Archives of Microbiology

, Volume 157, Issue 2, pp 148–154 | Cite as

Anaerobic degradation of trans-cinnamate and ω-phenylalkane carboxylic acids by the photosynthetic bacterium Rhodopseudomonas palustris: evidence for a β-oxidation mechanism

  • Douglas J. E. Elder
  • Philip Morgan
  • David J. Kelly
Original Papers


The mechanism responsible for the initial steps in the anaerobic degradation of trans-cinnamate and ω-phenylalkane carboxylates by the purple non-sulphur photosynthetic bacterium Rhodopseudomonas palustris was investigated. Phenylacetate did not support growth and there was a marked CO2 dependence for growth on acids with greater side-chain lengths. Here, CO2 was presumably acting as a redox sink for the disposal of excess reducing equivalents. Growth on benzoate did not require the addition of exogenous CO2. Aromatic acids with an odd number of side-chain carbon atoms (3-phenylpropionate, 5-phenylvalerate, 7-phenylheptanoate) gave greater apparent molar growth yields than those with an even number of side-chain carbon atoms (4-phenylbutyrate, 6-phenylhexanoate, 8-phenyloctanoate). HPLC analysis revealed that phenylacetate accumulated and persisted in the culture medium during growth on these latter compounds. Cinnamate and benzoate transiently accumulated in the culture medium during growth on 3-phenylpropionate, and benzoate alone accumulated transiently during the course of trans-cinnamate degradation. The transient accumulation of 4-phenyl-2-butenoic acid occurred during growth on 4-phenylbutyrate, and phenylacetate accumulated to a 1:1 molar stoichiometry with the initial 4-phenylbutyrate concentration. It is proposed that the initial steps in the anaerobic degradation of trans-cinnamate and the group of acids from 3-phenylpropionate to 8-phenyloctanoate involves β-oxidation of the side-chain.

Key words

Anaerobic degradation Aromatic compounds Rhodopseudomonas palustris ω-Phenylalkane carboxylic acids trans-cinnamic acid 3-Phenylpropionic acid 4-Phenylbutyric acid β-Oxidation 



3-phenylpropionic acid


4-phenylbutyric acid


5-phenylvaleric acid


6-phenylhexanoic acid


7-phenylheptanoic acid


8-phenyloctanoic acid


4-phenyl-2-butenoic acid


Gas chromatography/Mass spectrometry


High-pressure liquid chromatography


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Balba MT, Evans WC (1977) The methanogenic fermentation of aromatic compounds. Biochem Soc Trans 5: 302–304CrossRefGoogle Scholar
  2. Balba MT, Evans WC (1979) The methanogenic fermentation of ω-phenyl alkane carboxylic acids. Biochem Soc Trans 7: 403–405CrossRefGoogle Scholar
  3. Colberg PJ (1988) Anaerobic microbial degradation of cellulose, lignin, oligolignols, and monoaromatic lignin derivatives. In: Zehnder AJB (ed) Biology of anaerobic microorganisms. Wiley-Interscience, Chichester, pp 333–372Google Scholar
  4. Dagley S (1984) Microbial metabolism of aromatic compounds. In: Cooney CL, Humphrey AE (eds) Comprehensive Biotechnology, vol. 1. Pergamon Press, Oxford, pp 483–505Google Scholar
  5. Dangel W, Brackman R, Lack A, Mohamed M, Koch J, Oswald B, Seyfried B, Tschech A, Fuchs G (1991) Differential expression of enzyme activities initiating anoxic metabolism of various aromatic compounds via benzoyl-CoA. Arch Microbiol 155: 256–262CrossRefGoogle Scholar
  6. Dutton PL, Evans WC (1968) The photometabolism of benzoic acid by Rhodopseudomonas palustris: a new pathway of aromatic ring metabolism. Biochem J 109: 5PCrossRefGoogle Scholar
  7. Dutton PL, Evans WC (1969) The metabolism of aromatic compounds by Rhodopseudomonas palustris. Biochem J 113: 525–536CrossRefGoogle Scholar
  8. Evans WC, Fuchs G (1988) Anaerobic degradation of aromatic compounds. Ann Rev Microbiol 42: 289–317CrossRefGoogle Scholar
  9. French CJ, Vance CP, Neil Towers GH (1976) Conversion of p-coumaric acid to p-hydroxybenzoic acid by cell free extracts of potato tubers and Polyporus hispidus. Phytochem 15: 564–566CrossRefGoogle Scholar
  10. Geissler JF, Harwood CS, Gibson J (1988) Purification and properties of benzoate-coenzyme A ligase, a Rhodopseudomonas palustris enzyme involved in the anaerobic degradation of benzoate. J Bacteriol 170: 1709–1714CrossRefGoogle Scholar
  11. Gross GG, Zenk MH (1974) Isolation and properties of hydroxycinnamate: CoA ligase from lignifying tissues of Forsythia. Eur J Biochem 42: 453–459CrossRefGoogle Scholar
  12. Guyer M, Hegeman G (1969) Evidence for a reductive pathway for the anaerobic metabolism of benzoate. J Bacteriol 99: 906–907PubMedPubMedCentralGoogle Scholar
  13. Hagel P, Kindl H (1975) p-Hydroxybenzoate Synthase: a complex associated with mitochondrial membranes of roots of Cucumis sativus. FEBS Lett 59: 120–124CrossRefGoogle Scholar
  14. Harwood CS, Gibson J (1986) Uptake of benzoate by Rhodopseudomonas palustris grown anaerobically in light. J Bacteriol 165: 504–509CrossRefGoogle Scholar
  15. Harwood CS, Gibson J (1988) Anaerobic and aerobic metabolism of diverse aromatic compounds by the photosynthetic bacterium Rhodopseudomonas palustris. Appl Environ Microbiol 54: 712–717PubMedPubMedCentralGoogle Scholar
  16. Healy JB JR, Young LY, Reinhard M (1980) Methanogenic decomposition of ferulic acid, a model lignin derivative. Appl Environ Microbiol 39: 436–444PubMedPubMedCentralGoogle Scholar
  17. Hillmer P, Gest H (1977) H2 metabolism in the photosynthetic bacterium Rhodopseudomonas capsulata: H2 production by growing cultures. J Bacteriol 129: 724–731PubMedPubMedCentralGoogle Scholar
  18. Hutber GN, Ribbons DW (1983) Involvement of coenzyme A esters in the metabolism of benzoate and cyclohexanecarboxylate by Rhodopseudomonas palustris. J Gen Microbiol 129: 2413–2420Google Scholar
  19. Imhoff-Stuckle D, Pfennig N (1983) Isolation and characterisation of a nicotinic acid-degrading sulfate-reducing bacterium, Desulfococcus niacini sp. nov. Arch Microbiol 136: 194–198CrossRefGoogle Scholar
  20. Lascelles J (1960) The formation of ribulose-1,5-diphosphate carboxylase by growing cultures of Athiorhodaceae. J Gen Microbiol 23: 499–510CrossRefGoogle Scholar
  21. Madigan MT, Gest H (1988) Selective enrichment and isolation of Rhodopseudomonas palustris using trans-cinnamic acid as sole carbon source. FEMS Microbiol Ecol 53: 53–58CrossRefGoogle Scholar
  22. vanNiel CB (1944) The culture, general physiology, morphology and classification of the non-sulphur purple bacteria. Bacteriol Rev 8: 1–118PubMedPubMedCentralGoogle Scholar
  23. Richardson DJ, King GF, Kelly DJ, McEwan AG, Ferguson SJ, Jackson JB (1988) The role of auxiliary oxidants in maintaining redox balance during phototrophic growth of Rhodobacter capsulatus on propionate or butyrate. Arch Microbiol 150: 131–137CrossRefGoogle Scholar
  24. Schennen U, Braun K, Knackmuss HJ (1985) Anaerobic degradation of 2-fluorobenzoate by benzoate-degrading denitrifying bacteria. J Bacteriol 161: 321–325PubMedPubMedCentralGoogle Scholar
  25. Seyfried B, Tschech A, Fuchs G (1991) Anaerobic degradation of phenylacetate and 4-hydroxyphenylacetate by denitrifying bacteria. Arch Microbiol. 155: 249–255CrossRefGoogle Scholar
  26. Shlomi ER, Lankhorst A, Prins RA (1978) Methanogenic fermentation of benzoate in an enrichment culture. Microbiol Ecol 4: 249–261CrossRefGoogle Scholar
  27. Toms A, Wood JM (1970) The degradation of trans-ferulic acid by Pseudomonas acidovorans. Biochem 9: 337–343CrossRefGoogle Scholar
  28. Weaver PF, Wall JD, Gest H (1975) Characterisation of Rhodopseudomonas capsulata. Arch Microbiol 105: 207–216CrossRefGoogle Scholar
  29. Webley DM, Duff RB, Farmer VC (1955) Beta-oxidation of fatty acids by Nocardia opaca. J Gen Microbiol 13: 361–369CrossRefGoogle Scholar
  30. Whittle PJ, Lunt DO, Evans WC (1976) Anaerobic photometabolism of aromatic compounds by Rhodopseudomonas sp. Biochem Soc Trans 4: 490–491CrossRefGoogle Scholar
  31. Zenk MH (1966) Biosynthesis of C6−C1 compounds. In: Billek G (ed) Biosynthesis of aromatic compounds. Proceedings of the 2nd meeting of the Federation of European Biochemical Societies, vol 3. Pergamon Press, Oxford, pp 45–60, presented 1964CrossRefGoogle Scholar
  32. Zenk MH (1978) Recent work on cinnamoyl CoA derivatives. In: Swain T, Harborne JB, VanSumere CF (eds) Recent advances in biochemistry, vol 12. Plenum Press, New York, pp 139–176Google Scholar
  33. Zenk MH, Ulbrich B, Busse J, Stockigt J (1980) Procedure for the enzymatic synthesis and isolation of cinnamoyl-CoA thiolesters using a bacterial system. Anal Biochem 101: 182–187CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 1992

Authors and Affiliations

  • Douglas J. E. Elder
    • 1
  • Philip Morgan
    • 2
  • David J. Kelly
    • 1
  1. 1.Robert Hill Institute, Department of Molecular Biology and Biotechnology Firth CourtUniversity of SheffieldSheffieldUK
  2. 2.Sittingbourne Research CentreShell Research LimitedSittingbourneUK

Personalised recommendations