First report of anti-inflammatory chromenyl derivatives from the spineless cuttlefish Sepiella inermis |
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Authors: | Soumya Krishnan Minju Joy |
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Affiliation: | 1. Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, Cochin, India;2. Department of Biosciences, Mangalore University, Mangalagangothri, Karnataka State, India |
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Abstract: | AbstractThe spineless cuttlefish Sepiella inermis encompasses a major share in the marine fisheries sector, and represents as a culinary delicacy in many cultures. Bioactivity-guided fractionation of methanol:ethyl acetate (MeOH:EtOAc, 1:1) extract of the edible parts of the species ensued in identification of two hexahydro chromenyl analogues namely, methyl 7-ethyl-hexahydro-8a-methyl-2H-chromene-4-carboxylate (1) and methyl 1-acetoxy-hexahydro-3-methyl-3-propyl-1H-isochromene-4-carboxylate (2). The isolated metabolites were checked for their radical scavenging and anti-inflammatory potentials by selective in vitro models. The isochromenyl derivative exhibited potential 2,2-diphenyl-1-picryl-hydrazil and 2,2′-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (IC50?0.45?mg mL?1) radical-scavenging capacities along with pro-inflammatory cyclooxygenase-2 (COX-2) (IC50 0.75?mg mL?1) and 5-lipoxygenase (5-LOX) (IC50 0.77?mg mL?1) inhibitory activities. The titled compounds displayed the selectivity indices (IC50 anti-COX-1/IC50 anti-COX-2) greater than 1.25, in comparison with synthetic anti-inflammatory drug ibuprofen (0.44), which attributed to their greater selectivity towards inducible pro-inflammatory enzyme COX-2. |
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Keywords: | hexahydro chromenyls pro-inflammatory cyclooxygenase 5-lipoxygenase Spineless cuttlefish Sepiella inermis |
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