Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 11, Pages 2084-2090Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901311
Keywords
Alkaloids; Fungi; Melanin; Natural products; Mycosis
Categories
Funding
- Deutsche Forschungsgemeinschaft (DFG) [SP 718/1-2, SP 718/1-3, 1160, MA 1839/5-1]
- Fonds der Chemischen Industrie
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Exophialin, a previously unknown indole alkaloid, was isolated from the human-pathogenic fungus Exophiala dermatitidis upon cultivation on a medium containing tryptophan as sole nitrogen source. Its structure has been elucidated by 1D and 2D NMR experiments and mass spectrometry. When the mutant strain Mel-1 was used in place of the wild-type strain, the new indole alkaloid 8-hydroxyexophialin was generated instead of exophialin. This result indicates that the aromatic moiety of exophialin originates from 2-hydroxyjuglone, a shunt product of the 1,8-dihydroxynaphthalene melanin biosynthesis, which is only produced by the wild-type strain, but not by the mutant. In contrast, the mutant accumulates flavioline, which acts as precursor leading to the generation of 8-hydroxyexophialin instead of exophialin.
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