Abstract
The decarboxylation of phthalic acids was studied with Bacillus sp. strain FO, a marine mixed culture ON-7, and Pseudomonas testosteroni. The mixed culture ON-7, when grown anaerobically on phthalate but incubated aerobically with chloramphenicol, quantitatively converted phthalic acid to benzoic acid. Substituted phthalic acids were also decarboxylated: 4,5-dihydroxyphthalic acid to protocatechuic acid; 4-hydroxyphthalic and 4-chlorophthalic acids to 3-hydroxybenzoic and 3-chlorobenzoic acids, respectively; and 3-fluorophthalic acid to 2-and 3-fluorobenzoic acids. Bacillus sp. strain FO gave similar results except that 4,5-dihydroxyphthalic acid was not metabolized, and both 3- and 4-hydroxybenzoic acids were produced from 4-hydroxyphthalic acid. P. testosteroni decarboxylated 4-hydroxyphthalate (to 3-hydroxybenzoate) and 4,5-dihydroxyphthalate but not phthalic acid and halogenated phthalates. Thus, P. testosteroni and the mixed culture ON-7 possessed 4,5-dihydroxyphthalic acid decarboxylase, previously described in P. testosteroni, that metabolized 4,5-dihydroxyphthalic acid and specifically decarboxylated 4-hydroxyphthalic acid to 3-hydroxybenzoic acid. The mixed culture ON-7 and Bacillus sp. strain FO also possessed a novel decarboxylase that metabolized phthalic acid and halogenated phthalates, but not 4,5-dihydroxyphthalate, and randomly decarboxylated 4-hydroxyphthalic acid. The decarboxylation of phthalic acid is suggested to involve an initial reduction to 1,2-dihydrophthalic acid followed by oxidative decarboxylation to benzoic acid.
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Selected References
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- Aftring R. P., Chalker B. E., Taylor B. F. Degradation of phthalic acids by denitrifying, mixed cultures of bacteria. Appl Environ Microbiol. 1981 May;41(5):1177–1183. doi: 10.1128/aem.41.5.1177-1183.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Autian J. Toxicity and health threats of phthalate esters: review of the literature. Environ Health Perspect. 1973 Jun;4:3–26. doi: 10.1289/ehp.73043. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Crawford R. L., Olson P. P. Microbial catabolism of vanillate: decarboxylation to guaiacol. Appl Environ Microbiol. 1978 Oct;36(4):539–543. doi: 10.1128/aem.36.4.539-543.1978. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Eaton R. W., Ribbons D. W. Metabolism of dibutylphthalate and phthalate by Micrococcus sp. strain 12B. J Bacteriol. 1982 Jul;151(1):48–57. doi: 10.1128/jb.151.1.48-57.1982. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Eaton R. W., Ribbons D. W. Metabolism of dimethylphthalate by Micrococcus sp. strain 12B. J Bacteriol. 1982 Jul;151(1):465–467. doi: 10.1128/jb.151.1.465-467.1982. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Eaton R. W., Ribbons D. W. Utilization of phthalate esters by micrococci. Arch Microbiol. 1982 Aug;132(2):185–188. doi: 10.1007/BF00508728. [DOI] [PubMed] [Google Scholar]
- Evans W. C. Biochemistry of the bacterial catabolism of aromatic compounds in anaerobic environments. Nature. 1977 Nov 3;270(5632):17–22. doi: 10.1038/270017a0. [DOI] [PubMed] [Google Scholar]
- Healy J. B., Young L. Y., Reinhard M. Methanogenic decomposition of ferulic Acid, a model lignin derivative. Appl Environ Microbiol. 1980 Feb;39(2):436–444. doi: 10.1128/aem.39.2.436-444.1980. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Keyser P., Pujar B. G., Eaton R. W., Ribbons D. W. Biodegradation of the phthalates and their esters by bacteria. Environ Health Perspect. 1976 Dec;18:159–166. doi: 10.1289/ehp.7618159. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Nakazawa T., Hayashi E. Phthalate and 4-hydroxyphthalate metabolism in Pseudomonas testosteroni: purification and properties of 4,5-dihydroxyphthalate decarboxylase. Appl Environ Microbiol. 1978 Aug;36(2):264–269. doi: 10.1128/aem.36.2.264-269.1978. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Nakazawa T., Hayashi E. Phthalate metabolism in Pseudomonas testosteroni: accumulation of 4,5-dihydroxyphthalate by a mutant strain. J Bacteriol. 1977 Jul;131(1):42–48. doi: 10.1128/jb.131.1.42-48.1977. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Peakall D. B. Phthalate esters: Occurrence and biological effects. Residue Rev. 1975;54:1–41. doi: 10.1007/978-1-4612-9857-1_1. [DOI] [PubMed] [Google Scholar]
- Peppercorn M. A., Goldman P. Caffeic acid metabolism by gnotobiotic rats and their intestinal bacteria. Proc Natl Acad Sci U S A. 1972 Jun;69(6):1413–1415. doi: 10.1073/pnas.69.6.1413. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Reiner A. M., Hegeman G. D. Metabolism of benzoic acid by bacteria. Accumulation of (-)-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid by mutant strain of Alcaligenes eutrophus. Biochemistry. 1971 Jun 22;10(13):2530–2536. doi: 10.1021/bi00789a017. [DOI] [PubMed] [Google Scholar]
- Reiner A. M. Metabolism of benzoic acid by bacteria: 3,5-cyclohexadiene-1,2-diol-1-carboxylic acid is an intermediate in the formation of catechol. J Bacteriol. 1971 Oct;108(1):89–94. doi: 10.1128/jb.108.1.89-94.1971. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Ribbons D. W., Evans W. C. Oxidative metabolism of phthalic acid by soil pseudomonads. Biochem J. 1960 Aug;76(2):310–318. doi: 10.1042/bj0760310. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Scheline R. R. The metabolism of drugs and other organic compounds by the intestinal microflora. Acta Pharmacol Toxicol (Copenh) 1968;26(4):332–342. doi: 10.1111/j.1600-0773.1968.tb00453.x. [DOI] [PubMed] [Google Scholar]
- Smith A. J., Hoare D. S. Acetate assimilation by Nitrobacter agilis in relation to its "obligate autotrophy". J Bacteriol. 1968 Mar;95(3):844–855. doi: 10.1128/jb.95.3.844-855.1968. [DOI] [PMC free article] [PubMed] [Google Scholar]