Identification and quantitation of 1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid in beer and wine

Bosin, Talmage R.; Krogh, Stephanie; Mais, Dale E.

doi:10.1021/jf00071a020

Cited by 49 publications

(30 citation statements)

References 11 publications

(17 reference statements)

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“…We have suggested that both compounds are naturally occurring substances readily produced during food production, processing and storage. Appreciable amounts of TH Cs have been reported in alcoholic and smoked products (Bosin et al 1986, Adachi et al 1991, Papavergou and Cli ord 1992, Herraiz and Ough 1993, 1994, Herraiz et al 1993, Sen et al 1995, Herraiz 1996, Gutsche and Herderich 1997. Obviously, dietary sources will provide TH Cs and these may accumulate in biological tissues and¯uids (Herraiz 1996 ).…”

mentioning

confidence: 99%

Tetrahydro-beta-carboline-3-carboxylic acid compounds in fish and meat: possible precursors of co-mutagenic beta-carbolines norharman and harman in cooked foods

Herraiz

2000

Food Additives and Contaminants

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The presence of tetrahydro-beta-carbolines and beta-carbolines was studied in raw, cooked and smoked fish and meat. 1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid (THCA) usually was the major beta-carboline found, whereas 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (MTCA) appeared in smoked and 'well done' cooked samples. THCA was detected in raw fish (nd-2.52 micrograms/g), cooked fish (nd-6.43 micrograms/g), cooked meats (nd-0.036 microgram/g), smoked fish (0.19-0.67 microgram/g) and smoked meats (0.02-1.1 micrograms/g). Smoked and cooked samples contained higher amounts of THCA and MTCA than raw products. Deep cooking of fish and meat increased both THCA and MTCA, and this was accompanied by the formation of more beta-carbolines, norharman and harman. The tetrahydro-beta-carbolines THCA and MTCA were chemical precursors of the co-mutagens norharman and harman during cooking. These and previous results confirm that foods are an important source of beta-carbolines in humans.

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confidence: 99%

Tetrahydro-beta-carboline-3-carboxylic acid compounds in fish and meat: possible precursors of co-mutagenic beta-carbolines norharman and harman in cooked foods

Herraiz

2000

Food Additives and Contaminants

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“…In addition to THβCs in fermented and matured foodstuffs such as beer and wine [16][17][18], stereoisomers of 1-(2-pyrrolidinethione)-3-yl)-1,2,3,4-THβC were found to be formed from tryptophan with 4-methylthio-3-butenyl isothiocyanate in fermented radish roots and were found to posses different mutagenic properties [19]. Besides the fermented foodstuffs, β-carbolin derivatives are also present in raw, cooked and smoked fish and meat, and they are possible chemical precursors of the co-mutagens norharman and harman [20].…”

Section: Resultsmentioning

confidence: 99%

“…It has been reported that formation of THβCs might occur during elaboration and the ripening process from a chemical condensation between tryptophan or tryptamine and aldehydes or pyruvic acid [16][17][18]21]. Acetaldehyde derived from alcohol is supposed to be a precursor of MTCCs in the fermented and matured foodstuffs such as beer and wine [16][17][18], whereas pyruvic acid is supposed to be a precursor of MTCdiCs [13,14].…”

Section: Resultsmentioning

confidence: 99%

“…Acetaldehyde derived from alcohol is supposed to be a precursor of MTCCs in the fermented and matured foodstuffs such as beer and wine [16][17][18], whereas pyruvic acid is supposed to be a precursor of MTCdiCs [13,14]. In the case of aged garlic extract produced by soaking slice garlic in an aqueous ethanol solution for more than 10 months, MTCCs reached a plateau at 10 months after the onset of the extraction process while MTCdiCs increased further during the aging process [13].…”

Section: Resultsmentioning

confidence: 99%

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Increased Level of Tetrahydro-β-Carboline Derivatives in Short-Term Fermented Garlic

Sato

Kohno

Niwano

2006

Plant Foods Hum Nutr

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In our previous study [1], we found that relatively short-term spontaneous fermentation (40 days at 60-70 degrees C, 85-95% relative humidity) potentiates anti-oxidative properties of garlic, in which scavenging activity against hydrogen peroxide was included. Since tetrahydro-beta-carboline derivatives (THbetaCs) that possess hydrogen peroxide scavenging activity have recently been identified in aged garlic extract, THbetaCs were quantitatively analyzed with liquid chromatography-mass spectrometry (LC-MS). (1R, 3S)-1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (MTCC) and (1S, 3S)-MTCC were found in the fermented garlic extract whereas only trace levels of MTCCs were detected in the row garlic extract. Therefore, it is suggested that relatively short-term fermentation potentiates scavenging activity of garlic against hydrogen peroxide by forming THbetaCs, especially MTCCs.

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“…MTCA and 1,2,3,4-tetrahydro-~-carboline-3-carboxylic acid (TCCA) are condensation products of tryptophan with aldehyde. As MTCA has been recognized as a new toxic substance and because of difficulty in analysis, the content of MTCA in foodstuffs has scarcely been investigated (Bosin et al 1986). …”

Section: Introductionmentioning

confidence: 99%

Endogenous formation of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in man as the possible causative substance of eosinophilia-myalgia syndrome associated with ingestion ofl-tryptophan

et al. 1991

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1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (MTCA) is now thought to be a possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan. In the present study a factor affecting endogenous formation of MTCA in 32 healthy men is studied. Urinary excretions of MTCA and 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (TCCA) were measured by high-performance liquid chromatography (HPLC) with fluorometric detection after administration of a high or low protein diet as well as peroral tryptophan (0.5 g) or ethanol (0.4 g/kg). Blood ethanol and acetaldehyde levels were determined by gas chromatography after ethanol consumption. Both, the high protein diet and tryptophan resulted in a significant rise of urinary TCCA. In contrast, ethanol intake caused increased excretion of MTCA, though a relationship between blood acetaldehyde level and urinary excretion of MTCA was not shown. We showed for the first time that an elevation of urinary excretion of MTCA following ethanol consumption in man without ingestion of L-tryptophan tablets implicated eosinophilia-myalgia syndrome.

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Identification and quantitation of 1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid in beer and wine

Cited by 49 publications

References 11 publications

Tetrahydro-beta-carboline-3-carboxylic acid compounds in fish and meat: possible precursors of co-mutagenic beta-carbolines norharman and harman in cooked foods

Tetrahydro-beta-carboline-3-carboxylic acid compounds in fish and meat: possible precursors of co-mutagenic beta-carbolines norharman and harman in cooked foods

Increased Level of Tetrahydro-β-Carboline Derivatives in Short-Term Fermented Garlic

Endogenous formation of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in man as the possible causative substance of eosinophilia-myalgia syndrome associated with ingestion ofl-tryptophan

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