title: 5-HT3 receptor blocking activity of arylalkanes isolated from the rhizome of Zingiber officinale.
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 approximately diacetyl-[6]-gingerdiol approximately [6]-dehydrogingerdione approximately [6]-shogaol > or = [8]-shogaol approximately [8]-gingerol > [10]-gingerol > or = [6]-gingerol > [4]-gingerol.
authors.affiliation: Department of Pharmacology, Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Germany.
authors.forename: H
authors.initials: H
authors.lastname: Abdel-Aziz
authors.forename: A
authors.initials: A
authors.lastname: Nahrstedt
authors.forename: F
authors.initials: F
authors.lastname: Petereit
authors.forename: T
authors.initials: T
authors.lastname: Windeck
authors.forename: M
authors.initials: M
authors.lastname: Ploch
authors.forename: E J
authors.initials: EJ
authors.lastname: Verspohl
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor / Q000187:drug effects / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D005260:Female; D020939:Zingiber officinale; D007082:Ileum / Q000187:drug effects; D008297:Male; D051379:Mice; D009447:Neuroblastoma; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D010938:Plant Oils / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D051381:Rats; D044406:Receptors, Serotonin, 5-HT3 / Q000187:drug effects*; D027343:Rhizome; D058831:Serotonin 5-HT3 Receptor Antagonists; D012702:Serotonin Antagonists / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use
chemical_list: D010936:Plant Extracts; D010938:Plant Oils; D044406:Receptors, Serotonin, 5-HT3; D058831:Serotonin 5-HT3 Receptor Antagonists; D012702:Serotonin Antagonists