Constituents of sage (Salvia officinalis) with in vitro affinity to human brain benzodiazepine receptor.
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.
Kavvadias
Dominique
D
Food Chemistry, University of Würzburg, Würzburg, Germany.
Monschein
Vanessa
V
Sand
Philipp
P
Riederer
Peter
P
Schreier
Peter
P
D002540:Cerebral Cortex / Q000187:drug effects* / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D004224:Diterpenes / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D005419:Flavonoids / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D018515:Plant Leaves; D011963:Receptors, GABA-A / Q000187:drug effects*; D027543:Salvia officinalis; D013329:Structure-Activity Relationship
D004224:Diterpenes; D005419:Flavonoids; D010936:Plant Extracts; D011963:Receptors, GABA-A