Frontiers in Chemistry (Jun 2022)

Synthesis of Benzylidene Analogs of Oleanolic Acid as Potential α-Glucosidase and α-Amylase Inhibitors

  • Jun-Jie Ke,
  • Jing Lin,
  • Xin Zhang,
  • Xiao-Zheng Wu,
  • Ying-Ying Zheng,
  • Chun-Mei Hu,
  • Yu Kang,
  • Kun Zhang,
  • Zhuang Xiong,
  • Zhi-Qiang Ma

DOI
https://doi.org/10.3389/fchem.2022.911232
Journal volume & issue
Vol. 10

Abstract

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A series of benzylidene analogs of oleanolic acid 4a∼4s were synthesized and assessed for their α-glucosidase and α-amylase inhibitory activities. The results presented that all synthesized analogs exhibited excellent-to-moderate inhibitory effects on α-glucosidase and α-amylase. Analog 4i showed the highest α-glucosidase inhibition (IC50: 0.40 μM), and analog 4o presented the strongest α-amylase inhibition (IC50: 9.59 μM). Inhibition kinetics results showed that analogs 4i and 4o were reversible and mixed-type inhibitors against α-glucosidase and α-amylase, respectively. Simulation docking results demonstrated the interaction between analogs and two enzymes. Moreover, analogs 4i and 4o showed a high level of safety against 3T3-L1 and HepG2 cells.

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