Anti-proliferative activity of aguerin B and a new rare nor-guaianolide lactone isolated from the aerial parts of Centaurea deflexa

Eur J Med Chem. 2011 Jul;46(7):3066-70. doi: 10.1016/j.ejmech.2011.03.011. Epub 2011 Mar 15.

Abstract

The phytochemical investigation of the aerial parts of Centaurea deflexa led to the identification of 21 compounds, among which three phenolic acids, one sterol, ten flavonoids, one phenylpropanoid derivative, two lignans and four sesquiterpene lactones. One of the latter compounds was a new, rare active principle (1) having an uncommon 15-nor-guaianolide skeleton. The biological investigation was carried out through a bio-guided assay fractionation of C. deflexa extracts and highlighted an anti-proliferative activity of two sesquiterpene lactones, aguerin B and the newly identified 15-nor-guaianolide (1) against human pancreatic and colonic cancer cells. Of the two compounds, only aguerin B showed to induce apoptotic cell death, confirming the role as pro-apoptotic moiety of the α-methylene-γ-lactone ring present in aguerin B but not in 1.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Centaurea / chemistry*
  • DNA Fragmentation / drug effects
  • Humans
  • Lactones / chemistry*
  • Lactones / isolation & purification
  • Lactones / pharmacology
  • Plant Components, Aerial / chemistry
  • Plant Extracts / chemistry*
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes, Guaiane / chemistry*
  • Sesquiterpenes, Guaiane / isolation & purification
  • Sesquiterpenes, Guaiane / pharmacology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Lactones
  • Plant Extracts
  • Sesquiterpenes
  • Sesquiterpenes, Guaiane
  • aguerin B