scholarly journals Antioxidant Properties of Camphene-Based Thiosemicarbazones: Experimental and Theoretical Evaluation

Molecules ◽  
2020 ◽  
Vol 25 (5) ◽  
pp. 1192
Author(s):  
Lijuan Yang ◽  
Haochuang Liu ◽  
Dasha Xia ◽  
Shifa Wang
Keyword(s):  
Density Functional ◽  
Peroxyl Radical ◽  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Theoretical Data ◽  
Hydrogen Atom Transfer ◽  
Theoretical Evaluation ◽  
Wide Range

The thiosemicarbazone derivatives have a wide range of biological activities, such as antioxidant activity. In this study, the antiradical activities of six camphene-based thiosemicarbazones (TSC-1~6) were investigated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and peroxyl radical scavenging capacity (PSC) assays, respectively, and the results reveal that TSC1~6 exhibited good abilities for scavenging free radicals in a dose-dependent way. Compound TSC-2 exhibited the best effect of scavenging DPPH radical, with the lowest EC50 (0.208 ± 0.004 mol/mol DPPH) as well as the highest bimolecular rate constant Kb (4218 M−1 s−1), which is 1.18-fold higher than that of Trolox. Meanwhile, TSC-2 also obtained the lowest EC50 (1.27 µmol of Trolox equiv/µmol) of scavenging peroxyl radical. Furthermore, the density functional theory (DFT) calculation was carried out to further explain the experimental results by calculating several molecular descriptors associated with radical scavenging activity. These theoretical data suggested that the electron-donating effect of the diethylamino group in TSC-2 leads to the enhancement of the scavenging activities and the studied compounds may prefer to undergo the hydrogen atom transfer process.

scholarly journals Antioxidant and UV-radiation absorption activity of aaptamine derivatives – Potential application for natural organic sunscreens

2021 ◽  
Author(s):  
Thi Le Anh Nguyen ◽  
Thi Hoai Nam Doan ◽  
Dinh Hieu Truong ◽  
Nguyen Thi Ai Nhung ◽  
Duong Tuan Quang ◽  
...  
Keyword(s):  
Density Functional ◽  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Hydrogen Atom Transfer ◽  
Radiation Absorption ◽  
Chelating Activity ◽  
Radical Adduct ◽  
Potential Applications

Antioxidant and UV absorption activities of three marine product originated - aaptamine derivatives including piperidine[3,2-b]demethyl(oxy)aaptamine (<b>C1</b>), 9-amino-2-ethoxy-8-methoxy-3H-benzo[de][1,6]naphthyridine-3-one (<b>C2</b>), and 2-(sec-butyl)-7,8-dimethoxybenzo[de]imidazo[4,5,1-ij][1,6]-naphthyridin-10(9H)-one (<b>C3</b>) were theoretically studied by density functional theory (DFT). Direct antioxidant activities of C1–C3 were firstly evaluated via their intrinsic thermochemical properties and radical scavenging activity of the potential antioxidants with the HOO●/HO● radicals via four mechanisms, including: hydrogen atom transfer (HAT), single electron transfer (SET), proton loss (PL) and radical adduct formation (RAF). Kinetic calculation reveals that HOO● scavenging in water is occurred via HAT mechanism with C1 (kapp, 7.13x10<sup>6</sup> M-1 s-1) while RAF is more dominant with C2 (k<sub>app</sub>, 1.40x10<sup>5</sup> M-1 s-1) and C3 (kapp, 2.90x10<sup>5</sup> M-1 s-1). Antioxidant activity of aaptamine derivatives can be classified as <b>C1 </b>> <b>C3 </b>> <b>C2</b>. Indirect antioxidant properties based on Cu(I) and Cu(II) ions chelating activity were also investigated in aqueous phase. All three studied compounds show spontaneous and favorable Cu(I) ion chelating activity with DG0 being -15.4, -13.7, and -15.7 kcal.mol-1, whereas DG0 for Cu(II) chelation are -10.4, -10.8, and -2.2 kcal.mol-1 for C1, C2 and C3, respectively. In addition, all compounds show UVA and UVB absorption; in which the excitations are determined mostly as π-π* transition. Overall, the results suggest the potential applications of the aaptamines in pharmaceutics and cosmetics, i.e. as sunscreen and antioxidant ingredient.<br>

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 Investigation of Reaction Mechanisms and Kinetics of the Radical Scavenging Ability of 5-Tert-Butylbenzene-1,2,3-Triol and 3,5-di-Tert-Butylbenzene-1,2-Diol Compounds Towards OOH Radical

2018 ◽  
Vol 43 (2) ◽  
pp. 101-111
Author(s):  
Anes El-Hadj Saïd ◽  
Sidi Mohamed Mekelleche
Keyword(s):  
Gas Phase ◽  
Density Functional ◽  
Radical Scavenging Activity ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Hydrogen Atom Transfer ◽  
System A ◽  
Radical Adduct ◽  
Scavenging Capacity ◽  
Radical Scavenging Ability

The antioxidant properties of the synthesised 5- tert-butylbenzene-1,2,3-triol (system A) and the designed 3,5-di -tert-butylbenzene-1,2-diol (system B) have been explored through density functional theory at the M05-2X/6-31+G(d,p) level of theory. The quantum mechanics-based test for overall free radical scavenging activity (QM- ORSA) protocol has been employed to account for their radical-scavenging capacity against the hydroperoxyl radical (HOO•) in the gas phase and in toluene solvent as a mimic lipid medium. The different mechanisms of the chemical reactions of the studied systems with HOO• have been considered, namely (i) the hydrogen atom transfer (HAT), (ii) the single electron transfer followed by proton transfer and (iii) the radical adduct formation. Our calculations provide evidence that HAT is the most favoured reaction mechanism in both the gas phase and in lipid media and the calculated thermodynamic and kinetic parameters indicate that the designed compound is more efficient than the synthesised system A and the reference system (α-tocopherol).

scholarly journals Synthesis, Antiproliferative Activity and Radical Scavenging Ability of 5-O-Acyl Derivatives of Quercetin

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1608
Author(s):  
Stephen Lo ◽  
Euphemia Leung ◽  
Bruno Fedrizzi ◽  
David Barker
Keyword(s):  
Antiproliferative Activity ◽  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Breast Cancer Cell Lines ◽  
Scavenging Activity ◽  
Plant Materials ◽  
Wide Range ◽  
Derivatives Of ◽  
Acyl Derivatives

Quercetin is a flavonoid that is found in many plant materials, including commonly eaten fruits and vegetables. The compound is well known for its wide range of biological activities. In this study, 5-O-acyl derivatives of quercetin were synthesised and assessed for their antiproliferative activity against the HCT116 colon cancer and MDA-MB-231 breast cancer cell lines; and their radical scavenging activity against the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical species. Four derivatives were found to have improved the antiproliferative activity compared to quercetin whilst retaining radical scavenging activity.

scholarly journals GC-MS Assisted Phytoactive Chemical Compounds Identification and Profiling with Mineral Constituents from Biologically Active Extracts of Aerva javanica (Burm. f) Juss. ex Schult.

2018 ◽  
Vol 46 (2) ◽  
pp. 517-524
Author(s):  
Kandhan KARTHISHWARAN ◽  
Subban KAMALRAJ ◽  
Chelliah JAYABASKARAN ◽  
Shyam S. KURUP ◽  
Sabitha SAKKIR ◽  
...  
Keyword(s):  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Biologically Active ◽  
Scavenging Activity ◽  
Medicinal Uses ◽  
Chemical Structures ◽  
Aerial Parts ◽  
Mineral Constituents

Aerva javanica (Burm. f) Juss. ex Schult. (Family: Amaranthaceae) family is one of the traditional medicinal plant growing in the United Arab Emirates. Apart from studies related to some medicinal properties, phytochemical, GC MS compound characterization and biological activities still to be investigated. An experiment was conducted to determine the possible bioactive components with their chemical structures and elucidation of phytochemicals from the aerial parts of the plant. The macro and micro-mineral constituents and antioxidant activities were also evaluated. Aerial parts of A. javanica were extracted sequentially with hexane, chloroform, ethyl acetate, acetone, methanol by cold percolation method. Free radical scavenging and antioxidant properties of methanolic extract were evaluated by using in vitro antioxidant assays such as hydroxyl radical scavenging activity, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, superoxide radical scavenging activity and ABTS radical scavenging activity. Primary phytochemical and micro-macro element was tested using standard protocol. The chemical characterization was done with the help of Gas Chromatography-Mass Spectrometry (GC–MS), and the mass spectra of the total compounds in the extract were matched with the National Institute of Standard and Technology (NIST) library. Mineral constituents were identified and estimated by ICP-OES. Ninety-nine metabolites were obtained by GC-MS anslysis; indole was found to be major components followed by 2-Chlorallyl diethyldithiocarbamate (CDEC), Carbaril, Bis(2-ethylhexyl) phthalate, Quinoline, 4H-Cyclopenta[def]phenanthrene,2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide, Phenobarbital, 1H-Indole, 2-methyl-, 2,3,7,8-Tetrachlorodibenzo-p-dioxin Disulfide, diphenyl. The presence of various bioactive compounds in the extract validates the traditional medicinal uses of this plant.

scholarly journals RELATIONSHIP BETWEEN ANTIOXIDANT PROPERTIES AND NUTRITIONAL COMPOSITION OF SOME GALACTOPOIETICS HERBS USED IN INDONESIA: A COMPARATIVE STUDY

2016 ◽  
Vol 8 (12) ◽  
pp. 236 ◽  
Author(s):  
Ade Chandra Iwansyah ◽  
Rizal M. Damanik ◽  
Lilik Kustiyah ◽  
Muhammad Hanafi
Keyword(s):  
Antioxidant Activity ◽  
Chemical Composition ◽  
Total Phenolics ◽  
Radical Scavenging Activity ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Nutritional Composition ◽  
Total Flavonoids ◽  
Wide Range ◽  
Phenolics Content

<p><strong>Objective: </strong>The objectives of this research were to evaluate and compare the antioxidant activity; phenolics and flavonoids contents; and chemical composition of some galactopoietic herbs used in Indonesia and to find a possible relationship between antioxidant activity; phenolics, flavonoids and chemical composition of these plants.</p><p><strong>Methods: </strong>A wide range of analytical parameters was studied, including yield; pH; water activity (a<sub>w</sub>); total color difference; phenolics and flavonoids content; moisture; ash; protein; fat; carbohydrate; fiber; calcium; zinc; magnesium; potassium; iron content; and the data were analyzed by partial least squares (PLS) regression analysis and principal component analysis (PCA) to evaluate the correlation between the parameters and classification of the plants. Folin–cioceltaeu assay, aluminum chloride assay and DPPH scavenging assay were used to evaluate of total phenolics content and free radical scavenging activity of the ethanolic extract of galactopoietic herbs.</p><p><strong>Results: </strong>All of the galactagogue herbs, <em>viz</em>. <em>Plectranthus amboinicus </em>(Lour.) (PA), <em>Sauropus androgynus</em> (SA), <em>Moringa oleifera</em> (MO), and <em>Carica papaya</em> leaves (CP) exhibited good results of TPC, TFC and antioxidant activity. MO contained the highest average of total phenolics content (53.89 mg GAE/g). SA with a ratio of total flavonoids to total phenolics (TF/TP) which is 1.59 contained the highest average of total flavonoids and antioxidant activity (IC<sub>50</sub>), 43.63 mg QE/g and 126.13 μg/ml, respectively, followed by MO&gt;CA&gt;PA. Based on PLS and PCA analysis, antioxidant activity correlated with fat, protein, phenolics content, flavonoids content and pH, but only the total flavonoids content correlated strongly with antioxidant activity.<strong></strong></p><p><strong>Conclusion: </strong>This provides useful data about the studied relationships and chemical patterns in some galactopoietic herbs used and provides a helpful tool for understanding much more about the interpretation of results from the experiments and the mechanism of biosynthesis in plants.</p>

scholarly journals Radical-Scavenging and UV-Radiation Absorption Activities of Aaptamine Derivatives: DFT and TD-DFT Studies

2021 ◽  
Author(s):  
Thi Hoai Nam Doan ◽  
Thi Le Anh Nguyen ◽  
Nguyen Thi Ai Nhung ◽  
Duong Tuan Quang ◽  
Duy Quang Dao
Keyword(s):  
Density Functional ◽  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Hydrogen Atom Transfer ◽  
Radiation Absorption ◽  
Functional Theory ◽  
Radical Adduct ◽  
Td Dft ◽  
Potential Applications

Antioxidant and UV absorption activities of three aaptamine derivatives including piperidine[3,2-b]demethyl(oxy)aaptamine (C1), 9-amino-2-ethoxy-8-methoxy-3H-benzo[de][1,6]naphthyridine-3-one (C2), and 2-(sec-butyl)-7,8-dimethoxybenzo[de]imidazo[4,5,1-ij][1,6]-naphthyridin-10(9H)-one (C3) were theoretically studied by density functional theory (DFT). Optimized geometries of C1C3 and theirs intrinsic thermochemical properties such as bond dissociation energy, proton affinity, and ionization potential were calculated at DFT/M05-2X/6-311++G(d,p) level of theory in vacuo and in water. The results show that C1C3 exhibited similar potent antioxidant activities, which are comparable to well-known antioxidants such as Trolox or cembrene. The radical scavenging activity of the antioxidants were then investigated by evaluation the Gibbs free energy (ΔrG0) of the reaction between C1C3 and the HOO●/HO● radicals via four mechanisms, including: hydrogen atom transfer (HAT), single electron transfer (SET), proton loss (PL) and radical adduct formation (RAF). Kinetic calculation reveals that HOO● scavenging in water is occurred via HAT mechanism with C1@C19 while RAF is more dominant with C2 and C3. Antioxidant activity of aaptamine derivatives can be classified as C1 > C3 > C2. In addition, all compounds are active in UV-Vis absorption; the excitations of which are determined as π-π* transition. Overall, the results suggest the potential applications of the aaptamines in pharmaceutics and cosmetics, i.e. as sunscreen and antioxidant ingredient<br>

scholarly journals Gold Nanoparticles Using Ecklonia stolonifera Protect Human Dermal Fibroblasts from UVA-Induced Senescence through Inhibiting MMP-1 and MMP-3

Marine Drugs ◽  
2020 ◽  
Vol 18 (9) ◽  
pp. 433
Author(s):  
Eun-Sook Jun ◽  
Yeong Jin Kim ◽  
Hyung-Hoi Kim ◽  
Sun Young Park
Keyword(s):  
Gold Nanoparticles ◽  
Cellular Senescence ◽  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Dermal Fibroblasts ◽  
G1 Arrest ◽  
Human Dermal Fibroblasts ◽  
Ecklonia Stolonifera

The effect of gold nanoparticles (GNPs) synthesized in marine algae has been described in the context of skin, where they have shown potential benefit. Ecklonia stolonifera (ES) is a brown algae that belongs to the Laminariaceae family, and is widely used as a component of food and medicine due to its biological activities. However, the role of GNPs underlying cellular senescence in the protection of Ecklonia stolonifera gold nanoparticles (ES-GNPs) against UVA irradiation is less well known. Here, we investigate the antisenescence effect of ES-GNPs and the underlying mechanism in UVA-irradiated human dermal fibroblasts (HDFs). The DPPH and ABTS radical scavenging activity of ES extracts was analyzed. These analyses showed that ES extract has potent antioxidant properties. The facile and optimum synthesis of ES-GNPs was established using UV-vis spectra. The surface morphology and crystallinity of ES-GNPs were demonstrated using high resolution transmission electron microscopy (HR-TEM), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD), and Fourier-transform infrared spectroscopy (FT-IR). ES-GNPs presented excellent photocatalytic activity, as shown by the photo-degradation of methylene blue and rhodamine B. A cellular senescence model was established by irradiating HDFs with UVA. UVA-irradiated HDFs exhibited increased expression of senescence-associated β-galactosidase (SA-β-galactosidase). However, pretreatment with ES-GNPs resulted in reduced SA-β-galactosidase activity in UVA-irradiated HDFs. Intracellular ROS levels and G1 arrest in UVA-irradiated HDFs were checked against the background of ES-GNP treatment to investigate the antisenescence effects of ES-GNPs. The results showed that ES-GNPs significantly inhibit UVA-induced ROS levels and G1 arrest. Importantly, ES-GNPs significantly downregulated the transcription and translation of MMP (matrix metalloproteinases)-1/-3, which regulate cellular senescence in UVA-irradiated HDFs. These findings indicate that our optimal ES-GNPs exerted an antisenescence effect on UVA-irradiated HDFs by inhibiting MMP-1/-3 expression. Collectively, we posit that ES-GNPs may potentially be used to treat photoaging of the skin.

scholarly journals Bioactive Compounds of Selected Fruit Juices

2009 ◽  
Vol 4 (5) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Aneta Wojdyłto ◽  
Jan Oszmiański
Keyword(s):  
Antioxidant Activity ◽  
Phenolic Compounds ◽  
Fruit Juice ◽  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Sea Buckthorn ◽  
Quercetin Derivatives ◽  
Reducing Ability ◽  
Wide Range

Fruits are one of the most important sources of phenolic compounds in our diet. Many of these compounds exhibit a wide range of biological activities, especially antioxidant activity. The objective of this study was to determine the composition and antioxidant activity of phenolic compounds found in fruit juice obtained from buckthorn, flowering quince, rowanberry and hawthorn. Hydroxycinnamic acids (neochlorogenic and chlorogenic acid) and procyanidins were the main phenolics in rowanberry juice. The highest level of flavonols (quercetin derivatives) was found in sea buckthorn. All juices showed strong free-radical scavenging activity against ABTS•+ radicals and ferric reducing ability measured by the FRAP method. The strongest antioxidant activity was found in rowanberry juice, but the lowest was measured in hawthorn and sea buckthorn juices.

scholarly journals DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3

2019 ◽  
Vol 20 (6) ◽  
pp. 1450 ◽  
Author(s):  
Yan-Zhen Zheng ◽  
Geng Deng ◽  
Rui Guo ◽  
Da-Fu Chen ◽  
Zhong-Min Fu
Keyword(s):  
Antioxidant Activity ◽  
Density Functional ◽  
Radical Scavenging Activity ◽  
Resonance Effect ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Dft Method ◽  
Functional Theory ◽  
The Density Functional Theory ◽  
Selection Of

The radical scavenging activity of a flavonoid is largely influenced by its structure. The effects of the substituents at C3 position on the antioxidant activity of naringenin were carried out using the density functional theory (DFT) method. The reaction enthalpies related with the three well-established mechanisms were analyzed. Excellent correlations were found between the reaction enthalpies and Hammett sigma constants. Equations obtained from the linear regression can be helpful in the selection of suitable candidates for the synthesis of novel naringenin derivatives with enhanced antioxidant properties. In the gas and benzene phases, the antioxidant activity of naringenin was enhanced by the electron-donating substituents via weakening the bond dissociation enthalpy (BDE). In the water phase, it was strengthened by electron-withdrawing groups—via lowering the proton affinity (PA). The electronic effect of the substituent on the BDE of naringenin is mainly governed by the resonance effect, while that on the ionization potential (IP) and PA of naringenin is mainly controlled by the field/inductive effect.

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