Constituents of sage (Salvia officinalis) with in vitro affinity to human brain benzodiazepine receptor

Planta Med. 2003 Feb;69(2):113-7. doi: 10.1055/s-2003-37712.

Abstract

Benzodiazepine receptor binding assay-guided fractionation of the methanol extract from sage leaves ( Salvia officinalis L.) revealed three flavones and two abietane diterpenes functioning as benzodiazepine receptor-active components. Structural elucidation of the isolated pure compounds was performed by UV, EI-MS, ESI(pos)-MS/MS, as well as 1H- and 13C-NMR techniques. The flavones apigenin, hispidulin and cirsimaritin competitively inhibited 3H-flumazenil binding to the benzodiazepine receptor with IC50 values of 30, 1.3 and 350 microM, respectively. In addition, the affinities of the newly discovered diterpene receptor ligands, i. e., 7-methoxyrosmanol and galdosol, were characterized. 7-Methoxyrosmanol exhibited an IC50 value of 7.2 microM and galdosol showed the strongest binding activity to the benzodiazepine receptor with an IC50 value of 0.8 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cerebral Cortex / drug effects*
  • Cerebral Cortex / metabolism
  • Chromatography, High Pressure Liquid
  • Diterpenes / administration & dosage
  • Diterpenes / chemistry
  • Diterpenes / pharmacology
  • Diterpenes / therapeutic use
  • Flavonoids / administration & dosage
  • Flavonoids / chemistry
  • Flavonoids / pharmacology
  • Flavonoids / therapeutic use
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Phytotherapy*
  • Plant Extracts / administration & dosage
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Extracts / therapeutic use
  • Plant Leaves
  • Receptors, GABA-A / drug effects*
  • Salvia officinalis*
  • Structure-Activity Relationship

Substances

  • Diterpenes
  • Flavonoids
  • Plant Extracts
  • Receptors, GABA-A