A model system study of the inhibition of heterocyclic aromatic amine formation by organosulfur compounds

Han Seung Shin, Gale M. Strasburg, J. Ian Gray

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Abstract

Organosulfur compounds and sodium bisulfite significantly inhibited (P < 0.05) heterocyclic aromatic amine (HAA) formation in model systems containing phenylalanine, creatinine, and glucose. There was, however, no inhibition by the same compounds in a model system containing only phenylalanine and creatinine. Diallyl disulfide (DAD) and dipropyl disulfide (DPD) concentrations in the model systems were significantly decreased (P < 0.05) after heating for 10 min at 180 °C. Only very low concentrations of sulfhydryl groups (4.19 and 4.00 μmol) were produced on heating DAD and DPD for 30 min. Reaction of glucose and DAD produced several sulfur-containing compounds. After 10 min of heating at 180 °C, HAA formation in the control model systems was increased significantly, and DAD was an effective inhibitor during this heating period. Tetrahydrothiophene-3-one (THT) and tetrahydrothiophene (THP); two products resulting from the interaction of glucose and DAD, had no direct influence on HAA formation in the model systems.

Original languageEnglish
Pages (from-to)7684-7690
Number of pages7
JournalJournal of Agricultural and Food Chemistry
Volume50
Issue number26
DOIs
StatePublished - 18 Dec 2002

Keywords

  • Heterocyclic aromatic amine
  • Model system
  • Sulfur compound
  • Tetrahydrothiophene
  • Tetrahydrothiophene-3-one

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