New bisabolane sesquiterpenes and coumarin from Leontopodium longifolium

Chem Biodivers. 2006 Jul;3(7):783-90. doi: 10.1002/cbdv.200690080.

Abstract

From the roots of Leontopotium longifolium, three new bisabolane sesquiterpenes, rel-(1S,4R,5S,6R)-4,5-diacetoxy-6-[(R)-1,5-dimethylhexa-3,5-dienyl]-3-methylcyclohex-2-enyl (Z)-2-methylbut-2-enoate (1), rel-(1S,4R,5S,6R)-4,5-diacetoxy-6-[(R)-5-hydroxy-1,5-dimethylhex-3-enyl]-3-methylcyclohex-2-enyl (Z)-2-methylbut-2-enoate (2), rel-(1R,2S,4R,5S)-4-acetoxy-2-[(R)-5-hydroxy-1,5-dimethylhex-3-enyl]-5-methylcyclohexyl (Z)-2-methylbut-2-enoate (3), and a new coumarin, 2,3-dihydro-5-hydroxy-2-(1-methylethenyl)-7H-pyrano[2,3-g][1,4]benzodioxin-7-one (4) together with nine known compounds have been isolated. The structures of these compounds were established by spectroscopic methods. Compounds 1 and 2 exhibited moderate cytotoxic activities against human promyelocytic leukemia (HL-60) cells.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / toxicity
  • Asteraceae / chemistry*
  • Asteraceae / metabolism
  • Cell Survival / drug effects
  • HL-60 Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / metabolism
  • Sesquiterpenes / toxicity

Substances

  • Antineoplastic Agents
  • Sesquiterpenes