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New azaphilones from Aspergillus neoglaber.

Thomas Isbrandt1, Jens C Frisvad1, Anja Madsen1

  • 1Department of Biotechnology and Biomedicine, Technical University of Denmark, Kongens Lyngby, Denmark.

AMB Express
|August 18, 2020
PubMed
Summary

Three novel azaphilone compounds, sassafrin E, sassafrin F, and sassafrinamine A, were identified from Aspergillus neoglaber. These findings expand the known diversity of fungal secondary metabolites.

Keywords:
Aspergillus neoglaberAzaphilonesPigmentsStructural elucidationTandem mass spectrometry

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Area of Science:

  • Natural Product Chemistry
  • Mycology
  • Organic Chemistry

Background:

  • Azaphilones are a class of fungal secondary metabolites with diverse biological activities.
  • The fungus Aspergillus neoglaber is a known source of various bioactive compounds.

Purpose of the Study:

  • To isolate and characterize novel azaphilone compounds from Aspergillus neoglaber.
  • To elucidate the structures of these new compounds and compare them to known analogues.

Main Methods:

  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation via Nuclear Magnetic Resonance (NMR) spectroscopy.
  • High-resolution tandem mass spectrometry (HR-MS/MS) and deuterium exchange experiments for structural confirmation.

Main Results:

  • Three new azaphilones, sassafrin E (1), sassafrin F (2), and sassafrinamine A (3), were isolated.
  • Compounds 1 and 2 are oxygen-containing azaphilones.
  • Compound 3, sassafrinamine A, contains a nitrogen atom from an aminoethanol moiety and exhibits a purple color due to extensive conjugation.

Conclusions:

  • The discovery of sassafrin E, F, and sassafrinamine A expands the structural diversity of azaphilones.
  • These compounds represent novel analogues within the sassafrin and berkchaetoazaphilone classes.
  • The unique structural features of sassafrinamine A, including its conjugation and color, warrant further investigation.