Tetrahydroanthraquinone derivatives from the endophytic fungus Stemphylium globuliferum

Yang Liu, Andreas Marmann, Mohamed S. Abdel-Aziz, Chang Yun Wang, Werner E.G. Müller, Wen Han Lin, Attila Mándi, T. Kurtán, Georgios Daletos, Peter Proksch

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14 Citations (Scopus)

Abstract

Four new tetrahydroanthraquinone derivatives, namely, dihydroaltersolanol B (1), dihydroaltersolanol C (2), and the atropisomers acetylalterporriol D (3) and acetylalterporriol E (4), were obtained from the endophytic fungus Stemphylium globuliferum, which was isolated from Juncus acutus growing in Egypt. The structures of the new compounds were unambiguously elucidated on the basis of one- and two-dimensional NMR spectroscopy, as well as by high-resolution mass spectrometry and electronic circular dichroism (ECD) spectroscopy. In addition, seven known anthraquinone derivatives 5-11 were isolated and identified on the basis of their spectral characteristics and by comparison with literature data. Compounds 2, 4-7, 9, and 11 showed strong cytotoxicity against the murine lymphoma cell line L5178Y with IC50 values ranging from 1.25 to 10.4 μM. Compounds 1-4 were also tested for their antibacterial activity against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. Only 2 exhibited moderate growth inhibition against S. aureus with a minimum inhibitory concentration (MIC) of 49.7 μM. Four tetrahydroanthraquinone derivatives 1-4 were obtained from the endophytic fungus Stemphylium globuliferum, which was isolated from Juncus acutus in Egypt. Their structures were determined by extensive NMR and electronic circular dichroism (ECD) spectroscopic analysis. The isolated compounds show IC50 values of 1.25 to 10.4 μM against the murine lymphoma cell line L5178Y.

Original languageEnglish
Pages (from-to)2646-2653
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number12
DOIs
Publication statusPublished - Apr 1 2015

Keywords

  • Antibacterial activity
  • Atropisomerism
  • Cytotoxicity
  • Endophytic fungi
  • Natural products
  • Quinones

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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  • Cite this

    Liu, Y., Marmann, A., Abdel-Aziz, M. S., Wang, C. Y., Müller, W. E. G., Lin, W. H., Mándi, A., Kurtán, T., Daletos, G., & Proksch, P. (2015). Tetrahydroanthraquinone derivatives from the endophytic fungus Stemphylium globuliferum. European Journal of Organic Chemistry, 2015(12), 2646-2653. https://doi.org/10.1002/ejoc.201500079