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  • First report of antioxidative 2H-chromenyl derivatives from the intertidal red seaweed Gracilaria salicornia as potential anti-inflammatory agents

    Phytochemical investigation on biologically active compounds of an intertidal red seaweed Gracilaria salicornia (family Gracilariaceae) guided to the separation of two previously undisclosed 2H-chromenyl derivatives. The compounds were characterised as 40-[100-[7-hydroxy-2,8-dimethyl-6-(pentyloxy)- 2H-chromen-2-yl]ethyl]-30,40-dimethyl-cyclohexanone (1) and 30-[100-(8-hydroxy-5-methoxy-2,6,7-trimethyl-2H-chromen- 2-yl)ethyl]-30-methyl-20-methylene cyclohexyl butyrate (2) by extensive spectroscopic experiments. The studied metabolites recorded prospective bioactivities against 5-lipoxygenase (IC50<2.50mM), whereas their selectivity indices were significantly greater (?1) than ibuprofen (0.89) (p<0.05), which attributed higher anti-inflammatory selectivity of 2Hchromenyl compounds against inducible cyclooxygenase-2 than its constitutive pro-inflammatory isoform of cyclooxygenase- 1. The radical scavenging potential of 2 against oxidants, 2,2-diphenyl-1-picrylhydrazyl and 2,20-azino-bis-3 ethylbenzothiozoline-6-sulfonic acid were higher (IC50< 1.35mM) than standard antioxidant, a-tocopherol (IC50 1.42- 1.79mM). The greater hydrogen bond interactions and binding affinity of 2 (?7.35 kcal mol?1) bearing 2H-chromenyl ethyl-30-methyl-40-methylenecyclohexyl butyrate moiety with 5-lipoxygenase, along with higher electronic properties and permissible hydrophobic-hydrophilic balance, manifested towards its greater anti-inflammatory activity than 1.


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