Pityrialactone- a new fluorochrome from the tryptophan metabolism of M. alassezia furfur |
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Authors: | Peter Mayser Heike Stapelkamp Hans-Joachim Krämer Monika Podobinska Werner Wallbott Bernhard Irlinger Wolfgang Steglich |
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Affiliation: | 1. Zentrum für Dermatologie und Andrologie, Justus Liebig Universit?t, Gaffkystr. 14, Giessen, D-35385, Germany 2. Klinische Pharmakologie, Justus Liebig Universit?t, Gaffkystr. 14, Giessen, D-35385, Germany 3. Institut für Chemie, Justus Liebig Universit?t, Heinrich Buff Ring 58, Giessen, D-35392, Germany 4. Institut für Organische Chemie, Ludwig Maximilians Universit?t, Butenandtstr. 5-13 (F), München, 81377, Germany
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Abstract: | As the main nitrogen source in Malassezia (M.) furfur, tryptophan induces the formation of fluorochromes and pigments, which makes the yeast less sensitive towards UV light. For the investigation of the fluorochromes, M. furfur (CBS1878) was incubated at 32 °C for 14 days on a pigment-inducing medium, and the agar extract was purified by column chromatography, preparative TLC and HPLC. The structures of the pure metabolites were determined by mass spectrometry and NMR spectroscopy. A pale yellow compound eluting from the column with 22% acetonitrile was found to exhibit a strong green-yellow fluorescence. The fluorochrome is a new bisindolyl compound (C20H12N2O3, MW 328.33) named pityrialactone because of its furan-2,3-dione structure. The UV protective properties (λmax 352, 292, 276, 224 nm) of this metabolite were confirmed in a yeast model. As shown by the fluorescence spectrum, pityrialactone appears to be responsible for the green-yellow fluorescence of pityriasis versicolor lesions under Wood light. Pityrialactone is accompanied by the isomeric bisindolylmaleic anhydride (pityriaanhydride), which has not yet been described as a natural product but is a known intermediate in the total synthesis of bisindolylmaleimides. This revised version was published online in August 2006 with corrections to the Cover Date. |
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Keywords: | Bisindolyl derivatives Fluorescence Malassezia furfur Pityrialactone Pityriasis versicolor |
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