First report of two new antioxidative meroterpeno 2H-pyranoids from short-necked yellow-foot clam Paphia malabarica (family: Veneridae) with bioactivity against pro-inflammatory cyclooxygenases and lipoxygenase

Joy, Minju and Chakraborty, Kajal (2016) First report of two new antioxidative meroterpeno 2H-pyranoids from short-necked yellow-foot clam Paphia malabarica (family: Veneridae) with bioactivity against pro-inflammatory cyclooxygenases and lipoxygenase. Natural Product Research. pp. 1-11. ISSN 1478-6427 (Online)

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Official URL: https://www.ncbi.nlm.nih.gov/pubmed/27471883
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    Abstract

    Two new meroterpeno 2H-pyranoids were isolated from the EtOAc:MeOH extract of yellow-foot clam Paphia malabarica. The structures of these newly reported compounds were elucidated based on spectroscopic interpretations. This is the first report of biogenic 2H-pyrans bearing decadienyl and allyloxy-(isopentanyl)-cyclohexene skeletons from marine biota. The extended C18 sesquiterpenoid with prenylated irregular farnesene framework was characterised as 2-((E)-deca-1,8-dien-10-yl)-11,12-dihydro-13-propyl-2H-pyran (1). The compound 2, 1′-((10E)-10-(10-(pentan-4-yl)-cyclohex-4-enyl)- allyloxy)-tetrahydro-2′,2′-dimethyl-2H-pyran represents the first example of naturally occurring C21 prenylated bisabolene-type meroterpenoid, whereas tetrahydro-2′,2′-dimethyl-2H-pyran remains attached at C-2′ position of rearranged bisabolene framework formed by allyloxy linkage. The antioxidant activities (DPPH/ABTS+) of 1 and 2 were comparable (IC50 < 1.0 mg/mL) with α-tocopherol. In addition, these compounds exhibited greater activity against cyclooxygenase-2 than COX-1, and the selectivity indices were significantly lesser (~1.1). No significant differences in anti-5-lipoxygenase activity of 1 and 2 (IC50 1.02–1.06 mg/mL) than ibuprofen (IC50 0.93 mg/mL) indicated the potential anti-inflammatory properties of title compounds.

    Item Type: Article
    Uncontrolled Keywords: Paphia malabarica; meroterpeno 2Hpyranoids; antioxidative; anti-inflammatory; cyclooxygenases; lipoxygenase
    Subjects: Molluscan Fisheries > Clam
    Biochemistry > Bioactive compounds
    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: 09 Dec 2016 07:16
    Last Modified: 09 Dec 2016 07:16
    URI: http://eprints.cmfri.org.in/id/eprint/11338

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