A novel mutagen, 2-(5-hydroxy-4,6-dinitroindolyl) ethanol, formed in the reaction between 5-hydroxytryptamine and nitrite under acid conditions, especially in the presence of L-cysteine.
Mutat Res
; 588(2): 172-6, 2005 Dec 30.
Article
en En
| MEDLINE
| ID: mdl-16307901
We examined the mutagenic activity of each of 29 amino acids mixed under acidic conditions with 5-hydroxytryptamine (5-HT) and nitrite using Salmonella typhimurium strain TA 100 with or without a metabolic activation system (S9 mix). The reaction mixture containing L-cysteine was strongly mutagenic without S9 mix. We subjected an ethyl acetate extract of the reaction mixture to HPLC, isolated a mutagenic component, and investigated its chemical structure by LC-mass spectrometry (MS), high-resolution fast atom bombardment (HRFAB)-MS, and 1H and 13C NMR. We identified the mutagen as 2-(5-hydroxy-4,6-dinitro-3-indolyl) ethanol (2HDIE). We injected 8 mg/kg 2HDIE i.p. into male ICR mice and found that the compound increased the frequency of micronuclei in peripheral reticulocytes. Our results suggest that 2HDIE might be formed in vivo by consumption of 5-HT, nitrite and L-cysteine in foods, and might act as a mutagen.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Serotonina
/
Cisteína
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Indoles
/
Mutágenos
/
Nitritos
Límite:
Animals
Idioma:
En
Revista:
Mutat Res
Año:
2005
Tipo del documento:
Article
País de afiliación:
Japón
Pais de publicación:
Países Bajos