Triterpenoid saponins from the roots of two Gypsophila species

Phytochemistry. 2014 Jun:102:182-8. doi: 10.1016/j.phytochem.2014.02.018. Epub 2014 Apr 8.

Abstract

Two triterpenoid saponins with two known ones have been isolated from the roots of Gypsophila arrostii var. nebulosa, and two new ones from the roots of Gypsophila bicolor. Their structures were established by extensive NMR and mass spectroscopic techniques as 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosylquillaic acid 28-O-β-d-xylopyranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-fucopyranosyl ester (1), 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosylgypsogenin 28-O-β-d-xylopyranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-fucopyranosyl ester (2), 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosylgypsogenin 28-O-β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-β-d-quinovopyranosyl-(1→4)]-β-d-fucopyranosyl ester (3), gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-{6-O-[3-hydroxy-3-methylglutaryl]-β-d-glucopyranosyl-(1→6)}-β-d-galactopyranosyl ester (4). Three compounds were evaluated against one human colon cancer cell line SW480 and one rat cardiomyoblast cell line H9c2.

Keywords: 2D NMR; Caryophyllaceae; Gypsophila arrostii; Gypsophila bicolor; Triterpenoid saponins.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Caryophyllaceae / chemistry*
  • Cell Line
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Conformation
  • Plant Roots / chemistry*
  • Rats
  • Saponins / chemistry
  • Saponins / isolation & purification
  • Saponins / pharmacology*
  • Species Specificity
  • Stereoisomerism
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • Antineoplastic Agents
  • Saponins
  • Triterpenes