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

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

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

10.26434/chemrxiv.14493846.v2 ◽

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 (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). 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, 7.13x106 M-1 s-1) while RAF is more dominant with C2 (kapp, 1.40x105 M-1 s-1) and C3 (kapp, 2.90x105 M-1 s-1). Antioxidant activity of aaptamine derivatives can be classified as C1 > C3 > C2. 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.

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Density Functional Theory Calculations of the Radical Scavenging Activity of Alkannin Derivatives

Applied Mechanics and Materials ◽

10.4028/www.scientific.net/amm.189.225 ◽

2012 ◽

Vol 189 ◽

pp. 225-231

Author(s):

Xiang Peng Guo ◽

Rui Fa Jin

Keyword(s):

Density Functional ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Density Functional Theory Calculations ◽

Hydrogen Atom Transfer ◽

Scavenging Activity ◽

Functional Theory ◽

Hydrogen Bond Formation ◽

Structural And Electronic Properties ◽

The One

The structural and electronic properties of alkannin and its derivatives and their radicals were investigated at density functional level. It turned out that the presence of the dihydroxy functionality increases the radical stability through hydrogen bond formation. The hydrogen atom transfer for alkannin derivatives is difficult to occur compared with zero compound phenol. However, alkannin derivatives appear to be good candidates for the one-electron-transfer, particularly for alkannin derivatives with –OCOCH=CH(CH3)2 and –OCOCH2CH(CH3)2 groups. It suggests that 1–7 are expected to be the promising candidates for radical scavenging activity compounds because The ionization potential (IP) values of 1–7 are lower than that of the zero compound phenol.

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Scavenging of hydroxyl radical by kinsenoside originated from anoectochilus roxburghii: A DFT approach

Journal of Science and Technology Issue on Information and Communications Technology ◽

10.31130/jst-ud2019-135e ◽

2020 ◽

pp. 72-76

Author(s):

Nguyen Minh Thong Nguyen

Keyword(s):

Hydroxyl Radical ◽

Density Functional ◽

Energy Surface ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Hydrogen Atom Transfer ◽

Single Electron Transfer ◽

Functional Theory ◽

Anoectochilus Roxburghii ◽

Radical Scavenging Properties

- A density functional theory (DFT) study on the hydroxyl radical scavenging properties of Kinsenoside originated from Anoectochilus roxburghii is presented. Two mechanisms, single electron transfer (SET) and hydrogen atom transfer (HAT) are considered. The thermochemical results demonstrate that the SET mechanism is not plausible to occur. With respect to the HAT, the interaction of OH• radical with Kinsenoside is also studied in detail by establishing potential energy surface (PES). This result strongly confirms that the C8H bond decides the radical scavenging activity of Kinsenoside with activation Gibbs free energy (∆G≠) and rate constants (k) of 1.1 kcal/mol and 5.9×10-8 cm3/molecules, respectively

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COMBINED EXPERIMENTAL AND COMPUTATIONAL STUDY OF THE RADICAL SCAVENGING ACTIVITY OF LUTEOLIN

Journal of Theoretical and Computational Chemistry ◽

10.1142/s0219633613500211 ◽

2013 ◽

Vol 12 (05) ◽

pp. 1350021 ◽

Cited By ~ 3

Author(s):

ABDULLAH G. AL-SEHEMI ◽

AHMAD IRFAN ◽

SALHA MANA ALJUBIRI ◽

KAMEL HUSSEIN SHAKER

Keyword(s):

Density Functional Theory ◽

Absorption Spectra ◽

Density Functional ◽

Computational Study ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

2D Nmr ◽

Hydrogen Atom Transfer ◽

Functional Theory ◽

Polarized Continuum Model

The luteolin has been extracted from Euphorbia schimperiana then 1H NMR, 13C NMR and 2D NMR spectra were measured. The ground-state geometries have been computed by using density functional theory (DFT) at B3LYP/6-31G* and M06/6-31++G** level of theories. The time dependent density functional theory (TD-DFT) has been applied to compute the absorption spectra with and without solvent. The absorption spectra have been computed in methanol to check the effect of solvent using the polarized continuum model (PCM). On the basis of bond dissociation enthalpy (BDE) and the adiabatic ionization potential (IP), we have explained the antioxidant activity of luteolin and its rotamer/positional isomer. Two mechanisms have been explained for the radical scavenging processes, i.e. hydrogen atom transfer and one-electron transfer.

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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

Progress in Reaction Kinetics and Mechanism ◽

10.3184/146867818x15161889114484 ◽

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).

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Sorbicillasins A–B and Scirpyrone K from a Deep-Sea-Derived Fungus, Phialocephala sp. FL30r

Marine Drugs ◽

10.3390/md16070245 ◽

2018 ◽

Vol 16 (7) ◽

pp. 245 ◽

Cited By ~ 6

Author(s):

Zhenzhen Zhang ◽

Xueqian He ◽

Qian Che ◽

Guojian Zhang ◽

Tianjiao Zhu ◽

...

Keyword(s):

Deep Sea ◽

Density Functional ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Time Dependent ◽

Scavenging Activity ◽

Functional Theory ◽

Ic50 Value ◽

Td Dft ◽

Dependent Density

Two new nitrogen-containing sorbicillinoids named sorbicillasins A and B (1 and 2) and a new 3,4,6-trisubstituted α-pyrone derivative, scirpyrone K (3), together with two known biosynthetically related polyketides (4–5), were isolated from the deep-sea-derived fungus Phialocephala sp. FL30r by using the OSMAC (one strain-many compounds) method. The structures of 1–3, including absolute configurations, were deduced based on MS, NMR, and time-dependent density functional theory (TD-DFT) calculations of specific ECD (electronic circular dichroism) spectra. Compounds 1 and 2 possessed a novel hexahydropyrimido[2,1-a] isoindole moiety, and compound 3 exhibited weak radical scavenging activity against DPPH (2,2-diphenyl-1-picrylhydrazyl) with an IC50 value of 27.9 μM.

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DPPH Radical Scavenging Activity of Tricin and Its Conjugates Isolated from “Njavara” Rice Bran: A Density Functional Theory Study

Journal of Agricultural and Food Chemistry ◽

10.1021/jf204826e ◽

2012 ◽

Vol 60 (14) ◽

pp. 3693-3699 ◽

Cited By ~ 26

Author(s):

Manjaly J. Ajitha ◽

Smitha Mohanlal ◽

Cherumuttathu H. Suresh ◽

Ananthasankaran Jayalekshmy

Keyword(s):

Density Functional Theory ◽

Density Functional ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Scavenging Activity ◽

Density Functional Theory Study ◽

Dpph Radical ◽

Dpph Radical Scavenging Activity ◽

Functional Theory ◽

Dpph Radical Scavenging

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

International Journal of Molecular Sciences ◽

10.3390/ijms20061450 ◽

2019 ◽

Vol 20 (6) ◽

pp. 1450 ◽

Cited By ~ 3

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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