Antiasthmatic acetophenones — an in vivo study on structure activity relationship

W. Dorsch, A. Müller, V. Christoffel, H. Stuppner, S. Antus, A. Gottsegen, H. wagner

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The recently isolated acetophenone glucoside androsin, as the major antiasthmatic principle of Picrorhiza kurroa Royle ex Benth. (Scrophulariaceae), was used as a lead compound for detailed structure-activity relationship studies. More than 25 synthesized or commercially available acetophenones with modified substitution patterns were screened in the Plethysmographic guinea pig model using PAF and/or ovalbumin as challenging agents for the generation of bronchial constriction. Whereas the aglycones in most cases were more effective than the corresponding glycosides, substitution patterns in position 3 and 4 of the phenyl ring and the keto function attached to the phenyl ring were found to be essential for marked antiasthmatic effect. 3,5-Dimethoxy-4-hydroxy-acetophenone (acetosyringenin) showed the highest activity of all tested compounds. Initial in vitro studies on the mode of action could not sufficiently explain the mechanism of antiasthmatic activity.

Original languageEnglish
Pages (from-to)47-54
Number of pages8
JournalPhytomedicine
Volume1
Issue number1
DOIs
Publication statusPublished - Jan 1 1994

Keywords

  • Natural and synthetic acetophenones
  • Picrorhiza kurroa
  • plethysmographic guinea pig model
  • prevention of ovalbumin- and PAF-induced bronchoconstriction

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine

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    Dorsch, W., Müller, A., Christoffel, V., Stuppner, H., Antus, S., Gottsegen, A., & wagner, H. (1994). Antiasthmatic acetophenones — an in vivo study on structure activity relationship. Phytomedicine, 1(1), 47-54. https://doi.org/10.1016/S0944-7113(11)80022-X