scholarly journals Synthesis, In Vitro, and In Silico Analysis of the Antioxidative Activity of Dapsone Imine Derivatives

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5747
Author(s):  
Ricardo Guzmán-Ávila ◽  
Mayra Avelar ◽  
Edgar A. Márquez ◽  
Julio C. Rivera-Leyva ◽  
José R. Mora ◽  
...  

Dapsone (DDS) is an antibacterial drug with well-known antioxidant properties. However, the antioxidant behavior of its derivatives has not been well explored. In the present work, the antioxidant activity of 10 dapsone derivatives 4-substituted was determined by an evaluation in two in vitro models (DPPH radical scavenging assay and ferric reducing antioxidant power). These imine derivatives 1–10 were obtained through condensation between DDS and the corresponding aromatic aldehydes 4-substuited. Three derivatives presented better results than DDS in the determination of DPPH (2, 9, and 10). Likewise, we have three compounds with better reducing activity than dapsone (4, 9, and 10). In order to be more insight, the redox process, a conceptual DFT analysis was carried out. Molecular descriptors such as electronic distribution, the total charge accepting/donating capacity (I/A), and the partial charge accepting/donating capacity (ω+/ω−) were calculated to analyze the relative donor-acceptor capacity through employing a donor acceptor map (DAM). The DFT calculation allowed us to establish a relationship between GAPHOMO-LUMO and DAM with the observed antioxidant effects. According to the results, we concluded that compounds 2 and 3 have the lowest Ra values, representing a good antioxidant behavior observed experimentally in DPPH radical capturing. On the other hand, derivatives 4, 9, and 10 display the best reducing capacity activity with the highest ω− and Rd values. Consequently, we propose these compounds as the best antireductants in our DDS imine derivative series.

2021 ◽  
Vol 10 (4) ◽  
pp. 408-414
Author(s):  
Oluwaseun Ruth Olasehinde ◽  
Olakunle Bamikole Afolabi ◽  
Benjamin Olusola Omiyale ◽  
Oyindamola Adeniyi Olaoye

Introduction: Diabetes mellitus (DM) has been recognized as the seventh leading cause of global mortality; however, researchers seek alternative means to manage the menace. The current study sought to investigate antioxidant potentials, α-amylase, and α-glucosidase inhibitory activities of ethanolic extract of Moringa oleifera flower in vitro. Methods: Antioxidant properties of the extract were appraised by assessing its inhibition against 1,1-diphenyl-2-picrylhydrazyl (DPPH), hydroxyl (OH•), and hydrogen peroxide (H2O2) free radicals, as well as ferric reducing antioxidant power (FRAP), the antidiabetic activity was evaluated by α-amylase and α-glucosidase inhibition.Results: In this study, ethanolic extract of M. oleifera flower demonstrated a significant (P < 0.05) inhibition against DPPH free radical (43.57–83.56%) in a concentration-dependent manner, while FRAP (101.76 ± 1.63 mg/100 g), OH• scavenging ability (71.62 ± 0.95 mg/100 g), and H2O2 free radical scavenging capacity (15.33 ± 1.20 mg/100 g) were also observed. In the same manner, ethanolic extract of M. oleifera flower revealed a significant (P < 0.05) inhibition against α-amylase (IC50= 37.63 mg/mL) and α-glucosidase activities (IC50= 38.30 mg/mL) in the presence of their respective substrates in a concentration-dependent manner in comparison with acarbose. Conclusion: Ethanoic extract of M. oleifera flower could be useful as an alternative phytotherapy in the management of DM, having shown a strong antioxidative capacity and substantial inhibition against the activities of key enzymes involved in carbohydrate hydrolysis in vitro.


Antioxidants ◽  
2019 ◽  
Vol 8 (12) ◽  
pp. 592 ◽  
Author(s):  
Chengli Hou ◽  
Liguo Wu ◽  
Zhenyu Wang ◽  
Elena Saguer ◽  
Dequan Zhang

In this study, sheep plasma was submitted to Alcalase-hydrolysis and peptides with better antioxidant properties measured through both the ferric-reducing antioxidant power (FRAP) and the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging ability assays were isolated and identified. After hydrolysate ultrafiltration and semi-preparative reverse-phase high-performance liquid chromatography, nine fractions (F1–F9) were obtained, with the two first (F1 and F2) showing the greatest antioxidant potential. These two fractions were further separated by the AKTA purifier system to generate four (F1-1–F1-4) and five (F2-1–F2-5) fractions, respectively, with two of them (F1-2 and F2-1) exhibiting appreciable FRAP activity and DPPH radical scavenging ability. Using liquid chromatography-tandem mass spectrometry, three antioxidant peptides were identified. From their amino acid sequences (QTALVELLK, SLHTLFGDELCK, and MPCTEDYLSLILNR), which include amino acids that have been previously reported as key contributors to the peptide antioxidant properties, it can be maintained that they come mainly from serum albumin. These results suggested that the sheep plasma protein can be considered as a good source of antioxidant peptides and bring forth new possibilities for the utilization of animal blood by-products.


2018 ◽  
Vol 2018 ◽  
pp. 1-6 ◽  
Author(s):  
Gauhar Rehman ◽  
Muhammad Hamayun ◽  
Amjad Iqbal ◽  
Saif Ul Islam ◽  
Saba Arshad ◽  
...  

The antidiabetic and antioxidant potential of ethanolic extract ofCassia nemophilapod (EECNP) was evaluated by three in vitro assays, including yeast glucose uptake assay, glucose adsorption assay, and DPPH radical scavenging activity. The result revealed that the extracts have enhanced the uptake of glucose through the plasma membrane of yeast cells. A linear increase in glucose uptake by yeast cells was noticed with gradual increase in the concentration of the test samples. Moreover, the adsorption capacity of the EECNP was directly proportional to the molar concentration of glucose. Also, the DPPH radical scavenging capacity of the extract was increased to a maximum value of 43.3% at 80 μg/ml, which was then decreased to 41.9% at 100 μg/ml. From the results, it was concluded that EECNP possess good antidiabetic and antioxidant properties as shown by in vitro assays.


2012 ◽  
Vol 48 (1) ◽  
pp. 31-37 ◽  
Author(s):  
Ariana Costa-Mugica ◽  
Ana Elsa Batista- Gonzalez ◽  
Diadelis Mondejar ◽  
Yosdel Soto-López ◽  
Victor Brito-Navarro ◽  
...  

LDL oxidation and oxidative stress are closely related to atherosclerosis. Therefore, natural antioxidants have been studied as promising candidates. In the present study, the LDL oxidation inhibition activity of bioactive compounds from Halimeda incrassata seaweed. associated to antioxidant capacity, was evaluated in vitro. Experimental work was conducted with lyophilized aqueous extract and phenolic-rich fractions of the seaweed and their effect on LDL oxidation was evaluated using heparin-precipitated LDL (hep-LDL) with exposure to Cu2+ ions and AAPH as the free radical generator. H. incrassata had a protective effect for hep-LDL in both systems and the presence of phenolic compounds contributed to the activity where phenolic-rich fractions showed significant capacity for inhibition of oxidation mediated by Cu2+ ions. The observed effect could be related to the antioxidant potential of polar fractions evidenced by reducing activity and DPPH• radical scavenging. The results obtained in vitro further support the antioxidant and LDL oxidation inhibition properties of H. incrassata and further knowledge toward future phytotherapeutic application of the seaweed.


2020 ◽  
Vol 13 (9) ◽  
pp. 240 ◽  
Author(s):  
Cezary Pawlukianiec ◽  
Małgorzata Ewa Gryciuk ◽  
Kacper Maksymilian Mil ◽  
Małgorzata Żendzian-Piotrowska ◽  
Anna Zalewska ◽  
...  

Meloxicam is a non-steroidal anti-inflammatory drug, which has a preferential inhibitory effect to cyclooxyganase-2 (COX-2). Although the drug inhibits prostaglandin synthesis, the exact mechanism of meloxicam is still unknown. This is the first study to assess the effect of meloxicam on protein glyco-oxidation as well as antioxidant activity. For this purpose, we used an in vitro model of oxidized bovine serum albumin (BSA). Glucose, fructose, ribose, glyoxal and methylglyoxal were used as glycating agents, while chloramine T was used as an oxidant. We evaluated the antioxidant properties of albumin (2,2-di-phenyl-1-picrylhydrazyl radical scavenging capacity, total antioxidant capacity and ferric reducing antioxidant power), the intensity of protein glycation (Amadori products, advanced glycation end products) and glyco-oxidation (dityrosine, kynurenine, N-formylkynurenine, tryptophan and amyloid-β) as well as the content of protein oxidation products (advanced oxidation protein products, carbonyl groups and thiol groups). We have demonstrated that meloxicam enhances the antioxidant properties of albumin and prevents the protein oxidation and glycation under the influence of various factors such as sugars, aldehydes and oxidants. Importantly, the antioxidant and anti-glycating activity is similar to that of routinely used antioxidants such as captopril, Trolox, reduced glutathione and lipoic acid as well as protein glycation inhibitors (aminoguanidine). Pleiotropic action of meloxicam may increase the effectiveness of anti-inflammatory treatment in diseases with oxidative stress etiology.


2020 ◽  
Vol 2020 ◽  
pp. 1-10
Author(s):  
Beatrice Muthoni Guchu ◽  
Alex King’ori Machocho ◽  
Stephen Kiruthi Mwihia ◽  
Mathew Piero Ngugi

Oxidative stress is the result of the disparity between pro-oxidants and antioxidants in an organism, and it is important in the pathogenesis of several degenerative disorders, such as arthritis, Alzheimer’s, cancer, and cardiovascular diseases. Free radicals can damage biomolecules, such as nucleic acids, lipids, proteins, polyunsaturated fatty acids, and carbohydrates, and the DNA leading to mutations. The use of antioxidants is effective in delaying the oxidation of biomolecules. Antioxidants are complexes found in the food that can retard or deter oxidation by preventing the initiation and propagation of oxidizing chain reactions. Medicinal plants have been used for centuries by man to manage diseases and have a host of antioxidant complexes. Traditionally, Caesalpinia volkensii, Vernonia lasiopus, and Acacia hockii have folkloric remedies against associated oxidative stress-mediated complications. However, the upsurge in its use has not been accompanied by scientific validations to support these claims. In this study, in vitro antioxidant activity of Caesalpinia volkensii, Vernonia lasiopus, and Acacia hockii collected from Embu County (Kenya) were determined by radical scavenging activities of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl radical in addition to ferric reducing antioxidant power analyzed against that of L-ascorbic acid as the standard. The obtained results revealed remarkable antioxidant activities of the studied plant extracts as evidenced by the low IC50 and EC50 values. These antioxidant activities could be due to the presence of antioxidants phytochemicals such as flavonoids, phenols, terpenoids, and saponins among others. Therefore, the therapeutic potential of this plant could be due to their antioxidant properties. This study recommends bioassay of the extracts against oxidative stress-related disorders for development of phytomedicine with antioxidant properties.


2017 ◽  
Vol 2017 ◽  
pp. 1-14 ◽  
Author(s):  
Murni Nazira Sarian ◽  
Qamar Uddin Ahmed ◽  
Siti Zaiton Mat So’ad ◽  
Alhassan Muhammad Alhassan ◽  
Suganya Murugesu ◽  
...  

The best described pharmacological property of flavonoids is their capacity to act as potent antioxidant that has been reported to play an important role in the alleviation of diabetes mellitus. Flavonoids biochemical properties are structure dependent; however, they are yet to be thoroughly understood. Hence, the main aim of this work was to investigate the antioxidant and antidiabetic properties of some structurally related flavonoids to identify key positions responsible, their correlation, and the effect of methylation and acetylation on the same properties. Antioxidant potential was evaluated through dot blot, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, ABTS+radical scavenging, ferric reducing antioxidant power (FRAP), and xanthine oxidase inhibitory (XOI) assays. Antidiabetic effect was investigated throughα-glucosidase and dipeptidyl peptidase-4 (DPP-4) assays. Results showed that the total number and the configuration of hydroxyl groups played an important role in regulating antioxidant and antidiabetic properties in scavenging DPPH radical, ABTS+radical, and FRAP assays and improved bothα-glucosidase and DPP-4 activities. Presence of C-2-C-3 double bond and C-4 ketonic group are two essential structural features in the bioactivity of flavonoids especially for antidiabetic property. Methylation and acetylation of hydroxyl groups were found to diminish thein vitroantioxidant and antidiabetic properties of the flavonoids.


2016 ◽  
Vol 2 (2) ◽  
pp. 77 ◽  
Author(s):  
Tomisin Happy Ogunwa ◽  
Tolulope Tosin Adeyelu ◽  
Rotimi Yemi Fasimoye ◽  
Mary Bose Oyewale ◽  
Taiwo Ademola Ademoye ◽  
...  

ABSTRACTClerodenrum volubile is an important locally used medicinal plant. It is one of the essential herbs nature has provided for mankind to be consumed as spices, vegetable and also used in the treatment of diseases. Qualitative phytoconstituent screening of the plant revealed the presence of steroids, flavonoids, tannins, saponins, and phenolic compound while chalcones, alkaloid and anthraquinone were absent. Quantitative phytochemical evaluation showed values of 8.29±1.26mg/g rutin equivalent for flavonoids, 3.53±0.05mg/g gallic acid equivalent for phenol, 3.97±0.03mg/g tannic acid equivalent for tannins and 13.67±1.27% for saponin per dry weight. As it is imperative to extend research work on therapeutic effects of the arsenal of plants nature has given to us in Africa so as to obtain a cure for various diseases attacking human’s health, antioxidant properties of the plant was evaluated. Antioxidant models used include iron chelating, DPPH radical, superoxide ion, hydrogen peroxide, ABTS radical, hydroxyl radical scavenging activities and ferric ion reducing properties. The obtained IC50 values against DPPH radical were 141.342 and 120.349µg/mL for Clerodendrum volubile and trolox respectively. The chelating effect of the plant extract at 50% inhibition was close to that of ascorbic acid (standard) with 134.34 and 131.19µg/mL concentration respectively. Overall, the aqueous extract of the plant showed antioxidant potential which was close to the effects exerted by known standard antioxidants (ascorbic acid, trolox and EDTA). The plant could hence provide natural antioxidants which are needed to combat numerous free radical-mediated diseases and complications such as aging, cancer, atherosclerosis, which are linked with oxidative stress. 


2019 ◽  
Vol 15 (7) ◽  
pp. 700-706
Author(s):  
Mehdi Zarei ◽  
Ali Fazlara ◽  
Maedeh S. Hamedani

Background: All over the world, the quality of commercial honeys varies greatly depending on many factors. Hence, this study was conducted to evaluate the physicochemical and antioxidant properties of Iranian commercial honeys to confirm their nutritional and economical quality. Methods: Fifty three honey samples from six different types, including alfalfa, milkvetch, lotus, thyme, coriander and multifloral honeys, were analyzed for pH, free acidity, electrical conductivity, Ash, moisture, hydroxymethylfurfural, reducing sugars, glucose, fructose, proline, color, total phenolic content, ferric reducing antioxidant power and DPPH radical-scavenging activity. Results: : In total, physicochemical properties of different honey types were in the range of 4.3 ± 0.49 to 5.2 ± 0.49 for pH, 13.81 ± 2.5 to 26.22 ± 2.8 for free acidity (meq/kg), 15.95 ± 0.45 to 17.98 ± 0.97 for moisture (%), 282.2 ± 50.3 to 578 ± 47 for electrical conductivity (µS/cm), 0.14 ± 0.04 to 0.38 ± 0.03 for ash (g/100 g), 68.66 ± 4.3 to 72.09 ± 6.4 for reducing sugars (g/100 g), 34.67 ± 2.6 to 36.7 ± 2.2 for glucose (g/100 g), 31.9 ± 4.75 to 37.04 ± 4.0 for fructose (g/100 g), 6.1 ± 5.8 to 22.85 ± 10.9 for hydroxymethylfurfural (mg/kg), 426.7 ± 53.91 to 593.9 ± 108.6 for proline (mg/kg), 46.27 ± 4.3 to 96.04 ± 14.4 for color (mm) and 245.4 ± 48.45 to 573.9 ± 69.3 for total phenolic (mg/kg) content. In terms of antioxidant capacity, lotus and thyme honeys were preferable, while the highest level of DPPH radical scavenging activity and ferric reducing antioxidant power were observed in lotus and thyme honeys. Conclusion: These results confirmed that the Iranian commercial honeys meet the quality standards established by national and international regulatory agencies.


Antioxidants ◽  
2021 ◽  
Vol 10 (9) ◽  
pp. 1434
Author(s):  
Shingo Kasamatsu ◽  
Somei Komae ◽  
Kana Matsukura ◽  
Yuki Kakihana ◽  
Koji Uchida ◽  
...  

There is substantial evidence for the antioxidant functions of imidazole-containing dipeptides (IDPs), including carnosine and anserine, under physiological and pathological conditions in vivo. However, the detailed mechanism underlying the antioxidant functions is still poorly understood. Recently, we discovered the endogenous production of 2-oxo-imidazole-containing dipeptides (2-oxo-IDPs), such as 2-oxo-carnosine and 2-oxo-anserine, as novel derivatives of IDPs in mouse tissues and revealed that the antioxidant capacity of 2-oxo-carnosine was much greater than that of carnosine. However, the antioxidant capacity of 2-oxo-IDPs still remains unclear. In this study, we evaluated 2-oxo-carnosine and 2-oxo-anserine by multiple in vitro assays, such as 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, ferric reducing/antioxidant power, and oxygen radical absorbance capacity assays in comparison with the corresponding IDPs, carnosine and anserine. All the assays employed herein demonstrated that 2-oxo-carnosine and 2-oxo-anserine exhibited a greater antioxidant capacity than that of the corresponding IDPs. Quantitative high-performance liquid chromatography tandem mass spectrometry revealed that commercial IDPs standards were contaminated with a certain amount of 2-oxo-IDPs, which was correlated with the antioxidant capacity. DPPH radical scavenging assay revealed that the elimination of contaminated 2-oxo-IDPs from the IDPs standards caused a significant decrease in the antioxidant capacity compared to the original IDPs standards. These results suggest that the main driver of the antioxidant capacity of IDPs is 2-oxo-IDPs; accordingly, the conversion of IDPs to 2-oxo-IDPs may be a critical step in the antioxidant functions.


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