ChemInform Abstract: NEUROPHARMACOLOGICAL STUDIES OF A NEW ANTIDOPAMINERGIC TETRAHYDRO‐β‐CARBOLINE

Kehr, W.; Horowski, R.; Schulte‐Sienbeck, Hildegard; Rehse, Klaus

doi:10.1002/chin.197907348

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“…Numerous THβC and βC derivatives show binding to the benzodiazepine receptor (Cain et al, 1982). Furthermore, premutagenicity (Kinae et al, 1986), inhibitory activity on monoamine oxidase (Ho, 1972), and membrane translocation mechanisms (Kehr et al, 1978) and psychotropic effects (Naranjo, 1969) have been reported besides others.…”

Section: Introductionmentioning

confidence: 99%

Formation of Tetrahydro-β-carbolines and β-Carbolines during the Reaction of l-Tryptophan with d-Glucose

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Bergmüller

et al. 2000

J. Agric. Food Chem.

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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, PHP-THbetaC 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 degrees 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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Section: Introductionmentioning

confidence: 99%

Formation of Tetrahydro-β-carbolines and β-Carbolines during the Reaction of l-Tryptophan with d-Glucose

Rönner

Lerche

Bergmüller

et al. 2000

J. Agric. Food Chem.

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ChemInform Abstract: NEUROPHARMACOLOGICAL STUDIES OF A NEW ANTIDOPAMINERGIC TETRAHYDRO‐β‐CARBOLINE

Abstract: Durch 2‐[2‐(3,4‐Dimethoxyphenyl)‐ethyl]‐1,2,3,4‐tetrahydro‐β‐carbolin wird bei Mäusen die Wirkung von Clonidin, Noradrenalin und Apomorphin anta‐ ′ gonisiert (Dosen zwischen 6 ‐ 50mg/ kg i.p.).

Cited by 1 publication

References 1 publication

Formation of Tetrahydro-β-carbolines and β-Carbolines during the Reaction of l-Tryptophan with d-Glucose

Formation of Tetrahydro-β-carbolines and β-Carbolines during the Reaction of l-Tryptophan with d-Glucose

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