Inhibition of nitrosamine formation by ascorbic acid.
Nitrosation occurs under a wide variety of conditions by reaction of most types of amines with any of a large number of nitrosating species. Nitrite can be formed in vivo via bacterial reduction of nitrate and by activated macrophages and endothelial cells. The mechanism of nitrite formation by mammalian cells is via enzymatic oxidation of arginine to NO followed by oxidation to N2O3 and N2O4. Nitrosatable amines are found in many foods and some, eg, dimethylamine, are synthesized in the body. Precursors of N-nitroso compounds are thus almost constantly present together under favorable reaction conditions in vivo and there is, consequently, considerable interest concerning possible human health risks arising from endogenous formation of this class of compounds. Among many nitrosation inhibitors, most attention has focused on ascorbic acid, which reacts with many nitrosating agents and which is virtually nontoxic. This presentation discusses the chemistry of ascorbic acid inhibition of nitrosation reactions.
Tannenbaum
S R
SR
Massachusetts Institute of Technology, Cambridge 02139.
Wishnok
J S
JS
Leaf
C D
CD
D000588:Amines / Q000378:metabolism; D000818:Animals; D001205:Ascorbic Acid / Q000494:pharmacology*; D001419:Bacteria / Q000378:metabolism; D006801:Humans; D008264:Macrophages / Q000378:metabolism; D009566:Nitrates / Q000378:metabolism; D009573:Nitrites / Q000378:metabolism; D009585:Nitrogen Dioxide / Q000378:metabolism; D009602:Nitrosamines / Q000378:metabolism*; D015538:Nitrosation / Q000187:drug effects; D009603:Nitroso Compounds / Q000378:metabolism; D010084:Oxidation-Reduction
D000588:Amines; D009566:Nitrates; D009573:Nitrites; D009602:Nitrosamines; D009603:Nitroso Compounds; D001205:Ascorbic Acid; D009585:Nitrogen Dioxide