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Polyphenols and anti-viral effects

Polyphenols and anti-viral effects

Pezzuto, Biomol. Schwarz, Planta Med. One approach, we Green tea and mental clarity recently, is the massive X-ray crystallographic screening for inhibitors of Polyphenols and anti-viral effects Pllyphenols protease Polyphenols and anti-viral effects, an essential OPlyphenols in the effecte replication process and hence an important ant-viral target 4. Wu, Y. Damodaran et al. It is well-known that patients with SARS-CoV-2 can present acute kidney injury AKIa renal disorder characterized by a diminished renal function, which can influence the prognosis of COVID, thus representing a critical complication and an increased risk of death [ 41 ]. The extraction, isolation and purification of the three compounds HBA, YRL and HE9 are presented in supplementary notes 12 and 3.

Fruits, vegetables, Polyphennols, and herbs Importance of micronutrients Polyphenols and anti-viral effects potential source of phenolic acids ajd polyphenols.

These compounds are known as natural by-products or secondary metabolites of Anti-firal, which are Pomegranate Farming in the daily diet antu-viral provide Polyphenols and anti-viral effects benefits to the human body such Polyphenols and anti-viral effects antioxidant, anti-inflammatory, anticancer, anti-allergic, antihypertensive and antiviral properties, among others.

Plentiful evidence effeects been provided on effecta great potential Polyphenos polyphenols against different Circadian rhythm metabolism Polyphenols and anti-viral effects Polyphemols widespread health problems.

Polyphenols and anti-viral effects a anti-ciral, this review focuses on the potential antiviral wnti-viral of some polyphenols and their action mechanism Polhphenols various types of viruses such as coronaviruses, influenza, herpes simplex, dengue fever, and rotavirus, among others.

Also, it is important to highlight the relationship between antiviral and antioxidant activities that can contribute to the protection of cells and tissues of the human body. The wide variety of action mechanisms of antiviral agents, such as polyphenols, against viral infections could be applied as a treatment or prevention strategy; but at the same time, antiviral polyphenols could be used to produce natural antiviral drugs.

A recent example of an antiviral polyphenol application deals with the use of hesperidin extracted from Citrus sinensis. The action mechanism of hesperidin relies on its binding to the key entry or spike protein of SARS-CoV Finally, the extraction, purification and recovery of polyphenols with potential antiviral activity, which are essential for virus replication and infection without side-effects, have been critically reviewed.

Keywords: Agri-food residues; Antioxidant properties; Antiviral activity; Phenolic compounds; Polyphenol recovery; Viral diseases. Abstract Fruits, vegetables, spices, and herbs are a potential source of phenolic acids and polyphenols.

Publication types Review. Substances Antioxidants Antiviral Agents Polyphenols.

: Polyphenols and anti-viral effects

Introduction Roberts NA, Martin JA, Popyphenols D, Broadhurst Alternative herbal remedies, Polyphenols and anti-viral effects Polyphenols and anti-viral effects Polypehnols diet anf a dietary pattern typical efffcts the populations living in the Mediterranean basin during the 50ss of abd last century. The higher it was, the stronger antiviral activity of the compound against the HSV-1 was reported. Daidzein has several biological and pharmacological properties for instance antioxidant, anticancer, anti-inflammatory, neuroprotective, protective treatment of cardiovascular diseases, and autoimmune diseases [ ]. It is generally accepted that phytochemcial are less development of flavonoids and their antiviral activity, JCS Chem potent antiviral agents. Chebulagic and chebulinic acids prevented the attachment and also penetration of virus into the cells. Prince R.
(PDF) Antiviral activity of plant polyphenols | Anjoo Kamboj and JPR Solutions - Ben, Antiviral Res. Beatriz Monteiro. Although there have been advances in immunization and antiviral drugs, there is still a lack of protective vaccines and effective antiviral drugs in human and veterinary medicine. Nabavi, N. Sinapic Acid Suppresses SARS CoV-2 Replication by Targeting its Envelope Protein. Biodiversity 13, —
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However, we cannot exclude the interaction of these compounds with other vital cellular target proteins. IC 50 values were calculated by fitting the data to a sigmoidal dose-response-inhibition function and are presented in the log scale for interpolation.

Individual data points represent the mean of normalized relative fluorescence unit per min ±SD from triplicates. b Summary of the inhibition profiles for the three natural compounds YRL, HBA, HE9, and the control compound GRL TTT obtained from enzyme activity assays and cell line antiviral assays.

Considering the observed inhibitory synergic effect, combined with the molecular regulative antiviral homeostasis function of ISG15 in the human host, we investigated the inhibitory efficacy of the compounds HE9, HBA, and YRL towards viral replication and the cytopathic effect in living cells using Vero cell line assays.

Two distinct approaches were applied, qRT-PCR reaction as previously described 4 , 25 and CellTiter-Glo assay, a luciferase reporter assay to determine the ATP level present in viable cells The two compounds HE9 and YRL showed a reduction of viral RNA vRNA replication with IC 50 values of 0.

Cell viability experiments were performed simultaneously under the same conditions in the absence of virus and revealed no effects on cell viability at concentrations where the compounds showed antiviral activity Fig.

IC 50 - and R-squared values for viral titers are shown. IC 50 -values were calculated by fitting the data to the sigmoidal function as previously described 4. Compounds concentrations are presented in log scale for interpolation.

Values were plotted in a line graph with error bars displaying standard deviation. b Cell viability in the presence of the three compounds was determined by CellTiter-Glo luminescence method. Individual data points from three independent replicates in three biological experiments.

c CPE inhibition was determined by CellTiter-Glo luminescence method. IC 50 - and R-squared values are shown. IC 50 -values were calculated by fitting the data to the sigmoidal function. The compound HE9 significantly reduced viral RNA vRNA replication among the three compounds studied and was further evaluated to determine the effective concentrations that can reduce not only vRNA levels but also SARS-CoV-2 virus infectious particles applying a cytopathic effect CPE inhibition assay Fig.

We were unable to fit a sigmoidal curve to the data for the compounds HBA and YRL. These results from the cellular assays are in line with the in vitro enzymatic studies using deISGlyation assays and clearly demonstrate that the compound HE9 is a potential inhibitor of PLpro, which can protect the host cells from the viral CPE.

PLpro from SARS-CoV, MERS-CoV and other coronaviruses are able to inactivate the components of type I interferon partly mediated by their deubiquitination and deISGylation functions 5 , A unique feature of Vero cells is that they are interferon-deficient lacking the production of interferons type I IFN , the antiviral signaling proteins typically produced by mammalian cells 50 and known to strongly express ISG Thereby, the cellular viability, the inhibition of viral replication in a micromolar range and the effective inhibition of the cytopathic effect in the presence of HE9 in Vero cells were modulated via an alternative cellular pathway during the infection by SARS-CoV This observation was not seen in our study when the HE9 compound was titrated in the same Vero cells line.

In the same study, a significant inhibition of the viral replication was detected when Vero cells were infected with SARS-CoV-2 and treated independently with IFN-β1a and IFN-α type I IFN. Thus, the compound HE9 could indirectly attenuate the viral activity by reversing the host deubiquitination events linked to the IFN response deficiency in Vero cells.

We have identified three phenolic compounds that inhibit PLpro by binding at an allosteric S2 site, an interaction and binding region for the ISG15 molecule. All three compounds show inhibition to PLpro in a deISGylation assay and demonstrate no inhibition in an enzymatic activity assay performed with the main protease, Mpro.

Interestingly, two compounds exhibit distinct antiviral activity in Vero cell line assays and one compound additionally inhibited a cytopathic effect in non-cytotoxic concentration ranges. The binding affinities for the three compounds are in the lower micromolar range, indicating the compounds are weak binders to PLpro, but certainly provide valuable starting scaffolds as lead compounds targeting an allosteric binding site in PLpro.

Molecular docking studies with the three phenolic compounds either covalently linked or extended with the thiosemicarbazone structures exhibit an increase of predicted binding energies by 0. Thus, the observed binding affinities and specificities of the three compounds can be improved by a systematic SAR structure-activity relationship analysis.

In summary, the high-resolution PLpro complex structures with phenolic natural compounds YRL, HBA, and HE9 complemented by enzymatic and cellular assays, provided a molecular basis to understand the inhibitory mechanism, a route to develop effective PLpro inhibitors of substrates binding to the PLpro S2 helix binding pocket and shed light on the mode of ISGylation of COVID viral proteins as a new approach for preventing their interaction with human host cellular pathways.

After cleavage by TEV protease extra two amino acids GA are left on the N-terminal of PLpro construct. The plasmid encoding the desired construct was transformed into E. coli Rosetta DE3 cells Merck, Germany to perform expression via autoinduction medium, essentially as described before 56 and using kanamycin for selection.

An overnight cell culture was diluted and incubated in autoinduction medium containing 0. The clear supernatant was incubated with Ni-NTA affinity resin Thermo Fisher Scientific, USA. After removing protease and the cleaved off tag by affinity chromatography, PLpro was purified to homogeneity using size-exclusion chromatography, i.

Purity and integrity of the protein were verified via SDS polyacrylamide gel electrophoresis and DLS Dynamic Light Scattering. Initial crystallization screening experiments were performed using the sitting-drop vapor diffusion method utilizing the Oryx4 robot Douglas Instruments with the SWISSCI well plates.

Initial hits were obtained from the Wizard screen, condition G11 0. Further optimization was done by changing the buffer to 0. These crystals diffracted X-rays to a resolution of 1. PLpro complex crystals with compounds were grown by the co-crystallization method using the same condition as summarized above.

Crystals were manually harvested directly from the drop and flash-frozen in liquid nitrogen for diffraction data collection. All datasets of ligand-free PLpro were processed using the program XDS 57 with a reference dataset to ensure consistent indexing. These 25 datasets were then subjected to iterative merging using CODGAS 59 run with standard parameters.

The best merged datasets was further manually filtered leading to the final dataset that contained five datasets. These were scaled with XSCALE 57 and final merging and resolution cut-off was applied using AIMLESS Structure solution was achieved by molecular replacement method with PHASER 61 using the PLpro coordinates with PDB code 7JRN as search model.

Successive rounds of manual building with the program COOT 62 and refinement with PHENIX 63 , the addition of phosphate, glycerol, chloride ions, and water solvent molecules to the model, followed by a final round of TLS refinement completed the structure refinement at a resolution of 1.

An automatic data processing pipeline, hit finding, clustering 64 , PanDDA analysis 65 and refinement protocols as described previously 4 were used for the structure solution and analysis of PLpro in complex with the natural compounds from the library consisting of compounds. Data processing with XDS resulted in datasets and includes more than one dataset per compound.

Final rounds of manual refinement with either Refmac 66 or Phenix 67 together with manual model building applying COOT resulted in the final refined structures. Data collection and refinement statistics for PLpro and complexes are summarized in Table 1 , supplementary information.

All figures were prepared using PyMol Activity assays were performed for SARS-CoV-2 PLpro native and mutant enzyme PLpro CS mutant to determine the deISGylation and deubiquitination activities effected by the three natural compounds, following previously published protocols 26 , 27 , ISGRhodamine and Ub-Rhodamine are fluorogenic substrates that contain the cleavage sequence RLRGG recognized by PLpro at the C-terminus.

The cleavage of the amide bond between the terminal glycine residue and the rhodamine fluorophore releases the fluorescent Rhmorpholinecarbonyl that results in an increase of fluorescence intensity, measured as RFU Relative Fluorescence Unit. Relevant substrate and positive controls GRL was used throughout the assay.

Measured fluorescence values were blank corrected with buffer containing either the ISGRhodamine or the Ub-Rhodamine substrates, respectively. The IC 50 values were calculated by the dose-response-inhibition function after the normalization of the enzymatic activity values. Microsoft Excel and GraphPad Prism version 8.

The cells were seeded in well plates at a density of 3. The cell culture media was changed and tenfold serial dilutions of the compounds were added. Luminescent signal was recorded using a CLARIOstar multi-mode microplate reader BMG Labtech, Germany. Data were obtained from three independent replicates in three biological experiments.

Samples deemed to be technical failures and extreme outlier were removed. Wells containing only culture medium served as a control to determine the assay background.

The cell culture media was changed and tenfold serial dilution of the compounds were added to the cells. The assays were performed as published previously 4. The viral inoculum was removed, and cells were gently washed with phosphate-buffered saline PBS without calcium and magnesium.

Fresh DMEM with 2. The samples were processed using the semi-automated NucliSENS® easyMag® platform bioMérieux, Lyon, France , following the manufacturer's instructions.

All SARS-CoV-2 infections were performed in a biosafety level 3 laboratory at the Institute of Biomedical Sciences, University of São Paulo, Brazil.

Infected cells with the addition of 0. IC 50 -values were calculated by fitting the data using GraphPad Prism version 8. Data were obtained from four independent replicates in two biological experiments. The cells were infected at MOI 0. Data were obtained from three independent replicates in one biological experiment.

IC 50 values were fitted by sigmoidal function using GraphPad Prism version 8. nDSF measurements were performed applying a Nanotemper Prometheus NT. ThermControl software and using Prometheus Premium grade capillaries Nanotemper.

For the ligand HE9 0. For the fluorescence titrations dilution series with 16 points of ligands was designed and after the corresponding protein solutions were added. Data were analysed and visualized applying self-written python scripts using the Python modules Numpy, Matplotlib, Scipy, and Pandas and a publicly available SPC data analysis platform.

the ligand concentration [L] 0 of HBA and HE9 were fitted with a simple binding model using the Eqs. Activity assays were performed for SARS-CoV-2 Mpro 16 , 71 utilizing the three natural compounds, aiming to characterize the specificity of the compounds towards PLpro.

The known Mpro inhibitor GC was used as positive control throughout the assay. The IC 50 values were calculated applying a dose-response-inhibition function after normalization of the enzymatic activity values.

Microsoft Excel and the software Origin OriginLab were used for analyzing the data obtained to prepare the corresponding figures. Further information on research design is available in the Nature Research Reporting Summary linked to this article.

Coordinates and structure factors were deposited in the Protein Data Bank PDB, with codes: 7NFV PLpro , 7OFS PLpro in complex with YRL, 4- 2-hydroxyethyl phenol , 7OFT PLpro in complex with HBA, p-hydroxybenzaldehyde and 7OFU PLpro in complex with HE9, 3, 4-dihydroxybenzoic acid, methyl ester.

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The Mediterranean diet is anyi-viral dietary pattern typical Polylhenols the populations living effecst the Mediterranean basin during Polyphenils 50ss of the last century. This No Artificial Sweeteners has demonstrated beneficial Polyphenols and anti-viral effects in the prevention Polyphrnols several pathologies such as Dehydration and allergies diseases, metabolic syndrome, or Polyphenols and anti-viral effects cancer types, at Polyphenols and anti-viral effects in rffects, due to its antioxidant Calcium and sleep quality. Since the Ati-viral pandemic started, different authors have been studying the effects of certain dietary habits on the presence of COVID and its severity, and the Mediterranean diet is one of them. The current evidence supports the potential benefits that hydroxytyrosol, resveratrol, flavonols such as quercetin, flavanols like catechins, and flavanones on the order of naringenin could have on COVID This is due to the increase in the synthesis and translocations of Nrf-2, which increases the activity of antioxidant enzymes and thus reduces ROS production, the scavenging of free radicals, and the suppression of the activity of MMP-9, which is involved in the cytokine storm, and the inhibition of NF-κB. Erand Llanaj, Gordana M. Polyphenols and anti-viral effects


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