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

β-Carboline Alkaloids: Biochemical and Pharmacological Functions

“…Undoubtedly, the ingestion of these compounds during foods and beverages comsumption that could be partially responsible for their further endogenous presence in various mammals' tissues, organs and physiological fluids [235][236][237][238][239] besides certain endogenous formation itself by putative biosynthesis pathway.…”

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

“…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].…”

“…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].…”

“…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].…”

Quantitation of Thioprolines in Grape Wine by Isotope Dilution–Liquid Chromatography–Tandem Mass Spectrometry

“…Previous research reported that acetaldehyde is a dominant reactive carbonyl (>90%) and can be found in most beverages. 38,39 For example, in the study by Herraiz et al, 37 the acetaldehyde concentration in grape wine samples was found to range from 80 to 220 mg/L together with an abundant methyl-l,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, which is the condensation product of acetaldehyde and indole amine. However, the concentration of the condensation product of formaldehyde and indole amine was merely one percentage of the condensation product of acetaldehyde.…”