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

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

JOURNAL=Frontiers in Chemistry

VOLUME=10

YEAR=2022

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2022.911232

DOI=10.3389/fchem.2022.911232

ISSN=2296-2646

ABSTRACT=<p>A series of benzylidene analogs of oleanolic acid <bold>4a∼4s</bold> were synthesized and assessed for their <italic>α</italic>-glucosidase and <italic>α</italic>-amylase inhibitory activities. The results presented that all synthesized analogs exhibited excellent-to-moderate inhibitory effects on <italic>α</italic>-glucosidase and <italic>α</italic>-amylase. Analog <bold>4i</bold> showed the highest <italic>α</italic>-glucosidase inhibition (IC<sub>50</sub>: 0.40 μM), and analog <bold>4o</bold> presented the strongest <italic>α</italic>-amylase inhibition (IC<sub>50</sub>: 9.59 μM). Inhibition kinetics results showed that analogs <bold>4i</bold> and <bold>4o</bold> were reversible and mixed-type inhibitors against <italic>α</italic>-glucosidase and <italic>α</italic>-amylase, respectively. Simulation docking results demonstrated the interaction between analogs and two enzymes. Moreover, analogs <bold>4i</bold> and <bold>4o</bold> showed a high level of safety against 3T3-L1 and HepG2 cells.</p>