Biogenic antioxidative and anti-inflammatory aryl polyketides from the venerid bivalve clam Paphia malabarica

Joy, Minju and Chakraborty, Kajal (2017) Biogenic antioxidative and anti-inflammatory aryl polyketides from the venerid bivalve clam Paphia malabarica. Food Chemistry, 237. pp. 169-180.

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    Abstract

    Chemical investigation of ethyl acetate-methanol extract of the venerid bivalve clam Paphia malabarica led to isolation of three unprecedented aryl polyketide derivatives, characterized as (E)-12-(17-ethyl-tet rahydro-16-hydroxy-15-(methyl pentanoate)-14-oxo-2H-pyran-13-yl)-9-methyl-but-11-enyl benzoate (1), isobutyl-13-(6-(benzoyloxy)-10-methylpentyl)-tetrahydro-13-methyl-2H-pyran-17-carboxylate (2) and (13-(methoxycarbonyl)-11-((E)-18-ethylhexa-16,19-dienyl)-12-propyl-cyclohex-10-enyl)-methyl-3 -hydroxy benzoate (3). The structures of the polyketides were assigned by extensive spectroscopic experiments. Compound 1 displayed comparatively greater 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical quenching potential (50% inhibitory concentration, IC50 �0.59 mg/mL) than commercially available atocopherol (IC50 0.63 mg/mL). Potential pro-inflammatory 5-lipoxygenase (5-LOX) inhibition potential (IC50 0.76–0.92 mg/mL) of the polyketides in consonant with significantly greater anti-inflammatory selectivity indices (anti-cyclooxygense-1IC50/anti-cyclooxygense-2IC50 > 1) than non-steroidal antiinflammatory agent ibuprofen (0.44) described the safety profile of the title compounds. Putative biosynthetic route by means of polyketide synthatase biocatalyzed pathways unambiguously established the structural assignments of the previously undescribed polyketide analogues. The potential of hitherto undescribed polyketides from P. malabarica as natural antioxidative and anti-inflammatory functional food ingredients was demonstrated in the present study.

    Item Type: Article
    Subjects: Molluscan Fisheries > Clam
    Biochemistry > Biochemical composition
    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 May 2017 10:16
    Last Modified: 10 Jul 2017 09:03
    URI: http://eprints.cmfri.org.in/id/eprint/11874

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