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Polyether macrocyclic polyketide from the muricid gastropod Chicoreus ramosus attenuates pro-inflammatory 5-lipoxygenase

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Relation http://eprints.cmfri.org.in/14686/
https://link.springer.com/article/10.1007/s00044-020-02614-4
https://doi.org/10.1007/s00044-020-02614-4
 
Title Polyether macrocyclic polyketide from the muricid gastropod
Chicoreus ramosus attenuates pro-inflammatory 5-lipoxygenase
 
Creator Salas, Soumya
Chakraborty, Kajal
 
Subject Bioactive compounds
Gastropods
Molluscan Fisheries
 
Description 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-diene-
4,8-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.
 
Date 2020
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/14686/1/Medicinal%20Chemistry%20Research_2020_Kajal%20Chakraborty_Polyether%20macrocyclic%20polyketide%20from%20the%20muricid%20gastropod%20Chicoreus%20ramosus.pdf
Salas, Soumya and Chakraborty, Kajal (2020) Polyether macrocyclic polyketide from the muricid gastropod Chicoreus ramosus attenuates pro-inflammatory 5-lipoxygenase. Medicinal Chemistry Research, 29. pp. 1976-1985.