Gracilone, a new sesquiterpene lactone from Tanacetum gracile (Tansies)

Nat Prod Res. 2016 Oct;30(20):2291-8. doi: 10.1080/14786419.2016.1164701. Epub 2016 Mar 27.

Abstract

The methanolic extract of the Tanacetum gracile afforded the isolation of new sesquiterpene lactone, named gracilone (1) along with four known compounds as 14α-taraxeran-3-one (2), 14α-taraxeran-3-ol (3), apigenin (4) and β-sitosterol (5). The structure of compound 1 was elucidated on the basis of 1D, 2D NMR and MS spectroscopic analysis. Antimicrobial, antioxidant and anticancer activities of all compounds were evaluated, from which gracilone (1) showed a moderate antibacterial activity, while apigenin (4) showed comparatively more antibacterial activity against both gram-positive and gram-negative tested strains.

Keywords: Tanacetum gracile; antibacterial; anticancer activity; antioxidant; gracilone.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology*
  • Cell Line, Tumor
  • Drug Evaluation, Preclinical / methods
  • Humans
  • Inhibitory Concentration 50
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Sitosterols / isolation & purification
  • Sitosterols / pharmacology
  • Tanacetum / chemistry*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents, Phytogenic
  • Antioxidants
  • Lactones
  • Sesquiterpenes
  • Sitosterols
  • gracilone
  • gamma-sitosterol