Triterpene Glycosides from the Stems and Leaves of Lonicera japonica

Five new triterpene glycosides, namely lonicerosides F-J (1-5), together with five known ones, were isolated from the stems and leaves of Lonicera japonica. Based on extensive spectroscopic analysis, including two-dimensional (2D)-NMR experiments, and the results of hydrolysis, the structures of the new compounds were determined to be 3β-[(β-D-glucopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-β-D-glucopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl ester (loniceroside F), 3β-[(β-D-glucopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-(3-O-acetyl-β-D-xylopyranosyl)-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl ester (loniceroside G), 3β-[(β-D-glucopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-(4-O-acetyl-β-D-xylopyranosyl)-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl ester (loniceroside H), 3β[(α-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-(3-O-acetyl-β-D-xylopyranosyl)-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl ester (loniceroside I), and 3β[(α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl)oxy]-olean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(l→2)-[β-D-xylopyranosyl-(1→6)]-β-D-glucopyranosyl ester (loniceroside J).