Activation of a Sweet Taste Receptor by Oleanane-Type Glycosides from Wisteria sinensis
Résumé
The phytochemical study of Wisteria sinensis (Sims) DC. (Fabaceae), commonly known as the Chinese Wisteria, led to the isolation of seven oleanane-type glycosides from an aqueous-ethanolic extract of the roots. After successive purifications by various chromatographic methods, like solid/liquid chromatographic methods, vacuum liquid chromatography (VLC), medium pressure liquid chromatography (MPLC), on normal and reverse phase (RP-18 silica gel), and size exclusion chromatography on Sephadex L, their structures were elucidated by an extensive 600 MHz NMR analysis including 1D and 2D NMR experiments as well as ESI-MS. Among the seven isolated saponins, two have never been reported before : 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl-22-O-acetylolean-12-ene-3β,16β,22β,30-tetrol, and 3-O-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl wistariasapogenol A. Moreover, five additional known compounds were obtained, namely 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl wistariasapogenol A (wistariasaponin A), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl-(1→2)-β-D- glucuronopyranosyl soyasapogenol E (wistariasaponin D), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol E (dehydroazukisaponin V), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl 3b,22b,24-trihydroxyolean-12-ene (astragaloside VIII) et 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl 3b,22b,24-trihydroxyolean-12-ene soyasapogenol B (azukisaponin V). Based on the close structures between the saponins from W. sinensis, and the glycyrrhizin from licorice, the stimulation of the sweet testing receptors hTAS1R2/TAS1R3 by these latter was evaluated.