Malassezin--A novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur

Bioorg Med Chem. 2001 Apr;9(4):955-60. doi: 10.1016/s0968-0896(00)00319-9.

Abstract

The yeast Malassezia furfur converts tryptophan into several indole compounds. One of these, malassezin, was identified as 2-(1H-indol-3-ylmethyl)-1H-indole-3-carbaldehyde (1). It was synthesized from N-Boc-indole-3-carbaldehyde in five steps with 12% overall yield. The compound easily cyclizes to indolo[3,2-b]carbazole (7) which is known to interact with the arylhydrocarbon receptor (AHR). Similarly, malassezin was found to induce cytochrome P450 as an agonist of AHR (EC50 = 1.57 microM) in rat hepatocytes.

MeSH terms

  • Animals
  • Chromatography, Thin Layer
  • Cytochrome P-450 CYP1A1 / antagonists & inhibitors
  • Cytochrome P-450 CYP1A1 / metabolism
  • Enzyme Inhibitors / pharmacology
  • Hepatocytes / drug effects
  • Hepatocytes / enzymology
  • Indicators and Reagents
  • Indoles / isolation & purification
  • Indoles / pharmacology*
  • Malassezia / chemistry*
  • Male
  • Models, Molecular
  • Monophenol Monooxygenase / antagonists & inhibitors
  • Rats
  • Rats, Wistar
  • Receptors, Aryl Hydrocarbon / agonists*

Substances

  • Enzyme Inhibitors
  • Indicators and Reagents
  • Indoles
  • Receptors, Aryl Hydrocarbon
  • malassezin
  • Cytochrome P-450 CYP1A1
  • Monophenol Monooxygenase