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Applied and Environmental Microbiology, October 2005, p. 6121-6125, Vol. 71, No. 10
0099-2240/05/$08.00+0     doi:10.1128/AEM.71.10.6121-6125.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.

Formation of Catechols via Removal of Acid Side Chains from Ibuprofen and Related Aromatic Acids

Robert W. Murdoch1 and Anthony G. Hay1,2*

Institute for Comparative and Environmental Toxicology,1 Department of Microbiology, Cornell University, Ithaca, New York 148502

Received 20 January 2005/ Accepted 31 May 2005

Although ibuprofen [2-(4-isobutylphenyl)-propionic acid] is one of the most widely consumed drugs in the world, little is known regarding its degradation by environmental bacteria. Sphingomonas sp. strain Ibu-2 was isolated from a wastewater treatment plant based on its ability to use ibuprofen as a sole carbon and energy source. A slight preference toward the R enantiomer was observed, though both ibuprofen enantiomers were metabolized. A yellow color, indicative of meta-cleavage, accumulated transiently in the culture supernatant when Ibu-2 was grown on ibuprofen. When and only when 3-flurocatechol was used to poison the meta-cleavage system, isobutylcatechol was identified in the culture supernatant via gas chromatography-mass spectrometry analysis. Ibuprofen-induced washed-cell suspensions also metabolized phenylacetic acid and 2-phenylpropionic acid to catechol, while 3- and 4-tolylacetic acids and 2-(4-tolyl)-propionic acid were metabolized to the corresponding methyl catechols before ring cleavage. These data suggest that, in contrast to the widely distributed coenzyme A ligase, homogentisate, or homoprotocatechuate pathway for metabolism of phenylacetic acid and similar compounds, Ibu-2 removes the acidic side chain of ibuprofen and related compounds prior to ring cleavage.

* Corresponding author. Mailing address: Institute for Comparative and Environmental Toxicology, Cornell University, Ithaca, NY 14850. Phone: (607) 255-8471. Fax: (607) 255-3904. E-mail: agh5{at}cornell.edu.

Applied and Environmental Microbiology, October 2005, p. 6121-6125, Vol. 71, No. 10
0099-2240/05/$08.00+0     doi:10.1128/AEM.71.10.6121-6125.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.



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