First report of two new antioxidative meroterpeno 2H-pyranoids from short-necked yellow-foot clam Paphia malabarica (family: Veneridae) with bioactivity against pro-inflammatory cyclooxygenases and lipoxygenase
Two new meroterpeno 2H-pyranoids were isolated from the EtOAc:MeOH extract of yellow-foot clam Paphia malabarica. The structures of these newly reported compounds were elucidated based on spectroscopic interpretations. This is the first report of biogenic 2H-pyrans bearing decadienyl and allyloxy-(isopentanyl)-cyclohexene skeletons from marine biota. The extended C18 sesquiterpenoid with prenylated irregular farnesene framework was characterised as 2-((E)-deca-1,8-dien-10-yl)-11,12-dihydro-13-propyl-2H-pyran (1). The compound 2, 1′-((10E)-10-(10-(pentan-4-yl)-cyclohex-4-enyl)-allyloxy)-tetrahydro-2′,2′-dimethyl-2H-pyran represents the first example of naturally occurring C21 prenylated bisabolene-type meroterpenoid, whereas tetrahydro-2′,2′-dimethyl-2H-pyran remains attached at C-2′ position of rearranged bisabolene framework formed by allyloxy linkage. The antioxidant activities (DPPH/ABTS+) of 1 and 2 were comparable (IC50 < 1.0 mg/mL) with α-tocopherol. In addition, these compounds exhibited greater activity against cyclooxygenase-2 than COX-1, and the selectivity indices were significantly lesser (~1.1). No significant differences in anti-5-lipoxygenase activity of 1 and 2 (IC50 1.02–1.06 mg/mL) than ibuprofen (IC50 0.93 mg/mL) indicated the potential anti-inflammatory properties of title compounds.
