Derivatization in aqueous solution, isolation and separation of tetrahydro-β-carbolines and their precursors by liquid chromatography

Bosin, Talmage R.; Jarvis, Christine

doi:10.1016/s0378-4347(00)84042-6

Cited by 17 publications

(8 citation statements)

References 23 publications

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“…The analytical procedure used in this study has been described in detail (Bosin and Jarvis, 1985). The procedure is based on the aqueous derivatization of THBC compounds with methyl chloroformate and has been shown to facilitate the isolation of these compounds from an aqueous medium, to eliminate the potential for the artifactual formation of THBC compounds during sample preparation, and to markedly improve their high-performance liquid chromatographic (HPLC) separation.…”

Section: Resultsmentioning

confidence: 99%

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Identification and quantitation of 1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid in beer and wine

Bosin¹,

Krogh²,

Mais³

1986

J. Agric. Food Chem.

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Section: Resultsmentioning

confidence: 99%

“…Sample Preparation. A detailed presentation of the analytical method has been published (Bosin and Jarvis, 1985), and an abbreviated form appears below.…”

mentioning

confidence: 99%

Identification and quantitation of 1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid in beer and wine

Bosin¹,

Krogh²,

Mais³

1986

J. Agric. Food Chem.

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“…THβC-3-COOH gives rise to N-methoxycarbonyltetrahydroβ-carboline-3-carboxylic acid (N-MC-THβC-3-COOH) through reaction with methyl chloroformate (ClCOOCH 3) (Bosin and Jarvis, 1985;Herraiz, 1996). For this, aliquots (0.5 mL) of SCX-isolated fractions evaporated under a He stream up to ∼0.2 mL were derivatized and extracted as previously described (Bosin and Jarvis, 1985;Herraiz, 1996). The samples redissolved in phosphate buffer 0.4 M/methanol (1:1), pH 10, were injected into RP-HPLC as above.…”

Section: Methodsmentioning

confidence: 99%

“…The reagent methyl chloroformate (ClCOOCH 3 ) has been used in THβC analysis (Bosin and Jarvis, 1985;Herraiz, 1996). The resulting N-methoxycarbonyl derivatives (N-MC-THβC-3-COOH) exhibit fluorescence and higher HPLC retention times than parent compounds.…”

Section: Chromatographic Analysismentioning

confidence: 99%

Occurrence of 1,2,3,4-Tetrahydro-β-carboline-3-carboxylic Acid and 1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic Acid in Fruit Juices, Purees, and Jams

Herraiz

1998

J. Agric. Food Chem.

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1,2,3,4-Tetahydro-β-carboline-3-carboxylic acid (THCA) and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (MTCA) as two diastereoisomers (1S,3S and 1R,3S), occur in fruit juices, juices and fruit purees for infants, and jams. Concentrations in commercially prepared fruit juices were in the ranges 0.01−1.45, 0.02−9.1, and 0.01−2.48 μg/g for THCA, 1S,3S-MTCA, and 1R,3S-MTCA, respectively. The content was higher in citrus juices (orange, grapefruit) than in other juices (grape, apple, pineapple, peach, banana, pear, tomato). Commercially prepared infant juices contained 0.14, 0.52, and 0.16 μg/g on average, for THCA, 1S,3S-MTCA, and 1R,3S-MTCA, respectively. Commercial infant fruit purees averaged 0.04, 0.35, and 0.11 μg/g for THCA, 1S,3S-MTCA, and 1R,3S-MTCA. Jams and marmalades averaged 0.23, 0.76, and 0.25 μg/g for THCA, 1S,3S-MTCA, and 1R,3S-MTCA, respectively. The reported endogenous presence of these substances in humans could be influenced by their exogenous ingestion in the diet. This is the first specific report on THCA and MTCA in fruit products. Keywords: Tetrahydro-β-carboline-3-carboxylic acid; tetrahydro-β-carbolines; β-carbolines; alkaloids; tryptophan; aldehydes; fruit juices; infant purees; jams

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“…(123) Indolethylamines were condensed with an aldehyde or α-keto acid to form fluorescent carboline derivatives. (124) Thiamine (vitamin B 1 ) was oxidized with hexacyanoferrate(III) in base to give the fluorescent thiochrome in either the precolumn (125) or the postcolumn (126) mode. Riboflavin, already fluorescent, and thiamine, after precolumn oxidation to thiochrome using hexacyanoferrate(III), were determined by HPLC in a variety of food powders such as flour, milk, and beans.…”

Section: Aminesmentioning

confidence: 99%

Chemical Reagents and Derivatization Procedures in Drug Analysis

Danielson

Gallagher

Bao

2008

Encyclopedia of Analytical Chemistry

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This article describes both pre‐ and postcolumn derivatization chemistry used in conjunction with either chromatography or capillary electrophoresis (CE) to facilitate the determination of drugs. Generally, only prederivatization is used in gas chromatography (GC), principally to enhance the volatility, temperature stability, and/or detectability. The GC section considers derivatization of drugs by reagent class: alkylation, acylation, and silylation. The GC sample‐handling section describes an approach that combines the extraction and derivatization steps together. Both pre‐ and postcolumn derivatization are common approaches for high‐performance liquid chromatography (HPLC) and many of these methods have been adapted for CE. Derivatization for HPLC is often directed toward aliphatic amines, carboxylic acids, or alcohols that are difficult to detect at low levels by absorbance, luminescence, or electrochemical means. In addition, small hydrophilic molecules upon prederivatization are often converted into larger more hydrophobic compounds, making reversed‐phase HPLC easier or even feasible. The HPLC section considers derivatization of drugs based on the following types: alkaloids, amines, antibiotics, barbiturates, carbonyl compounds and carboxylic acids, catecholamines, hydroxy compounds, steroids, and sulfur compounds. For the GC and HPLC sections, tables are included, giving the structures of the more important derivatizing agents, the analytes, and the corresponding reaction products. A brief rationale for derivatization chemistry with CE concludes this article. For CE, derivatization is often done to improve detectability as the path length for absorbance detection is very short and fluorescence can be effective using laser‐based systems.

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Derivatization in aqueous solution, isolation and separation of tetrahydro-β-carbolines and their precursors by liquid chromatography

Cited by 17 publications

References 23 publications

Identification and quantitation of 1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid in beer and wine

Identification and quantitation of 1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid in beer and wine

Occurrence of 1,2,3,4-Tetrahydro-β-carboline-3-carboxylic Acid and 1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic Acid in Fruit Juices, Purees, and Jams

Chemical Reagents and Derivatization Procedures in Drug Analysis

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