Antioxidising activity of cinnamic acid derivatives against oxidative stress induced by oxidising radicals

Santos, Pedro M.P.; Vieira, Abel J. S. C.

doi:10.1002/poc.3104

Cited by 10 publications

(9 citation statements)

References 46 publications

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“…In practice, CO2 volumes equivalent to 9% of the total expected carbon were measured over three hours in the deoxygenated conditions, which, allowing for dissolution, is within a reasonable margin of error. It should be noted that the concentrations of 3 detected in our experiments do not match the amounts predicted if all of the CA was converted via this route but the difference can be attributed to some simultaneous degradation of 3 (via oxygen free routes in contrast to the reaction described in Scheme 2) and competition with hydroxylation of the aromatic ring which Santos et al 26 identified as a significant route for the reaction of cinnamic acid with hydroxyl radicals generated by gamma radiolysis.…”

Section: The Mechanism Of the Photocatalytic Decomposition Of Cinnamic Acidcontrasting

confidence: 85%

“…Scheme 3, for example shows competing pathways to products 2 and 3 arising from attack by the hydroxyl radical on different sides of the exocyclic C=C. Hydroxylation of the position α to the carboxylic acid moiety then leads to decarboxylation to a styryl alcohol that tautomerises to product 3, as suggested by Santos et al 26 Alternatively, hydroxylation at the other side of the double bond followed by attachment of oxygen or superoxide at the radical centre and a reverse-aldol reaction cleaving the C-C bond gives 2 and O=CH-CO2H. Note too, that the order of hydroxylation and dioxygen attack could be reversed and still give 2.…”

Section: The Mechanism Of the Photocatalytic Decomposition Of Cinnamic Acidmentioning

confidence: 88%

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The photocatalytic destruction of cinnamic acid and cinnamyl alcohol: Mechanism and the effect of aqueous ions

2020

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Cinnamic acid was chosen as an exemplar molecule to study the effect of potential contaminants on the kinetics and mechanism of the photocatalytic destruction of hydrocarbons in aqueous solutions. We identify the principal intermediates in the photocatalytic reaction of the acid and corresponding alcohol, and propose a mechanism that explains the presence of these species. The impact of two likely contaminants of aqueous systems, sulfate and chloride ions were also studied. Whereas sulfate ions inhibit the degradation reaction at all concentrations, chloride ions, up to a concentration of 0.5 M, accelerate the removal of cinnamic acid from solution by a factor of 1.6. However, although cinnamic acid is removed, the pathway to complete oxidation is blocked by the chloride, with the acid being converted (in the presence of oxygen) into new products including acetophenone, 2-chloroacetophenone, 1-(2-chlorophenyl)ethenone and 1,2-dibenzoylethane. We speculate that the formation of these products involves chlorine radicals formed from the reaction of chloride ions with the photoinduced holes at the catalyst surface. Interestingly, we have shown that the 1-(2-chlorophenyl)ethenone and 1,2-dibenzoylethane products form from 2chloroacetophenone when irradiated with 365 nm light in the absence of the catalyst. The formation of potentially dangerous side products in this reaction suggest that the practical implementation of the photocatalytic purification of contaminated water needs to considered very carefully if chlorides are likely to be present.

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Section: The Mechanism Of the Photocatalytic Decomposition Of Cinnamic Acidcontrasting

confidence: 85%

Section: The Mechanism Of the Photocatalytic Decomposition Of Cinnamic Acidmentioning

confidence: 88%

The photocatalytic destruction of cinnamic acid and cinnamyl alcohol: Mechanism and the effect of aqueous ions

2020

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“…Trans-2,3-dihydroxycinnamate is a derivative of cinnamic acid, which is an intermediate in the biosynthesis of lignin, flavonoids, and other secondary metabolites produced by plants like C. sativa (87). Cinnamic acid and its derivatives, like trans-2,3-dihydroxycinnamate, possess antioxidizing activity (88). Vanillic acid is a dihydroxybenzoic acid derivative commonly used as a flavoring agent.…”

Section: Hydroxycinnamic Acid Derivativesmentioning

confidence: 99%

Alteration of the Canine Metabolome After a 3-Week Supplementation of Cannabidiol (CBD) Containing Treats: An Exploratory Study of Healthy Animals

et al. 2021

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Despite the increased interest and widespread use of cannabidiol (CBD) in humans and companion animals, much remains to be learned about its effects on health and physiology. Metabolomics is a useful tool to evaluate changes in the health status of animals and to analyze metabolic alterations caused by diet, disease, or other factors. Thus, the purpose of this investigation was to evaluate the impact of CBD supplementation on the canine plasma metabolome. Sixteen dogs (18.2 ± 3.4 kg BW) were utilized in a completely randomized design with treatments consisting of control and 4.5 mg CBD/kg BW/d. After 21 d of treatment, blood was collected ~2 h after treat consumption. Plasma collected from samples was analyzed using CIL/LC-MS-based untargeted metabolomics to analyze amine/phenol- and carbonyl-containing metabolites. Metabolites that differed — fold change (FC) ≥ 1.2 or ≤ 0.83 and false discovery ratio (FDR) ≤ 0.05 — between the two treatments were identified using a volcano plot. Biomarker analysis based on receiver operating characteristic (ROC) curves was performed to identify biomarker candidates (area under ROC ≥ 0.90) of the effects of CBD supplementation. Volcano plot analysis revealed that 32 amine/phenol-containing metabolites and five carbonyl-containing metabolites were differentially altered (FC ≥ 1.2 or ≤ 0.83, FDR ≤ 0.05) by CBD; these metabolites are involved in the metabolism of amino acids, glucose, vitamins, nucleotides, and hydroxycinnamic acid derivatives. Biomarker analysis identified 24 amine/phenol-containing metabolites and 1 carbonyl-containing metabolite as candidate biomarkers of the effects of CBD (area under ROC ≥ 0.90; P < 0.01). Results of this study indicate that 3 weeks of 4.5 mg CBD/kg BW/d supplementation altered the canine metabolome. Additional work is warranted to investigate the physiological relevance of these changes.

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“…• OH-mediated reaction pathways. Hydroxylation at the other side of the double bond of cinnamic acid, followed by attaching the superoxide or oxygen at the radical center and a reverse-aldol reaction cleaving the C−C bond, produces benzaldehyde as well as O=CH−CO 2 H; this has been documented as an important pathway for the reaction of • OH with cinnamic acid (Santos and Vieira 2013). Benzaldehyde is a reactive chemical (Jin et al 1998), which exhibits bioreactive toxicity to increase the overall toxicity of the system.…”

Section: The Photochemical Degradation Mechanismmentioning

confidence: 99%

Insights into the Photodegradation of the Contact Allergen Fragrance Cinnamyl Alcohol: Kinetics, Mechanism, and Toxicity

Gao

Luo

et al. 2021

Enviro Toxic and Chemistry

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Fragrances can cause general health issues, and special concerns exist surrounding the issue of skin safety. Cinnamyl alcohol (CAL) is a frequent fragrance contact allergen that has various toxic effects on indiscriminate animals. In the present study, the photodegradation transformation mechanism of CAL and toxicity evolution during this process were examined. The results showed that CAL (50 μM) can be completely degraded after 90-min ultraviolet (UV) irradiation with a degradation rate of 0.086 min -1 . Increased toxicity on bioluminescent bacteria was observed during this process, with lethality increasing from 10.6% (0 min) to 50.2% (90 min) under UV light irradiation. Further, the photodegradation mechanisms of CAL were explored to find the reason behind the increased toxicity observed. Laser flash photolysis and quenching experiments showed that O 2•-, 1 O 2 , and • OH were mainly responsible for CAL photodegradation, together with 3 CAL* and e aq -. The 5 main photodegradation products were cinnamyl aldehyde, benzaldehyde, benzenepropanal, cinnamic acid, and toluene, as identified using gas chromatography-mass spectrometry and liquid chromatography-quadrupole-time-offlight-mass spectrometry. Once exposed to air, CAL was found to be easily oxidized to cinnamyl aldehyde and subsequently to cinnamic acid by O 2 •-or 1 O 2 -mediated pathways, leading to increased toxicity. Benzaldehyde exhibited bioreactive toxicity, increasing the toxicity through • OH-mediated pathways. Theoretical prediction of skin irritation indicated that cinnamyl aldehyde (0.83), benzenepropanal (0.69), cinnamyl aldehyde (0.69), and benzaldehyde (0.70) were higher than CAL (0.63), which may cause a profound impact on an individual's health and well-being. Overall, the present study advances the understanding of the photodegradation processes and health impacts of fragrance ingredients.

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Antioxidising activity of cinnamic acid derivatives against oxidative stress induced by oxidising radicals

Cited by 10 publications

References 46 publications

The photocatalytic destruction of cinnamic acid and cinnamyl alcohol: Mechanism and the effect of aqueous ions

The photocatalytic destruction of cinnamic acid and cinnamyl alcohol: Mechanism and the effect of aqueous ions

Alteration of the Canine Metabolome After a 3-Week Supplementation of Cannabidiol (CBD) Containing Treats: An Exploratory Study of Healthy Animals

Insights into the Photodegradation of the Contact Allergen Fragrance Cinnamyl Alcohol: Kinetics, Mechanism, and Toxicity

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