Document Detail

Taurine-nitrite interaction as a precursor of alkylation mechanisms.
MedLine Citation:
PMID:  23107717     Owner:  NLM     Status:  In-Data-Review    
Taurine (2-aminoethanesulphonic acid) is an amino acid-like-compound widely used as an ingredient in some nutraceuticals and energy drinks. Here the interaction of taurine (Tau) with nitrite was investigated. The reactions were carried out mimicking the conditions of the stomach lumen. The conclusions drawn are as follows: (i) Nitrite showed nitrosating capacity on Tau. The rate equation was ν(N)=k(obs)[Tau](o)[nitrite](o)(2), this result suggesting that the yield of nitrosation products in the human stomach would increase sharply with higher nitrate/nitrite intakes; (ii) the experimental results suggest a mechanism for the nitrosation, whose rate-limiting step is bimolecular attack by N(2)O(3); (iii) the nitrosation of taurine affords ethanesultone (ES), which displays alkylating capacity on the nucleophile 4-(p-nitrobenzyl)pyridine (NBP), a trap for alkylating agents with nucleophilic characteristics similar to those of DNA bases. Although the NBP alkylation rate for ethanesultone is much higher than those for carcinogenic four-membered ring lactones, resulting in the nitrosation of amino carboxylic acids, the fraction of ES-forming adduct with NBP is much smaller; (iv) in spite of the low risk to human health, since the stomach lumen conditions could be a favourable medium for Tau nitrosation, attention should be paid to potential situations of the concurrence of high contents of taurine and nitrite/nitrate in the diet.
Jorge Arenas-Valgañón; Rafael Gómez-Bombarelli; Marina González-Pérez; Mario González-Jiménez; Emilio Calle; Julio Casado
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Publication Detail:
Type:  Journal Article     Date:  2012-03-08
Journal Detail:
Title:  Food chemistry     Volume:  134     ISSN:  0308-8146     ISO Abbreviation:  Food Chem     Publication Date:  2012 Sep 
Date Detail:
Created Date:  2012-10-30     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7702639     Medline TA:  Food Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  986-91     Citation Subset:  IM    
Copyright Information:
Copyright © 2012. Published by Elsevier Ltd.
Departamento de Química física, Universidad de Salamanca, E-37008 Salamanca, Spain.
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