scholarly journals Enhanced Antioxidant Activity of Ursolic Acid by Complexation with Copper (II): Experimental and Theoretical Study

Materials ◽  
2021 ◽  
Vol 14 (2) ◽  
pp. 264
Author(s):  
Mariola Samsonowicz ◽  
Monika Kalinowska ◽  
Kamila Gryko

The copper (II) complex of ursolic acid (Cu(II) UA) was synthesized and discussed in terms of its infrared, UV–visible spectra, quantum-chemical calculations at B3LYP/6-31G(d) level and antioxidant capacity. The copper (II) complex was stable in methanolic solution with the molar ratio metal:ligand 1:1. The data obtained by FT-IR confirmed the metal ion coordination through the carboxylate anion. The antioxidant properties of ursolic acid and its complex with Cu were discussed on the basis of energy of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and values of chemical reactivity parameters. The antiradical properties of ursolic acid and the Cu (II) complex were examined against DPPH• and HO• radicals, and the ferric reducing antioxidant power (FRAP) was examined. The Cu(II) complex showed higher antioxidant activity than ursolic acid, i.e., in DPPH• assay, the EC50 for UA was 47.0 mM, whereas, for Cu(II), UA EC50 = 19.5 mM; the FRAP value for UA was 20.8 µMFe2+, and 35.4 µMFe2+ for Cu(II) UA (compound concentration 3 mM). Although there was no distinct difference in the antioxidant activity against HO• between these two chemicals, they were both better HO• scavengers than DPPH• and showed different kinetics in the reaction with DPPH•.

2018 ◽  
Author(s):  
Chanikan Sonklin ◽  
Natta Laohakunjit ◽  
Orapin Kerdchoechuen

Background Bioactive peptides can prevent damage associated with oxidative stress in the human body when consumed regularly. Recently year, peptides have attracted immense interest because of their beneficial functional properties, safety and little or no side effects when used at high concentration. Most antioxidant peptide has small size less than 1 kDa and contains high proportion of hydrophobic amino acid. Particularly Tyr, Leu, Ala, Ile, Val, Lys, Phe, Cys, Met and His exhibited high antioxidant activity. Mungbean protein contain high abundance of protein and hydrophobic amino acid contents, investigating its bioactivity is an important aspect of adding value to this by-product obtained from a growing industry. Therefore, the objectives of this study were to optimize the conditions used to generate MMPH with antioxidant activity form bromelain and to investigate the antioxidant activities of each molecular weight peptide fraction. Methods Response Surface Methodology (RSM) was used for screening the optimal conditions to produce Mungbean meal protein hydrolysate (MMPH). After that optimal MMPH was fractionated using ultrafiltration membranes with different molecular weight (MW) distribution. Crude-MMPH and four peptide fractions were investigated for five antioxidant activities: DPPH scavenging activity, Hydroxyl scavenging activity, Superoxide scavenging activity, Ferric reducing antioxidant power and metal ion chelation activity. Results The optimal condition of crude-MMPH production was 12 % (w/w) of bromelain and hydrolysis time for 12 h. The EC50 of DPPH was the highest for the F4 peptide fraction (MW<1 kDa) at 0.5320 mg/mL. Metal ion chelating activity was generally weak, except for the F4 that had a value of 43.94% at a protein concentration of 5 mg/mL. The F4 also exhibited high hydroxyl and superoxide radical scavenging activities (54 and 65.1%), but poor activity for ferric reducing antioxidant power (0.102 mM Fe2+/mg protein) compared to other peptide fractions and crude-MMPH. Molecular weight and amino acid were the main factors that determined the antioxidant activities of these peptide fractions. Results show that F4 have high antioxidant potentials. Discussion The lowest MW Fraction (less than 1 kDa) showed the highest DPPH activity, superoxide-, hydroxyl-scavenging activity and metal chelation activity. On the other hand, this fraction had poor ferric reducing power. This showed that low molecular weight has an important effect on antioxidant activities. According to the mechanism of the reaction, the potential of antioxidant activity was divided into two main groups: hydrogen atom transfer (HAT) and single electron transfer (SET). Therefore, this finding suggests that the antioxidant mechanism of peptides obtained mungbean could react with many species of free radicals by multiple mechanisms. Mungbean meal peptide can be developed into multiple functional foods which possess both antioxidant properties and aroma/taste.


2016 ◽  
Vol 70 (6) ◽  
Author(s):  
Mariola Samsonowicz ◽  
Ewa Regulska

AbstractThe analysis of the antioxidant activity of ethanol, methanol, acetone and aqueous extracts from the dried leaves and stems of savory is presented. The culinary herb used to study was procured from ecological agriculture in the Podlasie region of Poland. The antioxidant properties of extracts were calculated using the 1,1-diphenyl-2-picryl-hydrazyl radical (DPPH) and ferric-reducing antioxidant power (FRAP) (expressed as mg Trolox per g of dry mass) methods. In addition, the total phenolics contents of the herbal extracts were determined using the Folin–Ciocalteu reagent. The antioxidative activity of extracts as dependent on the type of solvent used for the extraction and concentration of savory in extracts is discussed. The influence of the concentration of different metal ion solutions on the anti-radicals’ properties of savory extracts was evaluated.


2018 ◽  
Author(s):  
Chanikan Sonklin ◽  
Natta Laohakunjit ◽  
Orapin Kerdchoechuen

Background Bioactive peptides can prevent damage associated with oxidative stress in the human body when consumed regularly. Recently year, peptides have attracted immense interest because of their beneficial functional properties, safety and little or no side effects when used at high concentration. Most antioxidant peptide has small size less than 1 kDa and contains high proportion of hydrophobic amino acid. Particularly Tyr, Leu, Ala, Ile, Val, Lys, Phe, Cys, Met and His exhibited high antioxidant activity. Mungbean protein contain high abundance of protein and hydrophobic amino acid contents, investigating its bioactivity is an important aspect of adding value to this by-product obtained from a growing industry. Therefore, the objectives of this study were to optimize the conditions used to generate MMPH with antioxidant activity form bromelain and to investigate the antioxidant activities of each molecular weight peptide fraction. Methods Response Surface Methodology (RSM) was used for screening the optimal conditions to produce Mungbean meal protein hydrolysate (MMPH). After that optimal MMPH was fractionated using ultrafiltration membranes with different molecular weight (MW) distribution. Crude-MMPH and four peptide fractions were investigated for five antioxidant activities: DPPH scavenging activity, Hydroxyl scavenging activity, Superoxide scavenging activity, Ferric reducing antioxidant power and metal ion chelation activity. Results The optimal condition of crude-MMPH production was 12 % (w/w) of bromelain and hydrolysis time for 12 h. The EC50 of DPPH was the highest for the F4 peptide fraction (MW<1 kDa) at 0.5320 mg/mL. Metal ion chelating activity was generally weak, except for the F4 that had a value of 43.94% at a protein concentration of 5 mg/mL. The F4 also exhibited high hydroxyl and superoxide radical scavenging activities (54 and 65.1%), but poor activity for ferric reducing antioxidant power (0.102 mM Fe2+/mg protein) compared to other peptide fractions and crude-MMPH. Molecular weight and amino acid were the main factors that determined the antioxidant activities of these peptide fractions. Results show that F4 have high antioxidant potentials. Discussion The lowest MW Fraction (less than 1 kDa) showed the highest DPPH activity, superoxide-, hydroxyl-scavenging activity and metal chelation activity. On the other hand, this fraction had poor ferric reducing power. This showed that low molecular weight has an important effect on antioxidant activities. According to the mechanism of the reaction, the potential of antioxidant activity was divided into two main groups: hydrogen atom transfer (HAT) and single electron transfer (SET). Therefore, this finding suggests that the antioxidant mechanism of peptides obtained mungbean could react with many species of free radicals by multiple mechanisms. Mungbean meal peptide can be developed into multiple functional foods which possess both antioxidant properties and aroma/taste.


2020 ◽  
Vol 6 (1) ◽  
Author(s):  
Chandravadivelu Gopi ◽  
Magharla Dasaratha Dhanaraju

Abstract Background The main aim of this work was to synthesise a novel N-(substituted phenyl)-2-(3-(hydroxyimino) methyl)-1H-indol-1-yl) acetamide derivatives and evaluate their antioxidant activity. These compounds were prepared by a condensation reaction between 1H-indole carbaldehyde oxime and 2-chloro acetamide derivatives. The newly synthesised compound structures were characterised by FT-IR, 1H-NMR, mass spectroscopy and elemental analysis. Furthermore, the above-mentioned compounds were screened for antioxidant activity by using ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) methods. Result The antioxidant activity result reveals that most of the compounds were exhibiting considerable activity in both methods and the values are very closer to the standards. Among the synthesised compounds, compound 3j, 3a and 3k were shown remarkable activity at low concentration. Conclusion Compounds 3j, 3a and 3k were shown highest activity among the prepared analogues due to the attachment of halogens connected at the appropriate place in the phenyl ring. Hence, these substituted phenyl rings considered as a perfect side chain for the indole nucleus for the development of the new antioxidant agents.


Processes ◽  
2021 ◽  
Vol 9 (8) ◽  
pp. 1262
Author(s):  
Shonisani Eugenia Ramashia ◽  
Felicia Matshepho Mamadisa ◽  
Mpho Edward Mashau

This study investigated the impact of Parinari curatellifolia peel flour on the nutritional, physical and antioxidant properties of formulated biscuits. Biscuits enriched with 5%, 10%, 15% and 20% of Parinari (P). curatellifolia peel flour were formulated and characterised. Thermal, physicochemical, polyphenolic compounds and antioxidant properties of flour and biscuits were determined. The incorporation of P. curatellifolia peel flour significantly increased (p < 0.05) thermal properties (onset, peak and conclusion temperatures) of flour. However, enthalpy of gelatinisation, viscosity and pH of flour samples decreased. Nutritional analysis revealed an increase in ash (0.74% to 2.23%) and crude fibre contents (0.39% to 2.95%) along with an increase of P. curatellifolia peel flour levels. Protein content and carbohydrates decreased while moisture content was insignificantly affected by the addition of P. curatellifolia peel flour. The L*, b* values and whiteness index of formulated biscuits decreased while parameter a* value (10.76 to 21.89) and yellowness index (69.84 to 102.71) decreased. Physical properties such as diameter (3.57 mm to 3.97 mm), spread ratio (2.67 to 3.45) and hardness (1188.13 g to 2432.60 g) increased with the inclusion levels of peel flour while weight and thickness decreased. The inclusion of P. curatellifolia improved the polyphenolic compounds and antioxidant activity of biscuits with values of total flavonoids content ranging from 0.028 to 0.104 mg CE/g, total phenolic content increasing from 20.01 mg to 48.51 mg GAE/g, ferric reducing antioxidant power (FRAP) increasing from 108.33 mg to 162.67 mg GAE/g and DPPH (2,2-diphenyl-1-picrylhydrazyl) from 48.70% to 94.72%. These results lead to the recommendation of the utilisation of P. curatellifolia peel flour to enhance the nutritional value, polyphenolic compounds and antioxidant activity of bakery products such as biscuits.


Molecules ◽  
2020 ◽  
Vol 25 (16) ◽  
pp. 3648
Author(s):  
Lucia Godočiková ◽  
Eva Ivanišová ◽  
Grzegorz Zaguła ◽  
Luis Noguera-Artiaga ◽  
Ángel A. Carbonell-Barrachina ◽  
...  

The biological activity of chocolates gains more and more attention of consumers. Its antioxidant properties depend, among other factors, mainly on the origin of cocoa and the characteristics that this origin gives to the final product. Therefore, the aim of the study was to measure and compare the total content of polyphenols, antioxidant activity, and key odorants of commercial chocolates made from blend cocoa with single-origin ones. The highest content of polyphenols was found in 90% blend cocoa chocolate and single-origin samples, while the lowest content was exhibited by 100% chocolate from blend cocoa mass. The highest antioxidant activity measured by 2,2′-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) and ferric reducing antioxidant power (FRAP) assays was observed in the sample of chocolate with 90% cocoa solids from blend mass, followed by single-origin chocolates. A high positive correlation between ABTS assay and the total polyphenol and phenolic acids’ content, as well as among the total content of polyphenols, flavonoids, and phenolic acids was found. Mineral composition analysis showed that dark chocolate is a valuable source of some elements, especially Mg, Fe, and Zn. Potentially toxic elements were not detected or below permitted limits. Moreover, it was noticed that the main volatile compound in all tested samples was acetic acid, but pyrazines were considered the most important group of chocolate odorants.


Materials ◽  
2020 ◽  
Vol 13 (17) ◽  
pp. 3745
Author(s):  
Monika Kalinowska ◽  
Justyna Sienkiewicz-Gromiuk ◽  
Grzegorz Świderski ◽  
Anna Pietryczuk ◽  
Adam Cudowski ◽  
...  

The structure of the Zn(II) complex of 5-caffeoylquinic acid (chlorogenic acid, 5-CQA) and the type of interaction between the Zn(II) cation and the ligand were studied by means of various experimental and theoretical methods, i.e., electronic absorption spectroscopy UV/Vis, infrared spectroscopy FT-IR, elemental, thermogravimetric and density functional theory (DFT) calculations at B3LYP/6-31G(d) level. DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), FRAP (ferric reducing antioxidant power), CUPRAC (cupric reducing antioxidant power) and trolox oxidation assays were applied in study of the anti-/pro-oxidant properties of Zn(II) 5-CQA and 5-CQA. The antimicrobial activity of these compounds against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, Salmonella enteritidis and Candida albicans was tested. An effect of Zn(II) chelation by chlorogenic acid on the anti-/pro-oxidant and antimicrobial activities of the ligand was discussed. Moreover, the mechanism of the antioxidant properties of Zn(II) 5-CQA and 5-CQA were studied on the basis of the theoretical energy descriptors and thermochemical parameters. Zn(II) chlorogenate showed better antioxidant activity than chlorogenic acid and commonly applied natural (L-ascorbic acid) and synthetic antioxidants (butylated hydroxyanisol (BHA) and butylated hydroxytoluene (BHT)). The pro-oxidant activity of Zn(II) 5-CQA was higher than the ligand and increased with the rise of the compound concentration The type of Zn(II) coordination by the chlorogenate ligand strongly affected the antioxidant activity of the complex.


Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4362 ◽  
Author(s):  
Luis Noguera-Artiaga ◽  
Joel Said García-Romo ◽  
Ema C. Rosas-Burgos ◽  
Francisco Javier Cinco-Moroyoqui ◽  
Reyna Luz Vidal-Quintanar ◽  
...  

Pistachio nuts are included among the foods with the highest antioxidant capacity. Stressed cultivating conditions, such as the use of regulated deficit irrigation (RDI), are expected to create a plant response that might increase the production of secondary metabolites. Fruits that are obtained under RDI treatments are commonly called hydroSOS products. The aim of this work was to study the influence of using different rootstocks (P. atlantica, P. integerrima, and P. terebinthus) and two RDI treatments on the antioxidant (ABTS, ferric reducing antioxidant power (FRAP), and DPPH), antimutagenic (Ames test), and cytotoxicity (MTT assay in five human cell lines) activities of pistachios. P. terebinthus showed the best antioxidant activity, and the RDI treatments maintained and improved the antioxidant properties of pistachios. Neither the rootstock nor the RDI had significant impact on the antimutagenic potential of pistachios. The nut extracts had no toxic effect on non-cancerous cells and the application of RDI did not reduce their cytoprotective capacity. Furthermore, neither rootstock nor RDI treatments affected the ability of the pistachio extracts of preventing the oxidative damage by H2O2. The application of RDI strategies, in addition to allowing irrigation water saving, led to obtaining pistachios with the same or even better biofunctional characteristics as compared to fully irrigated pistachios.


2014 ◽  
Vol 9 (1) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Rúben Silva ◽  
Isabel S. Carvalho

This study analyzed the antioxidant properties of Portulaca oleracea L., known as purslane. The samples (leaves, flowers and stems) were collected at two different locations in Portugal: Tavira (L1) and Vendas Novas (L2). Assays for total antioxidant activity, total phenolic content and ferric-reducing antioxidant power were conducted and, for both locations, significantly higher values ( P<0,05) were observed for stems (508.8 and 982.3 mg AAE/100 g DW, 1008.6 and 2285.5 mg GAE/100 g DW, 121.0 and 166.3 mg TE/100 g DW, respectively for each location), than in leaves or flowers. In the DPPH assay, the three-plant parts from L2 reached the 50% inhibition rate in lower concentrations than plants from L1. On the other hand, higher concentrations of total monomeric anthocyanins were found in samples from L1 (95.5, 88.8 and 86.0 mg/L) than in samples from L2 (81.7, 70.5 and 59.8 mg/L). The same was true for phenolic acids, estimated by liquid-chromatography, where methanol extracts were used. Phenolic extracts from all three-plant parts from both locations showed protective effects on DNA against hydroxyl radicals. This work suggests the possibility of benefit to human health from its consumption, related to the high antioxidant activity of purslane, even the stems, usually discarded in daily consumption.


2017 ◽  
Vol 24 (3) ◽  
pp. 251-263 ◽  
Author(s):  
Monika Šporin ◽  
Martina Avbelj ◽  
Boris Kovač ◽  
Sonja Smole Možina

Wheat bread was enriched with 6%, 10% and 15% dried and milled grape pomace flour from two grape cultivars: ‘Merlot’ and ‘Zelen’. Rheological, textural, sensory and antioxidant properties of the enriched dough and bread were evaluated, and compared to control samples. Grape cultivar had significant impact on the rheological characteristics of the dough, and on the sensory and antioxidant properties of the final bread. Development time and dough stability were longer when ‘Merlot’ grape pomace flour was added compared to ‘Zelen’ grape pomace flour and the control. Grape pomace flour addition affected bread volume, firmness, crumb and crust colour, and odour and taste intensity. Moreover, grape pomace flour addition resulted in a stickier and less springy crumb texture, and some negative sensorial properties, such as increased intensity of aftertaste and sand feeling in the mouth. The phenolic content and antioxidant activity of bread were positively correlated with grape pomace flour addition ( r = 0.987, p = 0.01 and r = 0.941, p = 0.01 between phenolic content and ferric reducing antioxidant power and phenolic content and 2,2-diphenyl-1-picrylhydrazyl, respectively). The highest total phenolic contents were 5.92 mg gallic acid equivalents (GAE)/g dw for ‘Merlot’ and 3.65 mg gallic acid equivalents /g dw for ‘Zelen’, which were seen for the bread prepared with the highest grape pomace flour addition (15%). The highest antioxidant activity determined by the 2,2-diphenyl-1-picrylhydrazyl and ferric reducing antioxidant power assays were seen for the bread prepared with the highest ‘Merlot’ grape pomace flour addition (15%). Dough characteristic and sensory profile are strongly influenced by cultivar of grape pomace flour. Based on results of sensory profiling, the variety ‘Zelen’ is suggested for use.


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