Preparation, urease inhibition mechanisms, and anti-Helicobacter pylori activities of hesperetin-7-rhamnoglucoside

Sharaf, Mohamed; Arif, Muhammad; Hamouda, Hamed I.; Khan, Samiullah; Abdalla, Mohnad; Shabana, Samah; Rozan, Hussein. E.; Khan, Tehsin Ullah; Chi, Zhe; Liu, Chenguang

doi:10.1016/j.crmicr.2021.100103

Cited by 18 publications

(12 citation statements)

References 67 publications

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“…HPLC was carried out using a GBC 1100 Series HPLC system equipped with a UV detector [ 59 ]. Bioactive phenolic components were identified in SRLe using a C18 column (250 mm × 4.6 mm; 5 μm).…”

Section: Methodsmentioning

confidence: 99%

In Situ Biosynthesis of Reduced Alpha Hematite (α-Fe2O3) Nanoparticles by Stevia Rebaudiana L. Leaf Extract: Insights into Antioxidant, Antimicrobial, and Anticancer Properties

et al. 2022

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In the present study, we utilized Stevia rebaudiana L. (SRLe) extract to in situ biosynthesize nanoscale alpha hematite (α-Fe 2 O 3 ) nanoparticles (NPs) with potent antioxidant, antimicrobial, and anticancer properties. SRLe-α-Fe 2 O 3 was characterized using physiochemical analyses, including UV/Vis, FTIR, XRD, DLS, EDX, SEM, and TEM studies. Among tested solvents, CHCl 3 /MeOH (2:1 v / v ) SRL extract (least polar solvent) contained the highest EY, TPC, and antioxidant capacity of ~3.5%, ~75 mg GAE/g extract, and IC 50 = 9.87 ± 0.7 mg/mL, respectively. FTIR confirmed the engagement of coating operation to the colloidal α-Fe 2 O 3 NPs. TEM, SEM, and DLS revealed that SRLe-α-Fe 2 O 3 has a spherical shape, uniform size distribution with aggregation for an average size of ~18.34 nm, and ζ = −19.4 mV, forming a repulsive barrier that helped to improve stability. The synthesized nanoparticles displayed considerable antibacterial activity against E. coli and S. aureus bacterial growth, and exhibited superior activity against the A549 lung cancer cell lines. These findings indicate that the increased availability of bioactive substances with antioxidant properties of SRLe makes it a potentially interesting material for the preparation of biologically active compounds and green synthesis of nanoparticles.

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Section: Methodsmentioning

confidence: 99%

In Situ Biosynthesis of Reduced Alpha Hematite (α-Fe2O3) Nanoparticles by Stevia Rebaudiana L. Leaf Extract: Insights into Antioxidant, Antimicrobial, and Anticancer Properties

et al. 2022

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“…In vitro screening and inhibitory studies on urease (Jack bean urease) were determined using the colored Berthelot phenols method, which measures the liberation of ammonia from the reaction [ 43 ]. Briefly, the assay mixture containing 1 unit of the enzyme was added to 650 µL of buffer solution (50 mmol phosphate buffer Ph 6.7, 400 mmol sodium salicylate, 10 mmol sodium nitroprusside, and 2 mmol EDTA/L) and mixed with 10 µL of different concentration 0.1–100 Mm of the tested compounds in DMF as a solvent.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Identification of New N,N-Disubstituted Thiourea, and Thiazolidinone Scaffolds Based on Quinolone Moiety as Urease Inhibitor

et al. 2022

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Synthesis of thiazolidinone based on quinolone moiety was established starting from 4-hydroxyquinol-2-ones. The strategy started with the reaction of ethyl bromoacetate with 4-hydroxyquinoline to give the corresponding ethyl oxoquinolinyl acetates, which reacted with hydrazine hydrate to afford the hydrazide derivatives. Subsequently, hydrazides reacted with isothiocyanate derivatives to give the corresponding N,N-disubstituted thioureas. Finally, on subjecting the N,N-disubstituted thioureas with dialkyl acetylenedicarboxylates, cyclization occurred, and thiazolidinone derivatives were obtained in good yields. The two series based on quinolone moiety, one containing N,N-disubstituted thioureas and the other containing thiazolidinone functionalities, were screened for their in vitro urease inhibition properties using thiourea and acetohydroxamic acid as standard inhibitors. The inhibition values of the synthesized thioureas and thiazolidinones exhibited moderate to good inhibitory effects. The structure−activity relationship revealed that N-methyl quinolonyl moiety exhibited a superior effect, since it was proved to be the most potent inhibitor in the present series achieving (IC50 = 1.83 ± 0.79 µM). The previous compound exhibited relatively much greater activity, being approximately 12-fold more potent than thiourea and acetohydroxamic acid as references. Molecular docking analysis showed a good protein−ligand interaction profile against the urease target (PDBID: 4UBP), emphasizing the electronic and geometric effect of N,N-disubstituted thiourea.

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“…The system is not in equilibrium when the RMSD of urease is increasing or decreasing after MD simulation. Thus, the duration of the MD simulation may be insufficient for robust analysis (Sharaf et al, 2022 ). The higher fluctuation of the RMSD of urease and higher average value in complex indicate that the urease–kaempferol complex structure is changed, thus suggesting bonding between the two.…”

Section: Methodsmentioning

confidence: 99%

Molecular dynamics simulations, molecular docking, and kinetics study of kaempferol interaction on Jack bean urease: Comparison of extended solvation model

Zolghadr

Behbehani

Pakbin

et al. 2022

Food Science & Nutrition

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Since the urease enzyme creates gastric cancer, peptic ulcer, hepatic coma, and urinary stones in millions of people worldwide, it is essential to find strong inhibitors to help patients. Natural products are well known for their beneficial effects on health and efforts are being made to isolate the ingredients, the so-called flavonoids. Flavonoids are now considered as an indispensable component in a variety of nutraceutical, pharmaceutical, and cosmetic applications. Kaempferol (KPF) is an antioxidant found in many fruits and vegetables. Many reports have explained the significant effects of dietary KPF in reducing the risk of chronic diseases such as cancer, ischemia, stroke, and Parkinson's. The current study aimed at investigating the inhibitory impact of KPF on Jack bean urease (JBU) using molecular dynamics (MD) simulations and molecular mechanics Poisson-Boltzmann surface area (MM-PBSA) calculations to confirm the results obtained from isothermal titration calorimetry (ITC), extended solvation model, and docking software. In addition, UV-VIS spectrophotometry was used to study the kinetics of urease inhibition. Calorimetric and spectrophotometric determinations of the kinetic parameters of this inhibition indicate the occurrence of a reversible and noncompetitive mode. Also, the docking and MD results indicated that the urease had well adapted to the kaempferol in the binding pocket, thereby forming a stable complex. Kaempferol displayed low binding energy during MMPBSA calculations. The inhibitory potential of kaempferol was confirmed by experimental and simulation data, but in vivo investigations are also recommended to validate our results.

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Preparation, urease inhibition mechanisms, and anti-Helicobacter pylori activities of hesperetin-7-rhamnoglucoside

Cited by 18 publications

References 67 publications

In Situ Biosynthesis of Reduced Alpha Hematite (α-Fe2O3) Nanoparticles by Stevia Rebaudiana L. Leaf Extract: Insights into Antioxidant, Antimicrobial, and Anticancer Properties

In Situ Biosynthesis of Reduced Alpha Hematite (α-Fe2O3) Nanoparticles by Stevia Rebaudiana L. Leaf Extract: Insights into Antioxidant, Antimicrobial, and Anticancer Properties

Synthesis and Identification of New N,N-Disubstituted Thiourea, and Thiazolidinone Scaffolds Based on Quinolone Moiety as Urease Inhibitor

Molecular dynamics simulations, molecular docking, and kinetics study of kaempferol interaction on Jack bean urease: Comparison of extended solvation model

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