Skip to main content
Applied Microbiology logoLink to Applied Microbiology
. 1975 Jan;29(1):7–12. doi: 10.1128/am.29.1.7-12.1975

Degradation of N-Nitrosamines by Intestinal Bacteria

I R Rowland 1, P Grasso 1
PMCID: PMC186900  PMID: 803287

Abstract

A major proportion of bacterial types, common in the gastrointestinal tract of many animals and man, were active in degrading diphenylnitrosamine and dimethylnitrosamine, the former being degraded more rapidly than the latter. At low nitrosamine concentrations (<0.05 μmol/ml), approximately 55% of added diphenylnitrosamine, 30% of N-nitrosopyrrolidine, and 4% of dimethylnitrosamine were degraded. The route of nitrosamine metabolism by bacteria appears to be different from that proposed for breakdown by mammalian enzyme systems in that carbon dioxide and formate were not produced. In bacteria, the nitrosamines were converted to the parent amine and nitrite ion and, in addition, certain unidentified volatile metabolites were produced from dimethylnitrosamine by bacteria. The importance of bacteria in reducing the potential hazard to man of nitrosamines is discussed.

Full text

PDF
7

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Alam B. S., Saporoschetz I. B., Epstein S. S. Formation of N-nitrosopiperidine from piperidine and sodium nitrite in the stomach and the isolated intestinal loop of the rat. Nature. 1971 Jul 9;232(5306):116–118. doi: 10.1038/232116a0. [DOI] [PubMed] [Google Scholar]
  2. Ayanaba A., Alexander M. Microbial formation of nitrosamines in vitro. Appl Microbiol. 1973 Jun;25(6):862–868. doi: 10.1128/am.25.6.862-868.1973. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. BROUWERS J. A., EMMELOT P. Microsomal N-demethylation and the effect of the hepatic carcinogen dimethylnitrosamine on amino acid incorporation into the proteins of rat livers and hepatomas. Exp Cell Res. 1960 Apr;19:467–474. doi: 10.1016/0014-4827(60)90056-2. [DOI] [PubMed] [Google Scholar]
  4. Beeken W. L., Kanich R. E. Microbial flora of the upper small bowel in Crohn's disease. Gastroenterology. 1973 Sep;65(3):390–397. [PubMed] [Google Scholar]
  5. Collins-Thompson D. L., Sen N. P., Aris B., Schwinghamer L. Non-enzymic in vitro formation of nitrosamines by bacteria isolated from meat products. Can J Microbiol. 1972 Dec;18(12):1968–1971. doi: 10.1139/m72-306. [DOI] [PubMed] [Google Scholar]
  6. Crosby N. T., Foreman J. K., Palframan J. F., Sawyer R. EWstimation of steam-volatile N-nitrosamines in foods at the 1 micro g-kg level. Nature. 1972 Aug 11;238(5363):342–343. doi: 10.1038/238342a0. [DOI] [PubMed] [Google Scholar]
  7. Drasar B. S., Shiner M., McLeod G. M. Studies on the intestinal flora. I. The bacterial flora of the gastrointestinal tract in healthy and achlorhydric persons. Gastroenterology. 1969 Jan;56(1):71–79. [PubMed] [Google Scholar]
  8. Drasar B. S., Shiner M. Studies on the intestinal flora. II. Bacterial flora of the small intestine in patients with gastrointestinal disorders. Gut. 1969 Oct;10(10):812–819. doi: 10.1136/gut.10.10.812. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Fong Y. Y., Chan W. C. Bacterial production of di-methyl nitrosamine in salted fish. Nature. 1973 Jun 15;243(5407):421–422. doi: 10.1038/243421a0. [DOI] [PubMed] [Google Scholar]
  10. Hawksworth G. M., Hill M. J. Bacteria and the N-nitrosation of secondary amines. Br J Cancer. 1971 Sep;25(3):520–526. doi: 10.1038/bjc.1971.66. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Heath D. F. The decomposition and toxicity of dialkylnitrosamines in rats. Biochem J. 1962 Oct;85(1):72–91. doi: 10.1042/bj0850072. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Klubes P., Jondorf W. R. Dimethylnitrosamine formation from sodium nitrite and dimethylamine by bacterial flora of rat intestine. Res Commun Chem Pathol Pharmacol. 1971 Jan;2(1):24–34. [PubMed] [Google Scholar]
  13. Magee P. N. Toxicity of nitrosamines: their possible human health hazards. Food Cosmet Toxicol. 1971 Apr;9(2):207–218. doi: 10.1016/0015-6264(71)90306-3. [DOI] [PubMed] [Google Scholar]
  14. Mirvish S. S. Kinetics of dimethylamine nitrosation in relation to nitrosamine carcinogenesis. J Natl Cancer Inst. 1970 Mar;44(3):633–639. [PubMed] [Google Scholar]
  15. Rowland I. R. Metabolism of di-(2-ethylhexyl) phthalate by the contents of the alimentary tract of the rat. Food Cosmet Toxicol. 1974 Jun;12(3):293–303. doi: 10.1016/0015-6264(74)90001-7. [DOI] [PubMed] [Google Scholar]
  16. Sander J. Nitrosaminsynthese durch Bakterien. Hoppe Seylers Z Physiol Chem. 1968 Apr;349(4):429–432. [PubMed] [Google Scholar]
  17. Sander J., Schweinsberg F., Menz H. P. Untersuchungen über die Entstehung cancerogener Nitrosamine im Magen. Hoppe Seylers Z Physiol Chem. 1968 Dec;349(12):1691–1697. [PubMed] [Google Scholar]
  18. Sen N. P., Smith D. C., Schwinghamer L. Formation of N-nitrosamines from secondary amines and nitrite in human and animal gastric juice. Food Cosmet Toxicol. 1969 Jul;7(4):301–307. doi: 10.1016/s0015-6264(69)80366-4. [DOI] [PubMed] [Google Scholar]
  19. Sen N. P. The evidence for the presence of dimethylnitrosamine in meat products. Food Cosmet Toxicol. 1972 Apr;10(2):219–223. doi: 10.1016/s0015-6264(72)80199-8. [DOI] [PubMed] [Google Scholar]
  20. Tabaqchali S., Booth C. C. Relationship of the intestinal bacterial flora to absorption. Br Med Bull. 1967 Sep;23(3):285–290. doi: 10.1093/oxfordjournals.bmb.a070573. [DOI] [PubMed] [Google Scholar]
  21. Thauer R. K., Rupprecht E., Jungermann K. Separation of 14C-formate from CO2 fixation metabolites by isoionic-exchange chromatography. Anal Biochem. 1970 Dec;38(2):461–468. doi: 10.1016/0003-2697(70)90471-9. [DOI] [PubMed] [Google Scholar]
  22. Wasserman A. E., Fiddler W., Doerr R. C., Osman S. F., Dooley C. J. Dimethylnitrosamine in frankfurters. Food Cosmet Toxicol. 1972 Oct;10(5):681–684. doi: 10.1016/s0015-6264(72)80148-2. [DOI] [PubMed] [Google Scholar]

Articles from Applied Microbiology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES