Specialized oxygenated heterocyclics from Villorita cyprinoides with cyclooxygenase-2 and 5-lipoxygenase inhibitory properties

Joy, Minju and Chakraborty, Kajal (2018) Specialized oxygenated heterocyclics from Villorita cyprinoides with cyclooxygenase-2 and 5-lipoxygenase inhibitory properties. Food Research International, 106. pp. 164-172. ISSN 0963-9969

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    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 (IC50 < 0.70 mg/mL) and anti-inflammatory activities against pro-inflammatory inducible 5-lipoxygenase (anti-5-LOX IC50 ≤0.80 mg/mL) and cyclooxygenase-2 (anti-COX-2 IC50 < 0.75 mg/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.

    Item Type: Article
    Uncontrolled Keywords: Villorita cyprinoides; Oxygenated heterocyclics; O-spirocyclic ether derivatives; Irregular meroterpenoid; Anti-inflammatory activity; Functional food
    Subjects: Fish Biotechnology > Bioactive compound
    Fish Biotechnology
    Divisions: CMFRI-Kochi > Marine Biotechnology
    Subject Area > CMFRI > CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology
    Subject Area > CMFRI-Kochi > Marine Biotechnology
    Depositing User: Arun Surendran
    Date Deposited: 12 Jan 2018 04:26
    Last Modified: 12 Jan 2018 04:26
    URI: http://eprints.cmfri.org.in/id/eprint/12474

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