Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (2): 613-621.DOI: 10.6023/cjoc202307027 Previous Articles     Next Articles



吴思敏a, 唐嘉欣b, 周于佳c, 徐学涛a,*(), 张昊星b,*(), 王少华c,*()   

  1. a 五邑大学生物科技与大健康学院 广东江门 529020
    b 深圳大学生命与海洋科学学院 广东深圳 518060
    c 兰州大学药学院 兰州 730000
  • 收稿日期:2023-07-31 修回日期:2023-10-10 发布日期:2023-10-23
  • 作者简介:
  • 基金资助:
    广东省教育厅基金(2021KCXTD044); 广东省教育厅基金(2021KTSCX135)

α-Glucosidase Inhibition Research of Derivatives Based on 2β-Acetoxyferruginol Scaffold Excluding Acetic Acid Group

Simin Wua, Jiaxin Tangb, Yujia Zhouc, Xuetao Xua(), Haoxing Zhangb(), Shaohua Wangc()   

  1. a School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020
    b College of Life Sciences and Oceanography, Shenzhen University, Shenzhen, Guangdong 518060
    c School of Pharmacy, Lanzhou University, Lanzhou 730000
  • Received:2023-07-31 Revised:2023-10-10 Published:2023-10-23
  • Contact: E-mail:;;
  • About author:
    These authors contributed equally to this work.
  • Supported by:
    Funds of Department of Education of Guangdong Province(2021KCXTD044); Funds of Department of Education of Guangdong Province(2021KTSCX135)

In this study, a series derivatives based on 2β-acetoxyferruginol scaffold excluding acetic acid group (1~24) were synthesized and their inhibitory activities on α-glucosidase were determined. The results showed that all compounds 1~24 had good α-glucosidase inhibitory activities. Among them, (3R,4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahy- drophenanthren-3-yl 4-(trifluoromethyl)benzoate (15) had the strongest inhibitory activity [IC50=(23.91±2.34) μmol/L], about 23.6-fold more active than acarbose. The structure activity relationship analysis showed that the introduction of trifluoromethyl was more conducive to enhance its activity. The kinetic results showed that compound 15 was a reversible and non competitive α-glucosidase inhibitor. The 3D fluorescence results indicated that the binding of α-glucosidase with compound 15 could change the conformation of α-glucosidase. The molecular docking results showed that compound 15 made hydrogen bonds with Asp68, Arg312, and Tyr313, and formed hydrophobic interactions with Phe177 and Phe300.

Key words: 2β-acetoxyferruginol, α-glucosidase, 3D fluorescence, molecular docking