title: Malassezin--A novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur.
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.
authors.affiliation: Department Chemie der Ludwig-Maximilians-Universität, München, Germany.
authors.forename: G
authors.initials: G
authors.lastname: Wille
authors.forename: P
authors.initials: P
authors.lastname: Mayser
authors.forename: W
authors.initials: W
authors.lastname: Thoma
authors.forename: T
authors.initials: T
authors.lastname: Monsees
authors.forename: A
authors.initials: A
authors.lastname: Baumgart
authors.forename: H J
authors.initials: HJ
authors.lastname: Schmitz
authors.forename: D
authors.initials: D
authors.lastname: Schrenk
authors.forename: K
authors.initials: K
authors.lastname: Polborn
authors.forename: W
authors.initials: W
authors.lastname: Steglich
mesh_terms: D000818:Animals; D002855:Chromatography, Thin Layer; D019363:Cytochrome P-450 CYP1A1 / Q000037:antagonists & inhibitors / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000494:pharmacology; D022781:Hepatocytes / Q000187:drug effects / Q000201:enzymology; D007202:Indicators and Reagents; D007211:Indoles / Q000302:isolation & purification / Q000494:pharmacology*; D008290:Malassezia / Q000737:chemistry*; D008297:Male; D008958:Models, Molecular; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors; D051381:Rats; D017208:Rats, Wistar; D018336:Receptors, Aryl Hydrocarbon / Q000819:agonists*
chemical_list: D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D007211:Indoles; D018336:Receptors, Aryl Hydrocarbon; C436511:malassezin; D019363:Cytochrome P-450 CYP1A1; D014442:Monophenol Monooxygenase