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