Skip to main content
NCBI home page
Biochemical Journal logoLink to Biochemical Journal
. 1974 Apr;140(1):31–45. doi: 10.1042/bj1400031

Microbial degradation of hydrocarbons. Catabolism of 1-phenylalkanes by Nocardia salmonicolor

F Sima Sariaslani 1, David B Harper 1,*, I John Higgins 1
PMCID: PMC1167968  PMID: 4451551

Abstract

1. Nocardia salmonicolor grew on a variety of alkanes, 1-phenylalkanes and 1-cyclo-hexylalkanes as sole carbon and energy sources. 2. Growth on 1-phenyldodecane in batch culture was diauxic. Isocitrate lyase activity was induced during lag phase, reaching a maximum activity in the first growth phase, during which both the aromatic ring and the side chain were degraded. However, 4-phenylbutyrate, 4-phenylbut-3-enoate, 4-phenylbut-2-enoate, 3-phenylpropionate, cinnamate and phenylacetate accumulated in the growth medium. These compounds disappeared at the onset of diauxic lag and four hydroxylated compounds accumulated; one was 4-(o-hydroxyphenyl)but-3-enoate and another was identified as 4-(o-hydroxyphenyl)butyrate. These compounds were utilized during the second growth phase. 3. Washed 1-phenyldodecane-grown cells oxidized acetate, cinnamate, 3,4-dihydroxyphenylacetate, homogentisate, o-, m- and p-hydroxyphenylacetate, phenylacetate, and 4-phenylbutyrate rapidly without lag. 4. Extracts of such cells rapidly oxidized homogentisate,3,4-dihydroxyphenylacetate, catechol and protocatechuate. 5. The organism grew readily on 4-phenylbutyrate, phenylacetate, o-hydroxyphenylacetate, homogentisate and 3,4-dihydroxyphenylacetate as sole carbon energy sources, but growth was slow on cinnamate and 4-phenylbut-3-enoate. 6. When cinnamate and phenylacetate were sole carbon sources for growth, phenylacetate and o-hydroxyphenylacetate respectively were detected in culture supernatants. 4-Phenylbut-3-enoate and 4-phenylbutyrate both yielded a mixture of cinnamate and phenylacetate. 7. It is proposed that 1-phenyldodecane is catabolized by ω-oxidation of the terminal methyl group, side-chain β-oxidation to 4-phenylbutyrate, both β- and α-oxidation to phenylacetic acid, hydroxylation to homogentisate via o-hydroxyphenylacetate and ring cleavage to maleylacetoacetate. Catabolism via 3,4-dihydroxyphenylacetate may also occur. 8. Growth on 1-phenylnonane was also diauxic and cinnamic acid, phenylpropionic acid, benzoic acid and hydroxyphenylpentanoic acid accumulated in the medium. Respirometric data and ring-cleavage enzyme activities showed similar patterns to those obtained after growth on 1-phenyldodecane. The results suggest that the main catabolic routes for 1-phenyldodecane and 1-phenylnonane may converge at cinnamate. 9. Possible reasons for diauxie are discussed.

Full text

PDF
31

Selected References

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

  1. ADACHI K., TAKEDA Y., SENOH S., KITA H. METABOLISM OF P-HYDROXYPHENYLACETIC ACID IN PSEUDOMONAS OVALIS. Biochim Biophys Acta. 1964 Dec 9;93:483–493. doi: 10.1016/0304-4165(64)90332-0. [DOI] [PubMed] [Google Scholar]
  2. BAUCHOP T., ELSDEN S. R. The growth of micro-organisms in relation to their energy supply. J Gen Microbiol. 1960 Dec;23:457–469. doi: 10.1099/00221287-23-3-457. [DOI] [PubMed] [Google Scholar]
  3. BLAKLEY E. R., SIMPSON F. J. THE MICROBIAL METABOLISM OF CINNAMIC ACID. Can J Microbiol. 1964 Apr;10:175–185. doi: 10.1139/m64-025. [DOI] [PubMed] [Google Scholar]
  4. Baggi G., Catelani D., Galli E., Treccani V. The microbial degradation of phenylalkanes. 2-Phenylbutane, 3-phenylpentane, 3-phenyldodecane and 4-phenylheptane. Biochem J. 1972 Mar;126(5):1091–1097. doi: 10.1042/bj1261091. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Blakley E. R., Kurz W., Halvorson H., Simpson F. J. The metabolism of phenylacetic acid by a Pseudomonas. Can J Microbiol. 1967 Feb;13(2):147–157. doi: 10.1139/m67-021. [DOI] [PubMed] [Google Scholar]
  6. Blakley E. R. Microbial conversion of p-hydroxyphenylacetic acid to homogentisic acid. Can J Microbiol. 1972 Aug;18(8):1247–1255. doi: 10.1139/m72-193. [DOI] [PubMed] [Google Scholar]
  7. CHAPMAN P. J., DAGLEY S. Oxidation of homogentistic acid by cell-free extracts of a vibrio. J Gen Microbiol. 1962 Jun;28:251–256. doi: 10.1099/00221287-28-2-251. [DOI] [PubMed] [Google Scholar]
  8. DAGLEY S., FEWSTER M. E., HAPPOLD F. C. The bacterial oxidation of aromatic compounds. J Gen Microbiol. 1953 Feb;8(1):1–7. doi: 10.1099/00221287-8-1-1. [DOI] [PubMed] [Google Scholar]
  9. DAGLEY S., WOOD J. M. OXIDATION OF PHENYLACETIC ACID BY A PSEUDOMONAS. Biochim Biophys Acta. 1965 May 18;99:383–385. doi: 10.1016/s0926-6593(65)80140-0. [DOI] [PubMed] [Google Scholar]
  10. DAVIS J. B., RAYMOND R. L. Oxidation of alkyl-substituted cyclic hydrocarbons by a Nocardia during growth on n-alkanes. Appl Microbiol. 1961 Sep;9:383–388. doi: 10.1128/am.9.5.383-388.1961. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. EL-BAGOURY S., FLETCHER S., MORRISON R. B. Effect of chloramphenicol in maintaining the viability of Escherichia coli. Nature. 1956 Dec 29;178(4548):1467–1467. doi: 10.1038/1781467a0. [DOI] [PubMed] [Google Scholar]
  12. Hochberg A. A., Stratman F. W., Zahlten R. N., Morris H. P., Lardy H. A. Binding of rat liver and hepatoma polyribosomes to stripped rough endoplasmic reticulum in vitro. Biological or an artifact? Biochem J. 1972 Nov;130(1):19–25. doi: 10.1042/bj1300019. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. KLUYVER A. J., VAN ZIJP J. C. The production of homogentisic acid out of phenylacetic acid by Aspergillus niger. Antonie Van Leeuwenhoek. 1951;17(5):315–324. doi: 10.1007/BF02062278. [DOI] [PubMed] [Google Scholar]
  14. Kornberg H. L. The role and control of the glyoxylate cycle in Escherichia coli. Biochem J. 1966 Apr;99(1):1–11. doi: 10.1042/bj0990001. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  16. LYNEN F., OCHOA S. Enzymes of fatty acid metabolism. Biochim Biophys Acta. 1953 Sep-Oct;12(1-2):299–314. doi: 10.1016/0006-3002(53)90149-8. [DOI] [PubMed] [Google Scholar]
  17. Trust T. J., Millis N. F. The isolation and characterization of alkane-oxidizing organisms and the effect of growth substrate on isocitric lyase. J Gen Microbiol. 1970 May;61(2):245–254. doi: 10.1099/00221287-61-2-245. [DOI] [PubMed] [Google Scholar]
  18. WEBLEY D. M., DUFF R. B., FARMER V. C. Beta-oxidation of fatty acids by Nocardia opaca. J Gen Microbiol. 1955 Oct;13(2):361–369. doi: 10.1099/00221287-13-2-361. [DOI] [PubMed] [Google Scholar]
  19. Willetts A. J., Cain R. B. Microbial metabolism of alkylbenzene sulphonates. Bacterial metabolism of undecylbenzene-p-sulphonate and dodecylbenzene-p-sulphonate. Biochem J. 1972 Sep;129(2):389–402. doi: 10.1042/bj1290389. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES