Citation: Xu Zhang, Jiang Li, Kai-Zhou Lu, Ya-Nan Yang, Jian-Shuang Jiang, Xiang Yuan, Zi-Ming Feng, Fei Ye, Pei-Cheng Zhang. Neosophoflavonoids A–C, A class of highly oxidized hybrid flavonoids from Sophora flavescens with antidiabetic effects[J]. Chinese Chemical Letters, ;2024, 35(10): 109456. doi: 10.1016/j.cclet.2023.109456 shu

Neosophoflavonoids A–C, A class of highly oxidized hybrid flavonoids from Sophora flavescens with antidiabetic effects

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

yefei@imm.ac.cn

pczhang@imm.ac.cn

Received Date: 13 October 2023
Revised Date: 19 December 2023
Accepted Date: 21 December 2023
Available Online: 26 December 2023

Figures(5)

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 heptacyclic 6/6/6/6/6/6/5 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 GIAO ¹³C 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 (IC₅₀) values 3.94 ± 0.01, 0.38 ± 0.13, and 0.70 ± 0.01 µmol/L, respectively. In addition, compared to a positive control fenofibrate (Feno) at 20 µmol/L, compounds 2a and 2b exhibited stronger inhibitory effects on lipid accumulation in the oleic acid (OA)-induced cell model at 5 and 10 µmol/L.
- Sophora flavescens,
- Highly oxidized hybrid flavonoids,
- Neosophoflavonoids A–C,
- PTP1B inhibition,
- Lipid accumulation inhibition
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