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

¹ Instituto de Fermentacions Industriales, Juan de la Cierva 3, 28006 Madrid, Spain
² Department of Viticulture and Enology, University of California, Davis, CA 95616-8749

1,2,3,4-Tetrahydro--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--carboline-3-carboxylic acid methyl esters. 1,2,3,4-Tetrahydro--carboline-3-carboxylic acid (THCA) and 1-methyl-l,2,3,4-tetrahydro--carboline-3-carboxylic acid (both diastereoisomers) were positively identified in wine samples. 1-Ethyl-1,2,3,4-tetrahydro--carboline-3-carboxylic acid (ETCA) and 1-isobutyl-1,2,3,4-tetrahydro--carboline-3-carboxylic acid (IBTCA) were not identified in the wines studied.

Key words: terahydro--carboline-3-carboxylate, wine, identification

Submitted on April 19, 1993