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The biotransformation of ibuprofen to trihydroxyibuprofen in activated sludge and by Variovorax Ibu-1

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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.

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Acknowledgments

R.W.M. was supported in part by NIH-NIEHS Environmental and Molecular Toxicology training grant ES 07052-27.

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  1. Robert W. Murdoch

    Present address: Environmental Engineering Department, Middle East Technical University, Dumlupınar Bulvarı, 06800, Ankara, Turkey

Authors and Affiliations

  1. Graduate Program in Environmental Toxicology, Institute for Comparative and Environmental Toxicology, Cornell University, Ithaca, NY, 14850, USA

    Robert W. Murdoch & Anthony G. Hay

  2. Department of Microbiology, Cornell University, B53A Wing Hall, Ithaca, NY, 14850, USA

    Anthony G. Hay

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Murdoch, R.W., Hay, A.G. The biotransformation of ibuprofen to trihydroxyibuprofen in activated sludge and by Variovorax Ibu-1. Biodegradation 26, 105–113 (2015). https://doi.org/10.1007/s10532-015-9719-4

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