Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana

Chakraborty, Kajal and Raola, Vamshi Krishna (2018) Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana. Medicinal Chemistry Research, 27. pp. 1679-1689.

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Kajal Chakraborty_2018_Medicinal Chemistry Research_Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials.pdf

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Official URL: https://link.springer.com/article/10.1007/s00044-0...
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    Abstract

    Previously undescribed oxygenated heterocyclic metabolites were purified from the ethyl acetate fraction of natural mangrove hybrid Rhizophora annamalayana. The purified metabolites were characterized as 11-(tetrahydro-14α-hydroxy- 13β-methylfuran-12-yl)-10β-methylbutyl benzoate (1), 13-(tetrahydro-15β,16α-dimethyl-18-oxo-2H-pyran-14-yl)-10β- methylhept-12(E)-enyl benzoate (2), and dihydro-11-((7E)-2-hydroxy-8β-methyl-2H-chromen-9-yl)-13-methylpent-12(E)- enyl)-17β-methylfuran-19(3H)-one (3) by the combined spectroscopic experiments. These metabolites were assessed for their antioxidant and anti-inflammatory activities, and compared with the commercially available standards. The purified compound 3 exhibited greater antioxidant activities as deduced by 2, 2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid and 2, 2-diphenyl-1-picrylhydrazyl quenching properties (IC50 2.10 and 2.22 mM, respectively) compared to the positive control (α-tocopherol, IC50 1.46 and 1.69 mM, respectively). Consequently, the anti-inflammatory activity of compound 3 with regard to the inhibitory property towards pro-inflammatory 5-lipoxygenase was greater (IC50 2.16 mM) than that exhibited by the synthetic anti-inflammatory drug ibuprofen (IC50 4.51 mM). Electronic and hydrophobic parameters were deduced to find the target bioactivities of the studied compounds. These oxygenated heterocyclic metabolites could be used as potential therapeutic lead compounds in the pharmaceutical applications.

    Item Type: Article
    Uncontrolled Keywords: Rhizophora annamalayana; Rhizophoraceae; Natural hybrid mangrove; Oxygenated heterocyclic metabolites Antioxidative ● Anti-inflammatory
    Subjects: Biochemistry > Bioactive compounds
    Biochemistry
    Marine Ecosystems > Mangroves
    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: 22 Jun 2017 07:12
    Last Modified: 22 May 2018 04:24
    URI: http://eprints.cmfri.org.in/id/eprint/11937

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