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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
Medicinal Chemistry Research ( IF 2.6 ) Pub Date : 2021-07-01 , DOI: 10.1007/s00044-021-02762-1
Shubhajit Dhara , Kajal Chakraborty

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.



中文翻译:

Turbinafuranone A–C,来自海洋大型藻 Turbinaria ornata 的新型 2-呋喃酮类似物作为前瞻性抗高血糖剂减弱酪氨酸磷酸酶-1B

对 Phaeophytan 海洋大型藻Turbinaria ornata(马尾藻科)的化学研究导致了三种 2-呋喃酮类似物的特征,其特征为 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), 和 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)。turbinafuranone B 对酪氨酸磷酸酶-1B 的抑制特性(IC 50 2.42 mM)明显高于标准药剂偏钒酸钠(IC 502.52 毫米)。更大的电子特性和分子对接实验证实了 turbinafuranone B 对蛋白质酪氨酸磷酸酶-1B 的衰减特性,与其他研究的类似物相比,显示出 -11.80 kcal/mol 的最小结合能。结果表明,未描述的 turbinafuranone B 可能用作预期的天然抗高血糖导致降低餐后血糖水平升高的可能性。

更新日期:2021-07-02
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