A novel tetrahydro-bêta-carboline, chemically identified as l-methyl-1,2,3,4-tetrahydro-bêta-carboline-3-carboxyl acid ethyl ester (ethyl 1-methyl-1,2,3,4-tetrahydro-bêta-carboline-3-carboxylate (MTCA-EE), has been found in alcoholic beverages ranging from an undetectable amount to 534 mug/l. RP-HPLC with fluorescence detection and GC-MS were used for characterization.
MTCA-EE occurred as two diastereoisomers 1 S, 3S and 1R, 3S with an average ratio (SS/RS) of 2.21.
The concentration of MTCA-EE (1S, 3S plus 1R, 3S) was 109.6-534 mug/l in sherry wines, 75.2-140.7 mug/l in sparkling wines, 3.4-161.65 mug/l in red and white wines, 32.7-47.2 mug/l in port wines, and 8.7-37.2 mug/l in sake.
MTCA-EE seemed to occur in some high alcohol beers at less than 10 mug/l. Most distilled alcoholic beverages did not contain MTCA-EE although, exceptionally, one brandy reached 28.6 mug/l. 1-Methyl-1,2,3,4-tetrahydro-bêta-carboline-3-carboxylic acid (MTCA) and L-tryptophan ethyl ester (L-TRP-EE) were two precursors leading to MTCA-EE.
Alcoholic drinks containing MTCA-EE and MTCA could be an exogenous source of bioactive bêta-carbolines found in vivo.
MTCA-EE is a structural analogue (reduced pyrido ring) of bêta-carboline-3-carboxylic acid ethyl ester (bêta-CCE), a potent benzodiazepine receptor inverse agonist.
Mots-clés Pascal : Vin blanc, Vin rouge, Analyse biochimique, Etude comparative, Récepteur benzodiazépinique, Ester, Acide carboxylique, Carboline dérivé, Diastéréoisomère, Xérès, Bière, Porto(vin), Saké, Boisson alcoolisée, Neuromodulateur, Indole dérivé, Vin mousseux, Etude expérimentale, Tryptophane, Activité biologique, Alcoolisme, Indole(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]), Analogue structural
Mots-clés Pascal anglais : White wine, Red wine, Biochemical analysis, Comparative study, Benzodiazepine receptor, Ester, Carboxylic acid, Carboline derivatives, Diastereomer, Xeres, Beer, Porto wine, Sake, Alcoholic beverage, Neuromodulator, Indole derivatives, Sparkling wine, Experimental study, Tryptophan, Biological activity, Alcoholism, Structural analogue
Notice produite par :
Inist-CNRS - Institut de l'Information Scientifique et Technique
Cote : 99-0485734
Code Inist : 002B30A02A. Création : 22/03/2000.