Reaction of Nitrite With Ascorbate and Its Relation to Nitrosamine Formation2

Archer, Michael C.; Tannenbaum, Steven R.; Fan, Tsai-Yi; Weisman, M.

doi:10.1093/jnci/54.5.1203

Cited by 100 publications

(40 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Accordingly, chlorogenic acid and quercetin (phenolics exhibiting a catechol moiety) were shown to enhance the production of U NO from nitrite at acidic pH [18,19]. On the other hand, ascorbic acid, a compound that exhibits a low redox potential, and actively secreted in the stomach, has also been shown to be an efficient one-electron reductant of nitrite [42,43].…”

Section: Discussionmentioning

confidence: 99%

Red wine-dependent reduction of nitrite to nitric oxide in the stomach

Gago

Lundberg

Barbosa

et al. 2007

Free Radical Biology and Medicine

158

111

View full text Add to dashboard Cite

Nitrite may be a source for nitric oxide ( U NO), particularly in highly acidic environments, such as the stomach. Diet products contribute also with reductants that dramatically increase the production of U NO from nitrite. Red wine has been attributed health promoting properties largely on basis of the reductive antioxidant properties of its polyphenolic fraction. We show in vitro that wine, wine anthocyanin fraction and wine catechol (caffeic acid) dose-and pH-dependently promote the formation of U NO when mixed with nitrite, as measured electrochemically. The production of U NO promoted by wine from nitrite was substantiated in vivo in healthy volunteers by measuring U NO in the air expelled from the stomach, following consumption of wine, as measured by chemiluminescence. Mechanistically, the reaction involves the univalent reduction of nitrite, as suggested by the formation of U NO and by the appearance of EPR spectra assigned to wine phenolic radicals. Ascorbic and caffeic acids cooperate in the reduction of nitrite to U NO. Moreover, reduction of nitrite is critically dependent on the phenolic structure and nitro-derivatives of phenols are also formed, as suggested by caffeic acid UV spectral modifications. The reduction of nitrite may reveal previously unrecognized physiologic effects of red wine in connection with U NO bioactivity.

show abstract

Section: Discussionmentioning

confidence: 99%

Red wine-dependent reduction of nitrite to nitric oxide in the stomach

Gago

Lundberg

Barbosa

et al. 2007

Free Radical Biology and Medicine

158

111

View full text Add to dashboard Cite

show abstract

“…The inhibiting effect of ascorbic acid on the artifactual nitrosamine formation has been described in several publications [33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Analysis of Volatile N-Nitrosamines in Mainstream and Sidestream Smoke from Cigarettes by GLC-TEA

Brunnemann

Fink

Moser³

1980

Oncology

View full text Add to dashboard Cite

Volatile N-nitrosamines were quantitatively determined in mainstream and sidestream smoke of commercial cigarettes using gas chromatography-thermal energy analysis (GLC-TEA). The smoke was trapped in ascorbic acid solution buffered at pH 4.5 and then extracted with dichloromethane; the organic phase was chromatographed on basic alumina and analyzed by GLC-TEA. The mainstream smoke of 22 different commercial cigarettes from Germany and Switzerland contained between 0.1 and 27 ng dimethylnitrosamine (DMN), 1.5 and 29 ng nitrosopyrrolidine (NPY) and traces of methylethylnitrosamine (MEN). The side-stream smoke of these cigarettes contained between 143 and 415 ng DMN, 3.1 and 27 ng MEN and 28 and 150 ng NPY. In a final experiment we measured the DMN concentration in a sealed experimental chamber as a function of the number of cigarettes smoked and recovered 68-87% of the DMN values found when using the sidestream collection device applied in the other experiments.

show abstract

“…For example, when ascorbic acid is oxidized to dehydroascorbic acid, nitrous anhydride, a potent nitrosating agent formed from sodium nitrite, is reduced to NO, which is not a nitrosating agent. Stoichiometrically, one molecule of ascorbic acid can reduce two molecules of acidified nitrite to NO [73,74]. However, in the presence of dissolved oxygen, NO can be oxidized back to nitrite/nitrous acid.…”

Section: Figurementioning

confidence: 99%

“…In other words, for every mole of nitrite, one mole of ascorbate is needed to yield one mole of nitric oxide, plus another 0.5 mole ascorbate to prevent the back reaction. The ratio of ascorbic acid to nitrite is recognized as a major determinant of the generation of N-nitroso compounds within the acidic lumen of the stomach [73]. Contemporary meat-curing methods use ascorbic acid or erythorbate to prevent Nnitrosation reactions and to facilitate the curing process.…”

Section: Figurementioning

confidence: 99%

Dietary Nitrite: from menace to marvel

Bryan¹

2016

FFHD

View full text Add to dashboard Cite

ABSTRACT:The health benefits of nitrite are now indisputable when administered in a clinical setting for specific diseases. Currently, most published reports identify the production of nitric oxide (NO) as the mechanism of action for nitrite. Basic science, in addition to clinical studies, demonstrate that nitrite and/or nitrate cannot restore NO homeostasis as an endothelium independent source of NO that may be a redundant system for endogenous NO production. Nitrate must first be reduced to nitrite by oral commensal bacteria; nitrite can then be further reduced to NO along the physiological oxygen gradient. But despite decades of rigorous research on sodium nitrate's safety and efficacy as a curing agent, sodium nitrite is still regarded by many as a toxic undesirable food additive. However, research within the biomedical science community has revealed enormous therapeutic benefits of nitrite which are being developed as novel therapies for conditions associated with nitric oxide insufficiency. Thus, this review will highlight the fundamental biochemistry of nitrite in human physiology and provide evidence that nitrite be considered an essential nutrient. Foods or diets enriched with nitrite can have profound positive health benefits.

show abstract

Reaction of Nitrite With Ascorbate and Its Relation to Nitrosamine Formation2

Cited by 100 publications

References 0 publications

Red wine-dependent reduction of nitrite to nitric oxide in the stomach

Red wine-dependent reduction of nitrite to nitric oxide in the stomach

Analysis of Volatile N-Nitrosamines in Mainstream and Sidestream Smoke from Cigarettes by GLC-TEA

Dietary Nitrite: from menace to marvel

Contact Info

Product

Resources

About