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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 2: 613 - 621

DOI: https://doi.org/10.6023/cjoc202307027

ARTICLES

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

  • Simin Wu ,
  • Jiaxin Tang ,
  • Yujia Zhou ,
  • Xuetao Xu ,
  • Haoxing Zhang ,
  • Shaohua Wang
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  • 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
† These authors contributed equally to this work.
* Corresponding authors. E-mail: ;
;

Received date: 2023-07-31

  Revised date: 2023-10-10

  Online published: 2023-10-26

Supported by

Funds of Department of Education of Guangdong Province(2021KCXTD044); Funds of Department of Education of Guangdong Province(2021KTSCX135)

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Abstract

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

Cite this article

Simin Wu , Jiaxin Tang , Yujia Zhou , Xuetao Xu , Haoxing Zhang , Shaohua Wang . α-Glucosidase Inhibition Research of Derivatives Based on 2β-Acetoxyferruginol Scaffold Excluding Acetic Acid Group[J]. Chinese Journal of Organic Chemistry, 2024 , 44(2) : 613 -621 . DOI: 10.6023/cjoc202307027

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