C -Nitrosation, C -Nitration, and Coupling of Flavonoids with N -Acetyltryptophan Limit This Amine N -Nitrosation in a Simulated Cured and Cooked Meat - Sécurité Qualité Produits d'Origine Végétale Access content directly
Journal Articles Journal of Agricultural and Food Chemistry Year : 2024

C -Nitrosation, C -Nitration, and Coupling of Flavonoids with N -Acetyltryptophan Limit This Amine N -Nitrosation in a Simulated Cured and Cooked Meat

Abstract

Nitrite is a common additive in cured meat formulation that provides microbiological safety, lipid oxidation management, and typical organoleptic properties. However, it is associated with the formation of carcinogenic N-nitrosamines. In this context, the antinitrosating capacity of selected flavonoids and ascorbate was evaluated in a simulated cooked and cured meat under formulation and digestion conditions. N-Acetyltryptophan was used as a secondary amine target. (-)-Epicatechin, rutin, and quercetin were all able to limit the formation of N-acetyl-N-nitrosotryptophan (NO-AcTrp) at pH 2.5 and pH 5 although (-)-epicatechin was 2 to 3-fold more efficient. Kinetics for the newly identified compounds allowed us to unravel common mechanistic pathways, which are flavonoid oxidation by nitrite followed by C-nitration and an original covalent coupling between NO-AcTrp and flavonoids or their nitro and nitroso counterparts. C-nitrosation of the A-ring was evidenced only for (-)-epicatechin. These major findings suggest that flavonoids could help to manage N-nitrosamine formation during cured meat processing, storage, and digestion.
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Wednesday, February 19, 2025
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Wednesday, February 19, 2025
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Dates and versions

hal-04524904 , version 1 (09-04-2024)

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Charlène Sirvins, Pascale Goupy, Aurélie Promeyrat, Claire Dufour. C -Nitrosation, C -Nitration, and Coupling of Flavonoids with N -Acetyltryptophan Limit This Amine N -Nitrosation in a Simulated Cured and Cooked Meat. Journal of Agricultural and Food Chemistry, 2024, 72 (9), pp.4777-4787. ⟨10.1021/acs.jafc.3c08445⟩. ⟨hal-04524904⟩
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