Antioxidative and anti-inflammatory pyranoids and isochromenyl analogues from Corbiculid bivalve clam, Villorita cyprinoides

Abstract

Bivalve black clam, Villorita cyprinoides is traditional seafood in Southwestern coast of Arabian Sea. In this study, bioactivity-guided purification of ethyl acetate:methanol extract of black clam was carried out. Two irregular meroterpenoids {tetrahydro-3-methoxy-5-((E)-8,12-dimethyloct-8-enyl)-pyran-2-one (1) and dihydro-5-(8-(9,12-dihydro-8-methyl-11-propyl-2H-pyran-8-yl)-ethyl)-furan-2(3H)-one (2)} and two hexahydro-isochromenyl-meroterpenoids (3–4) were identified. The structures were characterized by detailed spectroscopy and their antioxidant/anti-inflammatory potentials were evaluated. Compound 2 registered significantly greater 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging ability (IC50 <0.65 mg/mL) than other analogues (IC50 ≥0.70 mg/mL). Ferrous ion (Fe2+) chelating ability was higher for 1–2 (IC50 ∼0.84 mg/mL) than α-tocopherol (IC50 0.89 mg/mL). The 5-lipoxygenase inhibitory potential of furano-meroterpenoid analogue, 2 (IC50 0.76 mg/mL) was greater than other compounds (IC50 >0.90 mg/mL). An optimum hydrophobic-hydrophilic balance of furano-meroterpenoid and lesser steric bulk manifested towards its greater bioactivities compared to other compounds. These anti-inflammatory and antioxidant leads could be used as potential functional food components.