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Investigating the Role of Antioxidant Compounds in Riboflavin-Mediated Photo-Oxidation of Methionine: A (1)H-NMR Approach

[Image: see text] Riboflavin (RF) is a well-known photosensitizer, responsible for the light-induced oxidation of methionine (Met) leading to the spoilage of wine. An NMR approach was used to investigate the role of gallic acid (GA) and sulfur dioxide (SO(2)) in the RF-mediated photo-oxidation of Me...

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Autores principales: Fracassetti, Daniela, Tirelli, Antonio, Limbo, Sara, Mastro, Melissa, Pellegrino, Luisa, Ragg, Enzio M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7558052/
https://www.ncbi.nlm.nih.gov/pubmed/33073148
http://dx.doi.org/10.1021/acsomega.0c03845
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author Fracassetti, Daniela
Tirelli, Antonio
Limbo, Sara
Mastro, Melissa
Pellegrino, Luisa
Ragg, Enzio M.
author_facet Fracassetti, Daniela
Tirelli, Antonio
Limbo, Sara
Mastro, Melissa
Pellegrino, Luisa
Ragg, Enzio M.
author_sort Fracassetti, Daniela
collection PubMed
description [Image: see text] Riboflavin (RF) is a well-known photosensitizer, responsible for the light-induced oxidation of methionine (Met) leading to the spoilage of wine. An NMR approach was used to investigate the role of gallic acid (GA) and sulfur dioxide (SO(2)) in the RF-mediated photo-oxidation of Met. Water solutions of RF and Met, with and without GA or SO(2), were exposed to visible light for increasing time in both air and nitrogen atmospheres. Upon light exposure, a new signal appeared at 2.64 ppm that was assigned to the S(O)CH(3) moiety of methionine sulfoxide. Its formation rate was lower in a nitrogen atmosphere and even lower in the presence of GA, supporting the ability of this compound in quenching the singlet oxygen. In contrast, SO(2) caused relevant oxidation of Met, moderately observed even in the dark, making Met less available in donating electrons to RF. The competition of GA versus Met photo-oxidation was revealed, indicating effectiveness of this antioxidant against the light-dependent spoilage of wine. A pro-oxidant effect of SO(2) toward Met was found as a possible consequence of radical pathways involving oxygen.
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spelling pubmed-75580522020-10-16 Investigating the Role of Antioxidant Compounds in Riboflavin-Mediated Photo-Oxidation of Methionine: A (1)H-NMR Approach Fracassetti, Daniela Tirelli, Antonio Limbo, Sara Mastro, Melissa Pellegrino, Luisa Ragg, Enzio M. ACS Omega [Image: see text] Riboflavin (RF) is a well-known photosensitizer, responsible for the light-induced oxidation of methionine (Met) leading to the spoilage of wine. An NMR approach was used to investigate the role of gallic acid (GA) and sulfur dioxide (SO(2)) in the RF-mediated photo-oxidation of Met. Water solutions of RF and Met, with and without GA or SO(2), were exposed to visible light for increasing time in both air and nitrogen atmospheres. Upon light exposure, a new signal appeared at 2.64 ppm that was assigned to the S(O)CH(3) moiety of methionine sulfoxide. Its formation rate was lower in a nitrogen atmosphere and even lower in the presence of GA, supporting the ability of this compound in quenching the singlet oxygen. In contrast, SO(2) caused relevant oxidation of Met, moderately observed even in the dark, making Met less available in donating electrons to RF. The competition of GA versus Met photo-oxidation was revealed, indicating effectiveness of this antioxidant against the light-dependent spoilage of wine. A pro-oxidant effect of SO(2) toward Met was found as a possible consequence of radical pathways involving oxygen. American Chemical Society 2020-09-29 /pmc/articles/PMC7558052/ /pubmed/33073148 http://dx.doi.org/10.1021/acsomega.0c03845 Text en This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Fracassetti, Daniela
Tirelli, Antonio
Limbo, Sara
Mastro, Melissa
Pellegrino, Luisa
Ragg, Enzio M.
Investigating the Role of Antioxidant Compounds in Riboflavin-Mediated Photo-Oxidation of Methionine: A (1)H-NMR Approach
title Investigating the Role of Antioxidant Compounds in Riboflavin-Mediated Photo-Oxidation of Methionine: A (1)H-NMR Approach
title_full Investigating the Role of Antioxidant Compounds in Riboflavin-Mediated Photo-Oxidation of Methionine: A (1)H-NMR Approach
title_fullStr Investigating the Role of Antioxidant Compounds in Riboflavin-Mediated Photo-Oxidation of Methionine: A (1)H-NMR Approach
title_full_unstemmed Investigating the Role of Antioxidant Compounds in Riboflavin-Mediated Photo-Oxidation of Methionine: A (1)H-NMR Approach
title_short Investigating the Role of Antioxidant Compounds in Riboflavin-Mediated Photo-Oxidation of Methionine: A (1)H-NMR Approach
title_sort investigating the role of antioxidant compounds in riboflavin-mediated photo-oxidation of methionine: a (1)h-nmr approach
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7558052/
https://www.ncbi.nlm.nih.gov/pubmed/33073148
http://dx.doi.org/10.1021/acsomega.0c03845
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