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Tetrahydroanthraquinone Derivatives from the Endophytic Fungus Stemphylium globuliferum
Author(s) -
Liu Yang,
Marmann Andreas,
AbdelAziz Mohamed S.,
Wang Chang Yun,
Müller Werner E. G.,
Lin Wen Han,
Mándi Attila,
Kurtán Tibor,
Daletos Georgios,
Proksch Peter
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500079
Subject(s) - chemistry , atropisomer , circular dichroism , antibacterial activity , stereochemistry , staphylococcus aureus , two dimensional nuclear magnetic resonance spectroscopy , mass spectrometry , nuclear magnetic resonance spectroscopy , cytotoxicity , escherichia coli , bacteria , biochemistry , chromatography , biology , genetics , gene , in vitro
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 IC 50 values ranging from 1.25 to 10.4 μ M . 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 μ M .