Pityriazepin, a new indole alkaloid isolated from malassezia furfur yeasts

N Mexia; G Gaitanis; A Velegraki; AL Skaltsounis; P Magiatis

doi:10.1055/s-0032-1320757

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Planta Med 2012; 78 - PI70
DOI: 10.1055/s-0032-1320757

Pityriazepin, a new indole alkaloid isolated from malassezia furfur yeasts

N Mexia ¹, G Gaitanis ², A Velegraki ³, AL Skaltsounis ¹, P Magiatis ¹

¹Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, University of Athens, Greece
²Department of Skin and Venereal Diseases, University Hospital of Ioannina, Medical School, University of Ioannina, Greece
³Mycology Laboratory, Department of Microbiology, Medical School, University of Athens, Greece

Congress Abstract

Malassezia furfur strains isolated from diseased skin preferentially biosynthesize indole alkaloids that are active Aryl-hydrocarbon Receptor (AhR) inducers. Studying the induction of AhR by Malassezia yeasts, we envisaged the isolation of new metabolites produced by Malassezia when grown on L-tryptophan agar. Chemical investigation of the EtOAc extract of a M. furfur strain isolated from lessional skin revealed, by HPLC/UV, the presence of a yet unknown yellow compound. Isolation with Column Chromatography and preparative TLC and then structure elucidation with NMR 600MHz, combined with MS analysis, led us to propose for this metabolite a structure similar to that of pityriacitrin (1). Their difference is the transformation of pyridine to an azepine ring, where the carbonyl group is incorporated in the ring. In conclusion, this conversion afforded pityriazepin (2), a new natural molecule isolated from M. furfur yeasts. Furthermore, the fusion of indole with the azepine ring appears to offer a new natural skeleton.