Planta Med 2005; 71(7): 609-616
DOI: 10.1055/s-2005-871265
Original Paper
Pharmacology
© Georg Thieme Verlag KG Stuttgart · New York

5-HT3 Receptor Blocking Activity of Arylalkanes Isolated from the Rhizome of Zingiber officinale

H. Abdel-Aziz1 , A. Nahrstedt2 , F. Petereit2 , T. Windeck3 , M. Ploch3 , E. J. Verspohl1
  • 1Department of Pharmacology, Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Germany
  • 2Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Germany
  • 3Lichtwer Pharma AG, Berlin, Germany
Further Information

Publication History

Received: September 3, 2004

Accepted: February 15, 2005

Publication Date:
18 July 2005 (online)

Abstract

Different extracts (ethanolic, hexane, aqueous) of ginger (rhizomes of Zingiber officinale) and the essential oil were tested using [14C]guanidinium influx into N1E-115 cells and the isolated rat ileum in order to identify their activity in inhibiting 5-HT3 receptor function. The hexane extract proved to be the most active and yielded upon bioassay-guided fractionation nine constituents: [6]-, [8]-, [10]-gingerols, [6]- and [8]-shogaols which were previously shown as active in vivo against cytotoxic drug-induced emesis; [4]-gingerol, [6]-gingerdiol, diacetyl-[6]-gingerdiol and [6]-dehydrogingerdione have not been previously tested for anti-emetic or 5-HT3 receptor antagonistic effects. Even though the latter four compounds are only minor constituents, their identification contributed towards the characterisation of a structure-activity relationship of this class of compounds. The order of potency for the nine constituents in the N1E-115 cell system was [6]-gingerdiol ≈ diacetyl-[6]-gingerdiol ≈ [6]-dehydrogingerdione ≈ [6]-shogaol ≥ [8]-shogaol ≈ [8]-gingerol > [10]-gingerol ≥ [6]-gingerol > [4]-gingerol.

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Dr. Eugen J. Verspohl

Deptartment of Pharmacology

Institute of Pharmaceutical and Medicinal Chemistry

University of Münster

Hittorfstr. 58 - 62

48149 Münster

Germany

Email: verspoh@uni-muenster.de

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