First report of substituted 2H-pyranoids from brown seaweed Turbinaria conoides with antioxidant and anti-inflammatory activities.

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-21-yl-[5', 6'- dihydro-5'-yl-{54-(4-hydroxybenzoyl)-oxy-(52-methylbutyl)}-3'-methyl-2H-pyran]-21-methyl butanoate (1), 11-[(3', 6'-dihydro-4'-methyl-2'-oxo-2H-pyran-3'-yl)methyl]-10-methylhexyl benzoate (2), and [6-ethyl-3,4-dimethyl-(tetrahydro-2', 2', 6'-trimethyl-2H-pyran-3'-yl)-2,5-cycloheptadiene]-1-propanoate (3). The compounds 1 and 2 bearing 2H-pyranyl-4-hydroxybenzoyl and 2H-pyranyl-10-methylhexylbenzoate moieties exhibited potential antioxidant activities (IC50 0.54-0.69 mg mL-1) as commercial antioxidant (α-tocopherol IC50 0.63-0.73 mg mL-1). Likewise, potential bioactivity of the 2H-pyran derivative, 1 against 5-lipoxygenase (IC50 ∼ 1 mg mL-1) along with higher index of selectivity (COX-1 inhibitoryIC50/COX-2 inhibitoryIC50 1.88) indicated their selective anti-inflammatory properties against inducible inflammatory mediators than that displayed by commercially available non-steroidal anti-inflammatory 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. [Formula: see text].