Ceanothane- and lupane-type triterpene esters from the roots of Hovenia dulcis and their antiproliferative activity on HSC-T6 cells

Phytochemistry. 2017 Oct:142:60-67. doi: 10.1016/j.phytochem.2017.06.014. Epub 2017 Jul 4.

Abstract

Three ceanothane-type and three lupane-type triterpenoids, as well as three known compounds, were isolated from the roots of Hovenia dulcis (Rhamnaceae), based on LC-MS dereplication. The previously undescribed compounds were determined to be 27-O-protocatechuoyl-3-dehydroxyisoceanothanolic acid, 27-O-protocatechuoyl-3-dehydroxycolubrinic acid, 27-O-protocatechuoyl-3-dehydroxyepicolubrinic acid, 27-O-protocatechuoylbetulinic acid, 27-O-p-hydroxybenzoylbetulinic acid, and 27-O-syringoylbetulinic acid by 1D and 2D NMR spectroscopic and HR mass spectrometric data analysis. The isolates were examined for their antiproliferative activity in HSC-T6 hepatic stellate cells; compounds 1, 2, 3, and 6 showed IC50 values in the range of 15-50 μM.

Keywords: Antiproliferative activity; HSC-T6; Hovenia dulcis; Rhamnaceae; Triterpenoid.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Enterococcus faecalis / drug effects
  • Esters
  • Inhibitory Concentration 50
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry*
  • Rhamnaceae / chemistry*
  • Staphylococcus aureus / drug effects
  • Triterpenes / chemistry
  • Triterpenes / classification
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • 27-O-protocatechuoyl-3-dehydroxycolubrinic acid
  • 27-O-protocatechuoyl-3-dehydroxyepicolubrinic acid
  • 27-O-protocatechuoyl-3-dehydroxyisoceanothanolic acid
  • Anti-Bacterial Agents
  • Esters
  • Triterpenes
  • ceanothane
  • lupane