Hydrogen atom transfer in the reaction of hydroxycinnamic acids with OH and HO2 radicals: DFT study

Nsangou, Mama; Fifen, Jean Jules; Dhaouadi, Zoubeida; Lahmar, S.

doi:10.1016/j.theochem.2008.04.028

Cited by 22 publications

(16 citation statements)

References 44 publications

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“…So, in this state of molecules (complex) done spontaneously, it is good to know their antioxidant potency. Many studies have been carried out to search for and to develop antioxidants having natural origin [19,[27][28][29][30][31][32][33]. To evaluate the antioxidant activity of chelates (compounds resulting from the chelation), the reactions of Eqs.…”

Section: Introductionmentioning

confidence: 99%

Antioxidative Potency and UV–Vis spectra features of the compounds resulting from the chelation of Fe2+ by Caffeic Acid Phenethyl Ester and two of its derivatives

Holtomo

Nsangou

Fifen

et al. 2015

Computational and Theoretical Chemistry

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Section: Introductionmentioning

confidence: 99%

Antioxidative Potency and UV–Vis spectra features of the compounds resulting from the chelation of Fe2+ by Caffeic Acid Phenethyl Ester and two of its derivatives

Holtomo

Nsangou

Fifen

et al. 2015

Computational and Theoretical Chemistry

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“…Therefrom, it is noteworthy that the scavenging of hydroxyl radical by 3,4-DHPPA passes through a transition state (TS) while that of OBr − anion is barrierless. Moreover, it is well-known that the reaction of a phenolic acid (PhA) with neutral ROS leads to PCET mechanism while that with negatively charged ROS undergoes a barrierless PT mechanism [3,12,18,43,44]. This result may be generalized to PhAs which only have carbon, oxygen, and hydrogen in their skeleton (e.g., Quercetin may be a good candidate) and are involving the same RS or other.…”

Section: Resultsmentioning

confidence: 99%

“…PhAs and their derivatives are widely present in plants (vegetables, fruits, grains, and spices), many being metabolites and several functions being attributed to them [12]. PhAs may contribute to the dark colour, bitter taste, and objectionable flavour of some fruits, leaves, and seeds.…”

Section: Introductionmentioning

confidence: 99%

“…PhAs may contribute to the dark colour, bitter taste, and objectionable flavour of some fruits, leaves, and seeds. They have been considered as possible agents that influence toxicological, nutritional, sensory, and antioxidant properties of foods [12]. It has also been reported that phenolic acids may activate or inhibit microbial growth [12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

“…They have been considered as possible agents that influence toxicological, nutritional, sensory, and antioxidant properties of foods [12]. It has also been reported that phenolic acids may activate or inhibit microbial growth [12][13][14][15][16]. PhAs present antioxidant activity and exert this property through their capacity to donate hydrogen atoms, protons, and/or electrons to inhibit reactive oxygen species.…”

Section: Introductionmentioning

confidence: 99%

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Proton-Coupled Electron Transfer in the Reaction of 3,4-Dihydroxyphenylpyruvic Acid with Reactive Species in Various Media

Fifen

Dhaouadi

Nsangou

et al. 2015

International Journal of Chemical Physics

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The distinction of concerted proton-coupled electron transfer (CPCET) from sequential one as well as proton transfer-electron transfer (PT-ET) from electron transfer-proton transfer (ET-PT) in the O-H bond cleavage reactions in various media has always been a difficult task. In this work, the activation barrier of the CPCET mechanism, its rate constants, and reaction free energies related to ET-PT and PT-ET involving coreactive species were presented as good parameters to attempt the problem. DFT calculations were carried out studying the described pathways subsequent to the scavenging of• OH and OBr − by the 3,4-DHPPA in various media. The solvation was described in a hybrid manner using IEF-PCM model conjointly with a model that takes into account some solute-solvent interactions. As a result, we found that the scavenging of hydroxyl radical by 3,4-DHPPA is thermodynamically governed by a one-step hydrogen atom transfer (CPCET) from the acid to the radical in all media. In kinetic viewpoint, CPCET still dominates in the vacuum and in nonpolar solvents, but in polar solvents it could compete strongly with the ET-PT mechanism so that the latter could slightly dominate.

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Systems engineering Escherichia coli for efficient production p‐coumaric acid from glucose

Qiu,

Wang,

Zuo

et al. 2024

Biotech & Bioengineering

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P‐coumaric acid (p‐CA), a pant metabolite with antioxidant and anti‐inflammatory activity, is extensively utilized in biomedicine, food, and cosmetics industry. In this study, a synthetic pathway (PAL) for p‐CA was designed, integrating three enzymes (AtPAL2, AtC4H, AtATR2) into a higher l‐phenylalanine‐producing strain Escherichia coli PHE05. However, the lower soluble expression and activity of AtC4H in the PAL pathway was a bottleneck for increasing p‐CA titers. To overcome this limitation, the soluble expression of AtC4H was enhanced through N‐terminal modifications. And an optimal mutant, AtC4HL373T/G211H, which exhibited a 4.3‐fold higher kcat/Km value compared to the wild type, was developed. In addition, metabolic engineering strategies were employed to increase the intracellular NADPH pool. Overexpression of ppnk in engineered E. coli PHCA20 led to a 13.9‐folds, 1.3‐folds, and 29.1% in NADPH content, the NADPH/NADP+ ratio and p‐CA titer, respectively. These optimizations significantly enhance p‐CA production, in a 5‐L fermenter using fed‐batch fermentation, the p‐CA titer, yield and productivity of engineered strain E. coli PHCA20 were 3.09 g/L, 20.01 mg/g glucose, and 49.05 mg/L/h, respectively. The results presented here provide a novel way to efficiently produce the plant metabolites using an industrial strain.

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Hydrogen atom transfer in the reaction of hydroxycinnamic acids with OH and HO2 radicals: DFT study

Cited by 22 publications

References 44 publications

Antioxidative Potency and UV–Vis spectra features of the compounds resulting from the chelation of Fe2+ by Caffeic Acid Phenethyl Ester and two of its derivatives

Antioxidative Potency and UV–Vis spectra features of the compounds resulting from the chelation of Fe2+ by Caffeic Acid Phenethyl Ester and two of its derivatives

Proton-Coupled Electron Transfer in the Reaction of 3,4-Dihydroxyphenylpyruvic Acid with Reactive Species in Various Media

Systems engineering Escherichia coli for efficient production p‐coumaric acid from glucose

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