Bisanthraquinone glycosides of Hypericum perforatum with binding inhibition to CRH-1 receptors

Phytochemistry. 2000 Dec;55(8):941-7. doi: 10.1016/s0031-9422(00)00305-8.

Abstract

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.

MeSH terms

  • Acetylation
  • Amphibian Proteins
  • Binding, Competitive
  • Drug Interactions
  • Hypericum / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Peptide Hormones
  • Peptides / pharmacology
  • Plants, Medicinal*
  • Receptors, Corticotropin-Releasing Hormone / antagonists & inhibitors*
  • Receptors, Corticotropin-Releasing Hormone / metabolism
  • Vasodilator Agents / pharmacology

Substances

  • Amphibian Proteins
  • Peptide Hormones
  • Peptides
  • Receptors, Corticotropin-Releasing Hormone
  • Vasodilator Agents
  • CRF receptor type 1
  • sauvagine