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

Authors
Wille, G Mayser, P Thoma, W Monsees, T Baumgart, A Schmitz, HJ Schrenk, D Polborn, K Steglich, W
Citation
G. Wille et al., Malassezin - A novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur, BIO MED CH, 9(4), 2001, pp. 955-960
Citations number
27
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY
ISSN journal
09680896 → ACNP
Volume
9
Issue
4
Year of publication
2001
Pages
955 - 960
Database
ISI
SICI code
0968-0896(200104)9:4<955:M-ANAO>2.0.ZU;2-7
Abstract
The yeast Malassezia furfur converts tryptophan into several indole compoun ds. 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-carbalde hyde 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 arylhydrocar bon receptor (AHR). Similarly, malassezin was found to induce cytochrome P4 50 as an agonist of AHR(EC50 = 1.57 muM) in rat hepatocytes. (C) 2001 Elsev ier Science Ltd. All rights reserved.