First report of anti-inflammatory chromenyl derivatives from the spineless cuttlefish Sepiella inermis

Krishnan, Soumya and Chakraborty, Kajal and Joy, Minju (2020) First report of anti-inflammatory chromenyl derivatives from the spineless cuttlefish Sepiella inermis. Natural Product Research, 34 (17). pp. 2437-2447. ISSN 1478-6427 (Online)

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    The 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.

    Item Type: Article
    Uncontrolled Keywords: hexahydro chromenyls, pro-inflammatory cyclooxygenase, 5-lipoxygenase, Spineless cuttlefish, Sepiella inermis
    Subjects: Fish Biotechnology > Bioactive compound
    Marine Fisheries > Fish landing > New record
    Molluscan Fisheries > Cephalopods
    Fish Biotechnology
    Divisions: CMFRI-Kochi > Marine Biotechnology
    Subject Area > CMFRI > CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology
    Subject Area > CMFRI-Kochi > Marine Biotechnology
    Depositing User: Arun Surendran
    Date Deposited: 02 Sep 2020 04:59
    Last Modified: 06 Dec 2022 05:43

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