J. Agric. Food Chem., 54 (15), 5679 -5687, 2006. 10.1021/jf0604788 S0021-8561(06)00478-X
Web Release Date: June 29, 2006

Copyright © 2006 American Chemical Society

Partial Purification from Hot Dogs of N-Nitroso Compound Precursors and Their Mutagenicity after Nitrosation

Lin Zhou, James Haorah, Fulvio Perini, Steven G. Carmella, Takayuki Shibamoto, and Sidney S. Mirvish*

Eppley Institute for Research in Cancer and Departments of Pharmaceutical Sciences and of Biochemistry and Molecular Biology, University of Nebraska Medical Center, Omaha, Nebraska 68198, Cancer Center, University of Minnesota, Minneapolis, Minnesota 55455, and Department of Environmental Toxicology, University of California-Davis, Davis, California 95616

Received for review February 16, 2006. Revised manuscript received May 12, 2006. Accepted May 15, 2006. This research was supported by Grants RO1-CA-71483, RO1-CA-11753, and RO3-CA-11753 and Core Grant P30-CA-36727 from the National Cancer Institute and by Grant 94B28 from the American Institute for Cancer Research. Portions of these studies were presented at national meetings (42-44).

Abstract:

Hot dogs contain apparent N-nitroso compounds (ANC) and ANC precursors (ANCP). ANCP purification was followed by nitrosation, sulfamic acid treatment, and analysis for ANC. Aqueous hot dog extracts were adsorbed on silica gel, which was eluted with MeCN and MeOH. The MeOH eluate was adsorbed on cation exchange resin (H+ form) and eluted with NH4OH. Eluted ANCP traveled at moderate speeds in high-performance liquid chromatography (HPLC) on amino and Pb2+ columns. Gas chromatography-mass spectrometry (GC-MS) of trimethylsilyl (TMS) derivatives of crude water extract indicated the presence of glycerol, phosphate, lactic acid, and two monosaccharides. GC-MS of TMS derivatives of Pb2+ column HPLC eluates indicated that ANCP included 1-deoxy-N-1-glucosyl glycine. The nitrosated NH4OH eluate showed 4× background mutagenic activity for Salmonella typhimurium TA-100. Un-nitrosated fractions showed 2× background activity. Although tryptophan nitrosation gave 88% ANC yield, tryptophan is probably not a major ANCP in hot dogs. Hot dog patties prepared with or without sucrose or glucose showed similar ANC and ANCP levels. We discuss possible implications of these findings for the etiology of colon cancer.

Keywords: Hot dog; nitrite; mutagenicity


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