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Characterization of medium chain length (R)-3-hydroxycarboxylic acids produced by Streptomyces sp. JM3 and the evaluation of their antimicrobial properties

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Abstract

(R)-3-Hydroxycarboxylic acids, chiral enantiomers of bacterial polyhydroxyalkanoates (PHA), may be valuable synthons for the production of numerous industrial materials such as β-lactams, fungicides, flavors, pheromones and vitamins. In this study, (R)-3-hydroxycarboxylic acid [(R)-3HAs)] synthons were produced by Streptomyces sp. JM3 (JN166713) under batch fermentation. Initial confirmation of PHA production was achieved by matrix assisted laser desorption ionization-time of flight mass spectroscopy and gas chromatography/mass spectroscopy (GC/MS). Subsequently, (R)-3HAs were produced by in vivo depolymerization and the monomers were separated using acid precipitation and anion exchange chromatography. The (R)-3HAs were identified by GC/MS as 3-trimethylsiloxy esters of decanoic, octanoic and butanoic acids. This was further supported by 13C nuclear magnetic resonance spectrometry. The (R)-3HAs exhibited antimicrobial activity against Escherichia coli O157:H7, Listeria monocytogenes (ATCC 7644) and Salmonella typhimurium (ATCC 14028) with minimum inhibitory concentration ranging from 12.5 to 25 mg ml−1. However, the minimum bactericidal concentration data suggest that the (R)-3HAs may be bactericidal for E. coli O157:H7 and bacteriostatic for S. typhimurium and L. monocytogenes. Furthermore, the major purified synthon was shown to minimize the invasion of fibroblasts by S. typhimurium (ATCC 14028) [p < 0.05], using the MTT assay [(3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide)].

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Acknowledgments

We would like to express our sincere gratitude to Dr. Oumar Diall from the University of Mali for the gift of the Jatropha curcas oil. Some aspects of this work were supported through the Howard Hughes Core Laboratory at Howard University.

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Authors and Affiliations

  1. Department of Biology, Howard University, 415 College St. NW, Washington, DC, 20059, USA

    Adrian Douglas Allen, Patrick Daley, Ayelle Gugssa, Winston A. Anderson & Broderick. E. Eribo

  2. Department of Chemistry, Howard University, Washington, DC, 20059, USA

    Folahan O. Ayorinde

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  1. Adrian Douglas Allen
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  2. Patrick Daley
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  3. Folahan O. Ayorinde
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  4. Ayelle Gugssa
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  5. Winston A. Anderson
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  6. Broderick. E. Eribo
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Correspondence to Broderick. E. Eribo.

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Allen, A.D., Daley, P., Ayorinde, F.O. et al. Characterization of medium chain length (R)-3-hydroxycarboxylic acids produced by Streptomyces sp. JM3 and the evaluation of their antimicrobial properties. World J Microbiol Biotechnol 28, 2791–2800 (2012). https://doi.org/10.1007/s11274-012-1089-z

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  • DOI: https://doi.org/10.1007/s11274-012-1089-z

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