Potent HGF/c-Met axis inhibitors from Eucalyptus globulus: the coupling of phloroglucinol and sesquiterpenoid is essential for the activity

J Med Chem. 2012 Sep 27;55(18):8183-7. doi: 10.1021/jm3007454. Epub 2012 Sep 7.

Abstract

Eucalyptin A (1), together with two known compounds 2 and 3 exhibiting potent inhibition on HGF/c-Met axis, was discovered from the fruits of Eucalyptus globulus. 1 possessed an unprecedented carbon framework of phloroglucinol-coupled sesquiterpenoid, and its structure was elucidated by spectroscopic method and ECD calculation. A brief structure-activity relationship discussion indicated that the coupling of a phloroglucinol and a sesquiterpenoid is essential for the activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Movement / drug effects
  • Cell Proliferation / drug effects
  • Dogs
  • Eucalyptus / chemistry*
  • Hepatocyte Growth Factor / antagonists & inhibitors*
  • Hepatocyte Growth Factor / pharmacology
  • Humans
  • Madin Darby Canine Kidney Cells
  • Phloroglucinol / chemistry*
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology
  • Proto-Oncogene Proteins c-met / antagonists & inhibitors*
  • Sesquiterpenes / chemistry*
  • Structure-Activity Relationship
  • Urokinase-Type Plasminogen Activator / antagonists & inhibitors

Substances

  • Plant Extracts
  • Protein Kinase Inhibitors
  • Sesquiterpenes
  • Hepatocyte Growth Factor
  • Phloroglucinol
  • Proto-Oncogene Proteins c-met
  • Urokinase-Type Plasminogen Activator