Specialized oxygenated heterocyclics from Villorita cyprinoides with cyclooxygenase-2 and 5-lipoxygenase inhibitory properties.
Journal:
Food research international (Ottawa, Ont.)
PMID:
29579915
Abstract
Villorita cyprinoides is traditional seafood in the coastal regions of Arabian Sea. Bioactivity-guided purification of ethyl acetate:methanol extract of V. cyprinoides resulted in the identification of two O-spirocyclic ether derivatives (1-2) along with one O-heterocyclic irregular meroterpenoid (3). The structures and their relative stereochemistries were elucidated through comprehensive spectroscopic experiments. These specialized metabolites were found to exhibit potential antioxidative (IC<0.70mg/mL) and anti-inflammatory activities against pro-inflammatory inducible 5-lipoxygenase (anti-5-LOX IC≤0.80mg/mL) and cyclooxygenase-2 (anti-COX-2 IC<0.75mg/mL) enzymes. Molecular docking simulations were used to describe the interactions of the isolated compounds (ligands) with COX-2 and 5-LOX inflammation model. The permissible hydrophobic-hydrophilic balance and lesser steric bulk of spirocyclic ether derivative (compound 2), along with greater number of hydrogen bonding interactions in the active sites of COX-2 and 5-LOX manifested towards its greater bioactivities compared to other compounds isolated from V. cyprinoides.