Supercritical fluid extraction assisted isolation of sesquiterpene lactones with antiproliferative effects from Centipeda minima

Phytochemistry. 2012 Apr:76:133-40. doi: 10.1016/j.phytochem.2012.01.003. Epub 2012 Jan 23.

Abstract

Pseudoguaianolide sesquiterpene lactones minimolides A (1), B (2), C (3) and D (4) and two guaianolide sesquiterpene lactones minimolides E (5) and F (6), along with seven known ones (7-13), were isolated from the supercritical fluid extract of Centipeda minima. The structures of these compounds were elucidated by extensive spectroscopic methods (IR, UV, HRESIMS, 1D-NMR and 2D-NMR), and the complete structure and stereochemistry of 1 was further confirmed by X-ray diffraction analysis. Compounds 1, 5-8,11 and 13 displayed inhibitory activity against human nasopharyngeal cancer cells (CNE) with IC(50) values ranging from 1.1 to 20.3 μM. Compound 13 containing both α-methylene-γ-lactone and α, β-unsaturated cyclopentenone moieties exhibited even stronger inhibitory activity than that of cisplatin (positive control) through cell cycle arrest at G2/M phase. Isolation of six sesquiterpene lactones from Centipeda minima highlighted the potential of supercritical fluid extraction for enrichment of minor constituents for phytochemical study.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Asteraceae / chemistry*
  • Cell Cycle Checkpoints
  • Cell Line, Tumor
  • Chromatography, Supercritical Fluid / methods*
  • Cisplatin / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Lactones / chemistry
  • Lactones / isolation & purification
  • Lactones / pharmacology
  • Magnetic Resonance Spectroscopy / methods
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes, Germacrane / chemistry
  • Sesquiterpenes, Germacrane / isolation & purification*
  • Sesquiterpenes, Germacrane / pharmacology
  • Sesquiterpenes, Guaiane
  • Stereoisomerism
  • X-Ray Diffraction

Substances

  • (6S,7R,8S)-8,14-diacetoxy-15-hydroxygermacra-1(10),4,11(13)-trien-6, 12-olide
  • Antineoplastic Agents, Phytogenic
  • Lactones
  • Sesquiterpenes
  • Sesquiterpenes, Germacrane
  • Sesquiterpenes, Guaiane
  • florilenalin-2alpha-O-isobutyrate
  • helenalin
  • Cisplatin