Three New Highly Oxygenated Germacranolides from Carpesium Divaricatum and Their Cytotoxic Activity

Molecules. 2018 May 3;23(5):1078. doi: 10.3390/molecules23051078.

Abstract

Three new highly oxygenated (24), and two known (1 and 5) germacranolides, were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by detailed spectroscopic analysis. The absolute configuration of 1 was established using the circular dichroism (CD) method and X-ray diffraction, and the stereochemistry of the new compounds 24 were determined using similar CD spectra with 1. The new compound 2 and the known compound 5 exhibited potent cytotoxicity against hepatocellular cancer (Hep G2) and human cervical cancer (HeLa) cells, superior to those of the positive control cis-platin.

Keywords: Carpesium divaricatum; absolute configuration; cytotoxicity; germacranolides.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Asteraceae / chemistry*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Circular Dichroism
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Sesquiterpenes, Germacrane / chemistry*
  • Sesquiterpenes, Germacrane / isolation & purification
  • Sesquiterpenes, Germacrane / pharmacology*
  • Structure-Activity Relationship
  • X-Ray Diffraction

Substances

  • Antineoplastic Agents, Phytogenic
  • Sesquiterpenes, Germacrane
  • germacranolide