Malassezin--A novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur.
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.
Wille
G
G
Department Chemie der Ludwig-Maximilians-Universität, München, Germany.
Mayser
P
P
Thoma
W
W
Monsees
T
T
Baumgart
A
A
Schmitz
H J
HJ
Schrenk
D
D
Polborn
K
K
Steglich
W
W
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*
D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D007211:Indoles; D018336:Receptors, Aryl Hydrocarbon; C436511:malassezin; D019363:Cytochrome P-450 CYP1A1; D014442:Monophenol Monooxygenase