Three highly oxidized hybrid flavonoids neosophoflavonoids A–C(1,2a,and 2b)were isolated from the roots of Sophora flavescens.Neosophoflavonoid A possesses a unique highly oxidized heptacyclic6/6/6/6/6/6/5 system.Neo...Three highly oxidized hybrid flavonoids neosophoflavonoids A–C(1,2a,and 2b)were isolated from the roots of Sophora flavescens.Neosophoflavonoid A possesses a unique highly oxidized heptacyclic6/6/6/6/6/6/5 system.Neosophoflavonoids B and C are isomers and share the same highly oxidized hexacyclic 6/6/6/6/6/6 systems.Their planar structures were elucidated from 1D/2D nuclear magnetic resonance(NMR),ultraviolet spectroscopy(UV),infrared spectroscopy(IR),and high resolution electrospray ionization mass spectroscopy(HRESIMS)data.Their absolute configurations were determined by thorough GIAO13C NMR(DP4+)calculation protocol and electronic circular dichroism(ECD)calculation method.The plausible biosynthetic routes for the compounds were also proposed.All compounds exhibited significant protein tyrosine phosphatase-1B(PTP1B)inhibitory activity with half maximal inhibitory concentration(IC_(5)0)values 3.94±0.01,0.38±0.13,and 0.70±0.01μmol/L,respectively.In addition,compared to a positive control fenofibrate(Feno)at 20μmol/L,compounds 2a and 2b exhibited stronger inhibitory effects on lipid accumulation in the oleic acid(OA)-induced cell model at 5 and 10μmol/L.展开更多
基金supported by the National Natural Science Foundation of China(No.81973194)Biomedical High Performance Computing Platform,Chinese Academy of Medical Sciences。
文摘Three highly oxidized hybrid flavonoids neosophoflavonoids A–C(1,2a,and 2b)were isolated from the roots of Sophora flavescens.Neosophoflavonoid A possesses a unique highly oxidized heptacyclic6/6/6/6/6/6/5 system.Neosophoflavonoids B and C are isomers and share the same highly oxidized hexacyclic 6/6/6/6/6/6 systems.Their planar structures were elucidated from 1D/2D nuclear magnetic resonance(NMR),ultraviolet spectroscopy(UV),infrared spectroscopy(IR),and high resolution electrospray ionization mass spectroscopy(HRESIMS)data.Their absolute configurations were determined by thorough GIAO13C NMR(DP4+)calculation protocol and electronic circular dichroism(ECD)calculation method.The plausible biosynthetic routes for the compounds were also proposed.All compounds exhibited significant protein tyrosine phosphatase-1B(PTP1B)inhibitory activity with half maximal inhibitory concentration(IC_(5)0)values 3.94±0.01,0.38±0.13,and 0.70±0.01μmol/L,respectively.In addition,compared to a positive control fenofibrate(Feno)at 20μmol/L,compounds 2a and 2b exhibited stronger inhibitory effects on lipid accumulation in the oleic acid(OA)-induced cell model at 5 and 10μmol/L.
