Journal of Microbiology and Biotechnology

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
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Isolation, Purification, and Characterization of Five Active Diketopiperazine Derivatives from Endophytic Streptomyces SUK 25 with Antimicrobial and Cytotoxic Activities

  • Alshaibani, Muhanna M. (Programme of Biomedical Science, School of Diagnostic and Applied Health Sciences, Faculty of Health Sciences, Universiti Kebangsaan Malaysia) ;
  • MohamadZin, Noraziah (Programme of Biomedical Science, School of Diagnostic and Applied Health Sciences, Faculty of Health Sciences, Universiti Kebangsaan Malaysia) ;
  • Jalil, Juriyati (Drug and Herbal Research Centre, Faculty of Pharmacy, Universiti Kebangsaan Malaysia) ;
  • Sidik, Nik Marzuki (Faculty of Ago-based Industry, Universiti Malaysia Kelantan) ;
  • Ahmad, Siti Junaidah (Programme of Biomedical Science, School of Diagnostic and Applied Health Sciences, Faculty of Health Sciences, Universiti Kebangsaan Malaysia) ;
  • Kamal, Nurkhalida (Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde) ;
  • Edrada-Ebel, RuAngelie (Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde)
  • Received : 2016.08.13
  • Accepted : 2017.05.21
  • Published : 2017.07.28
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Abstract

In our search for new sources of bioactive secondary metabolites from Streptomyces sp., the ethyl acetate extracts from endophytic Streptomyces SUK 25 afforded five active diketopiperazine (DKP) compounds. The aim of this study was to characterize the bioactive compounds isolated from endophytic Streptomyces SUK 25 and evaluate their bioactivity against multiple drug resistance (MDR) bacteria such as Enterococcus raffinosus, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumanii, Pseudomonas aeruginosa, and Enterobacter spp., and their cytotoxic activities against the human hepatoma (HepaRG) cell line. The production of secondary metabolites by this strain was optimized through Thornton's medium. Isolation, purification, and identification of the bioactive compounds were carried out using high-performance liquid chromatography, high-resolution mass liquid chromatography-mass spectrometry, Fourier transform infrared spectroscopy, and nuclear magnetic resonance, and cryopreserved HepaRG cells were selected to test the cytotoxicity. The results showed that endophytic Streptomyces SUK 25 produces four active DKP compounds and an acetamide derivative, which were elucidated as $cyclo-({\text\tiny{L}}-Val-{\text\tiny{L}}-Pro)$, $cyclo-({\text\tiny{L}}-Leu-{\text\tiny{L}}-Pro)$, $cyclo-({\text\tiny{L}}-Phe-{\text\tiny{L}}-Pro)$, $cyclo-({\text\tiny{L}}-Val-{\text\tiny{L}}-Phe)$, and N-(7-hydroxy-6-methyl-octyl)-acetamide. These active compounds exhibited activity against methicillin-resistant S. aureus ATCC 43300 and Enterococcus raffinosus, with low toxicity against human hepatoma HepaRG cells. Endophytic Streptomyces SUK 25 has the ability to produce DKP derivatives biologically active against some MDR bacteria with relatively low toxicity against HepaRG cells line.

Keywords

References

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