Polyether macrocyclic polyketide from the muricid gastropod Chicoreus ramosus attenuates pro-inflammatory 5-lipoxygenase
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Medicinal Chemistry Research https://doi.org/10.1007/s00044-020-02614-4
ORIGINAL RESEARCH
Polyether macrocyclic polyketide from the muricid gastropod Chicoreus ramosus attenuates pro-inflammatory 5-lipoxygenase Soumya Salas1,2 Kajal Chakraborty ●
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Received: 11 April 2020 / Accepted: 10 August 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Macrocyclic compounds of multifaceted structural scaffolds are being increasingly reported from the marine environment, and gaining commercial importance due to their ability to inhibit the pro-inflammatory mediators. An unreported polyether macrocyclic polyketide characterized as 6-(butoxy)-13,15,22-trihydroxy-3,18-dioxatricyclo[18.3.1.011,16]tricosa-9,20-diene4,8-dione was isolated from the marine gastropod mollusc Chicoreus ramosus (family Muricidae). The compound displayed potential anti-inflammatory property by inhibiting 5-lipoxygenase (IC50 0.42 mg mL−1), which was analogous to the nonsteroidal anti-inflammatory agent aspirin (IC50 0.38 mg mL−1) and superior to ibuprofen (IC50 0.90 mg mL−1). Free radical scavenging abilities of the purified compound against oxidative agents (IC50 0.22 mg mL−1) were comparable to the commercially available antioxidants (butylated hydroxyanisole, IC50 0.25 mg mL−1; butylated hydroxytoluene, IC50 0.27 mg mL−1), and greater than α-tocopherol (IC50 0.60 mg mL−1). Molecular docking studies of the studied polyketide analog against 5-lipoxygenase indicated that the docked ligand could potentially bind to the target site of the enzyme with a less binding energy (−9.33 kcal mol−1) and docking score (−10.23 kcal mol−1). The present study recognized the potential of macrocyclic polyketide possessing tricosa-9, 20-diene-4,8-dione framework isolated from C. ramosus as a potential antioxidant and anti-inflammatory lead that could find its use in medicinal formulations. Keywords Gastropod mollusc Chicoreus ramosus Polyether macrocyclic polyketide Antioxidant Anti-inflammatory Pro-inflammatory 5-lipoxygenase ●
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Introduction Inflammation is an essential response to the human immunological system. However, the stage of chronic inflammation elicited without an actual stimulus has numerous adverse consequences in physiological responses leading to serious risk of chronic disorders and diseases. The statistics of
These authors contributed equally: Soumya Salas, Kajal Chakraborty Supplementary information The online version of this article (https:// doi.org/10.1007/s00044-020-02614-4) contains supplementary material, which is available to authorized users. * Kajal Chakraborty [email protected] 1
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Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North P.O., P.B. No. 1603, Cochin 682018, Kerala, India Present address: Department of Chemistry, St. Albert’s College (Autonomous), Ernakulam 682018, Kerala, India
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disorders, which are associated with the molecular intermediaries of inflammation, are increasing.
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