Bisanthraquinone glycosides of Hypericum perforatum with binding inhibition to CRH-1 receptors.
Four new bisanthraquinone glycosides, S-(+)-skyrin-6-O-beta-glucopyranoside (1), R-(-)-skyrin-6-O-beta-glucopyranoside (2), S-(+)-skyrin-6-O-beta-xylopyranoside (3) and S-(+)-skyrin-6-O-beta-alpha-arabinofuranoside (4), have been isolated from an ethanol-water (1:1, v/v) dry extract of the aerial parts of Hypericum perforatum L. The structures were elucidated by spectroscopic methods, mainly NMR and mass spectrometry. Circular dichroism was used to determine their axial stereochemistry revealing 1 and 2 to be atropisomers. 1 and 2 inhibited [125I]sauvagine binding to corticotropin releasing hormone (CRH-1) receptors.
Wirz
A
A
Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zurich.
Simmen
U
U
Heilmann
J
J
Calis
I
I
Meier
B
B
Sticher
O
O
D000107:Acetylation; D029845:Amphibian Proteins; D001667:Binding, Competitive; D004347:Drug Interactions; D020902:Hypericum / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D036361:Peptide Hormones; D010455:Peptides / Q000494:pharmacology; D010946:Plants, Medicinal; D018019:Receptors, Corticotropin-Releasing Hormone / Q000037:antagonists & inhibitors* / Q000378:metabolism; D014665:Vasodilator Agents / Q000494:pharmacology; D000099052:CRF Receptor, Type 1
D029845:Amphibian Proteins; D036361:Peptide Hormones; D010455:Peptides; D018019:Receptors, Corticotropin-Releasing Hormone; D014665:Vasodilator Agents; D000099052:CRF Receptor, Type 1; C025727:sauvagine