First report of substituted 2H-pyranoids from brown seaweed Turbinaria conoides with antioxidant and anti-inflammatory activities

Chakraborty, Kajal and Dhara, Subhajit (2020) First report of substituted 2H-pyranoids from brown seaweed Turbinaria conoides with antioxidant and anti-inflammatory activities. Natural Product Research, 34 (24). pp. 3451-3461. ISSN 1478-6427 (Online)

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    Abstract

    The organic extract of Turbinaria conoides, a brown seaweed harvested from the Gulf of Manner region of Indian peninsular was chromatographically fractionated to yield three substituted 2H-pyranoids, namely methyl-21-yl-[50, 60- dihydro-50-yl-{54-(4-hydroxybenzoyl)- oxy-(52-methylbutyl)}-30-methyl-2H-pyran]-21-methyl butanoate (1), 11-[(30, 60-dihydro-40-methyl-20-oxo-2H-pyran-30-yl)methyl]-10- methylhexyl benzoate (2), and [6-ethyl-3,4-dimethyl-(tetrahydro-20, 20, 60-trimethyl-2H-pyran-30-yl)-2,5-cycloheptadiene]-1-propanoate (3). The compounds 1 and 2 bearing 2H-pyranyl-4-hydroxybenzoyl and 2H-pyranyl-10-methylhexylbenzoate moieties exhibited potential antioxidant activities (IC50 0.54-0.69mg mL�1) as commercial antioxidant (a-tocopherol IC50 0.63-0.73mg mL�1). Likewise, potential bioactivity of the 2H-pyran derivative, 1 against 5-lipoxygenase (IC50 � 1mg mL�1) along with higher index of selectivity (COX-1 inhibitoryIC50/COX-2 inhibitoryIC50 1.88) indicated their selective antiinflammatory properties against inducible inflammatory mediators than that displayed by commercially available non-steroidal antiinflammatory drug (ibuprofen, 0.44). Structure activity relationship analysis of the studied compounds showed that the antioxidative and anti-inflammatory properties were directly proportional to their electronic properties. The previously undescribed 2H-pyranoids might constitute as potential antioxidative and anti-inflammatory pharmacophores for medicinal applications.

    Item Type: Article
    Uncontrolled Keywords: Turbinaria conoides; substituted pyran derivatives; 2H-pyranoids; anti-inflammatory; proinflammatory cyclooxygenase and lipoxygenase
    Subjects: CMFRI Departments > CMFRI-Kochi > Marine Biotechnology
    CMFRI > CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology

    Biochemistry > Bioprospecting
    Biochemistry
    Algae > Seaweed
    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: 08 Dec 2020 04:41
    Last Modified: 05 Jan 2021 08:49
    URI: http://eprints.cmfri.org.in/id/eprint/14743

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