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RF-3192C and other polyketides from the marine endophytic Aspergillus niger ASSB4: structure assignment and bioactivity investigation

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Abstract

Chemical investigation of the methanolic extract of endophytic Aspergillus niger SB4, isolated from the marine alga Laurencia obtuse, afforded the pentacyclic polyketide, RF-3192C (1), the dimeric coumarin orlandin (2), fonsecin B (3), TMC-256A1 (4), cyclo-(Leu-Ala) (5), and cerebroside A (6).The chemical structure of RF-3192C (1) is assigned herein for the first time using 1D/2D NMR and HRESI-MS. Additionally, the revision of the NMR assignments of orlandin (2) was reported herein as well. Investigation of the antimicrobial activities of isolated compounds revealed the high activity of RF-3192C (1) against Pseudomonas aeruginosa and Bacillus subtilis, and moderate activity against yeast. Moreover, an in vitro cytotoxic activity against liver (HEPG2), cervical (HELA), lung (A549), prostate (PC3), and breast (MCF7) cancer cell lines of the isolated compounds was evaluated. The isolation and taxonomical characterization of the producing fungus was reported as well.

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Acknowledgements

The authors are thankful to the NMR and MS Departments in Bielefeld University for the spectral measurements. We thank Carmela Michalek for her assistance in biological activity testing; Marco Wißbrock and Anke Nieß for technical assistance. This research work has been financed by the German Academic Exchange Service (DAAD) with funds from the German Federal Foreign Office in the frame of the Research Training Network “Novel Cytotoxic Drugs from Extremophilic Actinomycetes” (Project ID 57166072). This work was also supported by National Institutes of Health grant R01 GM115261 (JST), the Center of Biomedical Research Excellence (COBRE) in Pharmaceutical Research and Innovation (CPRI, NIH P20 GM130456), the University Of Kentucky College Of Pharmacy, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117 and UL1TR001998).

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Authors and Affiliations

  1. Pharmacognosy Department, Faculty of Pharmacy, Helwan University, Helwan, Cairo, 11795, Egypt

    Manar M, Mahmoud & Hesham S. M, Soliman

  2. Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501, Bielefeld, Germany

    Manar M, Mahmoud, Ahmed S, Abdel-Razek, Abdelaaty Hamed & Mohamed Shaaban

  3. Microbial Chemistry Department, Genetic Engineering and Biotechnology Research Division, National Research Centre, El-Buhouth St. 33, Dokki-Giza, 12622, Egypt

    Ahmed S, Abdel-Razek

  4. Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City-Cairo, 11884, Egypt

    Abdelaaty Hamed

  5. Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, Lexington, KY, 40536, USA

    Larissa V, Ponomareva, Jon S, Thorson & Khaled A, Shaaban

  6. Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY, 40536, USA

    Larissa V, Ponomareva, Jon S, Thorson & Khaled A, Shaaban

  7. Chemistry of Natural Compounds Department, Division of Pharmaceutical Industries, National Research Centre, El-Buhouth St. 33, Dokki-Giza, 12622, Egypt

    Mohamed Shaaban

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  1. Manar M, Mahmoud
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Correspondence to Mohamed Shaaban.

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JST is a co-founder of Centrose (Madison, WI, USA); except that the authors declare that they have no conflict of interest.

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Mahmoud, M.M., Abdel-Razek, A.S., Hamed, A. et al. RF-3192C and other polyketides from the marine endophytic Aspergillus niger ASSB4: structure assignment and bioactivity investigation. Med Chem Res 30, 647–654 (2021). https://doi.org/10.1007/s00044-020-02658-6

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