DFT Study of Structure and Radical Scavenging Activity of Natural Pigment Delphinidin and Derivatives

2021 ◽  
Author(s):  
Sumayya Pottachola ◽  
Arifa Kaniyantavida ◽  
Muraleedharan Karuvanthodiyil
Keyword(s):  
Antioxidant Activity ◽  
Electron Transfer ◽  
Gas Phase ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Scavenging Activity ◽  
Natural Pigment ◽  
Physiochemical Parameters ◽  
Dissociation Enthalpy ◽  
Spin Density Calculation

A theoretical evaluation of the antioxidant activity of natural pigment delphinidin (1a) and derivatives 1b, 1c, 1d & 1e was performed using the DFT-B3LYP/6–311 + G (d, p) level of theory. Three potential working mechanisms, hydrogen atom transfer (HAT), stepwise electron transfer proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET), have been investigated. The physiochemical parameters, including O–H bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA), and electron transfer enthalpy (ETE), have been calculated in the gas phase and aqueous phase. The study found that the most suitable mechanism for explaining antioxidant activity is HAT in the gas phase and SPLET in the aqueous medium in this level of theory. Spin density calculation and delocalization index of studied molecules also support the radical scavenging activity. When incorporated into natural pigment delphinidin, the gallate moiety can enhance the activity and stability of the compounds.

scholarly journals Radical Scavenging Activity of Puerarin: A Theoretical Study

Antioxidants ◽  
2019 ◽  
Vol 8 (12) ◽  
pp. 590 ◽  
Author(s):  
Huakang Zhou ◽  
Xiangzhou Li ◽  
Yaxuan Shang ◽  
Kai Chen
Keyword(s):  
Electron Transfer ◽  
Density Functional ◽  
Theoretical Study ◽  
Wide Spectrum ◽  
Radical Scavenging Activity ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Hydrogen Atom Transfer ◽  
Scavenging Activity ◽  
Dissociation Enthalpy

Puerarin is a C-glycoside of daidzein, one of the major bioactive ingredients isolated from the root of Pueraria lobata, which has a wide spectrum of pharmacological effects. Although puerarin is well-known for its effective antioxidant activity, there is seldom a systematic theoretical study on its radical scavenging activity. Herein, the free radical scavenging ability of puerarin was investigated systematically by density functional theory (DFT) calculations. The reaction activity was compared with daidzein as well. Three reaction pathways: hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) were discussed and compared by thermodynamic parameters such as bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA), and electron transfer enthalpy (ETE). The reaction kinetics of puerarin with special radicals •OH and •OOH were also studied. The results obtained may be of great significance for better understanding the relationship between the antioxidant properties and structural design of puerarin, as well as other antioxidants.

scholarly journals Antioxidant Activity in Rheum emodi Wall (Himalayan Rhubarb)

Molecules ◽  
2021 ◽  
Vol 26 (9) ◽  
pp. 2555
Author(s):  
Sang Koo Park ◽  
Yoon Kyung Lee
Keyword(s):  
Antioxidant Activity ◽  
Ethyl Acetate ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Ethyl Acetate Fraction ◽  
Total Phenolic ◽  
Scavenging Activity ◽  
Polyphenol Content ◽  
Abts Assay ◽  
Ic50 Values

Using natural products as antioxidant agents has been beneficial to replace synthetic products. Efforts have been made to profile the antioxidant capacities of natural resources, such as medicinal plants. The polyphenol content of Himalayan rhubarb, Rheum emodi wall, was measured and the antioxidant activity was determined using DPPH and ABTS+ assay, and the oxidative stress was assessed using SOD enzymatic assay. Five different solvent fractions, n-hexane, n-butanol, ethyl acetate, dichloromethane, and water, were used for screening the antioxidant capacity in effort to determine the optimum extraction solvent. The total phenolic contents for R. emodi fractions ranged from 27.76 to 209.21 mg of gallic acid equivalents (GAE)/g of dry weight. DPPH and ABTS+ assay results are presented into IC50 values, ranged from 21.52 to 2448.79 μg/mL and 90.25 to 1718.05 μg/mL, respectively. The ethyl acetate fraction had the highest antioxidant activity among other fractions. Also, n-butanol and water fractions showed significantly lower IC50 values than the positive control in DPPH radical scavenging activity. The IC50 values of SOD assay of fractions ranged from 2.31 to 64.78 μg/mL. A similar result was observed with ethyl acetate fraction showing the highest SOD radical scavenging activity. The study suggests that the ethyl acetate fraction of R. emodi possess the strongest antioxidant activity, thus the most efficient in extracting antioxidant contents. Moreover, a highly significant correlation was shown between total polyphenol content and antioxidant activity screening assays. The compounds related to the antioxidant activity of R. emodi were identified to myricitrin, myricetin 3-galloyl rhamnoside, and myricetin, which have not been reported in studies about R. emodi before.

scholarly journals Antiglycation and Antioxidant Properties of Ficus deltoidea Varieties

2020 ◽  
Vol 2020 ◽  
pp. 1-16
Author(s):  
Nur Sumirah Mohd Dom ◽  
Nurshieren Yahaya ◽  
Zainah Adam ◽  
Nik Mohd Afizan Nik Abd. Rahman ◽  
Muhajir Hamid
Keyword(s):  
Antioxidant Activity ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Reducing Power ◽  
Protein Carbonyl ◽  
Scavenging Activity ◽  
Dpph Radical ◽  
Dpph Radical Scavenging Activity ◽  
Ficus Deltoidea ◽  
Dpph Radical Scavenging

The present study aimed to evaluate the potential of standardized methanolic extracts from seven Ficus deltoidea varieties in inhibiting the formation of AGEs, protein oxidation, and their antioxidant effects. The antiglycation activity was analyzed based on the inhibition of AGEs, fructosamine, and thiol groups level followed by the inhibition of protein carbonyl formation. The antioxidant activity (DPPH radical scavenging activity and reducing power assay) and total phenolic contents were evaluated. After 28 days of induction, all varieties of Ficus deltoidea extracts significantly restrained the formation of fluorescence AGEs by 4.55–5.14 fold. The extracts also reduced the fructosamine levels by 47.0–86.5%, increased the thiol group levels by 64.3–83.7%, and inhibited the formation of protein carbonyl by 1.36–1.76 fold. DPPH radical scavenging activity showed an IC50 value of 66.81–288.04 μg/ml and reducing power activity depicted at 0.02–0.24 μg/ml. The extent of phenolic compounds present in the extracts ranged from 70.90 to 299.78 mg·GAE/g. Apart from that, correlation studies between the activities were observed. This study revealed that seven varieties of Ficus deltoidea have the potential to inhibit AGEs formation and possess antioxidant activity that might be attributed to the presence of phenolic compounds.

scholarly journals Composition, antimicrobial and antioxidant activity of the extracts of Eryngium palmatum Pančić and Vis. (Apiaceae)

2014 ◽  
Vol 9 (2) ◽  
pp. 149-155 ◽  
Author(s):  
Mirjana Marčetić ◽  
Silvana Petrović ◽  
Marina Milenković ◽  
Marjan Niketić
Keyword(s):  
Antioxidant Activity ◽  
Methanol Extract ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Chloroform Extract ◽  
Volatile Fraction ◽  
Scavenging Activity ◽  
Antioxidant Power ◽  
Aerial Parts ◽  
Antimicrobial And Antioxidant Activity

AbstractThe chemical composition, antimicrobial and antioxidant activity of Eryngium palmatum, an endemic plant species from the Balkan Peninsula, were investigated. The flavonoids apigenin (9.5±0.3 mg g−1) and apigenin 7-O-glucoside (2.4±0.1 mg g−1) were determined in a methanol extract of aerial parts using HPLC analysis. The methanol extract of roots contained catechin (5.0±0.1 mg g−1), epicatechin (2.9±0.1 mg g−1), chlorogenic acid (1.6±0.0 mg g−1), gallic acid (0.9±0.0 mg g−1) and rosmarinic acid (0.9±0.2 mg g−1). GC-FID and GCMS analysis of a chloroform extract of aerial parts showed that the main volatile constituents were falcarinol, linoleic acid, hexadecanoic acid and methyl linoleate (comprising 32.6%; 24.4%; 19.9; 13.2% of the volatile fraction, respectively), while octanoic acid, tetradecanol and dodecanol dominated in the chloroform extract of the roots (34.9%; 25.8%; 22.2% of the volatile fraction, respectively). Investigation of antimicrobial activity by broth microdilution showed that the methanol and chloroform extracts of aerial parts and roots exerted a significant effect (MIC 3.5–15.6 μg mL−1) against tested Gram-positive and Gram-negative bacteria. The methanol extracts of aerial parts or roots exerted moderate ferric reducing antioxidant power, DPPH radical scavenging activity and hydroxyl radical scavenging activity.

scholarly journals Antioxidant and Anticancer Activities of Wampee (Clausena lansium(Lour.) Skeels) Peel

2009 ◽  
Vol 2009 ◽  
pp. 1-6 ◽  
Author(s):  
K. Nagendra Prasad ◽  
Jing Hao ◽  
Chun Yi ◽  
Dandan Zhang ◽  
Shengxiang Qiu ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Ethyl Acetate ◽  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Reducing Power ◽  
Total Phenolic ◽  
Liver Carcinoma ◽  
Scavenging Activity ◽  
Anticancer Activities

Antioxidant activities of wampee peel extracts using five different solvents (ethanol, hexane, ethyl acetate, butanol and water) were determined by using in-vitro antioxidant models including total antioxidant capability, 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging activity, reducing power, and superoxide scavenging activity. Ethyl acetate fraction (EAF) exhibited the highest antioxidant activity compared to other fractions, even higher than synthetic antioxidant butylated hydroxyl toluene (BHT). In addition, the EAF exhibited strong anticancer activities against human gastric carcinoma (SGC-7901), human hepatocellular liver carcinoma (HepG-2) and human lung adenocarcinoma (A-549) cancer cell lines, higher than cisplatin, a conventional anticancer drug. The total phenolic content of wampee fraction was positively correlated with the antioxidant activity. This is the first report on the antioxidant and anticancer activities of the wampee peel extract. Thus, wampee peel can be used potentially as a readily accessible source of natural antioxidants and a possible pharmaceutical supplement.

scholarly journals EFFECT OF DIFFERENT SOLVENTS ON ANTIOXIDANT ACTIVITY OF LEAF EXTRACTS OF CALOTROPIS PROCERA AND AZADIRACHTA INDICA

2016 ◽  
Vol 10 (1) ◽  
pp. 268
Author(s):  
Sharmistha Banerjee ◽  
Shuchi Kaushik ◽  
Rajesh Singh Tomar
Keyword(s):  
Antioxidant Activity ◽  
Total Phenolics ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Calotropis Procera ◽  
Peroxide Radical ◽  
Scavenging Activity ◽  
Leaf Extracts ◽  
Dry Extract ◽  
Leaf Powder

ABSTRACTObjective: This study was performed to identify the phytochemicals and comparatively evaluate the antioxidant activity of Calotropis procera andAzadirachta indica by detection of total phenolics, hydrogen peroxide radical scavenging activity, and estimation of condensed tannins in differentsolvent systems and at different temperatures.Methods: Leaves of C. procera and A. indica were extracted in water, methanol by soaking dried leaf powder at room temperature and also by boilingthe leaf powder in water for 30 minutes. Phytochemical tests were performed in all of the extracts. The antioxidant activity was determined byhydrogen peroxide radical scavenging activity. Quantitative estimation of total phenolics and hydrolysable tannins was also performed.Results: The total phenolics in both leaf extracts was obtained maximum in boiled extract (40.7±1.20 mg gallic acid equivalent [GAE]/g dry extractin C. procera and 33.66±1.45 mg GAE/g dry extract in A. indica). The amount of hydrolysable tannins in both leaf extracts was found to be highest inmethanol (150±1.88 mg catechin equivalent/g dry extract in C. procera and 144.8±2.63 mg catechin equivalent/g dry extract in A. indica).Conclusion: The study showed promising results indicating that these plants are a good source of antioxidants. The majority of phytochemicals wereextracted in distilled water and methanol acts as a good solvent for extraction of tannins, whereas an increase in temperature leads to poor extractionof tannins.Keywords: Antioxidant, Phytochemicals, Phenolics, Radical, Tannins.© 2017 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (http://creativecommons.

DPPH Radical Scavenging Activity of Kaempferol

2013 ◽  
Vol 781-784 ◽  
pp. 1294-1297 ◽  
Author(s):  
Ping Liu ◽  
Yun Tao Gao ◽  
Jiao Jiao Yu ◽  
Jia Wei Cha ◽  
Dong Mei Zhao ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Absorption Spectrum ◽  
Reaction Time ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Scavenging Activity ◽  
Dpph Radical ◽  
Dpph Radical Scavenging Activity ◽  
Dpph Radical Scavenging

The UV-Vis absorption spectrum of kaempferol and DPPH was investigated, the optimum determination wavelength and reaction time for determining the DPPH radical scavenging activity of kaempferol was 517 nm and 30 min, respectively. Kaempferol exhibited strong DPPH radical scavenging activity with a IC50 value of 0.004349 mg·mL-1, which is smaller than that of rutin, indicating that kaempferol has a stronger antioxidant activity than rutin.

DFT study of free radical scavenging activity of erodiol

2013 ◽  
Vol 67 (11) ◽  
Author(s):  
Zoran Marković ◽  
Jelena Đorović ◽  
Milan Dekić ◽  
Milanka Radulović ◽  
Svetlana Marković ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Hydrogen Atom Transfer ◽  
Free Radical Scavenging ◽  
Single Electron Transfer ◽  
Transfer Energy ◽  
Dissociation Enthalpy ◽  
Proton Dissociation ◽  
Transfer Mechanisms

AbstractAntioxidant activity of erodiol was examined at the M05-2X/6-311+G(d,p) level of theory in the gas and aqueous phases. The structure and energy of radicals and anions of the most stable erodiol rotamer were analyzed. To estimate antioxidant potential of erodiol, different molecular properties were examined: bond dissociation enthalpy, proton affinity together with electron transfer energy, and ionization potential followed by proton dissociation enthalpy. It was found that hydrogen atom transfer is the prevailing mechanism of erodiol behavior in gas; whereas single electron transfer followed by proton transfer and sequential proton loss electron transfer mechanisms represent the thermodynamically preferred reaction paths in water.

scholarly journals HPLC Evaluation of Phenolic Profile, Nutritive Content, and Antioxidant Capacity of Extracts Obtained fromPunica granatumFruit Peel

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Sushil Kumar Middha ◽  
Talambedu Usha ◽  
Veena Pande
Keyword(s):  
Antioxidant Activity ◽  
Gallic Acid ◽  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Water Extract ◽  
Scavenging Activity ◽  
Fruit Peel ◽  
Phenolic Profile ◽  
Antioxidant Power

This study revealed polyphenolic content, nutritive content, antioxidant activity, and phenolic profile of methanol and aqueous extracts ofPunica granatumpeel extract. For this, extracts were screened for possible antioxidant activities by free radical scavenging activity (DPPH), hydrogen peroxide scavenging activity and ferric-reducing antioxidant power (FRAP) assays. The total phenolics and flavonoid recovered by methanolic (MPE) and the water extract (AQPE) were ranged from 185 ± 12.45 to 298.00 ± 24.86 mg GAE (gallic acid equivalents)/gm and 23.05 ± 1.54 to 49.8 ± 2.14 quercetin (QE) mg/g, respectively. The EC50of herbal extracts ranged from 100 µg/ml (0.38 quercetin equivalents), for AQPE, 168 µg/ml (0.80 quercetin equivalents), for MPE. The phenolic profile in the methanolic extracts was investigated by chromatographic (HPLC) method. About 5 different flavonoids, phenolic acids, and their derivatives including quercetin (1), rutin (2), gallic acid (3), ellagic acid (4), and punicalagin as a major ellagitannin (5) have been identified. Among both extracts, methanolic extract was the most effective. This report may be the first to show nutritive content and correlation analysis to suggest that phenols and flavonoids might contribute the high antioxidant activity of this fruit peel and establish it as a valuable natural antioxidant source applicable in the health food industry.

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