Anti-inflammatory triterpenoid saponins from the stem bark of Kalopanax pictus.

摘要

Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3 beta ,6 beta ,23-trihydroxyolean-12-en-28-oic acid 28-O- beta -D-glucopyranoside (3), 3-O-[2,3-di-O-acetyl- alpha -L-arabinopyranosyl]hederagenin 28-O- alpha -L-rhamnopyranosyl-(1->4)- beta -D-glucopyranosyl-(1->6)- beta -D-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl- alpha -L-arabinopyranosyl]hederagenin 28-O- alpha -L-rhamnopyranosyl-(1->4)- beta -D-glucopyranosyl-(1->6)- beta -D-glucopyranoside (5), as well as 10 known compounds (6-15), were isolated from the stem bark of Kalopanax pictus. Compounds 1-5 and 7-14 inhibited TNF alpha -induced NF- kappa B transcriptional activity in HepG2 cells in a dose-dependent manner, with IC₅₀ values ranging from 0.6to 16.4 micro M. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure-activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.