Tetrahydroanthraquinone Derivatives from the Endophytic Fungus Stemphylium globuliferum. Issue 12 (5th March 2015)

• Record Type: Journal Article
• Authors: Liu, Yang; Marmann, Andreas; Abdel‐Aziz, Mohamed S.; Wang, Chang Yun; Müller, Werner E. G.; Lin, Wen Han; Mándi, Attila; Kurtán, Tibor; Daletos, Georgios; Proksch, Peter
• Is Part Of: European journal of organic chemistry. Issue 12(2015)
• Page Start: 2646
• Page End: 2653
• Publication Date: 2015-03-05
• Subjects: Natural products -- Endophytic fungi -- Quinones -- Cytotoxicity -- Antibacterial activity -- Atropisomerism; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500079
• Languages: English
• ISSNs: 1434-193X

Abstract

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 derivatives5 –11 were isolated and identified on the basis of their spectral characteristics and by comparison with literature data. Compounds2, 4 –7, 9, and11 showed strong cytotoxicity against the murine lymphoma cell line L5178Y with IC50 values ranging from 1.25 to 10.4 μM . Compounds1 –4 were also tested for their antibacterial activity against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa . Only2 exhibited moderate growth inhibition against S. aureus with a minimum inhibitory concentration (MIC) of 49.7 μM . Abstract : Four tetrahydroanthraquinone derivatives1 –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.