Abstract
The conversion by a methanogenic consortium of phenol into phenylalanine, with benzoic and phenylpropionic acid as intermediates, was investigated. When (sup14)C-labelled phenol was fed to the consortium, the radioactivity was mostly transferred into methane and CO(inf2), but 4% of the radioactivity was found in the water fraction after extraction of the culture medium with an organic solvent. Utilization of labelled compounds and analysis by gas chromatography coupled with mass spectrometry revealed that a fraction of the benzoic acid produced was transformed into 3-phenylpropionic acid. When fully (sup13)C-labelled acetic acid was fed to the consortium, the labels were incorporated at the 1 and 2 positions of 3-phenylpropionic acid. When deuterium-labelled 3-phenylpropionic acid was fed to the consortium, part of the phenylalanine of the biomass was labelled. These metabolic transformations are reversible, since deuterium-labelled phenylalanine generated labelled 3-phenylpropionic acid. Cinnamic acid was also transformed into 3-phenylpropionic acid.
Full Text
The Full Text of this article is available as a PDF (204.2 KB).
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Bisaillon J. G., Lépine F., Beaudet R., Sylvestre M. Carboxylation of o-cresol by an anaerobic consortium under methanogenic conditions. Appl Environ Microbiol. 1991 Aug;57(8):2131–2134. doi: 10.1128/aem.57.8.2131-2134.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Bisaillon J. G., Lépine F., Beaudet R., Sylvestre M. Potential for carboxylation-dehydroxylation of phenolic compounds by a methanogenic consortium. Can J Microbiol. 1993 Jul;39(7):642–648. doi: 10.1139/m93-093. [DOI] [PubMed] [Google Scholar]
- Boyd S. A., Shelton D. R., Berry D., Tiedje J. M. Anaerobic biodegradation of phenolic compounds in digested sludge. Appl Environ Microbiol. 1983 Jul;46(1):50–54. doi: 10.1128/aem.46.1.50-54.1983. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Elder D. J., Kelly D. J. The bacterial degradation of benzoic acid and benzenoid compounds under anaerobic conditions: unifying trends and new perspectives. FEMS Microbiol Rev. 1994 Apr;13(4):441–468. doi: 10.1111/j.1574-6976.1994.tb00061.x. [DOI] [PubMed] [Google Scholar]
- Elsden S. R., Hilton M. G., Waller J. M. The end products of the metabolism of aromatic amino acids by Clostridia. Arch Microbiol. 1976 Apr 1;107(3):283–288. doi: 10.1007/BF00425340. [DOI] [PubMed] [Google Scholar]
- Genthner B. R., Price W. A., Pritchard P. H. Characterization of anaerobic dechlorinating consortia derived from aquatic sediments. Appl Environ Microbiol. 1989 Jun;55(6):1472–1476. doi: 10.1128/aem.55.6.1472-1476.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Giesel H., Machacek G., Bayerl J., Simon H. On the formation of 3-phenylpropionate and the different stereo-chemical course of the reduction of cinnamate by Clostridium sporogenes and Peptostreptococcus anaerobius. FEBS Lett. 1981 Jan 12;123(1):107–110. doi: 10.1016/0014-5793(81)80030-0. [DOI] [PubMed] [Google Scholar]
- Lack A., Tommasi I., Aresta M., Fuchs G. Catalytic properties of phenol carboxylase. In vitro study of CO2: 4-hydroxybenzoate isotope exchange reaction. Eur J Biochem. 1991 Apr 23;197(2):473–479. doi: 10.1111/j.1432-1033.1991.tb15934.x. [DOI] [PubMed] [Google Scholar]
- Londry K. L., Fedorak P. M. Benzoic acid intermediates in the anaerobic biodegradation of phenols. Can J Microbiol. 1992 Jan;38(1):1–11. doi: 10.1139/m92-001. [DOI] [PubMed] [Google Scholar]
- Moss C. W., Hatheway C. L., Lambert M. A., McCroskey L. M. Production of phenylacetic and hydroxyphenylacetic acids by clostridium botulinum type G. J Clin Microbiol. 1980 Jun;11(6):743–745. doi: 10.1128/jcm.11.6.743-745.1980. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Moss C. W., Lambert M. A., Goldsmith D. J. Production of hydrocinnamic acid by clostridia. Appl Microbiol. 1970 Feb;19(2):375–378. doi: 10.1128/am.19.2.375-378.1970. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Scott T. W., Ward P. F., Dawson R. M. The formation and metabolism of phenyl-substituted fatty acids in the ruminant. Biochem J. 1964 Jan;90(1):12–24. doi: 10.1042/bj0900012. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Zhang X., Wiegel J. Sequential anaerobic degradation of 2,4-dichlorophenol in freshwater sediments. Appl Environ Microbiol. 1990 Apr;56(4):1119–1127. doi: 10.1128/aem.56.4.1119-1127.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]