Mutagen formation in a model beef boiling system. III. Purification and identification of three heterocyclic amine mutagens-carcinogens

Journal Article · Mon Dec 31 23:00:00 EST 1984 · J. Environ. Sci. Health, Part A; (United States)

DOI:https://doi.org/10.1080/10934528509375216· OSTI ID:6168284

Taylor, R T; Fultz, E; Knize, M

An extensively boiled supernatant/sub 2/ (S/sub 2/) fraction from beef round steak contains two major Salmonella frameshift mutagens, designated as HPLC peaks A and B. These same mutagens arise, but in different proportions, when S/sub 2/ is boiled with creatine phosphate (CP), and they are produced in much greater quantities from a boiled mixture of S/sub 2/ + L-tryptophan (Trp) + CP + FeSO/sub 4/ (S/sub 2//sup */). A third mutagen, peak C, is also generated in the S/sub 2//sup */ mixture. Mutagen peaks A, B, and C were purified to homogeneity and shown by their absorption spectra, mass fragmentation patterns, and other data to be 2-amino-3-methylimidazo(4,5-f)quinoline (IQ), 3-amino-1-methyl-5H-pyrido(4,3-b)-indole (Trp-P-2), and 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole (Trp-P-1), respectively. This is the first demonstration that IQ, Trp-P-2, and Trp-P-1 can form under aqueous conditions at 100/sup 0/C from reactions between low molecular weight precursors that are present in meat juice. Further simplification of and studies with the S/sub 2/ fraction of beef muscle should provide relevant information about the mechanisms of frameshift mutagen formation during the cooking of meats and fish.

• Research Organization: Lawrence Livermore National Lab., CA
• DOE Contract Number: W-7405-ENG-48
• OSTI ID: 6168284
• Journal Information: J. Environ. Sci. Health, Part A; (United States), Journal Name: J. Environ. Sci. Health, Part A; (United States) Vol. A20:2; ISSN JESED
• Country of Publication: United States
• Language: English

Related Subjects

553000 -- Agriculture & Food Technology
560302* -- Chemicals Metabolism & Toxicology-- Microorganisms-- (-1987)
60 APPLIED LIFE SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AMINO ACIDS
AQUEOUS SOLUTIONS
AROMATICS
AZAARENES
AZINES
AZOLES
BACTERIA
BIOLOGICAL PATHWAYS
CARBOXYLIC ACIDS
DIET
DISPERSIONS
FOOD
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
INDOLES
MEAT
MICROORGANISMS
MIXTURES
MUTAGEN SCREENING
MUTAGENESIS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PRECURSOR
PYRIDINES
PYRROLES
QUINOLINES
SALMONELLA
SCREENING
SOLUTIONS
TRYPTOPHAN