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3,4-Dihydro-quinolin-2-one derivatives from extremophilic Streptomyces sp. LGE21

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Abstract

Three new naturally-occurring 3,4-dihydroquinoline-2-one derivatives: 8-Hydroxy-3,4-dihydro-1H-quinolin-2-one (1), 3,4-dihydro-1H-quinolin-2-one (2) and 8-methoxy-3,4-dihydro-1H-quinolin-2-one (3), together with linoleic acid, glycerol monolinoleate and phenyl acetic acid were isolated from the Streptomyces sp. LGE21, derived from Lemna gibba. Structures of the new alkaloids (1–3) were determined by extensive 1D and 2D NMR, and MS measurements. In vitro cytotoxic studies of 1–3 and linoleic acid, in comparison with the original extract were assayed against liver cancer HEPG2 cell line and the human cervix carcinoma cell line (KB-3-1). The antimicrobial activity of the strain extract and compounds 1–3 were achieved as well. The new metabolites exhibited weak cytotoxic activities against cancer cell lines and growth inhibitory activity against a panel of tested bacterial strains.

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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 biological activity testing and Marco Wißbrock 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” (ProjectID57166072).

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Authors and Affiliations

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

    Manar M. Mahmoud, Ahmed S. Abdel-Razek, Marcel Frese, Norbert Sewald & Mohamed Shaaban

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

    Manar M. Mahmoud & Hesham S. M. Soliman

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

    Ahmed S. Abdel-Razek

  4. Division of Pharmaceutical Industries, Chemistry of Natural Compounds Department, 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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  2. Ahmed S. Abdel-Razek
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Correspondence to Mohamed Shaaban.

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Mahmoud, M.M., Abdel-Razek, A.S., Frese, M. et al. 3,4-Dihydro-quinolin-2-one derivatives from extremophilic Streptomyces sp. LGE21. Med Chem Res 27, 1834–1842 (2018). https://doi.org/10.1007/s00044-018-2195-8

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  • DOI: https://doi.org/10.1007/s00044-018-2195-8

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