First report of spiro-compounds from marine macroalga Gracilaria salicornia: prospective natural anti-inflammatory agents attenuate 5- lipoxygenase and cyclooxygenase-2

Chakraborty, Kajal and Antony, Tima (2021) First report of spiro-compounds from marine macroalga Gracilaria salicornia: prospective natural anti-inflammatory agents attenuate 5- lipoxygenase and cyclooxygenase-2. Natural Product Research, 35 (5). pp. 770-781. ISSN 1478-6427 (Online)

[img] Text
Natural Product Research_2021_Kajal Chakraborty.pdf
Restricted to Registered users only

Download (1MB) | Request a copy | Please mail the copy request to cmfrilibrary@gmail.com
Official URL: https://www.tandfonline.com/doi/abs/10.1080/147864...
Related URLs:

    Abstract

    The inflammation pathology is an orchestrated biological process and the dual inhibition of pro-inflammatory enzymes 5-lipoxygenase and cyclooxygenase-2 has been found to be an effective approach against inflammation. This study involves the characterisation of two previously undescribed spiro[5.5]undecanes, 3-(hydroxymethyl)-7-(methoxymethyl)-3,11-dimethyl-9-oxospiro[5.5]undec-4-en-10-methylbutanoate (1) and 4-ethoxy-11,11-dimethyl-7-methylene-8-(propionyloxy)spiro[5.5]undec-2-en-104,106-dihydroxytetrahydro-2H-pyran-10-carboxylate (2) with potential anti-inflammatory properties, from seaweed Gracilaria salicornia by extensive-spectroscopic-experiments. These metabolites recorded prospective bioactivities against 5-lipoxygenase (IC50 < 2.80 mM), whereas their selectivity indices were significantly greater (∼1) than ibuprofen (0.89) (p < 0.05), which attributed selective anti-inflammatory potencies of the studied spiro[5.5]undecane derivatives against inducible cyclooxygenase-2 than constitutive cyclooxygenase-1. Radical scavenging potential of spiro[5.5]undec-2-en-104,106-dihydroxytetrahydro-2H-pyran-10-carboxylate analogue (2) against oxidants, 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis-3 ethylbenzothiozoline-6-sulfonic acid were found to be greater (IC50 < 1.25 mM) than commercial standard, α-tocopherol (IC50 1.42–1.79 mM). The greater hydrogen-bonding interactions and binding affinity of 2 (−10.13 kcal/mol) with 5-LOX appropriately corroborated its prospective anti-inflammatory activity.

    Item Type: Article
    Uncontrolled Keywords: Gracilaria salicornia; Gracilariaceae; spirocompounds; antiinflammatory; proinflammatory cyclooxygenase and lipoxygenase; molecular docking
    Subjects: Biochemistry > Bioprospecting
    Marine Fisheries > Fish landing > New record
    Biochemistry > Bioactive compounds
    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: 02 Mar 2021 04:32
    Last Modified: 06 Dec 2022 05:39
    URI: http://eprints.cmfri.org.in/id/eprint/14929

    Actions (login required)

    View Item View Item