Unprecedented antioxidative and anti-inflammatory aryl polyketides from the brown seaweed Sargassum wightii

Anusree, M and Chakraborty, Kajal (2017) Unprecedented antioxidative and anti-inflammatory aryl polyketides from the brown seaweed Sargassum wightii. Food Research International, 100. pp. 640-649. ISSN 0963-9969

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    Previously undescribed aryl polyketide lactones, 4-(8-ethyl-tetrahydro-7-oxo-2H-pyran-5-yl)-propyl-4′-methylbenzoate (compound 1) and methyl-2-(12-oxo-7-phenyl-8-vinyl-1-oxa-4,9-cyclododecadien-3-yl)-acetate (compound 2) were purified from ethyl acetate-methanol fraction of the brown seaweed Sargassum wightii. The structures were proposed based on their NMR and mass spectrometric data. The antioxidative activities of the lactones were significantly greater (P < 0.05) (IC50 1,1-diphenyl-2-picrylhydrazyl radical scavenging 0.24–0.32 mg/mL) than α-tocopherol (IC50 0.63 mg/mL). The title compounds displayed considerably greater 5- lipoxygenase inhibitory activity (IC50 0.56 and 0.29 mg/mL, respectively) in conjunction with higher selectivity indices (anti-cycloxygense-1IC50/anti-cycloxygense-2IC50> 1) compared to non-steroidal anti-inflammatory drugs (SIaspirin 0.03, SIibuprofen 0.43). Putative biosynthetic pathway of title polyketide products through polyketide synthase enzyme cascade catalyzed reactions substantiated the structural attributions of the hitherto unreported aryl polyketides. This is the first report of the occurrence and characterization of two rare skeletal types, oxo-2H-pyranyl and oxa-cyclododecadienyl macrolactone featuring the aryl substituent from marine organisms with potential antioxidative and anti-inflammatory activities.

    Item Type: Article
    Uncontrolled Keywords: Brown seaweedSargassum wightiiAryl polyketide lactones4-(8-ethyl-tetrahydro-7-oxo-2H-pyran-5-yl)-propyl-4′-methylbenzoateMethyl-2-(12-oxo-7-phenyl-8-vinyl-1-oxa-4, 9-cyclododecadien-3-yl)-acetateAnti-inflammatory activity
    Subjects: Fish Biotechnology > Bioactive compound
    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: 14 Sep 2017 09:19
    Last Modified: 14 Sep 2017 09:19
    URI: http://eprints.cmfri.org.in/id/eprint/12153

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