The organic extract of Turbinaria conoides, a brown seaweed harvested from the Gulf of Manner region of Indian peninsular was chromatographically fractionated to yield three substituted 2H-pyranoids, namely methyl-2 1 -yl-[5ʹ, 6ʹdihydro-5ʹ-yl-{5 4 -(4hydroxybenzoyl)-oxy-(5 2 -methylbutyl)}-3ʹ-methyl-2H-pyran]-2 1 -methyl butanoate (1), 11-[(3ʹ, 6ʹ-dihydro-4ʹ-methyl-2ʹ-oxo-2Hpyran-3ʹ-yl)methyl]-10-methylhexyl benzoate (2), and [6-ethyl-3,4-dimethyl-(tetrahydro-2ʹ, 2ʹ, 6ʹ-trimethyl-2H-pyran-3ʹ-yl)-2,5cycloheptadiene]-1ʹ-propanoate (3). The compounds 1 and 2 bearing 2H-pyranyl-4-hydroxybenzoyl and 2H-pyranyl-10methylhexylbenzoate moieties exhibited potential antioxidant activities (IC 50 0.54-0.69 mg mL -1 ) as commercial antioxidant (αtocopherol IC 50 0.63-0.73 mg mL -1 ). Likewise, potential bioactivity of the 2H-pyran derivative, 1 against 5-lipoxygenase (IC 50 ~ 1 mg mL -1 ) along with higher index of selectivity (COX-1 inhibitory IC50 /COX-2 inhibitory IC50 1.88) indicated their selective antiinflammatory properties against inducible inflammatory mediators than that displayed by commercially available non-steroidal antiinflammatory drug (ibuprofen, 0.44). Structure activity relationship analysis of the studied compounds showed that the antioxidative and anti-inflammatory properties were directly proportional to their electronic properties. The previously undescribed 2H-pyranoids might constitute as potential antioxidative and anti-inflammatory pharmacophores for medicinal applications.
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 (IC 50 1.2-1.4 mM) in comparison with commercial antioxidant (α-tocopherol, IC 50 > 1.40 mM). Attenuation property of sargilicixenicane against pro-inflammatory enzyme, 5-lipoxygenase (IC 50 4.70 mM) was comparable with that displayed by the non-steroidal anti-inflammatory agent ibuprofen (IC 50 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.
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