Formation of tetrahydro-ß-carbolines and ß-carbolines during the reaction of L-tryptophan with D-glucose
Rönner B, Lerche H, Freilinger C, Bergmüller W, Severin T, Pischetsrieder M (2000)
Publication Type: Journal article
Publication year: 2000
Journal
Publisher: American Chemical Society
Book Volume: 48
Pages Range: 2111-2116
DOI: 10.1021/jf991237l
Abstract
The reaction of L-tryptophan (Trp) with D-glucose under conditions that can occur during food
processing and preparation was studied by high-performance liquid chromatography with diode array detection (HPLC/DAD). Besides the well-established glucose-tryptophan Amadori product (AP), (1R,3S)-1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (PHP-THbetaC) was identified as an important product of this reaction. For preparation, PHPTH betaC was obtained in high yields when Trp and D-glucose were reacted under strongly acidic conditions after heating in methanol. At elevated reaction temperatures (150 °C) 1-acetyl-beta-carboline (acetyl-betaC), was detected in significant concentrations. The mixtures were heated under variations of reaction time and temperature, and AP, PHP-THbetaC, and acetyl-betaC were quantified. In the presence of air oxygen or mild, food relevant oxidants, such as L-dehydroascorbic acid, PHP-THbetaC was readily oxidized to a product that was identified as the previously unknown 1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)- beta-carboline (PHP-betaC). Formation of PHP-THbetaC and PHP-betaC in foodstuffs would deserve particular interest because multiple physiological activity of THbetaC and betaC derivatives has been shown previously.
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Germany (DE)How to cite
APA:
Rönner, B., Lerche, H., Freilinger, C., Bergmüller, W., Severin, T., & Pischetsrieder, M. (2000). Formation of tetrahydro-ß-carbolines and ß-carbolines during the reaction of L-tryptophan with D-glucose. Journal of Agricultural and Food Chemistry, 48, 2111-2116. https://dx.doi.org/10.1021/jf991237l
MLA:
Rönner, Birgit, et al. "Formation of tetrahydro-ß-carbolines and ß-carbolines during the reaction of L-tryptophan with D-glucose." Journal of Agricultural and Food Chemistry 48 (2000): 2111-2116.
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