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 3 beta-[(beta-D-glucopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-beta-D-glucopyranosyl(1 -> 6)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-D-glucopyranosyl ester (loniceroside F), 3 beta-[(beta-D-glucopyranosyl) oxy]-23-hydroxyolean-12-en-28-oic acid O-(beta-D-acetyl-beta-n-xylopyranosyl)-(1 -> 6)-[alpha-L-rhamnopyranosyl(1 -> 2)]1-D-glucopyranosyl ester (loniceroside G), 3 beta-[(beta-n-glucopyranosyl)oxy1-23-hydroxyolean-12-en-28oic acid O-(4-O-acetyl-beta-n-xylopyranosyl)-(1 -> 6)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-n-glucopyranosyl ester (loniceroside H), 3 beta-[(alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid 19-(3-O-acetyl-beta-nxylopyranosyl)-(1 -> 6)-k-L-rhamnopyranosyl-(1 ->alpha)14-n-glucopyranosyl ester (loniceroside I), and 3 beta-Ka-Lrhamnopyranosyl-(1 -> 2)-beta-n-glucopyranosyl)oxyFolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1 -> 2)-[beta-xylopyranosyl-(1 -> 6)]-beta-alpha-glucopyranosyl ester (loniceroside J).