28-Nor-oleanane-type triterpene saponins from Camellia japonica and their inhibitory activity on LPS-induced NO production in macrophage RAW264.7 cells

Four new 28-nor-oleanane-type triterpene oligoglycosides, camellenodiol 3-O-β-d-galactopyranosyl(1→2)[β-d-xylopyranosyl(1→2)-β-d-galactopyranosyl(1→3)]-β-d-glucuronopyranoside (2), camellenodiol 3-O-4′′-O-acetyl-β-d-galactopyranosyl(1→2)[β-d-xylopyranosyl(1→2)-β-d-galactopyranosyl(1→3)]-β-d-glucuronopyranoside (4), camellenodiol 3-O-(β-d-galactopyranosyl(1→2)[β-d-xylopyranosyl(1→2)-β-d-galactopyranosyl(1→3)]-6′-methoxy-β-d- glucuronopyranoside (5), and maragenin II 3-O-(β-d-galactopyranosyl(1→2)[β-d-xylopyranosyl(1→2)-β-d-galactopyranosyl(1→3)]-6′-methoxy-β-d-glucuronopyranoside (6), along with two known compounds, (1 and 3), were isolated from the stem bark of Camellia japonica. Their chemical structures were established mainly by 2D NMR techniques and mass spectrometry. The isolated compounds showed inhibitory effects on NO production in RAW264.7 macrophages.

Graphical abstractR1R2R3NO Production, IC50 value3HAcβ-d-Glu4.96 μM5CH3Hβ-d-Xyl5.19 μMFull-size tableTable optionsView in workspaceDownload as CSVFigure optionsDownload full-size imageDownload as PowerPoint slide