucidated to be 3 beta,24-dihydroxy-22 beta,30-epoxy-30-oxoolean-12-en 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl-(1 -> 2)-beta-D-glucuroilopyranoside, 1; 3 beta,24-dihydroxy-22 beta,30-epoxy-30-oxoolean-12-en 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-(3 ''-O-formyl)-galactopyranosyl-(1 -> 2)-beta-D-glucuronopyranoside, 2; 22-keto-3 beta,24-dihydroxy oleanane-12-ene 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-(3 ''-O-formyl)-galactopyranosyl-(1 -> 2)-beta-D-glucuronopyranoside, 3; 3 beta,22 beta,24-trihydroxy oxyolean-18(19)-ene-29-acid 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-(1 -> 2)-beta-D-glucuronopyranoside, 4; and punicanolic acid 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-(1 -> 2)-beta-D-glucuronopyranoside, 5 from the, spectroscopic data (IR, GTC/FID, HR-ESI-MS, and 1D and 2D NMR). The nitric oxide release inhibitions of compounds 1-10 in LPS-stimulated RAW264.7 cells were evaluated, and the data suggested that compounds 1, 2, and 5 might possess moderate, anti-inflammatory activities, with IC50 values of 18.8, 16.1, and 13.2 mu M, respectively.