Identification of Mutagens from the Cooking of Food

  • Frederick T. Hatch
  • James S. Felton
  • Daniel H. Stuermer
  • Leonard F. Bjeldanes

Keywords

Benzene DMSO Respiration Alkaloid Diazepam 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    R. Doll, General epidemiologic considerations in etiology of colorectal cancer, in:Colorectal Cancer: Prevention, Epidemiology, and Screening (S. Winawer, D. Schottenfeld, and P. Sherlock, eds.), p. 3–12, Raven Press, New York (1980).Google Scholar
  2. 2.
    J. H. Weisburger, N. E. Spingarn, Y. Y. Wang, and L. L. Vuolo, Assessment of the role of mutagens and endogenous factors in large bowel cancer,Cancer Bull. 33, 124–129 (1981).Google Scholar
  3. 3.
    R. Doll and R. Peto, The causes of cancer: Quantitative estimates of avoidable risks of cancer in the United States today,J. Natl. Cancer Inst. 66, 1191–1308 (1981).PubMedGoogle Scholar
  4. 4.
    J. H. Weisburger and G. M. Williams, Chemical carcinogenesis, in:Cancer Medicine (J. F. Holland and E. Frei III, eds.), pp. 42–95, Lea & Febiger, Philadelphia (1982).Google Scholar
  5. 5.
    J. H. Weisburger, On the etiology of gastro–intestinal tract cancers, with emphasis on dietary factors, in:Environmental Carcinogenesis. Occurrence, Risk Evaluation and Mechanisms (P. Emmelot and E. Kriek, eds.), pp. 215–240, Elsevier/North-Holland Biomedical Press, Amsterdam (1979).Google Scholar
  6. 6.
    E. L. Wynder and G. B. Gori, Contribution of the environment to cancer incidence: An epidemiologic exercise,J. Natl. Cancer Inst. 58, 825–832 (1977).PubMedGoogle Scholar
  7. 7.
    T. Sugimura, Tumor initiators and promoters associated with ordinary foods, in:Molecular Interrelations of Nutrition and Cancer ( M. S. Arnott, J. van Eys, and Y. M. Wang, eds.), pp. 3–42, Raven Press, New York (1982).Google Scholar
  8. 8.
    T. Sugimura, Mutagens, carcinogens, and tumor promoters in our daily food,Cancer 49, 1970–1984 (1982).PubMedGoogle Scholar
  9. 9.
    W. D. Powrie, C. H. Wu, M. P. Rosin, and H. F. Stich, Clastogenic and mutagenic activities of Maillard reaction model systems,J. Food Sci. 46, 1433–1445 (1981).Google Scholar
  10. 10.
    T. Sugimura and M. Nagao, Mutagenic factors in cooked foods,CRC Crit. Rev. Toxicol. 6, 189–209 (1979).PubMedGoogle Scholar
  11. 11.
    W. D. Powrie, C. H. Wu, M. P. Rosin, and H. F. Stich, Mutagens and carcinogens in food,Prog. Mutat. Res. 3, 187–199 (1982).Google Scholar
  12. 12.
    W. Lijinsky and P. Shubik, Benzo(α)pyrene and other polynuclear hydrocarbons in charcoal-broiled meat,Science 145, 53–55 (1964).PubMedGoogle Scholar
  13. 13.
    T. Sugimura, M. Nagao, T. Kawachi, M. Honda, T. Yahagi, Y. Seino, S. Sato, N. Matsukura, T. Matsushima, A. Shirai, M. Sawamura, and H. Matsumoto, Mutagen- carcinogens in foods with special reference to highly mutagenic pyrolytic products in broiled foods, in:Origins of Human Cancer (H. H. Hiatt, J. D. Watson, and J. A. Winsten, eds.), pp. 1561–1577, Cold Spring Harbor Laboratory, Cold Spring Harbor, New York (1977).Google Scholar
  14. 14.
    D. Yoshida and T. Matsumoto, Amino-a-carbolines as mutagenic agents in cigarette smoke condensate,Cancer Lett. 10, 141–149 (1980).PubMedGoogle Scholar
  15. 15.
    S. Mizusaki, H. Okamoto, A. Akiyama, and Y. Fukuhara, Relation between chemical constituents of tobacco and mutagenic activity of cigarette smoke condensate,Mutat. Res. 48, 319–326 (1977).PubMedGoogle Scholar
  16. 16.
    T. Matsumoto, D. Yoshida, S. Mizusaki, and H. Okamoto, Mutagenic activity of amino acid pyrolysates inSalmonella typhimurium TA 98,Mutat. Res. 48, 279–286 (1977).PubMedGoogle Scholar
  17. 17.
    T. Matsumoto, D. Yoshida, S. Mizusaki, and H. Okamoto, Mutagenicities of the pyrolysates of peptides and proteins,Mutat. Res. 56 , 281–288 (1978).PubMedGoogle Scholar
  18. 18.
    T. Matsumoto, D. Yoshida, and H. Tomita, Determination of mutagens, amino-a-carbolines in grilled foods and cigarette smoke condensate,Cancer Lett. 12, 105–110 (1981).PubMedGoogle Scholar
  19. 19.
    M. Nagao, M. Honda, Y. Seino, T. Yahagi, T. Kawachi, and T. Sugimura, Mutagenicities of protein pyrolysates,Cancer Lett. 2, 335–340 (1977).PubMedGoogle Scholar
  20. 20.
    M. Nagao, M. Honda, Y. Seino, T. Yahagi, and T. Sugimura, Mutagenicities of smoke condensates and the charred surface of fish and meat,Cancer Lett. 2, 221–226 (1977).PubMedGoogle Scholar
  21. 21.
    M. Nagao, T. Yahagi, T. Kawachi, Y. Seino, M. Honda, N. Matsukura, T. Sugimura, K. Wakabayashi, K. Tsuji, and T. Kosuge, Mutagens in foods, and especially pyrolysis products of protein, in:Progress in Genetic Toxicology: Proceedings of the Second International Conference on Environmental Mutagens, Edinburgh (July 1977), (D. Scott, B. A. Bridges, and F. H. Sobels, eds.), pp. 259–264, Elsevier (1977).Google Scholar
  22. 22.
    D. Yoshida, T. Matsumoto, and H. Nishigata, Effect of heating methods on mutagenic activity and yield of mutagenic compounds in pyrolysis products of protein,Agric. Biol. Chem. 44, 253–255 (1980).Google Scholar
  23. 23.
    D. Yoshida, T. Matsumoto, R. Yoshimura, and T. Matsuzaki, Mutagenicity of amino-α-carbolines in pyrolysis products of soybean globulin,Biochem. Biophys. Res. Commun. 83, 915–920 (1978).PubMedGoogle Scholar
  24. 24.
    D. Yoshida, H. Nishigata, and T. Matsumoto, Pyrolytic yields of 2-amino-9H-pyrido[2,3-b]indole and 3-amino-l-methyl-5H-pyrido[4,3-b]indole as mutagens from proteins,Agric. Biol. Chem. 43, 1769–1770 (1979).Google Scholar
  25. 25.
    T. Sugimura, M. Nagao, and K. Wakabayashi, Mutagenic heterocyclic amines in cooked food, in:Environmental Carcinogens, Selected Methods of Analysis (L. Fishbein, I. K. O’Neill, M. Castegnaro, and H. Bartsch, eds.), Vol. 4, pp. 251–267, International Agency for Research on Cancer, Lyon, France (1981).Google Scholar
  26. 26.
    M. Nagao, T. Yahagi, and T. Sugimura, Differences in effects of norharman with various classes of chemical mutagens and amounts of S-9,Biochem. Biophys. Res. Commun. 83, 373–378 (1978).PubMedGoogle Scholar
  27. 27.
    M. Nagao, T. Yahagi, T. Kawachi, T. Sugimura, T. Kosuge, K. Tsuji, K. Wakabayashi, S. Mizusaki, T. Matsumoto, Comutagenic action of norharman and harman,Proc. Jpn. Acad. B 53(2), 95–98 (1977).Google Scholar
  28. 28.
    T. Matsumoto, D. Yoshida, and S. Mizusaki, Enhancing effect of harman on mutagenicity inSalmonella, Mutat. Res. 56, 85–88 (1977).PubMedGoogle Scholar
  29. 29.
    B. Commoner, A. Vithayathil, and P. Dolara, Mutagenic analysis as a means of detecting carcinogens in foods,J. Food Protection , 996–1003 (1978).Google Scholar
  30. 30.
    B. Commoner, A. J. Vithayathil, P. Dolara, S. Nair, P. Madyastha, and G. C. Cuca, Formation of mutagens in beef and beef extract during cooking,Science 201, 913–916 (1978).PubMedGoogle Scholar
  31. 31.
    P. Dolara, B. Commoner, A. Vithayathil, G. Cuca, E. Tuley, P. Madyastha, S. Nair, an D. Kriebel, The effect of temperature on the formation of mutagens in heated beef stock and cooked ground beef,Mutat. Res. 60 , 231–237 (1979).PubMedGoogle Scholar
  32. 32.
    L. F. Bjeldanes, M. M. Morris, J. S. Felton, S. Healy, D. Stuermer, P. Berry, H. Timourian, and F. T. Hatch, Mutagens from the cooking of food II. Survey by Ames/Salmonella test of mutagen formation in the major protein–rich foods of the American diet,Food Chem. Toxicol. 20, 357–363 (1982).PubMedGoogle Scholar
  33. 33.
    L. F. Bjeldanes, M. M. Morris, J. S. Felton, S. Healy, D. Stuermer, P. Berry, H. Timourian, and F. T. Hatch, Mutagens from the cooking of food III. Secondary sources of cooked dietary protein,Food Chem. Toxicol. 20, 365–369 (1982).PubMedGoogle Scholar
  34. 34.
    L. F. Bjeldanes, M. M. Morris, H. Timourian, and F. T. Hatch, Effects of meat composition and cooking conditions on mutagenicity of fried ground beef,J. Agric. Food Chem. 31, 18–21 (1983).PubMedGoogle Scholar
  35. 35.
    J. Felton, S. Healy, D. Stuermer, C. Berry, H. Timourian, F. T. Hatch, M. Morris, and L. F. Bjeldanes, Mutagens from the cooking of food. (I). Improved isolation and characterization of mutagenic fractions from cooked ground beef,Mutat. Res. 88, 33–44 (1981).PubMedGoogle Scholar
  36. 36.
    H. Kasai, Z. Yamaizumi, K. Wakabayashi, M. Nagao, T. Sugimura, S. Yokoyama, T. Miyazawa, N. E. Spingarn, J. H. Weisburger, and S. Nishimura, Potent novel mutagens produced by broiling fish under normal conditions,Proc. Jpn. Acad. B 56(5), 278–283 (1980).Google Scholar
  37. 37.
    H. Kasai, Z. Yamaizumi, S. Nishimura, K. Wakabayashi, M. Nagao, T. Sugimura, N. E. Spingarn, J. H. Weisburger, S. Yokoyama, and T. Miyazawa, A potent mutagen in broiled fish. Part 1. 2-Amino-3-methyl-3H-imidazo[4,5-f]quinoline,J. Chem. Soc. 1981, 2290–2293.Google Scholar
  38. 38.
    M. W. Pariza, S. H. Ashoor, F. S. Chu, and D. B. Lund, Effects of temperature and time on mutagen formation in pan–fried hamburger,Cancer Lett. 7, 63–69 (1979).PubMedGoogle Scholar
  39. 39.
    N. E. Spingarn and J. H. Weisburger, Formation of mutagens in cooked food: I. Beef,Cancer Lett. 7, 259–264 (1979).PubMedGoogle Scholar
  40. 40.
    N. E. Spingarn, H. Kasai, L. L. Vuolo, S. Nishimura, Z. Yamaizumi, T. Sugimura, T. Matsushima, and J. H. Weisburger. Formation of mutagens in cooked foods. III. Isolation of a potent mutagen from beef,Cancer Lett. 9, 177–183 (1980).PubMedGoogle Scholar
  41. 41.
    W. A. Hargraves and M. W. Pariza, Purification and characterization of bacterial mutagens from commercial beef extracts and fried ground beef,Proc. Am. Assoc. Cancer Res. 23, 92 (1982).Google Scholar
  42. 42.
    M. W. Pariza, S. H. Ashoor, F. S. Chu, and D. B. Lund, Mutagens and inhibitors of mutagenesis in pan-fried hamburger,Proc. Am. Assoc. Cancer Res. 20, 39 (1979).Google Scholar
  43. 43.
    M. W. Pariza, Mutagens in heated foods,Food Technol. 1982 (March), 53–56.Google Scholar
  44. 44.
    M. W. Pariza, S. H. Ashoor, D. J. Raune, R. A. Dietrich, M. B. Hugdahl, and F. S. Chu, Formation of mutagens in cooked beef and in model systems,Proc. Am. Assoc. Cancer Res. 21, 87 (1980).Google Scholar
  45. 45.
    R. I. M. Chan, H. F. Stich, M. P. Rosin, and W. D. Powrie, Antimutagenic activity of browning reaction products,Cancer Lett. 15, 27–33 (1982).PubMedGoogle Scholar
  46. 46.
    N. E. Spingarn, L. A. Slocum, and J. H. Weisburger, Formation of mutagens in cooked foods. II. Foods with high starch content,Cancer Lett. 9, 7–12 (1980).PubMedGoogle Scholar
  47. 47.
    H. F. Stich, W. Stich, M. P. Rosin, and W. D. Powrie, Clastogenic activity of caramel and caramelized sugars,Mutat. Res. 91 , 129–136 (1981).PubMedGoogle Scholar
  48. 48.
    M. W. Pariza, S. H. Ashoor, and F. S. Chu, Mutagens in heat-processed meat, bakery and cereal products,Food Cosmet. Toxicol. 17, 429–430 (1979).PubMedGoogle Scholar
  49. 49.
    L. F. Bjeldanes and H. Chew, Mutagenicity of 1,2–dicarbonyl compounds: Maltol, kojic acid, diacetyl and related substances,Mutat. Res. 67, 367–371 (1979).PubMedGoogle Scholar
  50. 50.
    M. W. Pariza, ed., Selected abstracts on mutagens and carcinogens in cooked, smoked and charred foods, in:Oncology Overview, International Cancer Research Data Bank Program, National Cancer Institute, U. S. Department of Health and Human Services, National Institute of Health (1982).Google Scholar
  51. 51.
    T. Matsushima and T. Sugimura, Mutagen-carcinogens in amino acid and protein pyrolysates and in cooked food, in:Progress in Mutation Research (A. Kappas, ed.), Vol. 2, pp. 49–56 Elsevier/North-Holland Biomedical Press, Amsterdam (1981).Google Scholar
  52. 52.
    W. D. Powrie and S. Nakai, Processing effects on protein systems, in:Utilization of Protein Resources (D. W. Stanleyet al., eds.), Chapter 4, Food and Nutrition Press, Westport, Connecticut (1981).Google Scholar
  53. 53.
    T. Shibamoto, Heterocyclic compounds found in cooked meats,J. Agric. Food Chem. 58, 237–243 (1980).PubMedGoogle Scholar
  54. 54.
    Report of Committee on Diet, Nutrition, and Cancer, National Research Council, National Academy Press, Washington, D.C. (1982).Google Scholar
  55. 55.
    J.J. Hutton and C. Hackney, Metabolism of cigarette smoke condensates by human and rat homogenates to form mutagens detectable bySalmonella typhimurium TA 1538,Cancer Res. 35, 2461–2468 (1975).PubMedGoogle Scholar
  56. 56.
    T. Sugimura, T. Kawachi, M. Nagao, and T. Yahagi, Mutagens in food as causes of cancer,Prog. Cancer Res. Ther. 17, 59–71 (1981).Google Scholar
  57. 57.
    T. Sugimura, Naturally occurring genotoxic carcinogens, in:Naturally Occurring Carcinogen-Mutagens and Modulators of Carcinogenesis ( E. C. Miller, J. A. Miller, and I. Hirono, eds.), pp. 241–261, University Park Press, Baltimore, Maryland (1979).Google Scholar
  58. 58.
    K. Shinohara, R.-T. Wu, N. Jahan, M. Tanaka, N. Morinaga, H. Murakami, and H. Omura, Mutagenicity of the browning mixtures of amino-carbonyl reactions onSalmonella typhimurium TA 100,Agric. Biol. Chem. 44, 671 (1980).Google Scholar
  59. 59.
    H. F. Stich, W. Stich, M. Rosin, and W. Powrie, Mutagenic activity of pyrazine derivatives: A comparative study withSalmonella typhimurium, Saccharomyces cerevisiae and Chinese hamster ovary cells,Food Cosmet. Toxicol. 18, 581–584 (1980).PubMedGoogle Scholar
  60. 60.
    T. Shibamoto, Occurrence of mutagenic products in browning model systems,Food Technol. 1982 (March), 59–62.Google Scholar
  61. 61.
    N. E. Spingarn, C. T. Garvie-Gould, and L. A. Slocum, Formation of mutagens in sugar–amino acid model systems,J. Agric. Food Chem. 31, 301–304 (1983).PubMedGoogle Scholar
  62. 62.
    W. D. Powrie, C. H. Wu, and H. F. Stich, Browning reaction systems as sources of mutagens and modulators, in:Carcinogens and Mutagens in the Environment. Volume I Food Products (Hans F. Stich, ed.), pp. 121–133, CRC Press, Boca Raton, Florida (1982).Google Scholar
  63. 63.
    J. W. Howard and T. Fazio, A review of polycyclic aromatic hydrocarbons in foods,J. Agric. Food Chem. 17, 527–531 (1969).Google Scholar
  64. 64.
    C. Lintas, M. C. De Matthaeis, and F. Merli, Determination of benzo(a)pyrene in smoked, cooked and toasted food products,Food Cosmet. Toxicol. 17, 325–328 (1979).PubMedGoogle Scholar
  65. 65.
    T. Panalaks, Determination and identification of polycyclic aromatic hydrocarbons in smoked and charcoal-broiled food products by high pressure liquid chromatography and gas chromatography,J. Environ. Sci. Health Bull. 1976, 299–315.Google Scholar
  66. 66.
    L. O. MeiTein and E. Sandi, Polycyclic aromatic hydrocarbons (polynuclears) in foods,Residue Rev. 69, 35–86 (1978).Google Scholar
  67. 67.
    B. P. Dunn, Polycyclic aromatic hydrocarbons (PAH), in:Carcinogens and Mutagens in the Environment. Volume I Food Products (Hans F. Stich ed.), pp. 175–183, CRC Press, Boca Raton, Florida (1982).Google Scholar
  68. 68.
    W. Lijinksy, Carcinogenic and mutagenic N-nitroso compounds, in:Chemical Mutagens, Principles and Methods for Their Detection Vol. 4 (A. Hollaender, ed.), pp. 193–217, Plenum Press, New York (1976).Google Scholar
  69. 69.
    J. R. Iyengar, T. Panalaks, W. F. Miles, and N. P. Sen, A survey of fish products for volatile N–nitrosamines, in:Oncology Overview, Selected Abstracts on Mutagens and Carcinogens in Cooked, Smoked and Charred Foods (Michael W. Pariza, consulting reviewer), p. 8, U. S. Department of Health and Human Services, National Cancer Institute (1982).Google Scholar
  70. 70.
    T. Kawabata, H. Ohshima, T. Uibu, M. Nakamura, M. Matsui, and M. Hamano, Occurrence, formation, and precursors of N-nitroso compounds in Japanese diet, in:Oncology Overview, Selected Abstracts on Mutagens and Carcinogens in Cooked, Smoked and Charred Foods, p. 9 ( Michael W. Pariza, consulting reviewer), U. S. Department of Health and Human Services, National Cancer Institute (1982).Google Scholar
  71. 71.
    P. E. Hartman, Nitrates and nitrites: Ingestion, pharmacodynamics, and toxicology, in:Chemical Mutagens, Principles and Methods for Their Detection (F. J. de Serres and A. Hollaender, eds.), Vol. 7, pp. 211–294, Plenum Press, New York (1982).Google Scholar
  72. 72.
    L. Lakritz, R. A. Gates, A. M., Gugger, and A. E. Wasserman, Nitrosamine levels in human blood, urine and gastric aspirate following ingestion of foods containing potential nitrosamine precursors or preformed nitrosamines,Food Chem. Toxicol. 20, 455–459 (1982).PubMedGoogle Scholar
  73. 73.
    C. Plumlee, L. F. Bjeldanes, and F. Hatch, Priorities assessment for studies of mutagen production in cooked foods,J. Am. Diet. Assoc. 79, 446–449 (1981).PubMedGoogle Scholar
  74. 74.
    W. S. Barnes and J. H. Weisburger, Lipid content and mutagen formation in the cooking of beef,Proc. Am. Assoc. Cancer Res. 24, 65 (1983).Google Scholar
  75. 75.
    R. T. Taylor, E. Fultz, and V. Shore, Mutagen formation in a model beef boiling system. I. Conditions with soluble beef derived fraction,J. Environ. Sci. Health, in press (1984).Google Scholar
  76. 76.
    R. T. Taylor, V. Shore, and E. Fultz, Mutagen formation in a model beef boiling system. II. Effects of proteolysis and comparison of soluble fractions from several protein sources,J. Environ. Sci. Health, in press (1984).Google Scholar
  77. 77.
    R. T. Taylor, V. Shore, and E. Fultz, Mutagen formation in a model beef boiling system: Stimulation studies with amino acids and other agents,Environ. Mutagen. 4, 368 (1982).Google Scholar
  78. 78.
    H. Kasai, Z. Yamaizumi, T. Shiomi, S. Yokoyama, T. Miyazawa, K. Wakabayashi, M. Nagao, T. Sugimura, and S. Nishimura, Structure of a potent mutagen isolated from fried beef,Chem Lett. 485–488 (1981).Google Scholar
  79. 79.
    T. Sugimura, Mutagens in cooked food,Basic Life Sci. 21, 243–269 (1982).PubMedGoogle Scholar
  80. 80.
    T. Sugimura and S. Sato, Mutagens-carcinogens in foods,Cancer Res. (Suppl.) 43, 2415s–2421s (1983).Google Scholar
  81. 81.
    T. Ishikawa, S. Takayama, T. Kitagawa, T. Kawachi, and T. Sugimura, Induction of enzyme–altered islands in rat liver by tryptophan pyrolysis products,J. Cancer Res. Clin. Oncol. 94, 221–224 (1979).Google Scholar
  82. 82.
    T. Ishikawa, S. Takayama, T. Kitagawa, T. Kawachi, M. Kinebuchi, N. Matsukura, E. Uchida, and T. Sugimura,In vivo experiments on tryptophan pyrolysis products, in:Naturally Occurring Carcinogen-Mutagens and Modulators of Carcinogenesis (E. C. Miller, J. A. Miller, and I. Hirono, eds.), pp. 159–167, University Park Press, Baltimore, Maryland (1979).Google Scholar
  83. 83.
    S. Takayama, T. Hirakawa, M. Tanaka, Y. Katoh, and T. Sugimura, Transformation and neoplastic development of hamster embryo cells after exposure to tryptophan pyrolysis products in tissue culture, in:Naturally Occurring Carcinogen-Mutagens and Modulators of Carcinogenesis (E. C. Miller, J. A. Miller, and I. Hirono, eds.), pp. 151–157, University Park Press, Baltimore, Maryland (1979).Google Scholar
  84. 84.
    S. Hosaka, T. Matsushima, I. Hirono, and T. Sugimura, Carcinogenic activity of 3-amino-1-methyl-5H-pyrido[4,3-b] indole (Trp-P-2), a pyrolysis product of tryptophan,Cancer Lett. 13, 23–28 (1981).PubMedGoogle Scholar
  85. 85.
    N. Matsukura, T. Kawachi, K. Morino, H. Ohgaki, T. Sugimura, and S. Takayama, Carcinogenicity in mice of mutagenic compounds from a tryptophan pyrolyzate,Science 213, 346–347 (1981).PubMedGoogle Scholar
  86. 86.
    F. T. Hatch, J. S. Felton, L. H. Thompson, A. V. Carrano, S. K. Healy, E. P. Salazar, and J. L. Minkler, Comparative genotoxicity of the food mutagens Trp-P-2 and IQ inSalmonella and CHO cells,Environ. Mutagen. 4, 368 (1982).Google Scholar
  87. 87.
    L. H. Thompson, A. V. Carrano, E. Salazar, J. S. Felton, and F. T. Hatch, Comparative genotoxic effects of the cooked-food-related mutagens Trp-P-2 and IQ in bacteria and cultured mammalian cells,Mutat. Res. 117, 243–257 (1983).PubMedGoogle Scholar
  88. 88.
    T. Kosuge, K. Tsuji, K. Wakabayashi, T. Okamoto, K. Shudo, Y. Iitaka, A. Itai, T. Sugimura, T. Kawachi, M. Nagao, T. Yahagi, and Y. Seino, Isolation and structure studies of mutagenic principles in amino acid pyrolysates,Chem. Pharm. Bull. 26, 611–619 (1978).PubMedGoogle Scholar
  89. 89.
    M. Uyeta, T. Kanada, M. Mazaki, S. Taue, and S. Takahashi, Assaying mutagenicity of food pyrolysis products using the Ames test, in:Naturally Occurring Carcinogen-Mutagens and Modulators of Carcinogenesis (E. C. Miller, J. A. Miller, and I. Hirono, eds.), pp. 169–176, University Park Press, Baltimore, Maryland (1979).Google Scholar
  90. 90.
    Z. Yamaizumi, T. Shiomi, H. Kasai, S. Nishimura, Y. Takahashi, M. Nagao, and T. Sugimura, Detection of potent mutagens, Trp-P-1 and Trp-P-2, in broiled fish,Cancer Lett. 9, 75–83 (1980).PubMedGoogle Scholar
  91. 91.
    A.J. Vithayathil, B. Commoner, S. Nair, and P. Madyastha, Isolation of mutagens from bacterial nutrients containing beef extract,/.Toxicol. Environ. Health 4, 189–202 (1978).PubMedGoogle Scholar
  92. 92.
    W. A. Hargraves, R. Dietrich, and M. W. Pariza, A new chromatographic method for separating mutagens from commercial beef extract and fried ground beef, in:Carcinogens and Mutagens in the Environment. Volume I Food Products (Hans F. Stich, ed.), pp. 223–229, CRC Press, Boca Raton, Florida (1982).Google Scholar
  93. 93.
    W. A. Hargraves and M. W. Pariza, Purification and mass spectral characterization of bacterial mutagens from commercial beef extract,Cancer Res. 43, 1467–1472 (1983).PubMedGoogle Scholar
  94. 94.
    W. T. Iwaoka, C. A. Krone, J. J. Sullivan, and C. A. Johnson, Effect of pH and ammonium ions on mutagenic activity in cooked beef,Cancer Lett.12, 335–341 (1981).PubMedGoogle Scholar
  95. 95.
    W. T. Iwaoka, C. A. Krone, J. J. Sullivan, E. H. Meaker, C. A. Johnson, and L. S. Miyasato, A source of error in mutagen testing of foods,Cancer Lett. 11, 225–230 (1981).PubMedGoogle Scholar
  96. 96.
    W. T. Iwaoka and C. A. Krone, Problems associated with the extraction of mutagens from foods, in:Carcinogens and Mutagens in the Environment. Volume I Food Products (Hans F. Stich, ed.), pp. 211–221, CRC Press, Boca Raton, Florida (1982).Google Scholar
  97. 97.
    D. Moore and J. S. Felton, A microcomputer program for analyzing Ames test data,Mutat. Res. 119, 95–102 (1983).PubMedGoogle Scholar
  98. 98.
    L. F. Bjeldanes, K. R. Grose, P. H. Davis, D. H. Stuermer, S. K. Healy, and J. S. Felton, An XAD-2 resin method for efficient extraction of mutagens from fried ground beef,Mutat. Res. 105, 43–49 (1982).PubMedGoogle Scholar
  99. 99.
    B. N. Ames, J. McCann, and E. Yamasaki, Methods for detecting carcinogens and mutagens with theSalmonella/mammalian-microsome mutagenicity test,Mutat. Res. 31, 347–364 (1975).PubMedGoogle Scholar
  100. 100.
    D. W. Nebert, S. W. Bigelow, A. B. Okey, T. Yahagi, Y. Mori, M. Nagao, and T. Sugimura, Pyrolysis products from amino acids and protein: Highest mutagenicity requires cytochrome Pr450,Proc. Natl. Acad. Sci. USA 7(5, 5929–5933 (1979).Google Scholar
  101. 101.
    J. S. Felton, S. K. Healy, M. Knize, D. H. Stuermer, P. W. Berry, H. J. Timourian, F. T. Hatch, M. Morris, and L. F. Bjeldanes,In vitro human and rodent metabolism of mutagenic fractions from cooked ground beef,Environ. Mutagen. 3, 342 (1981).Google Scholar
  102. 102.
    J. S. Felton, S. K. Healy, M. Knize, D. H. Stuermer, P. W. Berry, H. Timourian, F. T. Hatch, L. F. Bjeldanes, and M. Morris, Metabolism of mutagenic fractions from cooked ground beef, J. Supramol. Structure Cell. Biochem. (Suppl. 5) 1981, 166.Google Scholar
  103. 103.
    M. Knize, B. Wuebbles, E. Fultz, M. Morris, R. Taylor, J. Felton, L. Bjeldanes, and F. Hatch, Characterization of the mutagens in cooked beef: Chromatographic patterns at different temperatures and cooking conditions,Fed. Proc. 42, 2089 (1983).Google Scholar
  104. 104.
    H. Kasai, S. Nishimura, M. Nagao, Y. Takahashi, and T. Sugimura, Fractionation of a mutagenic principle from broiled fish by high-pressure liquid chromatography,Cancer Lett. 7, 343–348 (1979).PubMedGoogle Scholar
  105. 105.
    Z. Yamaizumi, T. Shiomi, H. Kasai, K. Wakabayashi, M. Nagao, T. Sugimura, and S. Nishimura, Quantitative analysis of a novel potent mutagen, 2-amino-3-methyl- imidazo(4,5-f)quinoline, present in broiled food by GC/MS,Koenshu-Iyo Masu Kenk- yukai 5, 245–248 (1980).Google Scholar
  106. 106.
    Z. Yamaizumi, T. Shiomi, H. Sasai, K. Wakabayashi, T. Sugimura, and S. Nishimura, Quantitative measurement of IQ, Me-IQ and Me-IQx present in broiled foods by gas chromatography/mass spectrometry (GC/MS), in:Abstracts of the Third International Conference on Environmental Mutagens, p. 69 (1981).Google Scholar
  107. 107.
    M. Nagao, Y. Takahashi, T. Yahagi, T. Sugimura, K. Takeda, S. Shudo, and T. Okamoto, Mutagenicities of 7-carboline derivatives related to potent mutagens found in tryptophan pyrolysates,Carcinogenesis 1, 451–454 (1980).PubMedGoogle Scholar
  108. 108.
    M. Nagao, K. Wakabayashi, H. Kasai, S. Nishimura, and T. Sugimura, Effect of methyl substitution on mutagenicities of 2-amino-3-methylimidazo[4,5-f]quinoline, isolated from broiled sardine,Carcinogenesis, 2, 1147–1149 (1981).PubMedGoogle Scholar
  109. 108a.
    J. S. Felton, M. G. Knize, C. Wood, B. J. Wuebbles, S. K. Healy, D. H. Stuermer, L. F. Bjeldanes, B.J. Kimble, and F. T. Hatch, Isolation and characterization of new mutagens from fried ground beef,Carcinogenesis 5, 95–102 (1984).PubMedGoogle Scholar
  110. 109.
    T. Sugimura, T. Kawachi, M. Nagao, T. Yahagi, T. Okamoto, K. Shudo, T. Kosuge, K. Tsuji, K. Wakabayashi, Y. Iitaka, and A. Itai, Mutagenic principles in tryptophan and phenylalanine pyrolysis products,Proc. Jpn. Acad. 53, 58–61 (1977).Google Scholar
  111. 110.
    H. Akimoto, A. Kawai, H. Nomura, M. Nagao, T. Kawachi, and T. Sugimura, Synthesis of potent mutagens in tryptophan pyrolysates,Chem. Lett. 1977, 1061–1064.Google Scholar
  112. 111.
    K. Yamaguchi, K. Shudo, T. Okamoto, T. Sugimura, and T. Kosuge, Presence of 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole in broiled beef,Gann 71, 745–746 (1980).PubMedGoogle Scholar
  113. 112.
    J. H. Peters, K. E. Mortelmans, E. J. Reist, C. C. Sigman, R. J. Spanggord, and D. W. Thomas, Synthesis, chemical characterization, and mutagenic activities of pro-mutagens produced by pyrolysis of proteinaceous substances,Environ. Mutagen. 3, 639–649 (1981).Google Scholar
  114. 113.
    H. Tohda, A. Oikawa, T. Kawachi, and T. Sugimura, Induction of sister-chromatid exchanges by mutagens from amino acid and protein pyrolysates,Mutat. Res. 77, 65–69 (1980).PubMedGoogle Scholar
  115. 114.
    M. Sasaki, K. Sugimura, M. Yoshida, and T. Kawachi, Chromosome aberrations and sister chromatid exchanges induced by tryptophan pyrolysates, Trp-P-1 and Trp-P-2, in cultured human and Chinese hamster cells,Proc. Jpn. Acad. B 56, 332–336 (1980).Google Scholar
  116. 115.
    S. Takayama, T. Hirakawa, M. Tanaka, T. Kawachi, and T. Sugimura,In vitro transformation of hamster embryo cells with a glutamic acid pyrolysis product,Toxicol. Lett. 4, 281–284 (1979).Google Scholar
  117. 116.
    C. Hashida, K. Nagayama, and N. Takemura, Induction of bladder cancer in mice by implanting pellets containing tryptophan pyrolysis products,Cancer Lett. 17, 101–105 (1982).PubMedGoogle Scholar
  118. 117.
    K. Takeda, T. Ohta, K. Shudo, T. Okamoto, K. Tsuji, and T. Kosuge, Synthesis of a mutagenic principle isolated from tryptophan pyrolysate,Yakugaku Zasshi (J. Pharmaceutical Soc. Japan) 97, 2145–2146 (1977).Google Scholar
  119. 118.
    T. Sugimura, Mutagens, carcinogens, and tumor promoters in our daily food,Cancer 49, 1970–1984 (1982).PubMedGoogle Scholar
  120. 119.
    Y. Hashimoto, K. Shudo, and T. Okamoto, Structural identification of a modified base in DNA covalently bound with mutagenic 3-amino-1-methyl-5H-pyrido[4,3-b]indole,Chem. Pharm. Bull. 27, 1058–1060 (1979).PubMedGoogle Scholar
  121. 120.
    Y. Hashimoto, K. Shudo, and T. Okamoto, Modification of nucleic acids with muta– carcinogenic heteroaromatic aminesin vivo—identification of modified bases in DNA extracted from rats injected with 3-amino-1-methyl-5H-pyrido-[4,3-b]indole and 2-amino-6-methyldipyrido-[1,2 -a: 3’, 2’-d]-imidazole,Mutat. Res. 105, 9–13 (1982).PubMedGoogle Scholar
  122. 121.
    J. S. Felton and R. L. Dobson, The mouse oocyte toxicity assay, in:Short-Term Bioassays in the Analysis of Complex Environmental Mixtures III (M. Waters, S. Shandhu, J. Lewtas, L. Claxton, N. Chernoff, and S. Newsnow, eds.), pp. 245–255, Plenum Press, New York (1983).Google Scholar
  123. 122.
    S. Yokoyama, T. Miyazawa, H. Kasai, S. Nishimura, T. Sugimura, and Y. Iitaka, Crystal and molecular structures of 2-amino-3-methylimidazo-[4,5-f]quinoline, a novel potent mutagen found in broiled food,FEBS Lett. 122, 261–263 (1980.).PubMedGoogle Scholar
  124. 123.
    H. Kasai, S. Nishimura, K. Wakabayashi, M. Nagao, and T. Sugimura, Chemical synthesis of 1-amino-3-methylimidazo-[4,5-f]quinoline (IQ), a potent mutagen isolated from broiled fish,Proc. Jpn. Acad. 56(6), 382 (1980).Google Scholar
  125. 124.
    C.-S. Lee, Y. Hashimoto, K. Shudo, and T. Okamoto, Synthesis of mutagenic heteroaromatics: 2-Aminoimidazo[4,5-f]quinolines,Chem. Pharm. Bull. 30, 1857–1859 (1982).Google Scholar
  126. 125.
    Z. Yamaizumi, S. Tomoko, K. Hiroshi, K. Wakabayashi, M. Nagao, T. Sugimura, and S. Nishimura, Quantitative analysis of a novel potent mutagen 2-amino-3-methylimidazo(4,5-f)quinoline, present in broiled food by GC/MS,Chem. Abstr. 94, 137879d (1981).Google Scholar
  127. 126.
    J. Felton, S. Healy, L. Avalos, and B. Wuebbles, Comparison of mutagenicity of two cooking mutagens with three microbial bioassays,Environ. Mutagen. 5, 446 (1983).Google Scholar
  128. 127.
    H. Kasai, Z. Yamaizumi, K. Wakabayashi, M. Nagao, T. Sugimura, S. Yokoyama, T. Miyazawa, and S. Nishimura, Structure and chemical synthesis of ME-IQ, a potent mutagen isolated from broiled fish,Chem. Lett. 1980, 1391–1394.Google Scholar
  129. 128.
    H. Kasai and S. Nishimura, Syntheses of 2-amino-3,4-dimethyl-3H-imidazo[4,5- f]quinoline and its related compounds,Bull. Chem. Soc. Japan 55, 2233–2235 (1982).Google Scholar
  130. 129.
    H. S. Rosenkranz, E. D. McCoy, D. R. Sanders, M. Butler, D. K. Kiriazides, and R. Mermelstein, Nitropyrenes: Isolation, identification, and reduction of mutagenic impurities in carbon black and toners,Science 209, 1039–1043 (1980).PubMedGoogle Scholar
  131. 130.
    H. Kasai, T. Shiomi, T. Sugimura, and S. Nishimura, Synthesis of 2-amino-3,8- dimethylimidazo[4,5-f]quinoxaline (Me-IQx), a potent mutagen isolated from fried beef,Chem. Lett. 675–678 (1981).Google Scholar
  132. 131.
    T. Yamamoto, K. Tsuji, T. Kosuge, T. Okamoto, K. Shudo, K. Takeda, Y. Iitaka, K. Yamaguchi, Y. Seino, T. Yahagi, M. Nagao, and T. Sugimura, Isolation and structure determination of mutagenic substances inL–glutamic acid pyrolysate,Proc. Jpn. Acad. B 54, 248–250 (1978).Google Scholar
  133. 132.
    K. Takeda, K. Shudo, T. Okamoto, and T. Kosuge, Synthesis of mutagenic principles isolated fromL-glutamic acid pyrolysate,Chem. Pharm. Bull. 26, 2924–2925 (1978).Google Scholar
  134. 133.
    K. Tsuji, T. Yamamoto, H. Zenda, and T. Kosuge, Studies on active principles of tar. VII. Production of biological active substances in pyrolysis of amino acids. (2) Antifungal constituents in pyrolysis products of phenylalanine,Yakugaku Zasshi (J. Pharmaceutical Soc. Japan)98, 910–913 (1978).Google Scholar
  135. 134.
    Y. Hashimoto, K. Shudo, and T. Okamoto, Structure of a base in DNA modified by Glu-P-1,Chem. Pharm. Bull. 27, 2532–2534 (1979).PubMedGoogle Scholar
  136. 135.
    Y. Hashimoto, K. Shudo, and T. Okamoto, Metabolic activation of a mutagen, 2-amino-6-methyldipyrido[l,2-a:3’,2’-d] imidazole. Identification of 2-hydroxyamino-6-methyldipyrido[1,2-a:3’,2’-d] imidazole and its reaction with DNA,Biochem. Biophys. Res. Commun. 92, 971–976 (1980).PubMedGoogle Scholar
  137. 136.
    Y. Hashimoto, K. Shudo, and T. Okamoto, Modification of DNA with potent mutacarcinogenic 2-amino-6-methyldipyrido[1,2-a:3–,2–-d] imidazole isolated from a glutamic acid pyrolysate: Structure of the modified nucleic acid base and initial chemical event caused by the mutagen,J. Am. Chem. Soc. 104, 7636–7640 (1982).Google Scholar
  138. 137.
    K. Yamaguchi, K. Shudo, T. Okamoto, T. Sugimura, and T. Kosuge, Presence of 3-aminodipyrido(1,2-a:3’,2’-d)imidazole in broiled cuttlefish,Gann 71, 743–744 (1980).PubMedGoogle Scholar
  139. 138.
    D. Yoshida and T. Matsumoto, Isolation of 2-amino-9H-pyrido[2,3-b]indole and 2-amino-3-methyl-9H-pyrido[2,3-b]indole as mutagens from pyrolysis product of tryptophan,Agric. Biol. Chem. 43, 1155–1156 (1979).Google Scholar
  140. 139.
    T. Matsumoto, D. Yoshida, H. Tomita, and H. Matsushita, Synthesis of 2-amino-9H-pyrido[2,3b]indole isolated as a mutagenic principle from pyrolytic products of protein,Agric. Biol. Chem. 43, 675–677 (1979).Google Scholar
  141. 140.
    T. Matsumoto, D. Yoshida, and H. Tomita, Synthesis and mutagenic activity of alkyl derivatives of 2-amino-9H-pyrido[2,3-b]indole,Agric. Biol. Chern. 45, 2031–2035 (1981).Google Scholar
  142. 141.
    K. Wakabayashi, K. Tsuji, T. Kosuge, K. Yamaguchi, K. Shudo, K. Takeda, Y. Iitaka, T. Okamoto, T. Yahagi, M. Nagao, and T. Sugimura, Isolation and structure determination of a mutagenic substance in L-lysine pyrolysate,Proc.Jpn. Acad. B 54, 569–571 (1978).Google Scholar
  143. 142.
    M. Yokota, K. Narita, T. Kosuge, K. Wakabayashi, M. Nagao, T. Sugimura, K. Yamaguchi, K. Shudo, Y. Iitaka, and T. Okamoto, A potent mutagen isolated from a pyrolysate of L-ornithine,Chem. Pharm. Bull. 29, 1473–1475 (1981).PubMedGoogle Scholar

Copyright information

© Plenum Press, New York 1984

Authors and Affiliations

  • Frederick T. Hatch
    • 1
  • James S. Felton
    • 1
  • Daniel H. Stuermer
    • 1
  • Leonard F. Bjeldanes
    • 2
  1. 1.Biomedical and Environmental Research Program, Lawrence Livermore National LaboratoryUniversity of CaliforniaLivermoreUSA
  2. 2.Department of Nutritional SciencesUniversity of CaliforniaBerkeleyUSA

Personalised recommendations