An unreported polyether macrocyclic lactone with antioxidative and anti-lipoxygenase activities from the Babylonidae gastropod mollusc Babylonia spirata

AbstractA 16-member polyether macrocyclic lactone, with previously unreported framework was isolated as a result of the bioassay guided chromatographic fractionation of the ethyl acetate-methanol extract of the BabylonidaeBabylonia spirata collected from the southwestern coast of Indian peninsular. The compound was characterized as 10, 14-dihydroxy-4-(1 ′-propyl-1′(Z)-hexen-1 ′-yl)-7, 12-dioxapentadecanolide based on extensive spectral data analysis. The antioxidant activities evaluated byin vitro free radical scavenging capacities reported that the studied compound possessed greater activity (IC50 0.058 –0.065 × 10−2 M) than the commercial standards, butylated hydroxy anisole, butylated hydroxyl toluene andα-tocopherol (IC50 0.118 –0.189 × 10−2 M). The compound was found to possess greater anti-inflammatory potentials as recognized by its lower IC50 value for the 5-lipoxygenase inhibition assay (0.073  × 10−2 M) than the non steroidal anti-inflammatory drugs aspirin (0.211 × 10−2 M) and ibuprofen (0.436 × 10−2 M). Structure-activity studies showed that bioactivities of the polyether macrocyclic lactone were directed by electronic and lipophilic descriptors. The lipophilic parameter of octanol-water partition coefficient (log Pow) of the studied compound recorded a value as low as 2.76 when judged against commercial antioxidantα-tocopherol (log Pow 9.98), and was recognized as a primary physico-chemical descriptor dicta...
Source: Medicinal Chemistry Research - Category: Chemistry Source Type: research