The bacterial mutagenicity of three naturally occurring indoles after reaction with nitrous acid

Gatehouse, D.; Wedd, D.J.

doi:10.1016/0165-1218(83)90183-0

Cited by 19 publications

(10 citation statements)

References 23 publications

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“…1-NO-Trp is technically a nitrosamine, which is a class of compounds known to be highly carcinogenic in animals [37]. And similar to other nitrosamines, the 1-NO-Trp form of N-Ac-Trp (N-Ac-NO-Trp) was found to be mutagenic in numerous bacterial strains, including one strain of E. coli and two strains of S. typhimurium [38, 39]. However, it is still unclear whether 1-NO-Trp is also carcinogenic in animals, and if so, whether the accumulating cellular concentration of free 1-NO-Trp could ever rise to levels necessary to promote oncogenesis.…”

Section: Nitrotryptophan Formation In Vivomentioning

confidence: 99%

Protein nitrotryptophan: Formation, significance and identification

Nuriel

Hansler

Gross

2011

Journal of Proteomics

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Section: Nitrotryptophan Formation In Vivomentioning

confidence: 99%

Protein nitrotryptophan: Formation, significance and identification

Nuriel

Hansler

Gross

2011

Journal of Proteomics

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“…Besides the anticarcinogenic effects of indole-3-acetonitrile, it is also known to be a precursor of N-nitroso compounds (NOC) which have been isolated from nitritetreated Chinese cabbage and which exhibit direct mutagenic activity (Wakabayashi et al, 1985). Other workers have also shown indole compounds to be directly mutagenic to bacteria after nitrite treatment (Gatehouse and Wedd, 1983; Yang et al, 1984;Büchi et al, 1986;Ochiai et al, 1986;Tiedink et al, 1989). Approximately 75% of the nitrate ingested by humans is derived from vegetables (Ellen and Schuller, 1983), and part of this load will be converted to nitrite by bacteria in the oral cavity (Mirvish, 1983).…”

Section: Introductionmentioning

confidence: 99%

Role of glucosinolates in the formation of N-nitroso compounds

Tiedink¹,

Malingré²,

Broekhoven³

et al. 1991

J. Agric. Food Chem.

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The hydrolysis of the glucosinolates, sinigrin, gluconapin, glucobrassicanapin, progoitrin, glucotropaeolin, sinalbin, gluconasturtiin, glucobrassicin, and 4-hydroxyglucobrassicin, by myrosinase from white mustard (Sinapis alba) or acid was examined. While all glucosinolates were hydrolyzed by myrosinase, only 4-hydroxyglucobrassicin, glucosinalbin, gluconasturtiin, glucobrassicin, and progoitrin were partially hydrolyzed by acid (pH 2). When intact glucosinolates or myrosinase-treated glucosinolate products were treated with nitrite, only glucobrassicin and 4-hydroxyglucobrassicin formed -nitroso compounds. The nitrosated products of myrosinase-treated glucobrassicin alone were mutagenic and induced about 400 Salmonella typhimurium TA100 revertants/µ . The enzymic breakdown products of the alkyl and aryl glucosinolates were cytotoxic, but this activity was not affected by subsequent nitrite treatment. Given the levels at which indole glucosinolates occur in brassica vegetables, these findings suggest that their contribution to the observed mutagenic potential of these vegetables after nitrite treatment will be marginal. Further work is, however, needed to identify the exact chemical natures of both the -nitroso compounds formed in nitrite-treated brassicas and their naturally occurring precursors.

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“…46 The unnitrosated D-fructose-L-amino acid conjugates and the L-amino acid precursors were shown2L28330 a All compounds were administered in a 0.85% saline solution (Sigma Chemical Company). The average percentage weight change on days 5 and 10 was taken as a measure of drug toxicity.…”

Section: Resultsmentioning

confidence: 99%

“…Compounds were evaluated in vivo against the lymphocytic leukemia P388 and the lymphoid leukemia L1210 in mice following the NCI protocol. 46 The CDF, male mice (18-21 g weight), in groups of six, were inoculated ip either with 10' cells of P388 or with lo5 cells of L1210 tumor at day zero of the experiment.…”

Section: Methodsmentioning

confidence: 99%