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Synthesis and bioactivities evaluation of oleanolic acid oxime ester derivatives as α-glucosidase and α-amylase inhibitors.

ABSTRACT: Different oleanolic acid (OA) oxime ester derivatives (3a-3t) were designed and synthesised to develop inhibitors against α-glucosidase and α-amylase. All the synthesised OA derivatives were evaluated against α-glucosidase and α-amylase in vitro. Among them, compound 3a showed the highest α-glucosidase inhibition with an IC50 of 0.35 µM, which was ∼1900 times stronger than that of acarbose, meanwhile compound 3f exhibited the highest α-amylase inhibitory with an IC50 of 3.80 µM that was ∼26 times higher than that of acarbose. The inhibition kinetic studies showed that the inhibitory mechanism of compounds 3a and 3f were reversible and mixed types towards α-glucosidase and α-amylase, respectively. Molecular docking studies analysed the interaction between compound and two enzymes, respectively. Furthermore, cytotoxicity evaluation assay demonstrated a high level of safety profile of compounds 3a and 3f against 3T3-L1 and HepG2 cells.HighlightsOleanolic acid oxime ester derivatives (3a-3t) were synthesised and screened against α-glucosidase and α-amylase.Compound 3a showed the highest α-glucosidase inhibitory with IC50 of 0.35 µM.Compound 3f presented the highest α-amylase inhibitory with IC50 of 3.80 µM.Kinetic studies and in silico studies analysed the binding between compounds and α-glucosidase or α-amylase.

SUBMITTER: Deng XY 

PROVIDER: S-EPMC8757604 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Synthesis and bioactivities evaluation of oleanolic acid oxime ester derivatives as <i>α</i>-glucosidase and <i>α</i>-amylase inhibitors.

Deng Xu-Yang XY   Ke Jun-Jie JJ   Zheng Ying-Ying YY   Li Dong-Li DL   Zhang Kun K   Zheng Xi X   Wu Jing-Ying JY   Xiong Zhuang Z   Wu Pan-Pan PP   Xu Xue-Tao XT  

Journal of enzyme inhibition and medicinal chemistry 20221201 1

Different oleanolic acid (OA) oxime ester derivatives (<b>3a</b>-<b>3t</b>) were designed and synthesised to develop inhibitors against <i>α</i>-glucosidase and <i>α</i>-amylase. All the synthesised OA derivatives were evaluated against <i>α</i>-glucosidase and <i>α</i>-amylase <i>in vitro.</i> Among them, compound <b>3a</b> showed the highest <i>α</i>-glucosidase inhibition with an IC<sub>50</sub> of 0.35 µM, which was ∼1900 times stronger than that of acarbose, meanwhile compound <b>3f</b> exh  ...[more]

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