Show legend Show as text

Structure type: oligomer
Trivial name: ardisiacrispin A
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_983931,SB_192

• Article ID: 11674
  Jansaku C, Baumann H, Kenne L, Samuelsson G "Ardisiacrispin A and B, two utero-contracting saponins from Ardisia crispa" - Planta Medica 53(5) (1987) 405-409
  

  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

  NCBI PubMed ID: 3432422
  Publication DOI: 10.1055/s-2006-962758
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Department of Pharmacognosy, University of Uppsala, Biomedicum, Box 579, S-751 23 Uppsala, Sweden, Department of Biology, Faculty of Science, Prince of Songkla University, Haao-Yai, Thailand, Department of Organic Chemistry, University of Stockholm, Arrhenius Laboratory, Stockholm, Sweden
  Methods: 13C NMR, 1H NMR, GLC-MS, IR, TLC, GLC, HPLC, UV, molecular modeling, optical rotation measurement, acetylation, molecular mechanics, methylation analysis, COSY, NOESY, TFA hydrolysis
  
   
  
  Ardisia crispa
  CSDB ID 62476 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: ardisiacrispin B
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 11674
  Jansaku C, Baumann H, Kenne L, Samuelsson G "Ardisiacrispin A and B, two utero-contracting saponins from Ardisia crispa" - Planta Medica 53(5) (1987) 405-409
  

  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

  NCBI PubMed ID: 3432422
  Publication DOI: 10.1055/s-2006-962758
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Department of Pharmacognosy, University of Uppsala, Biomedicum, Box 579, S-751 23 Uppsala, Sweden, Department of Biology, Faculty of Science, Prince of Songkla University, Haao-Yai, Thailand, Department of Organic Chemistry, University of Stockholm, Arrhenius Laboratory, Stockholm, Sweden
  Methods: 13C NMR, 1H NMR, GLC-MS, IR, TLC, GLC, HPLC, UV, molecular modeling, optical rotation measurement, acetylation, molecular mechanics, methylation analysis, COSY, NOESY, TFA hydrolysis
  
   
  
  Ardisia crispa
  CSDB ID 62477 (all data & tools)
• Article ID: 12249
  Huang J, Ogihara Y, Zhang H, Shimizu N, Takeda T "Triterpenoid saponins from Ardisia mamillata" - Phytochemistry 54(8) (2000) 817-822
  

  Two saponins were isolated from the roots of Ardisia mamillata HANCE. Their structures were established on the basis of MALDI-TOFMS, 1H, 13C NMR and 2D NMR (COSY, HOHAHA, HETCOR, HMBC and ROESY) spectra, and on chemical evidence, to be ardisimamilloside A, 3-O-{α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-3β, 16α,28α-trihydroxy-13β,28-epoxy-oleanan-30-al; and ardisimamilloside B, 3-O-{α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-3β-hydroxy-13β,28-epoxy-oleanan-16-oxo-30-al.

  triterpenoid saponin, Myrsinaceae, Ardisia mamillata, ardisimamilloside A, ardisimamilloside B

  NCBI PubMed ID: 11014272
  Publication DOI: 10.1016/s0031-9422(00)00173-4
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: takeda-td@kyoritsu-ph.ac.jp
  Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan, School of Pharmaceutical Sciences, West China University of Medical Sciences, Chengdu, China, Department of Pharmacognosy, Kyoritsu College of Pharmacy, Tokyo, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, acid hydrolysis, GC, MALDI-TOF MS, HPLC, extraction, optical rotation measurement, acetylation, elemental analysis, reduction, CC, melting point determination, precipitation, derivatization, evaporation
  
   
  
  Ardisia mamillata
  CSDB ID 65871 (all data & tools)