Three newly identified lipophilic flavonoids in Tanacetum parthenium supercritical fluid extract penetrating the Blood-Brain Barrier

J Pharm Biomed Anal. 2018 Feb 5:149:488-493. doi: 10.1016/j.jpba.2017.11.029. Epub 2017 Nov 16.

Abstract

Feverfew (Tanacetum parthenium L.) as a perennial herb has been known for centuries due to its medicinal properties. The main sesquiterpene lactone, parthenolide is considered to be responsible for the migraine prophylactic effect, however the pharmacological benefits of the lipophilic flavonoid components can not be neglected. Supercritical fluid extraction (7% ethanol, 22MPa, 64°C) was carried out on the leaves of Tanacetum parthenium L. from which the presence of methylated flavonoids beside parthenolide and other sesquiterpene lactones were indicated by preliminary LC-MS analyses. Specific Parallel Artificial Membrane Permeability Assay (PAMPA) was applied to identify the components capable to cross the Blood-Brain Barrier (BBB). Three lipophilic flavonoids were detected on the acceptor side, that were isolated (Prep-HPLC) and identified as sudachitin, aceronin and nevadensin (LC-MS/MS, NMR). These flavonoids were also characterized individually by PAMPA-BBB model. The presence of sudachitin and nevadensin was proven in the Asteraceae family, but neither of the three flavonoids were reported in Tanacetum parthenium L.

Keywords: Methylated flavonoids; NMR; PAMPA-BBB; Supercritical fluid extraction; Tanacetum parthenium L.

MeSH terms

  • Blood-Brain Barrier / drug effects*
  • Chromatography, High Pressure Liquid / instrumentation
  • Chromatography, High Pressure Liquid / methods
  • Chromatography, Supercritical Fluid / instrumentation
  • Chromatography, Supercritical Fluid / methods
  • Flavones / chemistry
  • Flavones / pharmacokinetics
  • Flavonoids / chemistry
  • Flavonoids / pharmacokinetics*
  • Glycosides / chemistry
  • Glycosides / pharmacokinetics
  • Lipids / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacokinetics*
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Tanacetum parthenium / chemistry*
  • Tandem Mass Spectrometry / instrumentation
  • Tandem Mass Spectrometry / methods

Substances

  • Flavones
  • Flavonoids
  • Glycosides
  • Lipids
  • Plant Extracts
  • sudachitin
  • nevadensin