Chemical and technological factors determining tetrahydro-.beta.-carboline-3-carboxylic acid content in fermented alcoholic beverages

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].…”

Identification of 4-methylspinaceamine - a Pictet – Spengler condensation reaction product of histamine with acetaldehyde - in human urine

“…These compounds were identified in mammalian tissue and fluid samples (Peura et al, 1980;Airaksinen and Kari, 1981a;Melchior and Collins, 1982;Beck and Faull, 1986;Collins, 1988;Tsuchiya et al, 1994aTsuchiya et al, , 1994bHaber et al, 1996;Musshoff and Daldrup, 1998) and found to possess various neuropharmacological properties (Deitrich and Erwin, 1980;Buckholtz, 1980;Airaksinen and Kari, 1981b;Melchior and Collins, 1982;Nagatsu, 1997;Storch et al, 2002). The reactions of AA with indoleamines and dopamine have been extensively documented (Whaley and Govindachari, 1951;MacIsaac, 1961;Cohen and Collins, 1970;Herraiz and Ough, 1993;Callaway et al, 1994Callaway et al, , 1996Cox and Cook, 1995;Foppoli et al, 2002). Several reports suggested that the presence of MTBCs and SAL in mammalian tissue and fluid samples was caused by the reaction of AA with indoleamines and dopamine in vivo (MacIsaac, 1961;Cohen and Collins, 1970;Yamanaka et al, 1970;Collins et al, 1979;Callaway et al, 1996;Musshoff et al, 2000;Foppoli et al, 2002;Jamal et al, 2003) since the condensation reactions readily occur under physiological conditions (Whaley and Govindachari, 1951;MacIsaac, 1961;Cohen and Collins, 1970;Callaway et al, 1994Callaway et al, , 1996…”

Photoisomerization of 2-[3-(2-Thioxopyrrolidin-3-ylidene)methyl]-tryptophan, a Yellow Pigment in Salted Radish Roots

“…9,10) THCs are known to be produced during food processing and storage in the fermentation process. [11][12][13] In our recent study, 14) TPCC was found to change at weak acidic or neutral pH to a bright yellow pigment, which was identified as (E)-2-[3-(2-thioxopyrrolidine-3-ylidene)-methyl]-tryptophan ((E)-TPMT). In addition, we found that (E)-TPMT is probably the major naturally occurring substance in salted radish roots.…”