Iridoid glycosides from Gardeniae Fructus for treatment of ankle sprain

Abstract

The iridoid glycosides, genipin 1- O-β- d-isomaltoside ( 1) and genipin 1,10-di- O-β- d-glucopyranoside ( 2), together with six known iridoid glycosides, genipin 1- O-β- d-gentiobioside ( 3), geniposide ( 4), scandoside methyl ester ( 5), deacetylasperulosidic acid methyl ester ( 6), 6- O-methyldeacetylasperulosidic acid methyl ester ( 7), and gardenoside ( 8) were isolated from an EtOH extract of Gardeniae Fructus. The structures and relative stereochemistries of the metabolites were elucidated on the basis of 1D- and 2D-NMR spectroscopic techniques, high-resolution mass spectrometry, and chemical evidence. Geniposide ( 4), one of the main compounds of Gardeniae Fructus, was tested for treatment of ankle sprain using an ankle sprain model in rats. From the second to fifth day, the geniposide ( 4) (100 mg/ml) treated group exhibited significant differences ( p < 0.01) with ∼21–34% reduction in swelling ratio compared with those of the vehicle treated control group. This indicated the potential effect of geniposide ( 4) for the treatment of disorders such as ankle sprain.