Conoidecyclics A-C from marine macroalga Turbinaria conoides: Newly described natural macrolides with prospective bioactive properties

Chakraborty, Kajal and Dhara, Subhajit (2021) Conoidecyclics A-C from marine macroalga Turbinaria conoides: Newly described natural macrolides with prospective bioactive properties. Phytochemistry, 191. pp. 1-14.

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    Abstract

    Intertidal marine brown alga Turbinaria conoides (J.Agardh) Kützing (family Sargassaceae) is considered as one of the largely abundant species, available in the coastal zones of the Indian subcontinent. Bioactivity-guided chromatographic fractionation of the organic extract of T. conoides resulted in three previously undescribed macrocyclic lactone homologues, named as conoidecyclics A-C. Conoidecyclic A displayed greater attenuation potential against cyclooxygenase-2 (IC50 1.75 mM) and 5-lipoxygenase (IC50 4.24 mM) in comparison with other analogues. Conoidecyclic A exhibited higher attenuation potential against 5-lipoxygenase than that displayed by an anti-inflammatory agent, ibuprofen (IC50 4.51 mM). The higher selectivity index of conoidecyclic A (1.79) recognized its selective attenuation potential against the inducible cyclooxygenase-2 enzyme. Inhibition potential of conoidecyclic A against angiotensin converting enzyme-I (IC50 1.23 mM) and protein tyrosine phosphatase-1B (IC50 1.39 mM) were non-competitive, as deduced by kinetic studies. In-silico molecular modeling study of conoidecyclic A with the allosteric sites of the targeted enzymes exhibited least binding energy of -14.51 to -11.27 kcal mol-1 compared to those exhibited by other studied macrolide homologues. Reaction kinetic studies of conoidecyclic A coupled with lesser apparent Vmax inferred that it could efficiently bind with the allosteric site of targeted enzymes in a non-competitive manner to diminish the reaction velocity resulting in enzyme inhibition. Drug-likeness and predictive pharmacokinetic parameters of conoidecyclic A exhibited an acceptable oral bioavailability. These reports inferred that conoidecyclic A encompassing pentacosa macrocyclic moiety could be a promising therapeutic lead to inhibit the enzymes related to the development and progression of pathological conditions leading to inflammation, hypertension and type-2 diabetes.

    Item Type: Article
    Uncontrolled Keywords: Anti-diabetic; Anti-hypertensive; Anti-inflammatory; Conoidecyclics A-C; Macrocyclic lactones; Sargassaceae; Turbinaria conoides.
    Subjects: Biochemistry > Bioactive compounds
    Biochemistry
    Algae
    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 Aug 2021 07:34
    Last Modified: 30 Aug 2021 07:34
    URI: http://eprints.cmfri.org.in/id/eprint/15238

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