Identification and Occurrence of Tryptamine- and Tryptophan-Derived Tetrahydro-β-carbolines in Commercial Sausages

• Published in: Journal of agricultural and food chemistry 2004-05, Vol.52 (9), p.2652-2658
• Main Authors: Herraiz, Tomas, Papavergou, Ekaterini
• Format: Article
• Language: English
• Subjects: Aldehydes - chemistry; Animals; Biological and medical sciences; Carbolines - analysis; Carbolines - chemistry; chemical reactions; Chromatography, High Pressure Liquid; Fermentation; fermented foods; fermented sausages; food contamination; Food industries; food processing; Fundamental and applied biological sciences. Psychology; heat treatment; heterocyclic nitrogen compounds; Mass Spectrometry; Meat and meat product industries; meat composition; Meat Products - analysis; sausages; Smoke; smoked meats; smoked sausages; toxic substances; tryptamine; Tryptamines - chemistry; tryptophan; Tryptophan - chemistry
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf0354601

The identification and occurrence of tetrahydro-β-carbolines were studied in different kinds of commercial sausages including cooked, fresh, dry-fermented, and ripened sausages, such as salamis and Spanish chorizo, salchichon, fuet, and morcilla, both smoked and unsmoked. Four compounds were identified in several sausages by high-performance liquid chromatography−mass spectrometry (HPLC-MS):  1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1), 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid diastereoisomers (2a,b), 1,2,3,4-tetrahydro-β-carboline (3), and 1-methyl-1,2,3,4-tetrahydro-β-carboline (4). The latter two (3 and 4) are now reported for the first time in meat products. The presence and occurrence of tetrahydro-β-carbolines were highly variable depending on each particular sample of sausage, and it did not follow a single specific pattern. The concentration range taken as a sum of the four carbolines varied from undetectable levels to 33 μg/g, with the highest content found in ripened, dry-fermented, and smoked sausages (salami, chorizo, and morcilla) and the lowest in cooked sausages (Frankfurt). Formation of tetrahydro-β-carbolines might occur during elaboration and the ripening process from a chemical condensation between tryptophan or tryptamine and aldehydes (formaldehyde and acetaldehyde). Smoked samples had higher concentrations of formaldehyde-derived 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1) and 1,2,3,4-tetrahydro-β-carboline (tryptoline) (3) than those unsmoked. Also, 1 and 3 were more concentrated in the outer part of the sausage, likely to be in contact with smoke. It is concluded that some dry-fermented and/or smoked sausages may be significant dietary sources of tetrahydro-β-carbolines. Keywords: Tetrahydro-β-carbolines; sausages; fermented meats; smoking; tryptophan; tryptamine