Literature DB >> 11354679

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

G Wille1, P Mayser, W Thoma, T Monsees, A Baumgart, H J Schmitz, D Schrenk, K Polborn, W Steglich.   

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.

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Year:  2001        PMID： 11354679     DOI： 10.1016/s0968-0896(00)00319-9

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  15 in total

Review 1.  Ah receptor ligands and their impacts on gut resilience: structure-activity effects.

Authors:  Stephen Safe; Arul Jayaraman; Robert S Chapkin
Journal:  Crit Rev Toxicol       Date:  2020-06-29       Impact factor: 5.635

2.  Pityriazepin and other potent AhR ligands isolated from Malassezia furfur yeast.

Authors:  Nikitia Mexia; Georgios Gaitanis; Aristea Velegraki; Anatoly Soshilov; Michael S Denison; Prokopios Magiatis
Journal:  Arch Biochem Biophys       Date:  2015-02-24       Impact factor: 4.013

3.  A Biomimetic, One-Step Transformation of Simple Indolic Compounds to Malassezia-Related Alkaloids with High AhR Potency and Efficacy.

Authors:  Nikitia Mexia; Stamatis Koutrakis; Guochun He; Alexios-Leandros Skaltsounis; Michael S Denison; Prokopios Magiatis
Journal:  Chem Res Toxicol       Date:  2019-11-07       Impact factor: 3.739

4.  [UV radiation and skin pigmentation. Aryl hydrocarbon receptor - a "new kid on the block"].

Authors:  C Esser; J Krutmann
Journal:  Hautarzt       Date:  2010-07       Impact factor: 0.751

5.  Platinum-catalyzed tandem indole annulation/arylation for the synthesis of diindolylmethanes and indolo[3,2-b]carbazoles.

Authors:  Dongxu Shu; Gabrielle N Winston-McPherson; Wangze Song; Weiping Tang
Journal:  Org Lett       Date:  2013-08-05       Impact factor: 6.005

Review 6.  The Malassezia genus in skin and systemic diseases.

Authors:  Georgios Gaitanis; Prokopios Magiatis; Markus Hantschke; Ioannis D Bassukas; Aristea Velegraki
Journal:  Clin Microbiol Rev       Date:  2012-01       Impact factor: 26.132

7.  Malassezia yeasts produce a collection of exceptionally potent activators of the Ah (dioxin) receptor detected in diseased human skin.

Authors:  Prokopios Magiatis; Periklis Pappas; George Gaitanis; Nikitia Mexia; Eleni Melliou; Maria Galanou; Christophoros Vlachos; Konstantina Stathopoulou; Alexios Leandros Skaltsounis; Marios Marselos; Aristea Velegraki; Michael S Denison; Ioannis D Bassukas
Journal:  J Invest Dermatol       Date:  2013-02-28       Impact factor: 8.551

8.  Synthesis and biological evaluation of 2,3'-diindolylmethanes as agonists of aryl hydrocarbon receptor.

Authors:  Gabrielle N Winston-McPherson; Dongxu Shu; Weiping Tang
Journal:  Bioorg Med Chem Lett       Date:  2014-06-18       Impact factor: 2.823

9.  Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols.

Authors:  Hui Li; Xiaoxun Li; Hao-Yuan Wang; Gabrielle N Winston-McPherson; Hao-miao Julie Geng; Ilia A Guzei; Weiping Tang
Journal:  Chem Commun (Camb)       Date:  2014-10-21       Impact factor: 6.222

10.  Structural identification of Diindole agonists of the aryl hydrocarbon receptor derived from degradation of indole-3-pyruvic acid.

Authors:  Goutam Chowdhury; Miroslav Dostalek; Erin L Hsu; Linh P Nguyen; Donald F Stec; Christopher A Bradfield; F Peter Guengerich
Journal:  Chem Res Toxicol       Date:  2009-12       Impact factor: 3.739
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