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-(1→2)-[β- D -xylopyranosyl-(1→6)]-β- D -glucopyranosyl ester (loniceroside J).