Inhibition of glycosidase by ursolic acid: in vitro, in vivo and in silico study

Wang, Jing; Zhao, Jingjing; Yan, Yunhui; Liu, Dong; Wang, Chengtao; Wang, Hao

doi:10.1002/jsfa.10098

Cited by 34 publications

(16 citation statements)

References 36 publications

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“…This finding shows that ursolic acid was evaluated as a stronger inhibitor for α ‐glycosidase than acarbose, a commercial antidiabetic agent. In accordance with the results of the study, there were numerous reports on the potent inhibitory effects of ursolic acid isolated from various plant species on α ‐glycosidase [20,28,36,53–59] . Furthermore, the hyperglycemic property of ursolic acid isolated from Salvia polystachya was also confirmed by an in vivo study in DM2 mice [28] .…”

Section: Resultssupporting

confidence: 87%

“…Ursolic acid, a pentacyclic natural triterpenoid, is a secondary plant metabolite that is known to be involved in the plant's defense system against water loss and some pathogens. Today, there has been mounting experimental data that either pure ursolic acid or plant extracts rich in this compound exert various in vitro and in vivo therapeutic potentials, such as neuroprotective, neuropsychiatric, cardioprotective, hepatoprotective, antimicrobial, antidiabetic, anti‐oxidative, anti‐inflammatory, anticancer, etc [19–36] . In particular, the potential neuroprotective and neuropsychiatric potentials of this molecule, which have been revealed by both in vivo and in vitro studies, are quite remarkable [21–25,29,30,32–35] .…”

Section: Introductionmentioning

confidence: 99%

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Lavandula stoechas L. subsp. stoechas, a New Herbal Source for Ursolic Acid: Quantitative Analysis, Purification and Bioactivity Studies

Aydin¹,

Kaya

Gümüştaş

et al. 2023

Chemistry & Biodiversity

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In this study, methanol, ethanol, methanol‐dichloromethane (1 : 1, v/v), acetone, ethyl acetate, diethyl ether, and chloroform extracts of lavender (Lavandula stoechas L. subsp. stoechas) were prepared by maceration, and the ursolic acid contents in the extracts were determined quantitatively by HPLC analyses. The present results show that the methanol‐dichloromethane (1 : 1, v/v) solvent system is the most efficient solvent system for the extraction of ursolic acid from the plant sample with the highest yield (2.22 g/100 g plant sample). In the present study, a new practical method for the isolation of ursolic acid from polar extracts was also demonstrated for the first time. The inhibition effects of the extracts and ursolic acid were also revealed on α‐glycosidase, acetylcholinesterase, butyrylcholinesterase, and human carbonic anhydrase I and II enzymes by determining IC50 values for the first time. The extracts and ursolic acid acted as potent antidiabetic agents by strongly inhibiting the α‐glycosidase activity, whereas they were found to be very weak neuroprotective agents. In view of the present results, L. stoechas and its major metabolite, ursolic acid, can be recommended as a herbal source to control postprandial blood sugar levels and prevent diabetes by delaying the digestion of starch in food.

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Section: Resultssupporting

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Lavandula stoechas L. subsp. stoechas, a New Herbal Source for Ursolic Acid: Quantitative Analysis, Purification and Bioactivity Studies

Aydin¹,

Kaya

Gümüştaş

et al. 2023

Chemistry & Biodiversity

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“…Fluorescence spectroscopy is an effective technique for investigating the binding of ligands and proteins. [ 29 ] The endogenous fluorescence of Pin1 is mainly contributed by three tryptophan (Trp) residues and three tyrosine (Tyr) residues as described previously. [ 30 ] As shown in Figure 1d, the endogenous fluorescence intensity of Pin1 decreased gradually with increase in GA concentration.…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic and computational studies on the binding interaction between gallic acid and Pin1

et al. 2021

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Gallic acid (GA) is a natural ingredient in functional foods, which has various health‐promoting and antitumour effects. Peptidyl‐prolyl cis/trans isomerase Pin1 plays an important role in preventing the development of some malignant tumours. However, whether there was an interaction between Pin1 and GA remains unknown. In this work, the binding information of GA and Pin1 was investigated systematically using multiple spectral and computational methods. GA bound to Pin1 directly with moderate binding affinity in the order of 104 mol/L, therefore decreasing the activity of Pin1. Also, the binding process of GA to Pin1 was driven through weak van der Waals forces, hydrogen bonds, and electrostatic forces. In addition, the important residues Lys63, Arg68, and Arg69 played a significant role in maintaining the binding stability between Pin1 and GA. Interestingly, GA reduced the activity of Pin1 by affecting its conformational characteristics. Our present work showed that GA binds to Pin1 and inhibits its activity, affecting its structural and functional properties, which may contribute to the therapy of Pin1‐related diseases.

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“…The α ‐glucosidase activity was analyzed according to the method of Wang et al 14 . with minor modification.…”

Section: Methodsmentioning

confidence: 99%

“…The type of enzyme inhibition was determined according to the method of Wang et al 14 . with slight modifications.…”

Section: Methodsmentioning

confidence: 99%

Mechanistic study on the inhibition of α‐amylase and α‐glucosidase using the extract of ultrasound‐treated coffee leaves

Sun,

Cao,

Huang

et al. 2023

J Sci Food Agric

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BackgroundOur previous studies have shown that ultrasound‐treated γ‐aminobutyric acid (GABA)‐rich coffee leaves have higher angiotensin‐I‐converting enzyme inhibitory activity than their untreated counterpart. However, whether they have antidiabetic activity remains unknown. In this study, we aimed to investigate the inhibitory activities of coffee leaf extracts (CLEs) prepared with ultrasound (CLE‐U) or without ultrasound (CLE‐NU) pretreatment on α‐amylase and α‐glucosidase. Subsequently, we evaluated the binding interaction between CLE‐U and both enzymes using multi‐spectroscopic and in silico analyses.ResultsUltrasound pretreatment increased the inhibitory activities of CLE‐U against α‐amylase and α‐glucosidase by 21.78% and 25.13%, respectively. CLE‐U reversibly inhibits both enzymes, with competitive inhibition observed for α‐amylase and non‐competitive inhibition for α‐glucosidase. The static quenching of CLE‐U against both enzymes was primarily driven by hydrogen bond and van der Waals interactions. The α‐helices of α‐amylase and α‐glucosidase were increased by 1.8% and 21.3%, respectively. Molecular docking results showed that the key differential compounds, including mangiferin, 5‐caffeoylquinic acid, rutin, trigonelline, GABA, caffeine, glutamate, and others, present in coffee leaves interacted with specific amino acid residues located at the active site of α‐amylase (ASP197, GLU233, and ASP300). The binding of α‐glucosidase and these bioactive components involved amino acid residues, such as PHE1289, PRO1329, and GLU1397, located outside the active site.ConclusionUltrasound‐treated coffee leaves are potential anti‐diabetic substances, capable of preventing diabetes by inhibiting the activities of α‐amylase and α‐glucosidase, thus delaying starch digestion. Our study provides valuable information to elucidate the possible antidiabetic capacity of coffee leaves through the inhibition of α‐amylase and α‐glucosidase activities. © 2023 Society of Chemical Industry.

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Inhibition of glycosidase by ursolic acid: in vitro, in vivo and in silico study

Cited by 34 publications

References 36 publications

Lavandula stoechas L. subsp. stoechas, a New Herbal Source for Ursolic Acid: Quantitative Analysis, Purification and Bioactivity Studies

Lavandula stoechas L. subsp. stoechas, a New Herbal Source for Ursolic Acid: Quantitative Analysis, Purification and Bioactivity Studies

Spectroscopic and computational studies on the binding interaction between gallic acid and Pin1

Mechanistic study on the inhibition of α‐amylase and α‐glucosidase using the extract of ultrasound‐treated coffee leaves

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