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

A. Wirz; U. Simmen; J. Heilmann; I. Çalis; B. Meier; O. Sticher

doi:10.1016/S0031-9422(00)00305-8

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

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

Hacettepe University

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

Four new bisanthraquinone glycosides, S-(+)-skyrin-6-O-β-glucopyranoside (1), R-(-)-skyrin-6-O-β-glucopyranoside (2), S(+)-skyrin-6-O-β-xylopyranoside (3) and S-(+)-skyrin-6-O-β-α-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.

Original language	English
Pages (from-to)	941-947
Number of pages	7
Journal	Phytochemistry
Volume	55
Issue number	8
DOIs	https://doi.org/10.1016/S0031-9422(00)00305-8
Publication status	Published - 12 Dec 2000

Keywords

Bisanthraquinone glycosides
CRH-1 receptor
Hypericaceae
Hypericum perforatum
R-(-)-skyrin-6-O-β-glucopyran oside
S-(+)-skyrin-6-O-α-arabinofuranosid e
S-(+)-skyrin-6-O-β-glucopyranoside
S-(+)-skyrin-6-O-β-xylopyranoside

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10.1016/S0031-9422(00)00305-8

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title = "Bisanthraquinone glycosides of Hypericum perforatum with binding inhibition to CRH-1 receptors",

abstract = "Four new bisanthraquinone glycosides, S-(+)-skyrin-6-O-β-glucopyranoside (1), R-(-)-skyrin-6-O-β-glucopyranoside (2), S(+)-skyrin-6-O-β-xylopyranoside (3) and S-(+)-skyrin-6-O-β-α-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.",

keywords = "Bisanthraquinone glycosides, CRH-1 receptor, Hypericaceae, Hypericum perforatum, R-(-)-skyrin-6-O-β-glucopyran oside, S-(+)-skyrin-6-O-α-arabinofuranosid e, S-(+)-skyrin-6-O-β-glucopyranoside, S-(+)-skyrin-6-O-β-xylopyranoside",

author = "A. Wirz and U. Simmen and J. Heilmann and I. {\c C}alis and B. Meier and O. Sticher",

year = "2000",

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doi = "10.1016/S0031-9422(00)00305-8",

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T1 - Bisanthraquinone glycosides of Hypericum perforatum with binding inhibition to CRH-1 receptors

AU - Wirz, A.

AU - Simmen, U.

AU - Heilmann, J.

AU - Çalis, I.

AU - Meier, B.

AU - Sticher, O.

PY - 2000/12/12

Y1 - 2000/12/12

N2 - Four new bisanthraquinone glycosides, S-(+)-skyrin-6-O-β-glucopyranoside (1), R-(-)-skyrin-6-O-β-glucopyranoside (2), S(+)-skyrin-6-O-β-xylopyranoside (3) and S-(+)-skyrin-6-O-β-α-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.

AB - Four new bisanthraquinone glycosides, S-(+)-skyrin-6-O-β-glucopyranoside (1), R-(-)-skyrin-6-O-β-glucopyranoside (2), S(+)-skyrin-6-O-β-xylopyranoside (3) and S-(+)-skyrin-6-O-β-α-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.

KW - Bisanthraquinone glycosides

KW - CRH-1 receptor

KW - Hypericaceae

KW - Hypericum perforatum

KW - R-(-)-skyrin-6-O-β-glucopyran oside

KW - S-(+)-skyrin-6-O-α-arabinofuranosid e

KW - S-(+)-skyrin-6-O-β-glucopyranoside

KW - S-(+)-skyrin-6-O-β-xylopyranoside

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U2 - 10.1016/S0031-9422(00)00305-8

DO - 10.1016/S0031-9422(00)00305-8

M3 - Article

C2 - 11140529

AN - SCOPUS:0034642222

SN - 0031-9422

VL - 55

SP - 941

EP - 947

JO - Phytochemistry

JF - Phytochemistry

IS - 8

ER -

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

Abstract

Keywords

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