Formation of catechols via removal of acid side chains from ibuprofen and related aromatic acids.
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.
Murdoch
Robert W
RW
Institute for Comparative and Environmental Toxicology, Cornell University, Ithaca, NY 14850, USA.
Hay
Anthony G
AG
D002396:Catechols / Q000737:chemistry / Q000378:metabolism*; D003470:Culture Media; D007052:Ibuprofen / Q000737:chemistry / Q000378:metabolism*; D010648:Phenylacetates / Q000378:metabolism*; D012722:Sewage / Q000382:microbiology*; D020578:Sphingomonas / Q000145:classification / Q000235:genetics / Q000302:isolation & purification*; D013237:Stereoisomerism; D013379:Substrate Specificity
D002396:Catechols; D003470:Culture Media; D010648:Phenylacetates; D012722:Sewage; C025136:phenylacetic acid; C034221:catechol; D007052:Ibuprofen