First report of chromenyl derivatives from spineless marine cuttlefish Sepiella inermis: Prospective antihyperglycemic agents attenuate serine protease dipeptidyl peptidase‐IV

Soumya, Krishnan and Chakraborty, Kajal and Joy, Minju (2019) First report of chromenyl derivatives from spineless marine cuttlefish Sepiella inermis: Prospective antihyperglycemic agents attenuate serine protease dipeptidyl peptidase‐IV. Journal of Food Biochemistry, 43 (5). pp. 1-12.

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    Abstract

    The Asian green mussel, Perna viridis is a nutritious health food in the estuarine and coastal sea beds of the Arabian Sea along the west coast of India. In the present study, bioactivity‐guided purification of the chloroform fraction of the methanolic extract of P. viridis was carried out. The isolated secondary metabolites were characterized by spectroscopic experiments, and their antioxidative/antiinflammatory properties were evaluated. The titled compounds were characterized as 3‐hydroxy‐13‐vinyl‐dodecahydro‐11‐phenanthrenone (1), 4,4,9‐trimethyl‐13‐vinyl‐dodecahydro‐2‐phenanthrenone (2), 11,20‐dihydroxy‐6,6‐dimethyl‐decahydro‐5H‐benzo[h]naphtho[1,2‐c]chromene‐16‐carbaldehyde (3), 16‐acetyl‐20‐hydroxy‐6,6‐dimethyl‐dodecahydro‐5H‐benzo[h]naphtho[1,2‐c]chromen‐12‐one (4), cholest‐5‐en‐3β‐3‐yl‐(30‐hydroxy‐3‐methyl‐36‐methyleneundeca‐30E,34E‐dienoate) (5), and cholest‐5‐en‐3β‐3‐yl‐((E)‐33‐oxooct‐31‐enoate) (6). No significant differences in the antioxidant activities of the compounds with chromene‐16‐carbaldehyde (3) and chromen‐12‐one (4) functionalities (IC50 0.52–0.68 mg/ml) vis‐à‐vis the positive control, α‐tocopherol (IC50 0.65–0.76 mg/ml) were registered. The studied compounds, 1–4, displayed potential antiinflammatory activities against pro‐inflammatory 5‐lipoxygenase (5‐LOX) (IC50 < 1 mg/ml). The balanced hydrophilic–lipophilic properties and lower steric values of the studied compounds, 1–4, were correlated with their bioactive potentials.

    Item Type: Article
    Uncontrolled Keywords: antihyperglycemic, chromenyl derivatives, dipeptidyl peptidase‐IV, molecular docking simulations, Sepiella inermis
    Subjects: Fish Biotechnology > Bioactive compound
    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: 10 May 2019 06:53
    Last Modified: 10 May 2019 06:54
    URI: http://eprints.cmfri.org.in/id/eprint/13641

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