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Bioactive secondary metabolites from new terrestrial Streptomyces sp. TN82 strain: Isolation, structure elucidation and biological activity

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Abstract

An actinomycete strain designated TN82 was isolated from Tunisian Sahara soil and selected for its interesting antimicrobial activity against Gram positive and Gram negative bacteria and fungi. Based on the results of cultural characteristic, the 16S rRNA gene nucleotide sequence (1434 bp, accession n° LT608133) and the phylogenetic analysis, this new isolate was assigned as Streptomyces sp. TN82 strain. Two active compounds, 3-phenylpyrazin-2(1H)-one (1) and 3-O-methylviridicatin (2), described for the first time as natural product and bacterial compound respectively, together with four known bacterial metabolites; cyclo-(Leu, Pro) (3), anthranilic acid (4), indole-3-carbaldehyde (5) and p-hydroxybenzoic acid (6) were isolated from the culture broth of this strain. Structure of the natural compound (1) was confirmed by extensive 1D and 2D NMR and EI MS and ESI HR mass measurements, and by comparison with literature data. Minimum inhibitory concentrations of the two compounds (1) and (2) against the tested human pathogenic bacteria S. aureus, L. monocytogenes and S. typhimurium were significantly lower than those of kanamycin. For the natural compound 3-phenylpyrazin-2(1H)-one (1), MICs values were very interesting especially that against L. monocytogenes (1.0 μg/mL) which is 2 and 12 times lower than those of ampicillin (2.0 μg/mL) and kanamycin (12.50 μg/mL), respectively.

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Acknowledgements

The authors are thankful to the NMR and MS Departments in Bielefeld University for the spectral measurements. We thank Mr Marco Wißbrock for technical assistance. Thanks also to Mr. I. Hsairi, Mr. K. Bouchaala and Mr. M. Hmidi for their useful contribution to the fermentation experiments. 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 ID57166072) and by the Tunisian Ministry of Higher Education and Scientific Research “Contract Program (2015–2018) of the Laboratory of Microorganisms and Biomolecules (LMB) of the Centre of Biotechnology of Sfax (CBS)—Tunisia”.

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Authors and Affiliations

  1. Organic and Bioorganic Chemistry, Faculty of Chemistry, University Bielefeld, University Str. 25, 33615, Bielefeld, Germany

    Imene Zendah El Euch, Marcel Frese, Norbert Sewald & Mohamed Shaaban

  2. Laboratory of Microorganisms and Biomolecules of the Centre of Biotechnology of Sfax, Road of Sidi Mansour Km 6, P.O. Box 1177, 3018, Sfax, Tunisia

    Slim Smaoui & Lotfi Mellouli

  3. Chemistry of Natural Compounds Department, Pharmaceutical Industries Division, National Research Centre, El-Behoosst, Dokki-Cairo, 12622, Egypt

    Mohamed Shaaban

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  1. Imene Zendah El Euch
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  2. Marcel Frese
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  3. Norbert Sewald
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  4. Slim Smaoui
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  6. Lotfi Mellouli
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Correspondence to Lotfi Mellouli.

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El Euch, I.Z., Frese, M., Sewald, N. et al. Bioactive secondary metabolites from new terrestrial Streptomyces sp. TN82 strain: Isolation, structure elucidation and biological activity. Med Chem Res 27, 1085–1092 (2018). https://doi.org/10.1007/s00044-017-2130-4

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  • DOI: https://doi.org/10.1007/s00044-017-2130-4

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