Resumen de Identification and occurrence of 1,2,3,4-tetrahydro-ß-carboline-3-carboxylic acid: the main ß-carboline alkaloid in smoked foods
Ekaterini Papavergou, Tomas Herraiz
Tetrahydro-β-carboline alkaloids are biologically active compounds that occur in foodstuffs. 1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid, a tetrahydro-β-carboline derived from a Pictet–Spengler condensation reaction among l-tryptophan and formaldehyde, was identified by GC–MS as its N-methoxycarbonyl methyl ester derivative in smoked fish, sausage and cheese. The occurrence of this β-carboline was determined by RP-HPLC-fluorescence in numerous commercially available samples of these products and the concentrations ranges were 0.03–12.2 μg/g, 0.07–6.06 μg/g and 0.01–14.8 μg/g in smoked fish, smoked cheeses and smoked sausages and meats, respectively. These results showed that 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid is the main β-carboline in such products. Smoked foods contained a higher relative amount (2–7 fold) of this compound in their exterior part exposed to the smoke than in their interior counterpart suggesting a reaction involving formaldehyde from smoke and tryptophan. Smoked products appear to be one of the food stuffs with the highest amount of this particular tetrahydro-β-carboline.
