Isolation, purification, and characterization of five active diketopiperazine derivatives from endophytic Streptomyces SUK 25 with antimicrobial and cytotoxic activities

Muhanna M. Alshaibani, Noraziah Mohamad Zin, Juriyati Jalil, Nik Marzuki Sidik, Siti Junaidah Ahmad, Nurkhalida Kamal, Ruangelie Edrada-Ebel

Research output: Contribution to journalArticle

4 Citations (Scopus)

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-(L-Val-L-Pro), cyclo- (L-Leu-L-Pro), cyclo-(L-Phe-L-Pro), cyclo-(L-Val-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.

Original languageEnglish
Pages (from-to)1249-1256
Number of pages8
JournalJournal of Microbiology and Biotechnology
Volume27
Issue number7
DOIs
Publication statusPublished - 28 Jul 2017

Fingerprint

Diketopiperazines
Streptomyces
Enterococcus
Multiple Drug Resistance
phenylalanyl-valine
Hepatocellular Carcinoma
Staphylococcal Pneumonia
Bacteria
Cell Line
Enterobacter
Acinetobacter
Klebsiella pneumoniae
Fourier Transform Infrared Spectroscopy
Methicillin-Resistant Staphylococcus aureus
Human Activities
Liquid Chromatography
Pseudomonas aeruginosa
Mass Spectrometry
Magnetic Resonance Spectroscopy
High Pressure Liquid Chromatography

Keywords

  • Cytotoxicity
  • Diketopiperazines
  • Enterococcus raffinosus
  • HepaRG
  • MRSA
  • Streptomyces SUK 25

ASJC Scopus subject areas

  • Biotechnology
  • Applied Microbiology and Biotechnology

Cite this

Isolation, purification, and characterization of five active diketopiperazine derivatives from endophytic Streptomyces SUK 25 with antimicrobial and cytotoxic activities. / Alshaibani, Muhanna M.; Mohamad Zin, Noraziah; Jalil, Juriyati; Sidik, Nik Marzuki; Ahmad, Siti Junaidah; Kamal, Nurkhalida; Edrada-Ebel, Ruangelie.

In: Journal of Microbiology and Biotechnology, Vol. 27, No. 7, 28.07.2017, p. 1249-1256.

Research output: Contribution to journalArticle

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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-(L-Val-L-Pro), cyclo- (L-Leu-L-Pro), cyclo-(L-Phe-L-Pro), cyclo-(L-Val-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.",
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AU - Jalil, Juriyati

AU - Sidik, Nik Marzuki

AU - Ahmad, Siti Junaidah

AU - Kamal, Nurkhalida

AU - Edrada-Ebel, Ruangelie

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