Nitrosation of some food‐related tetrahydro‐β‐carboline‐3‐carboxylic acids

Salvi, Neeta A.; Choughuley, Ahmed S. U.

doi:10.1002/jsfa.2740520411

Cited by 5 publications

(3 citation statements)

References 23 publications

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“…In addition, the reversible reaction at indole nitrogen N -9 has been described ( − ). According to model reactions ( − ), one can expect the presence of N 2 -nitroso-tetrahydro- β -carbolines in nitrite-treated food samples as well as the endogenous formation of such metabolites in the digestive system. Rather surprisingly, tetrahydro- β -carbolines are common food constituents ( 17 and references therein), but only the occurrence of 2-nitroso-tetrahydro- β -carboline-3-carboxylic acid 9 in cured meat products and of 1-methyl-2-nitroso-tetrahydro- β -carboline-3-carboxylic acid 10a/b in soy sauce has been reported ( − ).…”

Section: Introductionmentioning

confidence: 99%

Degradation of Tetrahydro-β-carbolines in the Presence of Nitrite: HPLC−MS Analysis of the Reaction Products

Diem

Gutsche

Herderich

2001

J. Agric. Food Chem.

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Motivated by the identification of numerous novel tetrahydro-beta-carboline-carboxylic acids in food samples, we studied the reactions of tetrahydro-beta-carbolines in the presence of nitrosating agents. The anticipated formation of nitroso derivatives from unsubstituted tetrahydro-beta-carbolines, and from tetrahydro-beta-carboline-3-carboxylic acids was indicated by HPLC-MS/MS analysis and validated by the characteristic product ion spectra of the respective nitroso compounds. In addition, oxidative decarboxylation resulted in formation of the corresponding dihydro-beta-carbolines, and in the generation of the beta-carbolines harman or norharman. Subsequently, we studied the reactivity of tetrahydro-beta-carboline-1-carboxylic acids derived from the Pictet-Spengler condensation of indole amines with alpha-oxo acids. Again, in the presence of nitrosating agents the rapid disappearance of the starting material was obvious, but no nitroso derivatives could be observed. Instead, further HPLC-MS/MS studies demonstrated that dihydro-beta-carbolines were the major products of tetrahydro-beta-carboline-1-carboxylic acids. Finally, we demonstrated that freshly isolated nitroso-precursors spontaneously decomposed to yield harman alkaloids. In conclusion, we revealed that nitroso-tetrahydro-beta-carbolines can represent intermediates involved in the generation of beta-carbolines, and we established a novel pathway for the formation of harman alkaloids from nutritional tetrahydro-beta-carbolines.

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Section: Introductionmentioning

confidence: 99%

Degradation of Tetrahydro-β-carbolines in the Presence of Nitrite: HPLC−MS Analysis of the Reaction Products

Diem

Gutsche

Herderich

2001

J. Agric. Food Chem.

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“…THβC could react with nitrite already in foods, the mouth, or the stomach, giving rise to mutagenic compounds. Salvi and Choughuley (1990) and Sen et al (1991Sen et al ( , 1995 reported the nitrosation of some foodrelated THβC-3-COOHs.…”

Section: Introductionmentioning

confidence: 99%

Occurrence of Tetrahydro-β-carboline-3-carboxylic Acids in Commercial Foodstuffs

Herraiz

1996

J. Agric. Food Chem.

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The occurrence of tetrahydro-β-carboline-3-carboxylic acids (THβC-3-COOHs) in foodstuffs was investigated. Spectral and chromatographic data showed the occurrence of 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (THCA) and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (MTCA) in foodstuffs. The content of THβC-3-COOHs given as a sum of both THCA and MTCA was as follows: soy sauce, 94−517 mg/L; seasoning, 0.75−32.8 μg/g; table wine, 1.7−6.6 mg/L; beer, 0.3−17.9 mg/L; cider, 0.06−0.2 mg/L; liquor, 0−7.6 mg/L; wine vinegar, 3.9−9.7 mg/L; cider vinegar, 0.19−1 mg/L; yogurt, 0.05−0.15 μg/g; cheese, 0−3.4 μg/g; soft drinks, 0−0.45 mg/L; fruit juices, 0.1−5.1 mg/L; smoked fish, 0.08−0.4 μg/g; and bread, 0.16−3 μg/g. Usually MTCA was the major substance within THβC-3-COOHs, but bread and smoked fish contained more THCA. Experiments in which foodstuffs were spiked with formaldehyde and acetaldehyde proved the chemical formation of THCA and MTCA, respectively. It is concluded that the exogenous intake of these substances during the human ingestion of foods may be partially responsible of the reported endogenous presence of THβC-3-COOHs in the human biological tissues and fluids. Keywords: Tetrahydro-β-carboline-3-carboxylic acids; β-carbolines; l-tryptophan; foods; drinks; content; formation

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“…Tetrahydro-ßcarbolines can react with nitrite already in foods, in the mouth, or in the stomach, giving rise to mutagenic compounds. Salvi and Choughuley (1990) reported the nitrosation of some food-related tetrahydro-/3-carboline-3-carboxylic acids.…”

Section: Introductionmentioning

confidence: 99%

1,2,3,4-Tetrahydro-.beta.-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid in wines

Herraiz¹,

Huang²,

Ough³

1993

J. Agric. Food Chem.

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Nitrosation of some food‐related tetrahydro‐β‐carboline‐3‐carboxylic acids

Cited by 5 publications

References 23 publications

Degradation of Tetrahydro-β-carbolines in the Presence of Nitrite: HPLC−MS Analysis of the Reaction Products

Degradation of Tetrahydro-β-carbolines in the Presence of Nitrite: HPLC−MS Analysis of the Reaction Products

Occurrence of Tetrahydro-β-carboline-3-carboxylic Acids in Commercial Foodstuffs

1,2,3,4-Tetrahydro-.beta.-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid in wines

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