Synthesis and anti-α-glucosidase activity evaluation of betulinic acid derivatives

Wu, Xiao-Zheng; Zhu, Wen-Jian; Lu, Li; Hu, Chunmei; Zheng, Yingying; Zhang, Xin; Lin, Jing; Wu, Jing-Ying; Xiong, Zhuang; Zhang, Kun; Xu, Xuetao

doi:10.1016/j.arabjc.2023.104659

Cited by 38 publications

(16 citation statements)

References 40 publications

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“…Figure 3 B shows the Lineweaver–Burk plots of substrate concentration and residual enzyme activity under compound c27 (0~4 μM). It could be observed that all lines with different slopes intersected in the second quadrant, suggesting compound c27 is a mixed-type inhibitor [ 51 , 52 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Anti-Tyrosinase Activity, and Spectroscopic Inhibition Mechanism of Cinnamic Acid–Eugenol Esters

Min

Zheng

et al. 2023

Molecules

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Tyrosinase plays crucial roles in mediating the production of melanin pigment; thus, its inhibitors could be useful in preventing melanin-related diseases. To find potential tyrosinase inhibitors, a series of cinnamic acid–eugenol esters (c1~c29) was synthesized and their chemical structures were confirmed by 1H NMR, 13C NMR, HRMS, and FT-IR, respectively. The biological evaluation results showed that all compounds c1~c29 exhibited definite tyrosinase inhibitory activity; especially, compound c27 was the strongest tyrosinase inhibitor (IC50: 3.07 ± 0.26 μM), being ~4.6-fold stronger than the positive control, kojic acid (IC50: 14.15 ± 0.46 μM). Inhibition kinetic studies validated compound c27 as a reversible mixed-type inhibitor against tyrosinase. Three-dimensional fluorescence and circular dichroism (CD) spectra results indicated that compound c27 could change the conformation and secondary structure of tyrosinase. Fluorescence-quenching results showed that compound c27 quenched tyrosinase fluorescence in the static manner with one binding site. Molecular docking results also revealed the binding interactions between compound c27 and tyrosinase. Therefore, cinnamic acid–eugenol esters, especially c27, could be used as lead compounds to find potential tyrosinase inhibitors.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Anti-Tyrosinase Activity, and Spectroscopic Inhibition Mechanism of Cinnamic Acid–Eugenol Esters

Min

Zheng

et al. 2023

Molecules

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“…It has been suggested that chronic or intermittent hyperglycemia is linked to the development of diabetic complications ( Volpe et al, 2018 ; Wu et al, 2023 ). Several signaling pathways involved in diabetic complications may be directly triggered by hyperglycemia in different tissues, due to the production of ROS, the formation of AGEs and the secretion of pro-inflammatory cytokines ( Song et al, 2022 ; Yoshikawa et al, 2022 ).…”

Section: Discussionmentioning

confidence: 99%

N-p-coumaroyloctopamine ameliorates hepatic glucose metabolism and oxidative stress involved in a PI3K/AKT/GSK3β pathway

Huang,

Zhang,

et al. 2024

Front. Pharmacol.

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Type 2 diabetes mellitus is regarded as a chronic metabolic disease characterized by hyperglycemia. Long-term hyperglycemia may result in oxidative stress, damage pancreatic β-cell function and induce insulin resistance. Herein we explored the anti-hypoglycemic effects and mechanisms of action of N-p-coumaroyloctopamine (N-p-CO) in vitro and in vivo. N-p-CO exhibited high antioxidant activity, as indicated by the increased activity of SOD, GSH and GSH-Px in HL-7702 cells induced by both high glucose (HG) and palmitic acid (PA). N-p-CO treatment significantly augmented glucose uptake and glycogen synthesis in HG/PA-treated HL-7702 cells. Moreover, administration of N-p-CO in diabetic mice induced by both high-fat diet (HFD) and streptozotocin (STZ) not only significantly increased the antioxidant levels of GSH-PX, SOD and GSH, but also dramatically alleviated hyperglycemia and hepatic glucose metabolism in a dose-dependent manner. More importantly, N-p-CO upregulated the expressions of PI3K, AKT and GSK3β proteins in both HG/PA-induced HL-7702 cells and HFD/STZ-induced mice. These findings clearly suggest that N-p-CO exerts anti-hypoglycemic and anti-oxidant effects, most probably via the regulation of a PI3K/AKT/GSK3β signaling pathway. Thus, N-p-CO may have high potentials as a new candidate for the prevention and treatment of diabetes.

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“…Molecular docking was performed to simulate the binding of MY15–17 with PTP1B using SYBYL. , The structure of PTP1B (PDB: 1XBO) was optimized by the procedure, including removing water, adding hydrogen, adding charge, fixing side chains, and generating the active pocket in automatic mode. The protomol frid dimensions data ( x , y , z ) was 27 × 27 × 25.…”

Section: Methodsmentioning

confidence: 99%

Identification of 1,3,4-Thiadiazolyl-Containing Thiazolidine-2,4-dione Derivatives as Novel PTP1B Inhibitors with Antidiabetic Activity

Li,

Min

et al. 2024

J. Med. Chem.

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Forty-one 1,3,4-thiadiazolyl-containing thiazolidine-2,4dione derivatives (MY1−41) were designed and synthesized as protein tyrosine phosphatase 1B (PTP1B) inhibitors with activity against diabetes mellitus (DM). All synthesized compounds (MY1−41) presented potential PTP1B inhibitory activities, with half-maximal inhibitory concentration (IC 50 ) values ranging from 0.41 ± 0.05 to 4.68 ± 0.61 μM, compared with that of the positive control lithocholic acid (IC 50 = 9.62 ± 0.14 μM). The most potent compound, MY17 (IC 50 = 0.41 ± 0.05 μM), was a reversible, noncompetitive inhibitor of PTP1B. Circular dichroism spectroscopy and molecular docking were employed to analyze the binding interaction between MY17 and PTP1B. In HepG2 cells, MY17 treatment could alleviate palmitic acid (PA)-induced insulin resistance by upregulating the expression of phosphorylated insulin receptor substrate and protein kinase B. In vivo, oral administration of MY17 could reduce the fasting blood glucose level and improve glucose tolerance and dyslipidemia in mice suffering from DM.

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Synthesis and anti-α-glucosidase activity evaluation of betulinic acid derivatives

Cited by 38 publications

References 40 publications

Synthesis, Anti-Tyrosinase Activity, and Spectroscopic Inhibition Mechanism of Cinnamic Acid–Eugenol Esters

Synthesis, Anti-Tyrosinase Activity, and Spectroscopic Inhibition Mechanism of Cinnamic Acid–Eugenol Esters

N-p-coumaroyloctopamine ameliorates hepatic glucose metabolism and oxidative stress involved in a PI3K/AKT/GSK3β pathway

Identification of 1,3,4-Thiadiazolyl-Containing Thiazolidine-2,4-dione Derivatives as Novel PTP1B Inhibitors with Antidiabetic Activity

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