Atropisomeric dihydroanthracenones as inhibitors of multiresistant staphylococcus aureus

Robert Bara, Ilka Zerfass, Amal H. Aly, Heike Goldbach-Gecke, Vijay Raghavan, Peter Sass, Attila Mándi, Victor Wray, Prasad L. Polavarapu, Alexander Pretsch, Wenhan Lin, Tibor Kurtán, Abdessamad Debbab, Heike Brötz-Oesterhelt, Peter Proksch

Research output: Article

41 Citations (Scopus)


Two bisdihydroanthracenone atropodiastereomeric pairs, including homodimeric flavomannin A (1) and the previously unreported flavomannin B (2), two new unsymmetrical dimers (3 and 4), and two new mixed dihydroanthracenone/ anthraquinone dimers (5 and 6) were isolated from Talaromyces wortmannii, an endophyte of Aloe vera. The structures of 2-6 were elucidated by extensive NMR and mass spectrometric analyses. The axial chirality of the biaryls was determined using TDDFT ECD and VCD calculations, the combination of which however did not allow the assignment of the central chirality elements of 1. The compounds exhibited antibacterial activity against Staphylococcus aureus, including (multi)drug-resistant clinical isolates. Reporter gene analyses indicated induction of the SOS response for some of the derivatives, suggesting interference with DNA structure or metabolism. Fluorescence microscopy demonstrated defective segregation of the bacterial chromosome and DNA degradation. Notably, the compounds showed no cytotoxic activity, encouraging their further evaluation as potential starting points for antibacterial drug development.

Original languageEnglish
Pages (from-to)3257-3272
Number of pages16
JournalJournal of Medicinal Chemistry
Issue number8
Publication statusPublished - ápr. 25 2013

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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    Bara, R., Zerfass, I., Aly, A. H., Goldbach-Gecke, H., Raghavan, V., Sass, P., Mándi, A., Wray, V., Polavarapu, P. L., Pretsch, A., Lin, W., Kurtán, T., Debbab, A., Brötz-Oesterhelt, H., & Proksch, P. (2013). Atropisomeric dihydroanthracenones as inhibitors of multiresistant staphylococcus aureus. Journal of Medicinal Chemistry, 56(8), 3257-3272.