New sterols with anti-inflammatory potentials against cyclooxygenase-2 and 5-lipoxygenase from Paphia malabarica

Joy, Minju and Chakraborty, Kajal and Raola, Vamshi Krishna (2017) New sterols with anti-inflammatory potentials against cyclooxygenase-2 and 5-lipoxygenase from Paphia malabarica. Natural Product Research, 31. pp. 1286-1298. ISSN 1478-6427 (Online)

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Official URL: https://www.ncbi.nlm.nih.gov/pubmed/27736157
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    Abstract

    Marine bivalves occupy a leading share in the total edible molluscs at the coastline regions of south-eastern Asia, and are found to possess significant nutritional and biological potential. Various in vitro evaluation (antioxidant and anti-inflammatory) guided purification of ethyl acetate–methanol (EtOAc–MeOH) extract of bivalve clam, Paphia malabarica characterised two new sterol derivatives as 23-gem-dimethylcholesta-5-en-3β-ol (1) and (22E)- 241,242-methyldihomocholest-5,22-dien-3β-ol (2) collected from the south-west coast of Arabian Sea. Their structures were unambiguously assigned on the basis of 1D, 2D NMR spectroscopy and mass spectrometry. The antioxidant and anti-inflammatory activities of 2 as determined by DPPH/ABTS+ radical scavenging and anticyclooxygenase- 2/5-lipoxygenase assays were significantly greater (IC50 < 1 mg/mL) than 1 (IC50 > 1 mg/mL). Structure–activity relationship analysis revealed that the bioactivities of these compounds were directly proportional to the electronic and lipophilic parameters. This is the first report of the occurrence and characterisation of 23-gemdimethyl- 3β-hydroxy-Δ5-cholestane nucleus and C-30 dihomosterol from marine organisms.

    Item Type: Article
    Uncontrolled Keywords: (22E)-241,242-methyldihomocholest-5,22-dien-3β-ol; 23-gem-dimethylcholesta-5-en-3β-ol; Bivalve clam; Paphia malabarica; anti-inflammatory activity
    Subjects: Fish Biotechnology
    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 10:13
    Last Modified: 20 Feb 2017 05:44
    URI: http://eprints.cmfri.org.in/id/eprint/11342

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