1887

Abstract

Summary: The fatty acid composition of the cellular lipids of NCIMB 13064 grown on various long-chain haloalkanes has been investigated and the influence of halogen substituents, carbon chain length and the position of halogen substitution in the growth substrate explored. Of the total fatty acids present in cells grown on 1-chloro-, 1-bromo- and 1-iodohexadecane, 75, 90 and 81%, respectively, were substituted in the position by the corresponding halogen but only 1% of the fatty acids present after growth on 1-fluorotetradecane were fluorinated in this position. The extent of the halofatty acid incorporation with different halogen substituents in the growth substrate appears to reflect the degree to which oxygenase attack is restricted to the non-halogenated end of the haloalkane. Studies of the fatty acid composition of cells after growth on a series of 1-chloroalkanes containing an even number of carbon atoms between C and C indicated chlorofatty acid incorporation from C to C substrates at levels ranging from 21% with C to 75% with C. The chlorofatty acids formed by initial oxidation of the chloroalkane were chain-lengthened or chain-shortened by from two to eight carbon atoms, with accompanying desaturation in some instances. Substantial quantities of a methyl-branched C chlorofatty acid were also present with several chloroalkane substrates. When the fatty acid composition of cells after growth on 1-bromoalkanes containing an odd number of carbon atoms between C and C was examined, the incorporation of bromofatty acids was observed with C, C and C substrates; a maximum of 76% was recorded for the C bromoalkane. As with even chain-length chloroalkanes, both chain-lengthening and -shortening occurred predominantly via two-carbon units so that most bromoacids present possessed an odd number of carbon atoms. When 1-bromododecane or 2-bromododecane were substrates, overall incorporations of bromofatty acids into the lipid fraction were very similar, demonstrating that the position of halogen substitution in the haloalkane was not critical in determining the extent of incorporation of the haloacids into cellular lipids. The results of the study indicate a mechanism by which degradation products of chlorinated paraffins could enter the biological food chain.

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1995-10-01
2021-07-27
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References

  1. Campbell I., McConnell G. 1980; Chlorinated paraffins and the environment. 1. Environmental occurrence.. Environ Sci & Technol 14:1209–1214
    [Google Scholar]
  2. Curragh H., Flynn O., Larkin M.J., Stafford T.M., Hamilton J.T.G., Harper D.B. 1994; Haloalkane degradation and assimilation by Rhodococcus rhodochrous NCIMB 13064.. Microbiology 140:1433–1442
    [Google Scholar]
  3. Dunlap K.R., Perry J.J. 1967; Effect of substrate on the fatty acid composition of hydrocarbon-utilizing microorganisms.. J Bacterial 94:1919–1923
    [Google Scholar]
  4. Houghton K.L. 1991; Chlorinated paraffins.. In Encyclopedia of Chemical Technology, 4th edn. 6 pp. 78–87 Chichester:: J. Wiley & Sons.;
    [Google Scholar]
  5. King D.H., Perry J.J. 1975; Characterization of branched and unsaturated fatty acids in Mycobacterium vaccae strain JOBS.. Can J Microbiol 21:510–512
    [Google Scholar]
  6. Leach J.M., Thakore A.N. 1977; Compounds toxic to fish in pulp mill waste streams.. Prog Water Technol 9:787–798
    [Google Scholar]
  7. Madeley J.R., Birtley R.D.N. 1980; Chlorinated paraffins and the environment. 2. Aquatic and avian toxicology.. Environ Sci & Technol 14:1215–1221
    [Google Scholar]
  8. Murphy G.L., Perry J.J. 1983; Incorporation of chlorinated alkanes into fatty acids of hydrocarbon-utilizing mycobacteria.. J Bacterial 156:1158–1164
    [Google Scholar]
  9. Murphy G.L., Perry J.J. 1984; Assimilation of chlorinated alkanes by hydrocarbon-utilizing fungi.. J Bacteriol 160:1171–1174
    [Google Scholar]
  10. Omori T., Alexander M. 1978; Bacterial dehalogenation of halogenated alkanes and fatty acids.. Appl Environ Microbiol 35:867–871
    [Google Scholar]
  11. Omori T., Kimura T., Kodama T. 1987; Bacterial cometabolic degradation of chlorinated paraffins.. Appl Microbiol Biotechnol 25:533–557
    [Google Scholar]
  12. Sundin P., Wesén C., Mu H., Odham G. 1993; Are chlorinated fatty acids in fish lipids of natural origin?. Abstracts of Posters at the 1st International Conference on Naturally-produced Organohalogens pp. 31–33 Delft, The Netherlands:September 1993
    [Google Scholar]
  13. Wesén C., Mu H., Kvernheim A.L., Larsson P. 1992; Identification of chlorinated fatty acids in fish lipids by partitioning studies and by gas chromatography with Hall electrolytic conductivity detection.. J Chromatogr 625:257–269
    [Google Scholar]
  14. Wesén C., Mu H., Sundin P., Ringstad O., Odham G. 1995; Occurrence of halogenated fatty acids in bivalve lipids.. In Naturally-produced Organohalogens pp. 307–316 Grimvall A., de Leer E.W.B. Edited by Dordrecht:: Kluwer Academic Publishers.;
    [Google Scholar]
  15. White R.H., Hager R.H. 1977; Occurrence of fatty acid chlorohydrins in jellyfish lipids.. Biochemistry 16:4944–4948
    [Google Scholar]
  16. Yokata T., Fuse H., Omori T., Minoda Y. 1986; Microbial dehalogenation of haloalkanes mediated by oxygenase or halido-hydrolase.. Agric Biol Chem 50:453–460
    [Google Scholar]
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