Identification, Occurrence, and Mechanism of Formation of 1-Acetyl-β-carbolines Derived from l-Tryptophan and Methylglyoxal.

β-Carbolines (βCs) are bioactive compounds present in foods and biological systems. This work describes the identification, occurrence, and mechanism of formation of 1-acetyl-β-carbolines (1-acetyl-βCs) that result from the reaction of l-tryptophan with the α-dicarbonyl compound methylglyoxal. Two β-carbolines are characterized as 1-acetyl-β-carboline (AβC) and 1-acetyl-β-carboline-3-carboxylic acid (AβC-COOH).

Formation, Identification, and Occurrence of the Furan-Containing β-Carboline Flazin Derived from l-Tryptophan and Carbohydrates.

β-Carbolines (βCs) are bioactive indole alkaloids found in foods and in vivo. This work describes the identification, formation, and occurrence in foods of the βC with a furan moiety flazin (1-[5-(hydroxymethyl)furan-2-yl]-9-pyrido[3,4-]indole-3-carboxylic acid). Flazin was formed by the reaction of l-tryptophan with 3-deoxyglucosone but not with 5-hydroxymethylfurfural.

Synthesis and Biophysical and Biological Studies of -Phenylbenzamide Derivatives Targeting Kinetoplastid Parasites.

The AT-rich mitochondrial DNA (kDNA) of trypanosomatid parasites is a target of DNA minor groove binders. We report the synthesis, antiprotozoal screening, and SAR studies of three series of analogues of the known antiprotozoal kDNA binder 2-((4-(4-((4,5-dihydro-1-imidazol-3-ium-2-yl)amino)benzamido)phenyl)amino)-4,5-dihydro-1-imidazol-3-ium (). Bis(2-aminoimidazolines) (1) and bis(2-aminobenzimidazoles) (2) showed micromolar range activity against whereas bisarylimidamides (3) were submicromolar inhibitors of , and .

Identification, Formation, and Occurrence of Perlolyrine: A β-Carboline Alkaloid with a Furan Moiety in Foods.

β-Carbolines are naturally occurring bioactive alkaloids found in foods and . This research reports the identification, characterization, mechanism of formation, and occurrence of perlolyrine (1-(5-(hydroxymethyl)furan-2-yl)-9-pyrido[3,4-]indole), a β-carboline with a furan moiety. Perlolyrine did not arise from l-tryptophan and hydroxymethylfurfural but from the reaction of l-tryptophan with 3-deoxyglucosone, an intermediate of carbohydrate degradation.