Sesquiterpene lactones from Centaurea rhizantha C.A. Meyer

Nat Prod Res. 2019 Jul;33(14):2016-2023. doi: 10.1080/14786419.2018.1483926. Epub 2018 Jun 18.

Abstract

Two new sesquiterpene lactones, rhizantholide A (1) and rhizantholide B (2), together with five known compounds (3-7) have been isolated from the aerial parts of Centaurea rhizantha (Asteraceae). Sesquiterpene lactones belong to guaianolide class, and rhizantholide B is a rare guaianolide characterized by a free primary alcoholic function at C-10 along with a 3β,10β-epoxy function. Their structures have been established on the basis of 1D and 2D NMR experiments, as well as HR-ESIMS. The antimicrobial activity of compounds 1-7 has been evaluated against Gram-positive and Gram-negative strains. Only deacylcynaropicrin 8-O-[3'-hydroxy-2'-methylpropionate] (5) showed moderate antibacterial activity against Staphylococcus aureus with a MIC/MBC value of 500 μg/mL. All isolated compounds have been also evaluated for their cytotoxic activities against cancer cells. Among them, compound 5 showed the highest cytotoxic activity with IC50 values in the range 5.02-16.76 μg/mL.

Keywords: genus; Antimicrobial; Asteraceae; Cytotoxic activity; Sesquiterpene lactones.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Asteraceae / chemistry
  • Cell Line, Tumor
  • Centaurea / chemistry*
  • Drug Screening Assays, Antitumor
  • Humans
  • Lactones / chemistry*
  • Lactones / isolation & purification
  • Lactones / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Extracts / chemistry
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Lactones
  • Plant Extracts
  • Sesquiterpenes
  • deacylcynaropicrin