Anti-hyperglycemic Δ 5 steroids, marginoids A-C from marine veined octopus Amphioctopus marginatus (Octopodidae): Prospective natural leads inhibit serine exopeptidase dipeptidyl peptidase-4

Shilpa, K P and Chakraborty, Kajal (2022) Anti-hyperglycemic Δ 5 steroids, marginoids A-C from marine veined octopus Amphioctopus marginatus (Octopodidae): Prospective natural leads inhibit serine exopeptidase dipeptidyl peptidase-4. Steroids, 186. pp. 1-13. ISSN 0039-128X

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    Abstract

    Three Δ5 steroid analogues, marginoids A-C were purified from the organic extract of marine veined octopus Amphioctopus marginatus (Taki, 1964) (family Octopodidae) distributed on the Asian and Mediterranean coasts. Their structures were elucidated as (5Z)-3β-acetoxy-cholesta-5-en-25-ethylene-22β-hydroxy-23,26-lactone (marginoid A), (5Z, 25Z)-3β-yl-(1′-(E)-3′-hydroxy-4′-methyl-hex-5′-enoate)-22-oxo-26-furanyl-cholesta-5,25-diene (marginoid B), and (5Z)-3β-yl-(7′-methoxypropan-8′-yl)-tetrahydro-2H-pyran-2-one-cholesta-5,24-dien (marginoid C) based on extensive spectroscopic experiments. Marginoid B with hydroxyl-methyl-hexanoate at the C-3 position in conjunction with the heterocyclic furanyl ring displayed superior anti-hyperglycemic properties as acknowledged by its promising serine protease dipeptidyl peptidase-4 attenuation potential (IC50 3.49 µM) displaying comparable activity with the standard DPP-4 inhibitor (DPP-4i) diprotin A (IC50 4.53 µM). The anti-hyperglycemic properties were corroborated by the promising antioxidant activities (IC50 ∼ 0.8–1.0 mM) of these Δ5 steroids, marginoids A-C. Sizeably greater electronic properties, balanced hydrophobic-lipophilic properties (log POW 6.4–8.3), and comparatively lower steric factors were directly proportional to their bioactive properties. Molecular simulation studies in the binding sites of DPP-4 and lesser binding energy (-12.17 kcal/mol) and inhibition constant (Ki 1.20 nM) of marginoid B could be correlated with anti-hyperglycemic properties. Promising bioactivities of marginoid B isolated from A. marginatus are anticipated for nutraceutical applications against hyperglycemia.

    Item Type: Article
    Uncontrolled Keywords: Marine veined octopus Amphioctopus marginatus (Taki, 1964); Octopodidae; Marginoids A-CΔ5 steroid analogues; Anti-hyperglycemic; Dipeptidyl peptidase-4 inhibitor
    Subjects: Biochemistry > Bioactive compounds
    Biochemistry
    Molluscan Fisheries > Cephalopods
    Fish Biotechnology
    Molluscan Fisheries
    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: 30 Jul 2022 05:13
    Last Modified: 30 Jul 2022 05:13
    URI: http://eprints.cmfri.org.in/id/eprint/16125

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