title: The biotransformation of ibuprofen to trihydroxyibuprofen in activated sludge and by Variovorax Ibu-1.
abstract: A bacterium was isolated from activated sewage sludge that has the ability to use ibuprofen as its sole carbon and energy source. Phylogenetic analysis of the 16S rRNA gene sequence placed the strain in the Variovorax genus within the β-proteobacteria. When grown on ibuprofen it accumulated a transient yellow intermediate that disappeared upon acidification, a trait consistent with meta ring-fission metabolites. GC/MS analysis of derivatized culture supernatant yielded two spectra consistent with trihydroxyibuprofen bearing all three hydroxyl groups on the aromatic ring. These metabolites were only detected when 3-fluorocatechol, a meta ring-fission inhibitor, was added to Ibu-1 cultures and the supernatant was then derivatized with aqueous acetic anhydride and diazomethane. These findings suggest the possibility of ibuprofen metabolism proceeding via a trihydroxyibuprofen meta ring-fission pathway. Identical spectra, consistent with these putative ring-hydroxylated trihydroxyibuprofen metabolites, were also obtained from ibuprofen-spiked sewage sludge, but only when it was poisoned with 3-fluorocatechol. The presence of the same trihydroxylated metabolites in both spiked sewage sludge and culture supernatants suggests that this trihydroxyibuprofen extradiol ring-cleavage pathway for the degradation of ibuprofen may have environmental relevance.
authors: Graduate Program in Environmental Toxicology, Institute for Comparative and Environmental Toxicology, Cornell University, Ithaca, NY, 14850, USA, murdoch@metu.edu.tr.
authors: Robert W
authors: RW
authors: Murdoch
authors: Anthony G
authors: AG
authors: Hay
mesh_terms: D020562:Betaproteobacteria / Q000187:drug effects / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism*; D001673:Biodegradation, Environmental; D001711:Biotransformation; D002396:Catechols / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D005798:Genes, Bacterial; D006801:Humans; D006900:Hydroxylation; D007052:Ibuprofen / Q000378:metabolism*; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D012722:Sewage / Q000737:chemistry / Q000382:microbiology*; D014874:Water Pollutants, Chemical / Q000378:metabolism*
chemical_list: D002396:Catechols; D012336:RNA, Ribosomal, 16S; D012722:Sewage; D014874:Water Pollutants, Chemical; D007052:Ibuprofen