Identification and occurrence of tryptamine- and tryptophan-derived tetrahydro-beta-carbolines in commercial sausages.
The identification and occurrence of tetrahydro-beta-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-beta-carboline-3-carboxylic acid (1), 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid diastereoisomers (2a,b), 1,2,3,4-tetrahydro-beta-carboline (3), and 1-methyl-1,2,3,4-tetrahydro-beta-carboline (4). The latter two (3 and 4) are now reported for the first time in meat products. The presence and occurrence of tetrahydro-beta-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 microg/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-beta-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-beta-carboline-3-carboxylic acid (1) and 1,2,3,4-tetrahydro-beta-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-beta-carbolines.
Herraiz
Tomas
T
Instituto de Fermentaciones Industriales, CSIC, Juan de la Cierva, 3, 28006, Madrid, Spain. therraiz@ifi.csic.es
Papavergou
Ekaterini
E
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D002243:Carbolines / Q000032:analysis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005285:Fermentation; D013058:Mass Spectrometry; D008461:Meat Products / Q000032:analysis*; D012906:Smoke; D014363:Tryptamines / Q000737:chemistry*; D014364:Tryptophan / Q000737:chemistry*
D000447:Aldehydes; D002243:Carbolines; D012906:Smoke; D014363:Tryptamines; C030820:tryptamine; C009804:tryptoline; D014364:Tryptophan