Naproxen Is Transformed Via Acetogenesis and Syntrophic Acetate Oxidation by a Methanogenic Wastewater Consortium
Over-the-counter pharmaceutical compounds can serve as microbial substrates in wastewater treatment processes as well as in the environment. The metabolic pathways and intermediates produced during their degradation, however, are poorly understood. In this study, we investigate an anaerobic wastewater community that metabolizes naproxen via demethylation. Enriched cultures, established from anaerobic digester inocula receiving naproxen as the sole carbon source, transformed naproxen to 6-O-desmethylnaproxen (DMN) within 22 days. Continual enrichment and culture transfer resulted in consistent demethylation of naproxen with no loss of DMN observed. Methane was generated at 0.83 mmol per 1 mmol transformed naproxen. In addition to naproxen, the consortium readily demethylated syringic acid and vanillic acid. DNA analysis revealed a community of acetogenic bacteria and syntrophic acetate oxidizing archaea. Combined with the biotransformation data, this suggests the enriched consortium performs aromatic O-demethylation through a syntrophic relationship between specific acetogens, acetate oxidizers, and methanogens. The proposed model of carbon transfer through the anaerobic food web highlights the significance of linked community interactions in the anaerobic transformation of aromatic O-methyl compounds such as naproxen.
KeywordsNaproxen Anaerobic Microbial transformation Demethylation Wastewater Pharmaceutical
The authors gratefully acknowledge Tom Villani and the labs of Dr. James Simon and Dr. Alan Goldman for the analysis support. The nucleotide sequence data reported are available in the NCBI Sequence Read Archive under the BioSample accession numbers SAMN07237492 and SAMN07237493.
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Conflict of Interest
The authors declare that they have no conflict of interest.
- 9.Daniel SL, Keith ES, Yang H et al (1991) Utilization of methoxylated aromatic compounds by the acetogen Clostridium thermoaceticum: expression and specificity of the co-dependent O-demethylating activity. Biochem Biophys Res Commun 180:416–422. https://doi.org/10.1016/S0006-291X(05)81309-9CrossRefPubMedGoogle Scholar
- 16.Parks GS, Huffman HM (1932) The free energies of some organic compounds. Chemical Catalog Company, IncorporatedGoogle Scholar
- 26.Frazer AC (1994) O-demethylation and other transformations of aromatic compounds by acetogenic bacteria. In: Drake HL (ed) Acetogenesis. Springer US, pp 445–483Google Scholar
- 29.Muller V, Frerichs J (2013) Acetogenic bacteria. In eLS. John Wiley & Sons, Ltd: Chichester. https://doi.org/10.1002/9780470015902.a0020086.pub2
- 31.Oren A (2014) The family methanobacteriaceae. In: Rosenberg E, DeLong EF, Lory S et al (eds) The prokaryotes. Springer Berlin Heidelberg, Berlin, Heidelberg, pp 165–193Google Scholar
- 36.Westerholm M, Roos S, Schnürer A (2010) Syntrophaceticus schinkii gen. nov., sp. nov., an anaerobic, syntrophic acetate-oxidizing bacterium isolated from a mesophilic anaerobic filter. FEMS Microbiol Lett. https://doi.org/10.1111/j.1574-6968.2010.02023.x