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

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Relation http://eprints.cmfri.org.in/15279/
https://doi.org/10.1080/14786419.2020.1825426
 
Title Anti-inflammatory xenicane-type diterpenoid from the intertidal brown seaweed Sargassum ilicifolium
 
Creator Dhara, Subhajit
Chakraborty, Kajal
 
Subject Bioprospecting
Bioactive compounds
 
Description 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.
 
Publisher Taylor and Francis
 
Date 2020
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/15279/1/Natural%20Product%20Research_2020_Chakaraborty%20Kajal.pdf
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)