Oxidation of cinnamic acid derivatives: A pulse radiolysis and theoretical study

Yadav, Pooja; Mohan, Hari; Maity, Dilip Kumar; Suresh, Cherumuttathu H.; Rao, B. Sanjeeva

doi:10.1016/j.chemphys.2008.03.036

Cited by 9 publications

(4 citation statements)

References 37 publications

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“…Presumably the instability for both precursor and radical complexes would follow a monotonic increase from Complex (CHCl ·− ) to Complex (CHBr ·− ) to Complex (CHI ·− ) to Complex (CCl ·− 2 ) to Complex (CBr ·− 2 ) to Complex (CI ·− 2 ) because the investigated system is an ion-dipole complex. This is not inconsistent with the known result, 34 proposing the systems with the lowest S d is the most stable. More importantly, the S d values given above in CHX ·− abstractions are bigger than those in CX ·− 2 abstractions.…”

Section: Productssupporting

confidence: 65%

Theoretical study of the reactivity trends in the Cl-abstraction reactions of CHCl3 + CHX· − /CX2 · − (X = Cl, Br and I)

2011

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To better understand how and to what extent the halosubstituted carbene radical anions effect the chlorine abstraction of CHCl 3 , a detailed theoretical investigation has been performed at the UMP2/6-311++G (d, p)/RECP level of theory. The model system CHCl 3 + CHX ·− /CX ·− 2 (X = Cl, Br, and I) has been chosen for the present study. According to the detailed discussions of geometries and energetics of the optimized stationary points, our theoretical findings suggest that the Cl-abstraction reactions by CHX ·− are energetically favourable, indicating the less massive substitution X in CHX ·− the easier abstraction reaction, as compared to those by CX ·− 2 , which are energetically unfavourable and would be endothermic.

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Section: Productssupporting

confidence: 65%

Theoretical study of the reactivity trends in the Cl-abstraction reactions of CHCl3 + CHX· − /CX2 · − (X = Cl, Br and I)

2011

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“…It has been widely believed that other parts of the polyphenolic molecules contribute to antioxidant activity only insofar as they effect the stability of phenoxy radicals. ,− However, drawing on the well-known mechanism of styrene radical polymerization, it is not unreasonable to suspect that the α,β-unsaturated side chains of hydroxycinnamates could themselves be reactive toward radicals found in foods or biological systems. Furthermore, the radical reactivity of these unsaturated side chains has been demonstrated in theoretical systems involving neat ethanol, methanol, or aqueous solvents and pulse radiolysis. − Here we report for the first time that this side-chain reactivity is important in arresting the oxidation of a model wine, raising the question of how broadly applicable such antioxidant activity could be.…”

Section: Introductionmentioning

confidence: 79%

Novel Antioxidant Reactions of Cinnamates in Wine

Gislason

Currie

Waterhouse

2011

J. Agric. Food Chem.

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Plant-derived polyphenolic compounds have received much attention for their ability to sequester high-energy free radicals in a great variety of food-related and biological systems, protecting those systems from oxidative change. The ability of these compounds to scavenge free radicals has always been attributed to their phenolic functionality, from which a hydrogen atom can be easily abstracted. In this study, the cinnamates and the ubiquitous hydroxycinnamates were found to equally suppress the formation of oxidation products in wine exposed to the Fenton reaction (catalytic Fe(II) with hydrogen peroxide). Mechanistic investigations led to the unexpected discovery that the α,β-unsaturated side chain of cinnamic acids could efficiently trap 1-hydroxyethyl radicals, representing a newly discovered mode of antioxidant radical scavenging activity for these broadly occurring compounds in a food system. The proposed pathway is supported by prior fundamental studies with radiolytically generated radicals.

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“…Both cinnamic acid and its trans isomers are phenolic acids or intermediate compounds in the synthesis routes of flavonoids (Yadav et al, 2008). Phenolic acids have been reported to have antiviral effects against DENV, EHV-1 and HIV (Ichimura et al, 1999;Rees et al, 2008;Gravina et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

In vitro inhibition of canine distemper virus by flavonoids and phenolic acids: Implications of structural differences for antiviral design

Carvalho

Botelho

Ferreira

et al. 2013

Research in Veterinary Science

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Infection caused by canine distemper virus (CDV) is a highly contagious disease with high incidence and lethality in the canine population. Antiviral activity of flavonoids quercetin, morin, rutin and hesperidin, and phenolic cinnamic, trans-cinnamic and ferulic acids were evaluated in vitro against the CDV using the time of addition assay to determine which step of the viral replicative cycle was affected. All flavonoids displayed great viral inhibition when they were added at the times 0 (adsorption) and 1h (penetration) of the viral replicative cycle. Both quercetin and hesperidin presented antiviral activity at the time 2h (intracellular). In the other hand, cinnamic acid showed antiviral activity at the times 0 and 2h while trans-cinnamic acid showed antiviral effect at the times -1h (pre-treatment) and 0 h. Ferulic acid inhibited CDV replicative cycle at the times 0 and 1h. Our study revealed promising candidates to be considered in the treatment of CDV. Structural differences among compounds and correlation to their antiviral activity were also explored. Our analysis suggest that these compounds could be useful in order to design new antiviral drugs against CDV as well as other viruses of great meaning in veterinary medicine.

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Oxidation of cinnamic acid derivatives: A pulse radiolysis and theoretical study

Cited by 9 publications

References 37 publications

Theoretical study of the reactivity trends in the Cl-abstraction reactions of CHCl3 + CHX· − /CX2 · − (X = Cl, Br and I)

Theoretical study of the reactivity trends in the Cl-abstraction reactions of CHCl3 + CHX· − /CX2 · − (X = Cl, Br and I)

Novel Antioxidant Reactions of Cinnamates in Wine

In vitro inhibition of canine distemper virus by flavonoids and phenolic acids: Implications of structural differences for antiviral design

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