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

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Relation http://eprints.cmfri.org.in/16125/
https://www.sciencedirect.com/science/article/pii/S0039128X22001283?via%3Dihub
https://doi.org/10.1016/j.steroids.2022.109090
 
Title Anti-hyperglycemic Δ 5 steroids, marginoids A-C from marine veined octopus Amphioctopus marginatus (Octopodidae): Prospective natural leads inhibit serine exopeptidase dipeptidyl peptidase-4
 
Creator Shilpa, K P
Chakraborty, Kajal
 
Subject Bioactive compounds
Biochemistry
Cephalopods
Fish Biotechnology
Molluscan Fisheries
 
Description 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.
 
Publisher Elsevier
 
Date 2022
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/16125/1/Steroids_2022_Kajal%20Chakraborty.pdf
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