N-glucosyl-1H-indole derivatives from Cortinarius brunneus (Basidiomycetes).
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.
Teichert
Axel
A
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle/Saale.
Schmidt
Jürgen
J
Porzel
Andrea
A
Arnold
Norbert
N
Wessjohann
Ludger
L
D000363:Agaricales / Q000737:chemistry*; D017360:Arabidopsis; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007210:Indoleacetic Acids / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000187:drug effects
D005960:Glucosides; D026121:Indole Alkaloids; D007210:Indoleacetic Acids