Identification of biotransformation products of macrolide and fluoroquinolone antimicrobials in membrane bioreactor treatment by ultrahigh-performance liquid chromatography/quadrupole time-of-flight mass spectrometry |
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Authors: | Terzic Senka Senta Ivan Matosic Marin Ahel Marijan |
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Institution: | (1) Division of Marine and Environmental Research, Rudjer Boskovic Institute, 10000 Zagreb, Croatia;(2) Faculty of Food Technology and Biotechnology, University of Zagreb, 10000 Zagreb, Croatia; |
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Abstract: | Ultrahigh-performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry was applied for the identification
of transformation products (TPs) of fluoroquinolone (norfloxacin and ciprofloxacin) and macrolide (azithromycin, erythromycin,
and roxitromycin) antimicrobials in wastewater effluents from a Zenon hollow-fiber membrane bioreactor (MBR). The detected
TPs were thoroughly characterized using the accurate mass feature for the determination of the tentative molecular formulae
and MS-MS experiments for the structural elucidation of unknowns. Several novel TPs, which have not been previously reported
in the literature, were identified. The TPs of azithromycin and roxithromycin, identified in MBR effluent, were conjugate
compounds, which were formed by phosphorylation of desosamine moiety. Transformation of fluoroquinolones yielded two types
of products: conjugates, formed by succinylation of the piperazine ring, and smaller metabolites, formed by an oxidative break-up
of piperazine moiety to form the 7-(2-carboxymethyl)amino] group. A semi-quantitative assessment of these TPs suggested that
they might have contributed significantly to the overall balance of antimicrobial residues in MBR effluents and thus to the
overall removal efficiency. Determination of TPs during a period of 2 months indicated a conspicuous dynamics, which warrants
further research to identify microorganisms involved and treatment conditions leading to their formation. |
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