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Sharkquinone, a new ana-quinonoid tetracene derivative from marine-derived Streptomyces sp. EGY1 with TRAIL resistance-overcoming activity

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Abstract

A new ana-quinonoid tetracene metabolite, named sharkquinone (1), and the known SS-228R (2) have been isolated from the ethyl acetate extract of the culture of marine Streptomyces sp. EGY1. The strain was isolated from sediment sample collected from the Red Sea coast of Egypt. The structure of sharkquinone (1) was elucidated using detailed spectral (HRESI-MS, 1D and 2D NMR) analyses and quantum chemical calculations. This is the first report of the isolation of ana-quinonoid tetracene derivative from a natural source. Compound 1 showed the ability to overcome tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) resistance at a concentration of 10 μM in human gastric adenocarcinoma (AGS) cells.

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Acknowledgements

This work was supported financially by the Science and Technology Development Fund (STDF), Egypt (grant no. 4930).

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Authors and Affiliations

  1. Marine Natural Products Unit (MNPRU), Faculty of Science, Helwan University, Ain Helwan, Cairo, 11795, Egypt

    Mohamed S. Abdelfattah & Mohammed I. Y. Elmallah

  2. Chemistry Department, Faculty of Science, Helwan University, Ain Helwan, Cairo, 11795, Egypt

    Mohamed S. Abdelfattah, Mohammed I. Y. Elmallah & Adal A. Mohamed

  3. Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, 260-8675, Japan

    Masami Ishibashi

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  1. Mohamed S. Abdelfattah
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  2. Mohammed I. Y. Elmallah
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Correspondence to Mohamed S. Abdelfattah.

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Abdelfattah, M.S., Elmallah, M.I.Y., Mohamed, A.A. et al. Sharkquinone, a new ana-quinonoid tetracene derivative from marine-derived Streptomyces sp. EGY1 with TRAIL resistance-overcoming activity. J Nat Med 71, 564–569 (2017). https://doi.org/10.1007/s11418-017-1086-5

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