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 IC
50
of 0.35 µM, which was ∼1900 times stronger than that of acarbose, meanwhile compound
3f
exhibited the highest
α
-amylase inhibitory with an IC
50
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.
Highlights
Oleanolic 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.
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