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)-[O-β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-16α-hydroxy-13β,28-epoxyolean-30-al. Ardisiacrispin B is: 3β-O-{α-L-rhamnnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-[O-β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-16α-hydroxy-13β,28-epoxyolean-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).

Ardisia crispa, ardisiacrispin A, ardisiacrispin B, triterpenic saponin

• Compound ID: 30041
  

  b-D-Glcp-(1-2)-+ | b-D-Xylp-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst Subst = cyclamiretin A = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC[C@]45[C@]6([H])C[C@@](C)(C=O)CC[C@@](CO5)6{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H]

  Show graphically

  Show legend Show as text

  Structure type: oligomer
  Trivial name: ardisiacrispin A
  Compound class: saponin glycoside
  
   
  
  Ardisia crispa
  CSDB ID 62476 (all data & tools)
• Compound ID: 30042
  

  b-D-Glcp-(1-2)-+ | a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst Subst = cyclamiretin A = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC[C@]45[C@]6([H])C[C@@](C)(C=O)CC[C@@](CO5)6{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H]

  Show graphically

  Show legend Show as text

  Structure type: oligomer
  Trivial name: ardisiacrispin B
  Compound class: saponin glycoside, glycoside, triterpenoid glycoside
  
   
  
  Ardisia crispa
  CSDB ID 62477 (all data & tools)