Naturalproductman’s Blog

Hey, is that a natural product?!

Pleurocybellaziridine

Posted by naturalproductman on December 25, 2010

First things first:  Merry Christmas!  Happy holidays!

Toshiyuki Kan and co-workers from the University of Shizuoka have published in ACIEE on the evidence of an aziridine containing amino acid in a fungus called Angel’s wing.  They did some detective work because the aziridine containing amino acid dubbed pleurocybellaziridine is not stable enough for observation.  The carboxylic acid was not stable so they derivitized the natural product to the methyl ester form, which was more stable.  They also synthesized the aziridine containing amino acid to confirm the structures through spectral data.  The aziridine was synthesized via Mitsunobu conditions.  Interestingly the carboxylic acid form is more cytotoxic (87 micromolar, strong activity) compared to the methyl ester (233 micromolar, weak activity).  Pleurocybellaziridine damages the oligodendrocytes, which makes up the myelin sheath in the brain.

angel's wing

ACIEE paper

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