5-HT3 receptor blocking activity of arylalkanes isolated from the rhizome of Zingiber officinale

Planta Med. 2005 Jul;71(7):609-16. doi: 10.1055/s-2005-871265.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor / drug effects
  • Cell Line, Tumor / metabolism
  • Dose-Response Relationship, Drug
  • Female
  • Ileum / drug effects
  • Male
  • Mice
  • Neuroblastoma
  • Phytotherapy*
  • Plant Extracts / administration & dosage
  • Plant Extracts / pharmacology*
  • Plant Extracts / therapeutic use
  • Plant Oils / administration & dosage
  • Plant Oils / pharmacology*
  • Plant Oils / therapeutic use
  • Rats
  • Receptors, Serotonin, 5-HT3 / drug effects*
  • Rhizome
  • Serotonin 5-HT3 Receptor Antagonists
  • Serotonin Antagonists / administration & dosage
  • Serotonin Antagonists / pharmacology*
  • Serotonin Antagonists / therapeutic use
  • Zingiber officinale*

Substances

  • Plant Extracts
  • Plant Oils
  • Receptors, Serotonin, 5-HT3
  • Serotonin 5-HT3 Receptor Antagonists
  • Serotonin Antagonists