Pityrialactone- a new fluorochrome from the tryptophan metabolism of Malassezia furfur.
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 degrees 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 (C(20)H(12)N(2)O(3), MW 328.33) named pityrialactone because of its furan-2,3-dione structure. The UV protective properties (lambda(max) 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.
Mayser
Peter
P
Zentrum für Dermatologie und Andrologie, Justus Liebig Universität, Gaffkystr. 14, Giessen D-35385, Germany. Peter.Mayser@derma.med.uni-giessen.de
Stapelkamp
Heike
H
Krämer
Hans-Joachim
HJ
Podobinska
Monika
M
Wallbott
Werner
W
Irlinger
Bernhard
B
Steglich
Wolfgang
W
D002845:Chromatography / Q000379:methods; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000302:isolation & purification* / Q000378:metabolism*; D007211:Indoles / Q000378:metabolism; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008290:Malassezia / Q000737:chemistry* / Q000254:growth & development / Q000378:metabolism*; D008301:Maleimides / Q000378:metabolism; D013058:Mass Spectrometry; D014364:Tryptophan / Q000378:metabolism*; D014466:Ultraviolet Rays
D005456:Fluorescent Dyes; D007211:Indoles; D007783:Lactones; D008301:Maleimides; C481123:pityrialactone; D014364:Tryptophan; C088060:bisindolylmaleimide