N-glucosyl-1H-indole derivatives from Cortinarius brunneus (Basidiomycetes)

Chem Biodivers. 2008 Apr;5(4):664-9. doi: 10.1002/cbdv.200890062.

Abstract

Two new N-glucosylated indole alkaloids were isolated from fruiting bodies of the basidiomycete Cortinarius brunneus (Pers.) Fr. The structures were elucidated by means of the spectroscopic data. Additionally, the very recently reported compounds N-1-beta-glucopyranosyl-3-(carboxymethyl)-1H-indole (3) and N-1-beta-glucopyranosyl-3-(2-methoxy-2-oxoethyl)-1H-indole (4) could be detected. Compound 3 is the N-glucoside of the plant-growth regulator 1H-indole-3-acetic acid (IAA), but, in contrast, it does not exhibit auxin-like activity in an Arabidopsis thaliana tap root elongation assay.

MeSH terms

  • Agaricales / chemistry*
  • Arabidopsis
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology
  • Indoleacetic Acids / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / drug effects

Substances

  • Glucosides
  • Indole Alkaloids
  • Indoleacetic Acids