Absolute configuration and antibiotic activity of neosartorin from the endophytic fungus Aspergillus fumigatiaffinis

Antonius R.B. Ola, Abdessamad Debbab, Amal H. Aly, Attila Mandi, Ilka Zerfass, Alexandra Hamacher, Matthias U. Kassack, Heike Brötz-Oesterhelt, Tibor Kurtan, Peter Proksch

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22 Citations (Scopus)

Abstract

Neosartorin (1) was isolated from the endophytic fungus Aspergillus fumigatiaffinis. The absolute configuration of 1, including both axial and central chirality elements, was established as (aR,5S,10R,5′S,6′S, 10′R) for the first time on the basis of its electronic circular dichroism (ECD) spectra aided with TDDFT-ECD calculations. Neosartorin (1) exhibited substantial antibacterial activity against a broad spectrum of Gram-positive bacterial species including staphylococci, streptococci, enterococci, and Bacillus subtilis with minimal inhibitory concentrations in the range of 4-32 μg/mL. When the toxicity of 1 against eukaryotic cells was measured using a panel of different cancer cell lines such as HELA and BALB/3T3, the average IC50 values exceeded 32 μg/mL.

Original languageEnglish
Pages (from-to)1020-1023
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number5
DOIs
Publication statusPublished - Jan 29 2014

Keywords

  • Absolute configuration
  • Antibacterial activity
  • Aspergillus fumigatiaffinis
  • Neosartorin

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Ola, A. R. B., Debbab, A., Aly, A. H., Mandi, A., Zerfass, I., Hamacher, A., Kassack, M. U., Brötz-Oesterhelt, H., Kurtan, T., & Proksch, P. (2014). Absolute configuration and antibiotic activity of neosartorin from the endophytic fungus Aspergillus fumigatiaffinis. Tetrahedron Letters, 55(5), 1020-1023. https://doi.org/10.1016/j.tetlet.2013.12.070