Fermented Soy-Derived Bioactive Peptides Selected by a Molecular Docking Approach Show Antioxidant Properties Involving the Keap1/Nrf2 Pathway

Bioactive peptides are a group of molecules with health beneficial properties, deriving from food matrices. They are protein fragments consisting of 2–20 amino acids that can be released by microbial fermentation, food processing and gastrointestinal digestion. Once hydrolyzed from their native proteins, they can have different functions including antioxidant activity, which is important for cell protection by oxidant agents. In this work, fermented soy products were digested in vitro in order to improve the release of bioactive peptides. These were extracted, purified and analyzed in vitro and in a cellular model to assess their antioxidant activity. Peptide sequences were identified by LC-MS/MS analysis and a molecular docking approach was used to predict their ability to interact with Keap1, one of the key proteins of the Keap1/Nrf2 pathway, the major system involved in redox regulation. Peptides showing a high score of interaction were selected and tested for their antioxidant properties in a cellular environment using the Caco-2 cell line and examined for their capability to defend cells against oxidative stress. Our results indicate that several of the selected peptides were indeed able to activate the Keap1/Nrf2 pathway with the consequent overexpression of antioxidant and phase II enzymes.

Download Full-text

Molecular Docking Approaches to Suggest the Anti-Mycobacterial Targets of Natural Products

10.26434/chemrxiv.13325690.v1 ◽

2020 ◽

Author(s):

Rafael Baptista ◽

Sumana Bhowmick ◽

Shen Jianying ◽

Luis Mur

Keyword(s):

Natural Products ◽

Molecular Docking ◽

Free Energies ◽

Antibiotic Resistant ◽

Drug Lead ◽

Bisbenzylisoquinoline Alkaloids ◽

Docking Approach ◽

Global Threat ◽

Physicochemical And Structural Properties

Tuberculosis (TB) is a major global threat mostly due to the development of antibiotic resistant forms of Mycobacterium tuberculosis, the causal agent of the disease. Driven by the pressing need for new anti-mycobacterial agents, several natural products (NPs) have been shown to have in vitro activities against M. tuberculosis. The utility of any NP as a drug lead is augmented when the anti-mycobacterial target(s) is unknown. To suggest these, we used a molecular docking approach to predict the interactions of 53 selected anti-mycobacterial NPs against known ‘druggable’ mycobacterial targets ClpP1P2, DprE1, InhA, KasA, PanK, PknB and Pks13. The docking scores / binding free energies were predicted and calculated using AutoDock Vina along with physicochemical and structural properties of the NPs, using PaDEL descriptors. These were compared to the established inhibitor (control) drugs for each mycobacterial target. The specific interactions of the bisbenzylisoquinoline alkaloids 2-nortiliacorinine, tiliacorine and 13’-bromotiliacorinine against the targets PknB and DprE1 (-11.4, -10.9 and -9.8 kcal.mol-1 ; -12.7, -10.9 and -10.3 kcal.mol-1 , respectively) and the lignan αcubebin and Pks13 (-11.0 kcal.mol-1 ) had significantly superior docking scores compared to controls. Our approach can be used to suggest predicted targets for the NP to be validated experimentally but these in silico steps are likely to facilitate drug optimisation.

Download Full-text

Synthesis, Molecular Docking, in vitro Antiproliferative and Antioxidant Activity of Novel Pyrrolidinyl-Carbazole Derivatives

Current Organic Synthesis ◽

10.2174/1570179414666170606120934 ◽

2018 ◽

Vol 14 (8) ◽

Author(s):

Padmaja Pannala ◽

Pedavenkatagari Narayana Reddy ◽

Basireddy V. Subba Reddy ◽

Sunil Misra ◽

Koude Dhevendar ◽

...

Keyword(s):

Antioxidant Activity ◽

Molecular Docking ◽

Carbazole Derivatives

Download Full-text

Chemical Composition, In Vitro and In Silico Antioxidant Potential of Melissa officinalis subsp. officinalis Essential Oil

Antioxidants ◽

10.3390/antiox10071081 ◽

2021 ◽

Vol 10 (7) ◽

pp. 1081

Author(s):

Matilda Rădulescu ◽

Călin Jianu ◽

Alexandra Teodora Lukinich-Gruia ◽

Marius Mioc ◽

Alexandra Mioc ◽

...

Keyword(s):

Antioxidant Activity ◽

Chemical Composition ◽

Essential Oil ◽

In Silico ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Inhibitory Effect ◽

Melissa Officinalis ◽

Β Carotene

The investigation aimed to study the in vitro and in silico antioxidant properties of Melissa officinalis subsp. officinalis essential oil (MOEO). The chemical composition of MOEO was determined using GC–MS analysis. Among 36 compounds identified in MOEO, the main were beta-cubebene (27.66%), beta-caryophyllene (27.41%), alpha-cadinene (4.72%), caryophyllene oxide (4.09%), and alpha-cadinol (4.07%), respectively. In vitro antioxidant properties of MOEO have been studied in 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging, and inhibition of β-carotene bleaching assays. The half-maximal inhibitory concentration (IC50) for the radical scavenging abilities of ABTS and DPPH were 1.225 ± 0.011 μg/mL and 14.015 ± 0.027 μg/mL, respectively, demonstrating good antioxidant activity. Moreover, MOEO exhibited a strong inhibitory effect (94.031 ± 0.082%) in the β-carotene bleaching assay by neutralizing hydroperoxides, responsible for the oxidation of highly unsaturated β-carotene. Furthermore, molecular docking showed that the MOEO components could exert an in vitro antioxidant activity through xanthine oxidoreductase inhibition. The most active structures are minor MOEO components (approximately 6%), among which the highest affinity for the target protein belongs to carvacrol.

Download Full-text

Isobornylchalcones as Scaffold for the Synthesis of Diarylpyrazolines with Antioxidant Activity

Molecules ◽

10.3390/molecules26123579 ◽

2021 ◽

Vol 26 (12) ◽

pp. 3579

Author(s):

Svetlana A. Popova ◽

Evgenia V. Pavlova ◽

Oksana G. Shevchenko ◽

Irina Yu. Chukicheva ◽

Aleksandr V. Kutchin

Keyword(s):

Antioxidant Activity ◽

Antioxidant Properties ◽

Biological Properties ◽

High Reactivity ◽

Biologically Active ◽

Brain Lipids ◽

Wide Range ◽

Privileged Structure ◽

Vitro Model

The pyrazoline ring is defined as a “privileged structure” in medicinal chemistry. A variety of pharmacological properties of pyrazolines is associated with the nature and position of various substituents, which is especially evident in diarylpyrazolines. Compounds with a chalcone fragment show a wide range of biological properties as well as high reactivity which is primarily due to the presence of an α, β-unsaturated carbonyl system. At the same time, bicyclic monoterpenoids deserve special attention as a source of a key structural block or as one of the pharmacophore components of biologically active molecules. A series of new diarylpyrazoline derivatives based on isobornylchalcones with different substitutes (MeO, Hal, NO2, N(Me)2) was synthesized. Antioxidant properties of the obtained compounds were comparatively evaluated using in vitro model Fe2+/ascorbate-initiated lipid peroxidation in the substrate containing brain lipids of laboratory mice. It was demonstrated that the combination of the electron-donating group in the para-position of ring B and OH-group in the ring A in the structure of chalcone fragment provides significant antioxidant activity of synthesized diarylpyrazoline derivatives.

Download Full-text

Extraction of Antioxidant Compounds from Blueberry Fruit Waste and Evaluation of Their In Vitro Biological Activity in Human Keratinocytes (HaCaT)

Food Analytical Methods ◽

10.1007/s12161-021-02056-7 ◽

2021 ◽

Author(s):

Tomasz Piechowiak ◽

Bartosz Skóra ◽

Katarzyna Grzelak-Błaszczyk ◽

Michał Sójka

Keyword(s):

Antioxidant Activity ◽

Antioxidant Properties ◽

Waste Material ◽

Lower Amount ◽

Process Time ◽

Antioxidant Compounds ◽

Mass Unit ◽

Diet Supplements ◽

Study Results

AbstractThe purpose of this study was to investigate the biological properties of an extract obtained from the waste of blueberry fruit. The study covered the optimization of extraction of antioxidants from blueberry pomace and the determination of antioxidant properties of the extract using HaCaT as the model organism. Research showed that the yield of antioxidants extraction from blueberry waste was dependent on the applied extraction conditions. Based on the mathematical models, the optimal conditions of extraction process in which the maximum quantity of antioxidant compounds is achieved from the waste mass unit, i.e., the relation of the waste mass to the volume of ethanol equal to 1:17.36, and process time equal to 1000 s. The obtained extract was characterized by high antioxidant activity, which was shaped by high content of polyphenols, mainly anthocyanins. Moreover, the extract showed a high ability to protect HaCaT cells from the occurrence of oxidative stress induced by H2O2. Cells treated with the extract and H2O2 generated a lower amount of ROS than cells treated with H2O2 only. The obtained results will be base of further studies on applying the extract in production of diet supplements and functional foods with increased antioxidant activity. Moreover, the main research material is blueberry pomace which is a troublesome waste material for juice producers. Consequently, according to a sustainable development idea, the study results will provide an opportunity to increase interest in the problem of rational use of the waste material to a certain extent.

Download Full-text

Synthesis, Neuroprotection, and Antioxidant Activity of 1,1′-Biphenylnitrones as α-Phenyl-N-tert-butylnitrone Analogues in In Vitro Ischemia Models

Molecules ◽

10.3390/molecules26041127 ◽

2021 ◽

Vol 26 (4) ◽

pp. 1127 ◽

Cited By ~ 1

Author(s):

Beatriz Chamorro ◽

David García-Vieira ◽

Daniel Diez-Iriepa ◽

Estíbaliz Garagarza ◽

Mourad Chioua ◽

...

Keyword(s):

Antioxidant Activity ◽

Antioxidant Activities ◽

Antioxidant Properties ◽

Glucose Deprivation ◽

Oxygen Glucose Deprivation ◽

Human Neuroblastoma ◽

In Vitro Ischemia ◽

Lipoxygenase Inhibition ◽

Antioxidant Agent

Herein, we report the neuroprotective and antioxidant activity of 1,1′-biphenyl nitrones (BPNs) 1–5 as α-phenyl-N-tert-butylnitrone analogues prepared from commercially available [1,1′-biphenyl]-4-carbaldehyde and [1,1′-biphenyl]-4,4′-dicarbaldehyde. The neuroprotection of BPNs1-5 has been measured against oligomycin A/rotenone and in an oxygen–glucose deprivation in vitro ischemia model in human neuroblastoma SH-SY5Y cells. Our results indicate that BPNs 1–5 have better neuroprotective and antioxidant properties than α-phenyl-N-tert-butylnitrone (PBN), and they are quite similar to N-acetyl-L-cysteine (NAC), which is a well-known antioxidant agent. Among the nitrones studied, homo-bis-nitrone BPHBN5, bearing two N-tert-Bu radicals at the nitrone motif, has the best neuroprotective capacity (EC50 = 13.16 ± 1.65 and 25.5 ± 3.93 μM, against the reduction in metabolic activity induced by respiratory chain blockers and oxygen–glucose deprivation in an in vitro ischemia model, respectively) as well as anti-necrotic, anti-apoptotic, and antioxidant activities (EC50 = 11.2 ± 3.94 μM), which were measured by its capacity to reduce superoxide production in human neuroblastoma SH-SY5Y cell cultures, followed by mononitrone BPMN3, with one N-Bn radical, and BPMN2, with only one N-tert-Bu substituent. The antioxidant activity of BPNs1-5 has also been analyzed for their capacity to scavenge hydroxyl free radicals (82% at 100 μM), lipoxygenase inhibition, and the inhibition of lipid peroxidation (68% at 100 μM). Results showed that although the number of nitrone groups improves the neuroprotection profile of these BPNs, the final effect is also dependent on the substitutent that is being incorporated. Thus, BPNs bearing N-tert-Bu and N-Bn groups show better neuroprotective and antioxidant properties than those substituted with Me. All these results led us to propose homo-bis-nitrone BPHBN5 as the most balanced and interesting nitrone based on its neuroprotective capacity in different neuronal models of oxidative stress and in vitro ischemia as well as its antioxidant activity.

Download Full-text

In vitro and molecular docking analysis of chalconeimine derivatives with α-glucosidase

Bioinformation ◽

10.6026/97320630016949 ◽

2020 ◽

Vol 16 (11) ◽

pp. 949-957

Author(s):

R Asaithambi ◽

Keyword(s):

Antioxidant Activity ◽

Molecular Docking ◽

Docking Analysis ◽

Molecular Docking Analysis

It is known that α-glucosidase is linked with the antioxidant activity. Therefore, it is of interest to document the in- vitro and molecular docking analysis of chalconeimine derivatives with α-glucosidase (PDB ID: 2ZEO) for further consideration.

Download Full-text

Determination of in vitro antioxidant activity of the leaves extracts of Ehretia pubescens

International Journal of Research in Pharmaceutical Sciences ◽

10.26452/ijrps.v11i4.3308 ◽

2020 ◽

Vol 11 (4) ◽

pp. 6262-6267

Author(s):

Krishnamoorthy Meenakumari ◽

Giridharan Bupesh ◽

Mayur Mausoom Phukan

Keyword(s):

Antioxidant Activity ◽

Ethyl Acetate ◽

Radical Scavenging Activity ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Reducing Power ◽

Biological Properties ◽

Scavenging Activity ◽

Reducing Power Assay

The foods from plants were known to ensure against degenerative diseases and maturing because of their antioxidant activitycredited to their high content. Information on antioxidant activity of Indian medicinal plant is abundant. To the best of our knowledge, biological properties have not been accounted in the literature for this species of . As a point, this is the first results to assess the anti-oxidant activity of the plant which belongs to the family . The antioxidant activity of Methanol, , Ethyl acetate and Aqueous extracts of E. was determined using the DPPH free radical scavenging activity, ABTS radical scavenging activity and reducing power assay. The DPPH scavenging activity showed higher activity observed in extract (63%) of E. than (54%), (44%) and aqueous (30%). the ABTS assay inhibition in extract (58%) than (43%), (38%) and aqueous (32%) extracts. The reducing power assay of different extracts was increased in extract (54%) than (40%), (34%) and aqueous (28%) extracts. Overall, the and ethyl acetate extract had higher antioxidant properties than other extract. However, in this study, extracts exhibit great potential for antioxidant activity and may be useful for their nutritional and medicinal functions.

Download Full-text

Phytochemical Characterization, In Vitro Antioxidant Activity, and Quantitative Analysis by Micellar Electrokinetic Chromatography of Hawthorn (Crataegus pubescens) Fruit

Journal of Food Quality ◽

10.1155/2018/2154893 ◽

2018 ◽

Vol 2018 ◽

pp. 1-11 ◽

Cited By ~ 5

Author(s):

Francisco Erik González-Jiménez ◽

Juan Alfredo Salazar-Montoya ◽

Graciano Calva-Calva ◽

Emma Gloria Ramos-Ramírez

Keyword(s):

Antioxidant Activity ◽

Phenolic Compounds ◽

Micellar Electrokinetic Chromatography ◽

Antioxidant Properties ◽

Total Phenolic ◽

Electrokinetic Chromatography ◽

Polyphenol Profile ◽

Gallic Acid Equivalent ◽

Dry Fruit

Due to their antioxidant properties, polyphenolic compounds are considered beneficial for human health. In this work, we investigated the polyphenol profile and antioxidant activity of edible tejocote (Crataegus pubescens) fruit extracts by micellar electrokinetic chromatography (MEKC) and HPLC/UV. The major phenolic compounds in the pulp extracts were (+)-catechin (9.17 ± 0.20 mg/100 mg dry fruit), (−)-epicatechin (4.32 ± 0.11 mg/100 mg dry fruit), and chlorogenic acid (5.60 ± 0.24 mg/100 mg dry fruit). The total phenolic content was 168.6 ± 0.9 mg gallic acid equivalent/g dry fruit; the total proanthocyanidin content was 84.6 ± 1.4 mg cyanidin/100 g dry fruit; and the total flavonoid content was 55.89 ± 1.43 mg quercetin/g dry fruit. Interestingly, procyanidins (dimers, trimers, and tetramers of (−)-epicatechin and (+)-catechin) were detected in the extract. This is the first study reporting the presence of polymeric polyphenols in Crataegus pubescens fruit. Accordingly, these fruits demonstrate great potential as a natural source of antioxidant phenolic compounds and could therefore be used as a nutraceutical and functional food.

Download Full-text

Discovery of potential inhibitors of the receptor-binding domain (RBD) of pandemic disease-causing SARS-CoV-2 Spike Glycoprotein from Triphala through molecular docking

Current Chinese Chemistry ◽

10.2174/2666001601666210322121802 ◽

2021 ◽

Vol 01 ◽

Author(s):

Sharuk L. Khan ◽

Falak A. Siddiqui ◽

Mohd Sayeed Shaikh ◽

Nitin V. Nema ◽

Aijaz A. Shaikh

Keyword(s):

Molecular Docking ◽

Hydrogen Bonds ◽

Receptor Binding ◽

Chemical Constituents ◽

Antioxidant Properties ◽

Binding Domain ◽

Quality Data ◽

Receptor Binding Domain ◽

Spike Glycoprotein

Background: COVID-19 (SARS-CoV-2 infection) has affected almost every region of the world. Presently, there is no defined line of treatment available for it. Triphala is already proven to have a safe biological window and well known for its antioxidant and immunomodulatory properties. Objective: Present work has been carried out to study Triphala's effectiveness for the treatment of COVID-19. Methods: The Receptor-binding domain (RBD) of SARS-CoV-2 Spike Glycoprotein responsible for the invasion into the host cell, which leads to further infection. The molecular docking (MD) was performed to explore the binding affinities (kcal/mol) of Triphala's chemical constituents and compared them with the existing drugs under investigation for the treatment of COVID-19 epidemiology. Results: Chebulinic acid binding affinity -8.5 kcal/mol with the formation of 10 hydrogen bonds. Almost all the major chemical constituents have formed two or more hydrogen bonds with RBD of SARS-CoV-2 Spike Glycoprotein. Conclusion: The present study showed that Triphala might perform vital roles in the treatment of COVID-19 and expand its usefulness to physicians to treat this illness. There is a need to complete the in-vitro, in-vivo biological testing of Triphala on SARS-CoV-2 disease to create more quality data. The binding mode of Chebulinic acid in the allosteric cavity allows a better understanding of RBD of SARS-CoV-2 Spike Glycoprotein target and provides insight for the design of new inhibitors. Triphala is already proven to have a safe biological window, which indicates we can skip the pre-clinical trials. Apart from this, Triphala is well known for its antioxidant properties, which ultimately improves the immunity of the COVID-19 patient.

Download Full-text