Aryl-enclosed polyketides from mangrove sediment associated bacterium Bacillus amyloliquefaciens attenuating pro-inflamm
- PDF / 948,323 Bytes
- 9 Pages / 595.276 x 790.866 pts Page_size
- 12 Downloads / 175 Views
Medicinal Chemistry Research https://doi.org/10.1007/s00044-020-02618-0
ORIGINAL RESEARCH
Aryl-enclosed polyketides from mangrove sediment associated bacterium Bacillus amyloliquefaciens attenuating pro-inflammatory 5-lipoxygenase Kajal Chakraborty
1
●
Lakshmi Rajan2 Prima Francis1 ●
1234567890();,:
1234567890();,:
Received: 19 April 2020 / Accepted: 18 August 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
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. Keywords Mangrove sediment associated bacteria B. amyloliquefaciens Polyketides Antioxidant activity Antiinflammatory activity ●
Introduction Polyketides are structurally heterogeneous group of compounds isolated from the microorganisms and higher organisms with potential pharmacological properties (Winter et al. 2013). The elementary units of acyl co-enzyme A in the catalytic motif of polyketide synthetase gene (pks) may undergo chain elongation by varying sequences of molecular condensation resulting in the biosynthesis of
Supplementary information The online version of this article (https:// doi.org/10.1007/s00044-020-02618-0) contains supplementary material, which is available to authorized users. * Kajal Chakraborty [email protected] 1
Central Marine Fisheries Research Institute, Ernakulam North P.O., P.B. No. 1603, Cochin 682018, India
2
Department of Plant Biotechnology, College of Agriculture, Kerala Agricultural University, Thiruvanthapuram, India
●
●
●
structurally complex polyketide compounds (Hertweck 2009). Polyketides are structurally complex natural products, which have potential to bind with the biological target, usually protein or RNA, and can cross biological membranes, such as macrolides, polyethers, and polyphenols (Hill et al. 2017; Chakraborty et al. 2018). These characters have made polyketide natural product
Data Loading...
