Formation of heterocyclic N-nitrosamines from the reaction of nitrite and selected primary diamines and amino acids

Warthesen, J. J.; Scanlan, Richard A.; Bills, Donald D.; Libbey, Leonard M.

doi:10.1021/jf60201a004

Cited by 86 publications

(24 citation statements)

References 20 publications

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“…275-277~ C30H5202; M + 444; [a]~ 8~ -3 ~ (CHC13), obtained by NaBH 4 reduction of (1)] is in conformity with the above stereochemical assignment and therefore the structure 1 is the complete representation of antidesmanol which is a C-16 epimer of pachysonol (7) isolated earlier from Pachysandra terminalis 6 (Buxaceae). On the other hand, the observed dissimilarity between the diols 5 and 6, [m.p.…”

Section: -290~supporting

confidence: 71%

Inhibition of nitrosamine formation by ascorbic acid: participation of free radicals in its anaerobic reaction with nitrite

Kalus

Filby

1980

Experientia

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Section: -290~supporting

confidence: 71%

Inhibition of nitrosamine formation by ascorbic acid: participation of free radicals in its anaerobic reaction with nitrite

Kalus

Filby

1980

Experientia

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“…Apart from a direct effect in promoting the transformation of cells, histamine and polyamines subjected to heat can give rise to secondary amines that can combine with nitrites, their salts generating nitrosamines of known carcinogenic, mutagenic and teratogenic activity [85,86]. This is of particular importance in some fermented meat products to which nitrates and nitrites are added as preservatives [61].…”

Section: Putrescine and Polyaminesmentioning

confidence: 99%

Toxicological Effects of Dietary Biogenic Amines

Ladero¹,

Calles-Enríquez²,

Fernández³

et al. 2010

CNF

445

294

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Biogenic amines (BAs) are defined as low molecular weight organic bases with biological activity. They are formed and degraded as part of the normal metabolism of microorganisms, plants and animals, in which they have important physiological functions. In humans, BAs are involved in brain activity, the regulation of body temperature and stomach pH, gastric acid secretion, the immune response, and cell growth and differentiation etc. However, the consumption of foods with high concentrations of BAs can induce adverse reactions such as nausea, headaches, rashes and changes in blood pressure. The accumulation of BAs in the food matrix is mainly due to the presence of bacteria able to decarboxylate certain amino acids. The most common and powerful BAs found in food are histamine, tyramine and putrescine. Their contents vary, sometimes reaching over 2 g per kg. Histamine is the only BA for which

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“…It can potentiate the toxic effects of histamine by competing with it for the enzymes involved in the latter’s detoxification in the intestinal mucosa (diamine oxidase and N-methyltransferase) 7 , and may also increase the absorption of histamine into the bloodstream 13 . Dietary putrescine has also been associated with cancer, since it can form carcinogenic nitrosamines when it reacts with nitrites present in food 2,14 . Certainly it has been linked (along with the polyamines spermine and spermidine) to the appearance of colorectal adenoma 15 .…”

Section: Introductionmentioning

confidence: 99%

An altered gene expression profile in tyramine-exposed intestinal cell cultures supports the genotoxicity of this biogenic amine at dietary concentrations

Río

Redruello

Ladero

et al. 2018

Sci Rep

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Tyramine, histamine and putrescine are the most commonly detected and most abundant biogenic amines (BA) in food. The consumption of food with high concentrations of these BA is discouraged by the main food safety agencies, but legal limits have only been set for histamine. The present work reports a transcriptomic investigation of the oncogenic potential of the above-mentioned BA, as assessed in the HT29 human intestinal epithelial cell line. Tyramine had a greater effect on the expression of genes involved in tumorigenesis than did histamine or putrescine. Since some of the genes that showed altered expression in tyramine-exposed cells are involved in DNA damage and repair, the effect of this BA on the expression of other genes involved in the DNA damage response was investigated. The results suggest that tyramine might be genotoxic for intestinal cells at concentrations easily found in BA-rich food. Moreover, a role in promoting intestinal cancer cannot be excluded.

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Formation of heterocyclic N-nitrosamines from the reaction of nitrite and selected primary diamines and amino acids

Abstract: the reaction of several common primary amines and nitrite with regard to the formation of nitrosamines. EXPERIMENTAL PROCEDURES Amine Purity. Nitrosamine yields from primary amines were generally low, so it was necessary to establish the pu-

Cited by 86 publications

References 20 publications

Inhibition of nitrosamine formation by ascorbic acid: participation of free radicals in its anaerobic reaction with nitrite

Inhibition of nitrosamine formation by ascorbic acid: participation of free radicals in its anaerobic reaction with nitrite

Toxicological Effects of Dietary Biogenic Amines

An altered gene expression profile in tyramine-exposed intestinal cell cultures supports the genotoxicity of this biogenic amine at dietary concentrations

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