New azaphilones from Aspergillus neoglaber

Three new azaphilones, sassafrin E ( 1 ), sassafrin F ( 2 ), and sassafrinamine A ( 3 ), were isolated from the filamentous fungus Aspergillus neoglaber . The structures of the compounds were determined by nuclear magnetic resonance spectroscopy, and were found to be novel analogues of two already known compound classes; sassafrins and berkchaetoazaphilones. Sassafrin E and F were both oxygen containing, while sassafrinamine A additionally contained a nitrogen atom, originating from an aminoethanol moiety, as well as extensive conjugation resulting in an intense purple colour of the pure compound. The structure of sassafrin E was further confirmed using deuterium exchange experiments coupled with high-resolution tandem mass spectrometry.