Novel cinnamic acid magnolol derivatives as potent α-glucosidase and α-amylase inhibitors: Synthesis, in vitro and in silico studies

Hu, Chunmei; Wang, Wenjing; Ye, Yuan-Na; Kang, Yu; Lin, Jing; Wu, Panpan; Li, Dongli; Bai, Liping; Xu, Xuetao; Li, Bao-Qiong; Zhang, Kun

doi:10.1016/j.bioorg.2021.105291

Cited by 22 publications

(6 citation statements)

References 33 publications

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“…Molecular docking was performed using SYBYL software to investigate the interaction between inhibitors and target protein ( Zheng P.-F. et al, 2021 ; Hu, et al, 2021 ). The crystal structure of Saccharomyces cerevisiae α -glucosidase was not resolved so far.…”

Section: Methodsmentioning

confidence: 99%

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

Lin

Zhang

et al. 2022

Front. Chem.

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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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Section: Methodsmentioning

confidence: 99%

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

Lin

Zhang

et al. 2022

Front. Chem.

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“…The molecular docking between compounds 3d , 3f , and 3i and α-glucosidase were simulated with Sybyl-2.1.1 (Tripos, Shanghai, China) ( Hu et al, 2021 ). First, compounds 3d , 3f , and 3i were prepared by hydrogenation and energy minimization using the MM2 program.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of 5-Fluoro-2-Oxindole Derivatives as Potential α-Glucosidase Inhibitors

Lin

Liang

et al. 2022

Front. Chem.

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α-Glucosidase inhibitors are known to prevent the digestion of carbohydrates and reduce the impact of carbohydrates on blood glucose. To develop novel α-glucosidase inhibitors, a series of 5-fluoro-2-oxindole derivatives (3a ∼ 3v) were synthesized, and their α-glucosidase inhibitory activities were investigated. Biological assessment results showed that most synthesized compounds presented potential inhibition on α-glucosidase. Among them, compounds 3d, 3f, and 3i exhibited much better inhibitory activity with IC50 values of 49.89 ± 1.16 μM, 35.83 ± 0.98 μM, and 56.87 ± 0.42 μM, respectively, which were about 10 ∼ 15 folds higher than acarbose (IC50 = 569.43 ± 43.72 μM). A kinetic mechanism study revealed that compounds 3d, 3f, and 3i inhibited the α-glucosidase in a reversible and mixed manner. Molecular docking was carried out to simulate the affinity between the compound and α-glucosidase.

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“…Anti-α-glucosidase activity of cinnamic acid derivatives (1 ~ 6) was measured according to previous reports [31][32]. Test compound solution with different concentration was added into α-glucosidase solution and for 10 minutes, followed by the addition of p-NPG solution.…”

Section: A-glucosidase Inhibition and Kinetics Assaymentioning

confidence: 99%

Synthesis and evaluation of cinnamic acid derivatives as ɑ- glucosidase inhibitors

Zhong,

Zhu

2024

Preprint

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Six cinnamic acid derivatives (1 ~ 6) were synthesized for finding potential α-glucosidase inhibitors. The structure of derivatives (1 ~ 6) were confirmed by NMR and HRMS. Inhibitory activity screening results showed that cinnamic acid derivatives (1 ~ 6) exhibited potential α-glucosidase inhibitory activity. Compound 2 showed the highest α-glucosidase inhibitory activity with IC50 value of 39.91 ± 0.62 µM. SAR results showed that introduction of substituent groups in benzene ring of cinnamic acid enhanced the α-glucosidase inhibition activity, and methyl group had the optimal gain. Inhibitory kinetics results showed compound 2 was one reversible and mixed-type inhibitor. Molecular docking results revealed that compound 2 tightly bind to active pocket of α-glucosidase and formed hydrogen bond and hydrophobic interactions with α-glucosidase.

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Novel cinnamic acid magnolol derivatives as potent α-glucosidase and α-amylase inhibitors: Synthesis, in vitro and in silico studies

Cited by 22 publications

References 33 publications

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

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

Synthesis and Biological Evaluation of 5-Fluoro-2-Oxindole Derivatives as Potential α-Glucosidase Inhibitors

Synthesis and evaluation of cinnamic acid derivatives as ɑ- glucosidase inhibitors

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