Synthesis and biological evaluation of novel oleanolic acid analogues as potential α-glucosidase inhibitors

Zhong, Yingying; Chen, Hui‐Sheng; Wu, Panpan; Zhang, Bing-Jie; Yang, Yang; Zhu, Qi; Zhang, Chunguo; Zhao, Suqing

doi:10.1016/j.ejmech.2018.12.046

Cited by 46 publications

(12 citation statements)

References 32 publications

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“…The biocompatibility of gelatin/AEO nanofibers was measured according to our previous reported method by MTT assay [26]. NIH/3T3 cells were cultured in DMEM with 10% fetal bovine serum (FBS), 100 U/mL penicillin and streptomycin at 37 • C with 5% CO 2 in a humidified atmosphere incubator.…”

Section: Biocompatibility Study Of Gelatin/aeo Nanofibersmentioning

confidence: 99%

Angelica Essential Oil Loaded Electrospun Gelatin Nanofibers for Active Food Packaging Application

et al. 2020

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The development of food packaging possessing bioactivities which could extend the shelf life of food has gained increased interest in recent years. In this study, gelatin nanofibers with encapsulated angelica essential oil (AEO) were fabricated via electrospinning. The morphology of gelatin/AEO nanofibers was examined by scanning electron microscopy (SEM) and the addition of AEO resulted in the increase of fiber diameter. The proton nuclear magnetic resonance (1H-NMR) spectra were measured to confirm the presence of AEO in nanofibers. The hydrophobic property of gelatin nanofibers was also found to be improved with the addition of AEO. The nanofibers incorporated with AEO showed significant antioxidant activity and inhibitory effect against both Gram-negative and Gram-positive bacteria in a concentration dependent manner. Furthermore, the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay demonstrated that the developed gelatin/AEO nanofibers revealed no cytotoxicity effect. Thus, gelatin nanofibers incorporated with AEO can be used as potential food packaging.

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Section: Biocompatibility Study Of Gelatin/aeo Nanofibersmentioning

confidence: 99%

Angelica Essential Oil Loaded Electrospun Gelatin Nanofibers for Active Food Packaging Application

et al. 2020

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“…The inhibitory activities of embelin and its derivatives on a-glucosidase from baker's yeast were determined by the reported method 6,11 with slight modification using acarbose and ursolic acid as the positive reference compounds. As depicted in Table 1, the inhibitory activities of all compounds were screened at the concentration of 250 lM.…”

Section: A-glucosidase Inhibitory Activity and Sar Analysesmentioning

confidence: 99%

“…The management of Type 2 diabetes includes hyperglycaemia treatment, diabetic comorbidity prevention, and metabolism adjustment 6,7 . One therapeutic approach is to retard the absorption of glucose via inhibition of enzymes, such as a-glucosidase and a-amylase, in the digestive organs [8][9][10][11] . a-Glucosidase is an exo-type carbohydrase widely distributed in microorganisms, plants, and animal tissues.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and α-glucosidase inhibition study of novel embelin derivatives

Chen

Gao

Jian

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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Embelin is a naturally occurring para-benzoquinone isolated from Embelia ribes (Burm. f.) of the Myrsinaceae family. It was first discovered to have potent inhibitory activity (IC 50 ¼ 4.2 lM) against a-glucosidase in this study. Then, four series of novel embelin derivatives were designed, prepared and evaluated in a-glucosidase inhibition assays. The results show that most of the embelin derivatives synthesised are effective a-glucosidase inhibitors, with IC 50 values at the micromolar level, especially 10d, 12d, and 15d, the IC 50 values of which are 1.8, 3.3, and 3.6 lM, respectively. Structure-activity relationship (SAR) studies suggest that hydroxyl groups in the 2/5-position of para-benzoquinone are very important, and long-chain substituents in the 3-position are highly preferred. Moreover, the inhibition mechanism and kinetics studies reveal that all of 10d, 12d, 15d, and embelin are reversible and mixed-type inhibitors. Furthermore, docking experiments were carried out to study the interactions between 10d and 15d with a-glucosidase.

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“…The research found that the introduction of oxime-ester moiety into OA can improve its anti-tumour activity 15 , anti-inflammatory effect 16 , the inhibition of HIV-1 protease dimerisation and the inhibitory activity of glycogen phosphorylase compared with the parent compound 17 , 18 and other activities, which was presumably associated with the enhancement of the hydrophilic performance 19 . Furthermore, our group has been dedicated to the structural modification and derivation of OA skeleton at the C2, C3, C12, C13, or C28 position, simultaneously the inhibition of α-glucosidase and its mechanism have been explored in depth 20 , 21 .…”

Section: Introductionmentioning

confidence: 99%

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

Deng

Zheng

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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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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Synthesis and biological evaluation of novel oleanolic acid analogues as potential α-glucosidase inhibitors

Cited by 46 publications

References 32 publications

Angelica Essential Oil Loaded Electrospun Gelatin Nanofibers for Active Food Packaging Application

Angelica Essential Oil Loaded Electrospun Gelatin Nanofibers for Active Food Packaging Application

Design, synthesis and α-glucosidase inhibition study of novel embelin derivatives

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

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