Identification and occurrence of tryptamine- and tryptophan-derived tetrahydro-beta-carbolines in commercial sausages

J Agric Food Chem. 2004 May 5;52(9):2652-8. doi: 10.1021/jf0354601.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Animals
  • Carbolines / analysis*
  • Carbolines / chemistry
  • Chromatography, High Pressure Liquid
  • Fermentation
  • Mass Spectrometry
  • Meat Products / analysis*
  • Smoke
  • Tryptamines / chemistry*
  • Tryptophan / chemistry*


  • Aldehydes
  • Carbolines
  • Smoke
  • Tryptamines
  • tryptamine
  • tryptoline
  • Tryptophan