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Turbinafuranone A–C, new 2-furanone analogues from marine macroalga Turbinaria ornata as prospective anti-hyperglycemic agents attenuate tyrosine phosphatase-1B

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Abstract

Chemical investigation of Phaeophytan marine macroalga Turbinaria ornata (family Sargassaceae) resulted in the characterization of three 2-furanone analogues, which were characterized as 6, 7-dihydroxy-8-methyl-3-(5′-methyloct-4′-en-1′-yl)-hexahydrocyclooct-1-en-[1, 2-c]furan-11-one (turbinafuranone A), 4-hydroxy-3-isopropyl-7, 8-dimethyl-6-(pentan-2′-acetate)-hexahydrocycloocta-1-en-[1, 2-c]furan-11-one (turbinafuranone B), and 6-acetoxy-8-ethyl-5-methoxy-3-(2′-methylhex-4′-en-1′-yl)-pentahydrocycloocta-1, 7-dien-[1, 2-c]furan-11-one (turbinafuranone C). Inhibitory property of turbinafuranone B against tyrosine phosphatase-1B was significantly greater (IC50 2.42 mM) than standard agent sodium metavanadate (IC50 2.52 mM). Greater electronic properties along with molecular docking experiments corroborated the attenuation property of turbinafuranone B against protein tyrosine phosphatase-1B, by exhibiting minimum binding energy of −11.80 kcal/mol compared to other studied analogues. The results demonstrated that the undescribed turbinafuranone B might be used as prospective natural anti-hyperglycemic lead to alleviate the likelihood of higher postprandial blood glucose levels.

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Acknowledgements

The authors gratefully acknowledge the funding by the Indian Council of Agricultural Research (ICAR, New Delhi, India) under Central Marine Fisheries Research Institute (ICAR-CMFRI) project “Development of Bioactive Pharmacophores from Marine Organisms” (MBT/HLT/SUB23). The authors are grateful to the Director, ICAR-CMFRI, and Head, Marine Biotechnology Division of ICAR-CMFRI for facilitating the research activities. The authors are thankful to the Chairman, Department of Chemistry, Mangalore University (Karnataka, India) for providing with necessary support.

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SD and KC designed research, conducted experiments, and analyzed data. KC acquired funds and conceptualized the work. SD drafted the manuscript. KC reviewed and edited the manuscript. Both authors read and approved the manuscript.

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Correspondence to Kajal Chakraborty.

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Dhara, S., Chakraborty, K. Turbinafuranone A–C, new 2-furanone analogues from marine macroalga Turbinaria ornata as prospective anti-hyperglycemic agents attenuate tyrosine phosphatase-1B. Med Chem Res 30, 1635–1648 (2021). https://doi.org/10.1007/s00044-021-02762-1

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