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

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