Anti-inflammatory xenicane-type diterpenoid from the intertidal brown seaweed Sargassum ilicifolium

Dhara, Subhajit and Chakraborty, Kajal (2020) Anti-inflammatory xenicane-type diterpenoid from the intertidal brown seaweed Sargassum ilicifolium. Natural Product Research. pp. 1-11. ISSN 1478-6427 (Online)

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    Abstract

    Chemical analysis of the organic extract from intertidal brown seaweed Sargassum ilicifolium (family Sargassaceae) characterised an undescribed xenicane-type diterpenoid sargilicixenicane, elucidated as 3-(17-hydroxy-14-methylhept-13-en-10-yl)-6-methylhexahydro-1H-cyclonona[c]furan-4,19-diyl diacetate (compound 1). The studied compound exhibited prospective free radical quenching potential (IC50 1.2-1.4 mM) in comparison with commercial antioxidant (α-tocopherol, IC50 > 1.40 mM). Attenuation property of sargilicixenicane against pro-inflammatory enzyme, 5-lipoxygenase (IC50 4.70 mM) was comparable with that displayed by the non-steroidal anti-inflammatory agent ibuprofen (IC50 4.51 mM). Greater selectivity index displayed by the studied xenicane-type diterpenoid (1.42) than that exhibited by ibuprofen (0.44) recognised the selective attenuation potential of the former against the inducible cyclooxygenase-2 and 5-lipoxygenase enzymes. Higher electronic parameters (topological polar surface area, 82.06) and balanced hydrophobic-hydrophilic property (octanol-water partition coefficient 2.94) coupled with docking score (-11.17 kcal mol−1) and lower binding energy (-9.61 kcal mol−1) with the active site of 5-lipoxygenase supported the significant anti-inflammatory properties of the studied xenicane-type diterpenoid.

    Item Type: Article
    Uncontrolled Keywords: Sargassum ilicifolium; Sargassa ceaexenicane-type diterpenoid; cyclooxygenase ; lipoxygenaseanti-inflammatory
    Subjects: CMFRI Departments > CMFRI-Kochi > Marine Biotechnology
    CMFRI > CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology

    Biochemistry > Bioprospecting
    Biochemistry > Bioactive compounds
    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: 08 Sep 2021 08:52
    Last Modified: 09 Sep 2021 10:30
    URI: http://eprints.cmfri.org.in/id/eprint/15279

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