Abstract
The structures of xanthoradones A and B, new potentiators of imipenem activity against methicillin-resistant Staphylococcus aureus produced by Penicillium radicum FKI-3765-2, were elucidated by spectroscopic studies, including various NMR experiments. These compounds have an asymmetric biaryl skeleton, which contains dihydronaphthopyranone and naphthoquinone moieties.
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Yamazaki, H., Nonaka, K., Masuma, R., Ōmura, S. & Tomoda, H. Xanthoradones, new potentiators of imipenem activity against methicillin-resistant Staphylococcus aureus, produced by Penicillium radicum FKI-3765-2 I. Taxonomy, fermentation, isolation and biological properties. J. Antibiot. 62, 431–434 (2009).
Singh, S. B. et al. Isolation, structure, and HIV-1 integrase inhibitory activity of xanthoviridicatin E and F, two novel fungal metabolites produced by Penicillium chrysogenum. Helv. Chim. Acta. 86, 3380–3385 (2003).
Stack, M. E., Mazzola, E. P. & Eppley, R. M. Structure of xanthoviridicatins D and xanthoviridicatin G, metabolites of Penicillium viridicatum: application of proton and carbon-13 NMR spectroscopy. Tetrahedron Lett. 52, 4989–4992 (1979).
Bode, S. E., Drochner, D. & Muller, M. Synthesis, biosynthesis, and absolute configuration of vioxanthin. Angew. Chem. Int. Ed. Engl. 46, 5916–5920 (2007).
Durley, R. C., MacMillan, J., Simpson, T. J., Glen, A. T. & Turner, W. B. Fungal products. Part XIII. Xanthomegnin, viomellin, rubrosulphin, and viopurpurin, pigments from Aspergillus sulphureus and Aspergillus melleus. J. Chem. Soc. Perkin. Trans. 1 2, 163–169 (1975).
Mori, H., Kawai, K., Ohbayashi, F., Kitamura, J. & Nozawa, Y. Genotoxicity of quinone pigments from pathogenic fungi. Mutat. Res. 122, 29–34 (1983).
Acknowledgements
This work was supported by a grant-in-aid for Scientific Research (B) 21310146 (to HT) from the Ministry of Education, Culture, Sports, Science and Technology, Japan and the Sasakawa Scientific Research Grant (to HY) from The Japan Science Society. We express our thanks to Ms N Sato for performing NMR experiments, and Dr K Nagai and Ms A Nakagawa for measuring mass spectra.
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Yamazaki, H., Ōmura, S. & Tomoda, H. Xanthoradones, new potentiators of imipenem activity against methicillin-resistant Staphylococcus aureus, produced by Penicillium radicum FKI-3765-2 II. Structure elucidation. J Antibiot 62, 435–437 (2009). https://doi.org/10.1038/ja.2009.61
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DOI: https://doi.org/10.1038/ja.2009.61
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