Transformation of resveratrol under disinfection conditions

Detenchuk, Elena A.; Trebše, Polonca; Marjanović, Aleksandra; Kosyakov, D. S.; Ul’yanovskii, N. V.; Kralj, Mojca Bavcon; Lebedev, A. T.

doi:10.1016/j.chemosphere.2020.127557

Cited by 13 publications

(14 citation statements)

References 33 publications

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“…The protective role of antioxidants in disinfection conditions has been supported by another study, dealing with the behavior of resveratrol in chlorinated waters. It reported the formation of more than 80 products, expressing resveratrol's protective role and its high potential for acting as a scavenger of reactive oxygen species (ROS) in sunscreens [26], and confirms the comparison of pairs 5 and 6 in Table 4.…”

Section: Discussionsupporting

confidence: 66%

“…Antioxidants, added to sunscreens, may react under disinfection conditions as well. Over 80 transformation products of resveratrol were identified using GC-HRMS and UPLC-HRMS, with chlorinated phenols and biphenyls found to be the most relevant among them [ 26 ]. Furthermore, β-carotene-type terpenoids mostly form trihalomethanes (CHBrCl 2 , CHBr 2 Cl, CHBr 3 ) as final disinfection products, most likely through haloform reactions on methyl ketone groups in the complex suites of reaction intermediates.…”

Section: Introductionmentioning

confidence: 99%

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Analyzing the Photoprotection Efficiency of Sunscreens Containing Antioxidants under Disinfection Conditions

Sotler

Adamič²,

Jarni

et al. 2021

Antioxidants

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Sunscreens ensure thorough protection against sunburn. The delivery of UV filters into the stratum corneum and viable epidermis could be reduced by the use of antioxidants (such as β-carotene and trans-resveratrol, alone or combined). The presence/absence of antioxidants (trans-resveratrol and β-carotene) in formulations containing benzophenone-3 (UV-filter) and their efficiency under disinfection and neutral conditions are studied and compared. The trial was conducted on 38 people. The prepared ointments were applied to the participants’ forearms, irradiated and monitored by reflectance colorimetry after 0, 4, 6, and 8 min. Descriptive statistics were used to describe the skin color’s main characteristics and the F-ratio was used to test overall differences. The ointments containing antioxidants and benzophenone-3 were the most efficient, followed by those with benzophenone-3 alone. It was proven that photoprotection with benzophenone-3 is still effective, despite the formation of its chlorinated products. Due to the short time of exposure to disinfecting conditions, it could be assumed that benzophenone-3 was only partially chlorinated. This clinical study demonstrated that formulations containing antioxidants are likely to be more suitable for protecting skin against UVB irradiation than a UV filter alone.

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Section: Discussionsupporting

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Analyzing the Photoprotection Efficiency of Sunscreens Containing Antioxidants under Disinfection Conditions

Sotler

Adamič²,

Jarni

et al. 2021

Antioxidants

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“…The reactivity of the double bond becomes comparable to the reactivity of aromatic rings only in the presence of the most active substituents, which activate electrophilic aromatic substitution. In particular, the aqueous chlorination of resveratrol proceeds simultaneously at the double bond and at the rings with hydroxyl groups [ 97 ]. More than 80 DBPs, including polychlorinated biphenyls and monoaromatic compounds, were identified by GC/HRMS analysis; addition, substitution, ring-opening, and cyclization reactions took place ( Fig.…”

Section: Transformation Of Olefins and Compounds With C=c Bondsmentioning

confidence: 99%

Transformation of Organic Compounds during Water Chlorination/Bromination: Formation Pathways for Disinfection By-Products (A Review)

Mazur

Lebedev

2022

J Anal Chem

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The purity of drinking water is an important issue of the human life quality. Water disinfection has saved millions people from the diseases spread with water. However, that procedure has a certain drawback due to formation of toxic organic disinfection products. Establishing the structures of these products and the mechanisms of their formation and diminishing their levels in drinking water represent an important task for chemistry and medicine, while mass spectrometry is the most efficient tool for the corresponding studies. The current review throws light upon natural and anthropogenic sources of the formation of disinfection by-products (DBPs) and the mechanisms of their formation related to the structural peculiarities and the presence of functional groups. In addition to chlorination, bromination is discussed since it is used quite often as an alternative method of disinfection, particularly, for the purification of swimming pool water. The benefits of the contemporary GC/MS and LC/MS methods for the elucidation of DBP structures and study of the mechanisms of their formation are discussed. The reactions characteristic for various functional groups and directions of transformation of certain classes of organic compounds in conditions of aqueous chlorination/bromination are also covered in the review.

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“…Transformation of the antioxidant resveratrol by chlorine was explored by Detenchuk et al GC-HRMS and UPLC-HRMS were used to tentatively identify >80 DBPs, with several chlorinated phenols and biphenyls formed. Phenazone drugs and their metabolites were the focus of a study by Sieira et al, who investigated DBPs formed by chlorine and monochloramine .…”

Section: Drinking Water and Swimming Pool Disinfection Byproductsmentioning

confidence: 99%