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

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2020 Oct 19

PMID 33073148

Citations 3

Authors

Daniela Fracassetti

Antonio Tirelli

Sara Limbo

Melissa Mastro

Luisa Pellegrino

Enzio M Ragg

Affiliations

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Abstract

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) in the RF-mediated photo-oxidation of Met. Water solutions of RF and Met, with and without GA or SO, 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 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 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 toward Met was found as a possible consequence of radical pathways involving oxygen.

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References

. Properties and use of sulphur dioxide. Food Addit Contam. 1992; 9(5):399-404. DOI: 10.1080/02652039209374090. View

Briviba K, Devasagayam T, Sies H, Steenken S . Selective para hydroxylation of phenol and aniline by singlet molecular oxygen. Chem Res Toxicol. 1993; 6(4):548-53. DOI: 10.1021/tx00034a025. View

Fracassetti D, Limbo S, Pellegrino L, Tirelli A . Light-induced reactions of methionine and riboflavin in model wine: Effects of hydrolysable tannins and sulfur dioxide. Food Chem. 2019; 298:124952. DOI: 10.1016/j.foodchem.2019.124952. View

Yang S . Sulfoxide formation from methionine or its sulfide analogs during aerobic oxidation of sulfite. Biochemistry. 1970; 9(25):5008-14. DOI: 10.1021/bi00827a027. View

Godelmann R, Fang F, Humpfer E, Schutz B, Bansbach M, Schafer H . Targeted and nontargeted wine analysis by (1)h NMR spectroscopy combined with multivariate statistical analysis. Differentiation of important parameters: grape variety, geographical origin, year of vintage. J Agric Food Chem. 2013; 61(23):5610-9. DOI: 10.1021/jf400800d. View

Bosca F, Miranda M, Morera I, Samadi A . Involvement of type I and type II mechanisms in the linoleic acid peroxidation photosensitized by tiaprofenic acid. J Photochem Photobiol B. 2001; 58(1):1-5. DOI: 10.1016/s1011-1344(00)00102-0. View

Min D, Boff J . Chemistry and Reaction of Singlet Oxygen in Foods. Compr Rev Food Sci Food Saf. 2021; 1(2):58-72. DOI: 10.1111/j.1541-4337.2002.tb00007.x. View

Sheraz M, Kazi S, Ahmed S, Anwar Z, Ahmad I . Photo, thermal and chemical degradation of riboflavin. Beilstein J Org Chem. 2014; 10:1999-2012. PMC: 4168737. DOI: 10.3762/bjoc.10.208. View

Silva E, Barrias P, Fuentes-Lemus E, Tirapegui C, Aspee A, Carroll L . Riboflavin-induced Type 1 photo-oxidation of tryptophan using a high intensity 365 nm light emitting diode. Free Radic Biol Med. 2018; 131:133-143. DOI: 10.1016/j.freeradbiomed.2018.11.026. View

10.

Vignault A, Gonzalez-Centeno M, Pascual O, Gombau J, Jourdes M, Moine V . Chemical characterization, antioxidant properties and oxygen consumption rate of 36 commercial oenological tannins in a model wine solution. Food Chem. 2018; 268:210-219. DOI: 10.1016/j.foodchem.2018.06.031. View

11.

Mattivi F, Monetti A, Vrhovsek U, Tonon D, Andres-Lacueva C . High-performance liquid chromatographic determination of the riboflavin concentration in white wines for predicting their resistance to light. J Chromatogr A. 2000; 888(1-2):121-7. DOI: 10.1016/s0021-9673(00)00561-6. View

12.

Lagunes I, Trigos A . Photo-oxidation of ergosterol: indirect detection of antioxidants photosensitizers or quenchers of singlet oxygen. J Photochem Photobiol B. 2015; 145:30-4. DOI: 10.1016/j.jphotobiol.2015.02.014. View

13.

Feldmeier C, Bartling H, Magerl K, Gschwind R . LED-illuminated NMR studies of flavin-catalyzed photooxidations reveal solvent control of the electron-transfer mechanism. Angew Chem Int Ed Engl. 2014; 54(4):1347-51. DOI: 10.1002/anie.201409146. View

14.

Barata-Vallejo S, Ferreri C, Postigo A, Chatgilialoglu C . Radiation chemical studies of methionine in aqueous solution: understanding the role of molecular oxygen. Chem Res Toxicol. 2009; 23(1):258-63. DOI: 10.1021/tx900427d. View

15.

Limbo S, Pellegrino L, DIncecco P, Gobbi S, Rosi V, Fracassetti D . Storage of pasteurized milk in clear PET bottles combined with light exposure on a retail display case: A possible strategy to define the shelf life and support a recyclable packaging. Food Chem. 2020; 329:127116. DOI: 10.1016/j.foodchem.2020.127116. View

16.

Gennaris A, Ezraty B, Henry C, Agrebi R, Vergnes A, Oheix E . Repairing oxidized proteins in the bacterial envelope using respiratory chain electrons. Nature. 2015; 528(7582):409-412. PMC: 4700593. DOI: 10.1038/nature15764. View

17.

Grant-Preece P, Barril C, Schmidtke L, Scollary G, Clark A . Light-induced changes in bottled white wine and underlying photochemical mechanisms. Crit Rev Food Sci Nutr. 2015; 57(4):743-754. DOI: 10.1080/10408398.2014.919246. View

18.

Navaratna S, Hamblett I, Tonnesen H . Photoreactivity of biologically active compounds. XVI. Formation and reactivity of free radicals in mefloquine. J Photochem Photobiol B. 2000; 56(1):25-38. DOI: 10.1016/s1011-1344(00)00056-7. View

19.

Cardoso D, Libardi S, Skibsted L . Riboflavin as a photosensitizer. Effects on human health and food quality. Food Funct. 2012; 3(5):487-502. DOI: 10.1039/c2fo10246c. View

20.

Caceres-Mella A, Flores-Valdivia D, Laurie V, Lopez-Solis R, Pena-Neira A . Chemical and sensory effects of storing sauvignon Blanc wine in colored bottles under artificial light. J Agric Food Chem. 2014; 62(29):7255-62. DOI: 10.1021/jf501467f. View