Ardisiacrispin A and B, Two Utero-Contracting Saponins from Ardisia crispa

Abstract

The main utero-contracting activity of an aqueous extract of Ardisia crispa (Thunb.) A. DC. is due to two new triterpenic saponins called ardisiacrispin A and B, respectively. The saponins were isolated by extraction with n-butanol, followed by chromatography on silica gel columns. Final purification was obtained by reversed phase HPLC. ¹³C-NMR identified the aglycone of both saponins as cyclamiretin A. The structure of the ardisiacrispins was deduced by sugar and methylation analysis in combination with ¹H- and ¹³C-NMR spectral data.

Ardisiacrispin A is 3β-O-{-β-D-xylopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-[Oβ-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-16 α-hydroxy-13 β, 28-epoxy olean-30-al. Ardisiacrispin B is: 3β-O-{α-L-rhamnnopyranosyl-(1→2)-O-βD-glucopyranosyl-(1→4)-[O-β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-16 α-hydroxy-13 β, 28-epoxy olean-30-al. At a concentration in the bath of 8 µg/ml both saponins gave contractive responses of the isolated rat uterus corresponding to 84% of the contraction caused by a standard dose of acetyl choline (0.2 µg/ml).