Separation and Characterization of 1,2,3,4-Tetrahydro-β-Carboline-3-Carboxylic Acids by HPLC and GC-MS. Identification in Wine Samples

1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acids, products of the reaction of tryptophan and aldehydes in alcoholic fermented beverages (10), were isolated by solid phase extraction, analyzed by HPLC, and identified by gas chromatography and mass spectrometry after derivatization to form N-trifluoroacetyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl esters. 1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid (THCA) and 1-methyl-l,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (both diastereoisomers) were positively identified in wine samples. 1-Ethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (ETCA) and 1-isobutyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (IBTCA) were not identified in the wines studied.