scholarly journals Antioxidant Activity of Selected Phenolic Acids–Ferric Reducing Antioxidant Power Assay and QSAR Analysis of the Structural Features

Molecules ◽  
2020 ◽  
Vol 25 (13) ◽  
pp. 3088
Author(s):  
Maciej Spiegel ◽  
Karina Kapusta ◽  
Wojciech Kołodziejczyk ◽  
Julia Saloni ◽  
Beata Żbikowska ◽  
...  

Phenolic acids are naturally occurring compounds that are known for their antioxidant and antiradical activity. We present experimental and theoretical studies on the antioxidant potential of the set of 22 phenolic acids with different models of hydroxylation and methoxylation of aromatic rings. Ferric reducing antioxidant power assay was used to evaluate this property. 2,3-dihydroxybenzoic acid was found to be the strongest antioxidant, while mono hydroxylated and methoxylated structures had the lowest activities. A comprehensive structure–activity investigation with density functional theory methods elucidated the influence of compounds topology, resonance stabilization, and intramolecular hydrogen bonding on the exhibited activity. The key factor was found to be a presence of two or more hydroxyl groups being located in ortho or para position to each other. Finally, the quantitative structure–activity relationship approach was used to build a multiple linear regression model describing the dependence of antioxidant activity on structure of compounds, using features exclusively related to their topology. Coefficients of determination for training set and for the test set equaled 0.9918 and 0.9993 respectively, and Q2 value for leave-one-out was 0.9716. In addition, the presented model was used to predict activities of phenolic acids that haven’t been tested here experimentally.

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.


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.


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 ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2267
Author(s):  
Małgorzata Starowicz ◽  
Saruhan Arpaci ◽  
Joanna Topolska ◽  
Małgorzata Wronkowska

The aim of this study was to determine the phytochemicals and antioxidant activity in oat-buckwheat doughs and cookies with the addition of ten selected spices or herbs (2 g/100 g flours weight basis). The used spices and herbs, as was expected, showed a wide range of bioactive molecules, namely phenolic acids and flavonoids, and they are a rich source of components with antioxidant potential. All analysed oat-buckwheat dough showed higher antioxidant activity potential and higher total phenolic content (TPC) compared to cookies. The highest TPC was found in clove, both dough and cookies, with its addition showing the highest ferric reducing antioxidant power. Generally, cookies with the addition of spice/herbs showed higher phytochemical contents and antioxidant activity compared to oat-buckwheat cookies without the condiment. The technology of obtaining confectionery products, like oat-buckwheat cookies, that will favor the protection of bioactive compounds should still be improved.


Antioxidants ◽  
2021 ◽  
Vol 10 (2) ◽  
pp. 165
Author(s):  
Elisabetta Bravi ◽  
Giovanni De Francesco ◽  
Valeria Sileoni ◽  
Giuseppe Perretti ◽  
Fernanda Galgano ◽  
...  

The brewing industry produces high quantities of solid and liquid waste, causing disposal issues. Brewing spent grains (BSGs) and brewing spent hop (BSH) are important by-products of the brewing industry and possess a high-value chemical composition. In this study, BSG and BSH, obtained from the production process of two different types of ale beer (Imperial red and Belgian strong beer) were characterized in terms of valuable components, including proteins, carbohydrates, fat, dietary fiber, β-glucans, arabinoxylans, polyphenols, and phenolic acids, and antioxidant activity (Ferric Reducing Antioxidant Power Assay (FRAP), 2,2-Diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-Azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS)). Significant concentrations of total polyphenols were observed in both BSH and BSG samples (average of about 10 mg GAE/g of dry mass); however, about 1.5-fold higher levels were detected in by-products of Belgian strong ale beer compared with Imperial red. Free and bound phenolic acids were quantified using a validated chromatographic method. A much higher level of total phenolic acids (TPA) (about 16-fold higher) was found in BSG samples compared with BSHs. Finally, their antioxidant potential was verified. By-products of Belgian strong ale beer, both BSG and BSH, showed significantly higher antioxidative capacity (about 1.5-fold lower inhibitory concentration (IC50) values) compared with spent grains and hop from the brewing of Imperial red ale. In summary, BSG and BSH may be considered rich sources of protein, carbohydrates, fiber, and antioxidant compounds (polyphenols), and have the potential to be upcycled by transformation into value-added products.


2018 ◽  
Vol 10 (1) ◽  
pp. 407
Author(s):  
Dewi Kumala Putri ◽  
Berna Elya ◽  
Nuraini Puspitasari

Objective: To assess the antioxidant activity from another part of the plant, in this study, leaf extracts in n-hexane were fractionated.Methods: Ten fractions were obtained and tested in vitro for antioxidant activity using two methods, 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferricreducing antioxidant power (FRAP), to identify the most active fraction.Results: The IC50 of the most active fraction was 36.24 μg/mL using the DPPH method, and the EC50 was 39.54 μg/mL using the FRAP method. Themost active fraction was also shown to contain terpenoids.Conclusion: The most active fraction of an n-hexane extract of the leaves of Gacinia bancana Miq., which was tested by both DPPH and FRAP methodshad antioxidant activities with IC50 and EC50 values of 36.2482 μg/mL and 39.5442 μg/mL, respectively. Phytochemical screening showed that activefraction contains terpenoids.


Botanica ◽  
2020 ◽  
Vol 26 (1) ◽  
pp. 76-87
Author(s):  
Aziza Lfitat ◽  
Hind Zejli ◽  
Abdelkamel Bousselham ◽  
Yassine El Atki ◽  
Badiaa Lyoussi ◽  
...  

AbstractWe conducted this study to determine and compare the content of phenolic compounds and flavonoids in the argan and olive leaves as well as their antioxidant capacity in aqueous, methanolic, and ethyl acetate extracted fractions. In vitro antioxidant activity was evaluated in comparison with synthetic antioxidants by assessing DPPH• radical scavenging capacity, ferric reducing antioxidant power, scavenging ability by inhibiting the β-carotene/linoleic acid emulsion oxidation, and by the ABTS radical scavenging activity assay. Total phenolic content in argan samples ranged from 221.69 ± 2.07 to 1.32 ± 0.01 mg GAE/g DW and in olive samples from 144.61 ± 0.82 to 1.21 ± 0.02 mg GAE/g DW. Total flavonoids content in argan samples varied from 267.37 ± 1.12 to 25.48 ± 0.02 mg QE/g DW, while in olives from 96.06 ± 0.78 to 10.63 ± 0.05 mg QE/g DW. In vitro antioxidant studies strongly confirmed the antioxidant potency of argan and olive leaves and their richness in secondary metabolites that are effective in free radicals scavenging and metal chelating capacities, indicating their antioxidant power.


2021 ◽  
Vol 332 ◽  
pp. 08005
Author(s):  
Aminah Dalimunthe ◽  
Dewi Pertiwi ◽  
Mahatir Muhammad ◽  
Denny Satria

Free radicals also play a role in the pathology of various degenerative diseases such as cancer, rheumatism, coronary heart disease, cataracts, and others. Free radicals can come from within the body (endogenous) and outside the body (exogenous). Litsea cubeba (Lour,) is a Lauraceae family plant which have contents volatile oils which used as antimicrobial, anticancer on breast cancer, pesticide, antideppressants, antiinflammation, antioxidant, and neuro pharmacology. The extract was prepared using water with the soxhletation method. The antioxidant activity was determined with the 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2’-Azinobis [3-ethylbenzothiazoline-6)-sulfonic acid] -diammonium salt (ABTS) and Ferric Reducing Antioxidant Power (FRAP) methods. Total flavonoid and total phenolic content were determined with colorimetric methods. Antioxidant activity measured as IC50 was 23.37 ± 0.42 µg/mL; 111.21 ± 0.42 and 109.01 ± 0.28 respectively. The extract was found to contain high levels of total phenolic (282.93 ± 0.33 mg GAE/g) and total flavonoid 7.49 ± 0.51 mg QE/g). The results reveal that ethanol extract of Litsea cubeba Lour. Bark has antioxidant potential. The further analysis is to isolation antioxidant compound.


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