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Acetylcholinesterase Inhibitors from a Marine Fungus Talaromyces sp. Strain LF458

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Abstract

Two new oxaphenalenone dimers, talaromycesone A (1) and talaromycesone B (2), and a new isopentenyl xanthenone, talaroxanthenone (3), together with six known diphenyl ether derivatives, e.g., Δ1′,3′,-1′-dehydroxypenicillide (4), 1′,2′-dehydropenicillide (5), vermixocin A (6), vermixocin B (7), 3′-methoxy-1′2′-dehydropenicillide (8), and AS-186c (9), were isolated from the culture broth and mycelia of a marine fungus Talaromyces sp. strain LF458. Compound 2 represents the first example of 1-nor oxaphenalenone dimer carbon skeleton. All isolated compounds were subjected to bioactivity assays. Compounds 1, 2, and 9 exhibited potent antibacterial activities with IC50 3.70, 17.36, and 1.34 μM, respectively, against human pathogenic Staphylococcus strains. Compounds 1, 3, and 9 displayed potent acetylcholinesterase inhibitory activities with IC50 7.49, 1.61, and 2.60 μM, respectively. Interestingly, phosphodiesterase PDE-4B2 was inhibited by compounds 3 (IC50 7.25 μM) and 9 (IC50 2.63 μM).

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Acknowledgments

The authors thank Dr. Stefan Steffens and Dr. Karsten Schaumann for providing strain LF458. We gratefully thank G. Kohlmeyer-Yilmaz, M. Höftmann, as well as Prof. F. Sönnichsen (Otto Diels Institute of Organic Chemistry, Christian-Albrechts-Universität zu Kiel, Germany) for running and processing NMR experiments. The authors are also grateful to A. Erhard, R. Koppe, and A. Schneider for excellent technical assistance. Thanks to NSFC (81273386) for supporting Bin Wu.

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Authors and Affiliations

  1. Wirkstoff-Zentrum am GEOMAR Helmholtz-Zentrum für Ozeanforschung Kiel, Kiel, 24105, Germany

    Bin Wu, Birgit Ohlendorf, Vanessa Oesker, Jutta Wiese, Susann Malien, Rolf Schmaljohann & Johannes F. Imhoff

  2. Ocean College, Zhejiang University, Hangzhou, 310058, China

    Bin Wu

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  1. Bin Wu
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  2. Birgit Ohlendorf
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  3. Vanessa Oesker
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  4. Jutta Wiese
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  5. Susann Malien
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  6. Rolf Schmaljohann
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  7. Johannes F. Imhoff
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Correspondence to Johannes F. Imhoff.

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Wu, B., Ohlendorf, B., Oesker, V. et al. Acetylcholinesterase Inhibitors from a Marine Fungus Talaromyces sp. Strain LF458. Mar Biotechnol 17, 110–119 (2015). https://doi.org/10.1007/s10126-014-9599-3

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  • DOI: https://doi.org/10.1007/s10126-014-9599-3

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