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

Wirz A., Simmen U., Heilmann J., Calis I., Meier B., Sticher O.

PHYTOCHEMISTRY, vol.55, no.8, pp.941-947, 2000 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 55 Issue: 8
  • Publication Date: 2000
  • Doi Number: 10.1016/s0031-9422(00)00305-8
  • Journal Name: PHYTOCHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.941-947
  • Hacettepe University Affiliated: Yes

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 [(125) I]sauvagine binding to corticotropin releasing hormone (CRH-1) receptors. (C) 2000 Elsevier Science Ltd. All rights reserved.