Malassezin--A novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur |
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| Authors: | Wille G Mayser P Thoma W Monsees T Baumgart A Schmitz H J Schrenk D Polborn K Steglich W |
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| Affiliation: | 1. Department Chemie der Ludwig-Maximilians-Universität, Butenandtstr. 5-13 (F), 81377 München, Germany;2. Center for Dermatology and Andrology, Justus-Liebig-University, 35385 Gießen, Germany;3. Lebensmittelchemie und Umwelttoxikologie der Universität Kaiserslautern, 67663 Kaiserslautern, Germany;1. School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan;2. Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599-7568, United States;3. Screening Technologies Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, Frederick National Laboratory for Cancer Research, National Cancer Institute, Frederick, MD 21702, United States;4. Chinese Medicine Research and Development Center, China Medical University and Hospital, 2 Yuh-Der Road, Taichung 40447, Taiwan;1. Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi, 20131, Thailand;2. Department of Biochemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi, 20131, Thailand;1. Queen Astrid Military Hospital, Burn Wound Centre, Laboratory for Molecular and Cellular Technology, Bruynstraat 1, 1120 Brussels, Belgium;2. KU Leuven, Faculty of Pharmaceutical and Pharmacological Sciences, Herestraat 49, 3000 Leuven, Belgium;3. Royal Military Academy, Department of Behavioural Sciences, Renaissancelaan 30, 1000 Brussels, Belgium;1. KU Leuven, Centre for Intellectual Property Rights, Minderbroedersstraat 5, 3000 Leuven, Belgium;2. KU Leuven, Faculty of Pharmaceutical and Pharmacological Sciences, Herestraat 49, 3000 Leuven, Belgium;1. Department of Pharmaceutical Sciences, University of Perugia, via del Liceo 1, 06123, Perugia, Italy;2. Department of Experimental Medicine, University of Perugia, via Gambuli 1, 06132, Perugia, Italy;1. State Key Laboratory of Cellular Stress Biology, School of Life Sciences, Xiamen University, Xiamen, Fujian, 361005, China;2. State Key Laboratory of Marine Environmental Science, Xiamen University, Xiamen, Fujian, 361005, China |
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| 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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