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Previously undescribed antioxidative and anti-inflammatory chromenyls bearing 3H-isochromenone and furanyl-2H-chromenyl skeletons from the venerid clam, Paphia malabarica

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Abstract

Previously undescribed chromenyl derivatives, characterized as 7-(2′-ethyl-1′-hydroxynonan-2′-yl)-6,7,8,8a-tetrahydro-3H-isochromen-1-(5H)-one (1) and 61-(3-((E)-31b-(furan-2′-yl)-prop-31b-en-31-yl)-4a,5,6,8a-tetrahydro-8-methyl-2H-chromen-6-yl)-ethyl-5′′-methyl-hexanoate (2) were isolated from ethyl acetate-methanol extract of yellow-foot bivalve clam, Paphia malabarica. Their structures have skeletons composed of isochromen-(5H)-one and furanyl-2H-chromenyl moieties, which are reported for the first time in marine organism. These were characterized by extensive one and two-dimensional nuclear magnetic resonance, infrared, and high-resolution mass spectroscopic experiments. The title compounds were evaluated for therapeutic potentials with regard to anti-inflammatory and antioxidant properties compared to known standards. These compounds exhibited comparable 2, 2-diphenyl-1-picrylhydrazyl (DPPH) and 2, 2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS+) radical scavenging activities with α-tocopherol (IC50 ~0.6–0.7 mg/mL). The significantly higher anti-5-lipoxygenase activity of the title compounds (IC50 0.76–0.82 mg/mL) than ibuprofen (IC50 0.93 mg/mL) indicated their potential anti-inflammatory properties. The selectivity indices (IC50 anti-cyclooxygenase-1/IC50anti-cyclooxygenase-2) of compounds 1 (1.19) and 2 (1.31) well established its safety profiles as an anti-inflammatory when compared to known drug, ibuprofen (0.44). The target bioactivities of chromenyl derivatives were guided by hydrophobic and electronic parameters. These compounds can be used as potential bioactive leads in functional food and medicinal applications.

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Acknowledgements

This work was supported by funding under Indian Council of Agricultural Research Network Project Health Food (grant no. HF/ICAR 2012–2017). The authors are thankful to Indian Council of Agricultural Research (ICAR), New Delhi for providing facilities to carry out the work. The authors thank the Director, Central Marine Fisheries Research Institute for support. Thanks are due to the Head, Marine Biotechnology Division, Central Marine Fisheries Research Institute for facilitating the research activity. M.J. acknowledges ICAR, for the award of a scholarship.

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  1. Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P.B. No. 1603, Cochin, India

    Minju Joy & Kajal Chakraborty

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  1. Minju Joy
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  2. Kajal Chakraborty
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Correspondence to Kajal Chakraborty.

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Minju Joy and Kajal Chakraborty have equally contributed.

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Joy, M., Chakraborty, K. Previously undescribed antioxidative and anti-inflammatory chromenyls bearing 3H-isochromenone and furanyl-2H-chromenyl skeletons from the venerid clam, Paphia malabarica . Med Chem Res 26, 1708–1722 (2017). https://doi.org/10.1007/s00044-017-1886-x

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  • DOI: https://doi.org/10.1007/s00044-017-1886-x

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