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 three malassezin, was identified as 2-( 1H-indol-3-ylmethl)- 1 H-indole-3-carbaldehyde (I). 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 muM) in rat hepatocytes. (C) 2001 Elsevier Science Ltd. All rights reserved.