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

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.

Effects of sodium nitrite reduction, removal or replacement on cured and cooked meat for microbiological growth, food safety, colon ecosystem, and colorectal carcinogenesis in Fischer 344 rats.

Epidemiological and experimental evidence indicated that processed meat consumption is associated with colorectal cancer risks. Several studies suggest the involvement of nitrite or nitrate additives via N-nitroso-compound formation (NOCs). Compared to the reference level (120 mg/kg of ham), sodium nitrite removal and reduction (90 mg/kg) similarly decreased preneoplastic lesions in F344 rats, but only reduction had an inhibitory effect on Listeria monocytogenes growth comparable to that obtained using the reference nitrite level and an effective lipid peroxidation control. Among the three nitrite salt alternatives tested, none of them led to a significant gain when compared to the reference level: vegetable stock, due to nitrate presence, was very similar to this reference nitrite level, yeast extract induced a strong luminal peroxidation and no decrease in preneoplastic lesions in rats despite the absence of NOCs, and polyphenol rich extract induced the clearest downward trend on preneoplastic lesions in rats but the concomitant presence of nitrosyl iron in feces. Except the vegetable stock, other alternatives were less efficient than sodium nitrite in reducing L. monocytogenes growth.

Design of an In Vitro Model to Screen the Chemical Reactivity Induced by Polyphenols and Vitamins during Digestion: An Application to Processed Meat.

Processed meats' nutritional quality may be enhanced by bioactive vegetable molecules, by preventing the synthesis of nitrosamines from N-nitrosation, and harmful aldehydes from lipid oxidation, through their reformulation. Both reactions occur during digestion. The precise effect of these molecules during processed meats' digestion must be deepened to wisely select the most efficient vegetable compounds. The aim of this study was to design an in vitro experimental method, allowing to foresee polyphenols and vitamins' effects on the chemical reactivity linked to processed meats' digestion. The method measured the modulation of end products formation (specific nitroso-tryptophan and thiobarbituric acid reactive substances (TBARS)), by differential UV-visible spectrophotometry, according to the presence or not of phenolic compounds (chlorogenic acid, rutin, naringin, naringenin) or vitamins (ascorbic acid and trolox). The reactional medium was supported by an oil in water emulsion mimicking the physico-chemical environment of the gastric compartment. The model was optimized to uphold the reactions in a stable and simplified model featuring processed meat composition. Rutin, chlorogenic acid, naringin, and naringenin significantly inhibited lipid oxidation. N-nitrosation was inhibited by the presence of lipids and ascorbate. This methodology paves the way for an accurate selection of molecules within the framework of processed meat products reformulation.