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First report of dual cyclooxygenase-2 and 5-lipoxygenase inhibitory halogen derivatives from the thallus of intertidal seaweed Kappaphycus alvarezii

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Abstract

Two halogen derivatives, characterized as 2-butyl-7-4-(chloromethyl) cyclooct-1-enyl) hept-5-en-1-ol (compound 1) and 4-(2-chloroethyl)-5-7-(methoxymethyl) undec-3-enyl) cyclooct-4-enone (compound 2) were isolated from the ethyl acetate-methanol extract of the intertidal red seaweed Kappaphycus alvarezii. The studied compounds were evaluated for their inhibitory effects towards pro-inflammatory 5-lipoxygenase along with cyclooxygenases, and also were determined the free radical scavenging potential. The halogenated cyclooctenone (compound 2) displayed greater 5-lipoxygenase (IC50 0.90 mg mL−1) inhibitory activity when compared to the non steroidal anti-inflammatory drug ibuprofen (IC50 0.93 mg mL−1). Similarly selectivity indices of the studied compounds were higher (anti-cyclooxygense-1 IC50/anti-cyclooxygense-2 IC50 ~1.06–1.07) when compared to those displayed by ibuprofen (0.44) and aspirin (0.02). The antioxidative activities of the halogen derivatives were found to be greater (IC50 < 0.30 mg mL−1) in comparison with that exhibited by α-tocopherol (IC50 > 0.50 mg mL−1). This is the first report on structural characterization of unusual halogen analogues from K. alvarezii with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory activities.

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Acknowledgements

Financial support from the Science and Engineering Research Board (SERB) of Department of Science and Technology, Ministry of Science and Technology, New Delhi, India in the form of a research grant (SR/S1/OC-96/2012 SERB) is gratefully acknowledged. The authors thank the Director, Central Marine Fisheries Research Institute, for his guidance and support. Thanks are due to the Head, Marine Biotechnology Division, Central Marine Fisheries Research Institute for assisting the research activity. FM gratefully acknowledges SERB for the award of a fellowship.

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    Authors and Affiliations

    1. Department of Chemistry, Mangalore University, Mangalagangothri, Mangaluru, Karanataka, 574199, India

      Fasina Makkar

    2. Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, Post Box No. 1603, Cochin, Kerala, India

      Kajal Chakraborty

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    1. Fasina Makkar
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    2. Kajal Chakraborty
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    Correspondence to Kajal Chakraborty.

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    These authors contributed equally: Fasina Makkar, Kajal Chakraborty.

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    Makkar, F., Chakraborty, K. First report of dual cyclooxygenase-2 and 5-lipoxygenase inhibitory halogen derivatives from the thallus of intertidal seaweed Kappaphycus alvarezii. Med Chem Res 27, 2331–2340 (2018). https://doi.org/10.1007/s00044-018-2239-0

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