A model system study of the inhibition of heterocyclic aromatic amine formation by organosulfur compounds.
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 degrees C. Only very low concentrations of sulfhydryl groups (4.19 and 4.00 micromol) 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 degrees 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.
Shin
Han-Seung
HS
Department of Food Science and Human Nutrition, Michigan State University, East Lansing, Michigan 48824-1224, USA.
Strasburg
Gale M
GM
Gray
J Ian
JI
D000498:Allyl Compounds / Q000494:pharmacology; D000588:Amines / Q000737:chemistry*; D003404:Creatinine / Q000737:chemistry; D004220:Disulfides / Q000494:pharmacology; D005947:Glucose / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006358:Hot Temperature; D007093:Imidazoles / Q000032:analysis / Q000737:chemistry; D010649:Phenylalanine / Q000737:chemistry; D011810:Quinoxalines / Q000032:analysis / Q000737:chemistry; D013447:Sulfites; D013457:Sulfur Compounds / Q000494:pharmacology*; D014835:Volatilization
C432523:2-amino-3-methylimidazo(4,5-f)quinoxaline; D000498:Allyl Compounds; D000588:Amines; D004220:Disulfides; D006571:Heterocyclic Compounds; D007093:Imidazoles; D011810:Quinoxalines; D013447:Sulfites; D013457:Sulfur Compounds; D010649:Phenylalanine; C028009:diallyl disulfide; C036990:2-amino-3,8-dimethylimidazo(4,5-f)quinoxaline; C049584:2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine; D003404:Creatinine; C041288:n-propyl disulfide; D005947:Glucose; C009279:sodium bisulfite