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Aryl-enclosed polyketides from mangrove sediment associated bacterium Bacillus amyloliquefaciens attenuating pro-inflammatory 5-lipoxygenase

Medicinal Chemistry Research volume 29, pages 2011–2019 (2020)Cite this article

Abstract

Two aryl-enclosed polyketides were identified from the ethyl acetate extract of mangrove sediment associated bacterium Bacillus amyloliquefaciens, and were characterized as 1-(8-hydroxy-1-oxoisochroman-3-yl)propyl 4′-(6′-hydroxy-8′-oxotetrahydrofuran-5′-yl)acetate (compound 1) and 6′a-(3′-(1′-(8-hydroxy-1-oxoisochroman-3-yl)propoxy)-3′-oxoethyl)-8′-oxotetrahydrofuran-6′-yl butyrate (compound 2) by detailed spectroscopic techniques encompassing two-dimensional nuclear magnetic resonance and mass spectroscopic experiments. Polyketide compound 2 bearing oxotetrahydrofuran-6′-yl butyrate moiety exhibited potential antioxidant activities against the free radicals, 2,2-diphenyl-1-picrylhydrazyl radical and 2,2′-azino-bis-3-ethylbenzothiozoline-6-sulfonic acid (IC50 1.01 and 1.22 mM, respectively), and were found to be significantly greater than those displayed by polyketide 1 and standard (α-tocopherol IC50 1.45–1.63 mM, p < 0.05). Compound 2 also exhibited greater anti-inflammatory properties as determined by 5-LOX inhibitory assay (IC50 1.11 mM) than those displayed by compound 1 (IC50 1.23 mM) and standard (ibuprofen IC50 4.50 mM). Greater electronic parameters of compound 2 could further support its greater bioactive potentials.

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Acknowledgements

This work was funded by the College of Agriculture of Kerala Agricultural University, India under the B.Sc.–M.Sc. (Integrated) Biotechnology programme (Grant No. 2014-09-103). The authors are thankful to Indian Council of Agricultural Research (ICAR), New Delhi for providing facilities to carry out the work. The authors thank the Director, Central Marine Fisheries Research Institute, Course Director {B.Sc.–M.Sc. (Integrated) Biotechnology programme} and Head, Department of Plant Biotechnology, College of Agriculture, Kerala Agricultural University, Thiruvanthapuram, for providing with necessary support. Thanks are due to the Head, Marine Biotechnology Division, Central Marine Fisheries Research Institute for facilitating the research activities.

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Authors and Affiliations

  1. Central Marine Fisheries Research Institute, Ernakulam North P.O., P.B. No. 1603, Cochin, 682018, India

    Kajal Chakraborty & Prima Francis

  2. Department of Plant Biotechnology, College of Agriculture, Kerala Agricultural University, Thiruvanthapuram, India

    Lakshmi Rajan

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  1. Kajal Chakraborty
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  2. Lakshmi Rajan
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  3. Prima Francis
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Correspondence to Kajal Chakraborty.

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Chakraborty, K., Rajan, L. & Francis, P. Aryl-enclosed polyketides from mangrove sediment associated bacterium Bacillus amyloliquefaciens attenuating pro-inflammatory 5-lipoxygenase. Med Chem Res 29, 2011–2019 (2020). https://doi.org/10.1007/s00044-020-02618-0

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Keywords

  • Mangrove sediment associated bacteria
  • B. amyloliquefaciens
  • Polyketides
  • Antioxidant activity
  • Anti-inflammatory activity