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Identification of Enantiomeric Byproducts During Microalgae-Mediated Transformation of Metoprolol by MS/MS Spectrum Based Networking
Metoprolol (MPL) is a chiral β-blocker ubiquitously detected in various environments due to its low to moderate removal in wastewater treatment plants. This study was conducted to test the potential of using microalgae to degrade emerging contaminant MPL and to characterize the enantiomeric enrichme...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Frontiers Media S.A.
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6137207/ https://www.ncbi.nlm.nih.gov/pubmed/30245676 http://dx.doi.org/10.3389/fmicb.2018.02115 |
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author | Lv, Min Lo, Ching Hsu, Cheng-Chih Wang, Yuwen Chiang, Yin-Ru Sun, Qian Wu, Yang Li, Yan Chen, Lingxin Yu, Chang-Ping |
author_facet | Lv, Min Lo, Ching Hsu, Cheng-Chih Wang, Yuwen Chiang, Yin-Ru Sun, Qian Wu, Yang Li, Yan Chen, Lingxin Yu, Chang-Ping |
author_sort | Lv, Min |
collection | PubMed |
description | Metoprolol (MPL) is a chiral β-blocker ubiquitously detected in various environments due to its low to moderate removal in wastewater treatment plants. This study was conducted to test the potential of using microalgae to degrade emerging contaminant MPL and to characterize the enantiomeric enrichment during MPL degradation by microalgae. The results showed that PO(4)(3−)- P, NO(3)(−)- N and MPL could be simultaneously removed in the synthetic effluent by the targeted microalgae species, indicating microalgae were promising in wastewater treatment. Stereoselectivity was observed during MPL degradation by microalgae, with R-form enrichment. A marginal linear relationship between MPL degradation and enantiomeric enrichment was observed, implying that the enantiomeric tool, used as a quantitative indicator of biodegradation, could possibly be applied in MPL degradation by microalgae. An efficient liquid chromatograph tandem high resolution mass spectrometry (LC-HRMS/MS) chiral analytical method was developed to identify transformation products (TPs). The results showed that MS/MS spectral similarity networking could be used as a powerful tool to quickly identify unknown TPs. A total of 6 pairs of chiral TPs were identified, among which two new TPs of MPL including hydroxy{4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl}acetic acid (α-HMPLA) and 4-[2-Hydroxy-3-(isopropylamino)propoxy]benzaldehyde (DMPLD) were firstly reported, and proposed transformation pathways of MPL by microalgae were given. Considering the paired TPs detected and that the degradation of the two enantiomers followed first order kinetics, the two enantiomers likely had the same degradation mechanism. |
format | Online Article Text |
id | pubmed-6137207 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-61372072018-09-21 Identification of Enantiomeric Byproducts During Microalgae-Mediated Transformation of Metoprolol by MS/MS Spectrum Based Networking Lv, Min Lo, Ching Hsu, Cheng-Chih Wang, Yuwen Chiang, Yin-Ru Sun, Qian Wu, Yang Li, Yan Chen, Lingxin Yu, Chang-Ping Front Microbiol Microbiology Metoprolol (MPL) is a chiral β-blocker ubiquitously detected in various environments due to its low to moderate removal in wastewater treatment plants. This study was conducted to test the potential of using microalgae to degrade emerging contaminant MPL and to characterize the enantiomeric enrichment during MPL degradation by microalgae. The results showed that PO(4)(3−)- P, NO(3)(−)- N and MPL could be simultaneously removed in the synthetic effluent by the targeted microalgae species, indicating microalgae were promising in wastewater treatment. Stereoselectivity was observed during MPL degradation by microalgae, with R-form enrichment. A marginal linear relationship between MPL degradation and enantiomeric enrichment was observed, implying that the enantiomeric tool, used as a quantitative indicator of biodegradation, could possibly be applied in MPL degradation by microalgae. An efficient liquid chromatograph tandem high resolution mass spectrometry (LC-HRMS/MS) chiral analytical method was developed to identify transformation products (TPs). The results showed that MS/MS spectral similarity networking could be used as a powerful tool to quickly identify unknown TPs. A total of 6 pairs of chiral TPs were identified, among which two new TPs of MPL including hydroxy{4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl}acetic acid (α-HMPLA) and 4-[2-Hydroxy-3-(isopropylamino)propoxy]benzaldehyde (DMPLD) were firstly reported, and proposed transformation pathways of MPL by microalgae were given. Considering the paired TPs detected and that the degradation of the two enantiomers followed first order kinetics, the two enantiomers likely had the same degradation mechanism. Frontiers Media S.A. 2018-09-07 /pmc/articles/PMC6137207/ /pubmed/30245676 http://dx.doi.org/10.3389/fmicb.2018.02115 Text en Copyright © 2018 Lv, Lo, Hsu, Wang, Chiang, Sun, Wu, Li, Chen and Yu. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Microbiology Lv, Min Lo, Ching Hsu, Cheng-Chih Wang, Yuwen Chiang, Yin-Ru Sun, Qian Wu, Yang Li, Yan Chen, Lingxin Yu, Chang-Ping Identification of Enantiomeric Byproducts During Microalgae-Mediated Transformation of Metoprolol by MS/MS Spectrum Based Networking |
title | Identification of Enantiomeric Byproducts During Microalgae-Mediated Transformation of Metoprolol by MS/MS Spectrum Based Networking |
title_full | Identification of Enantiomeric Byproducts During Microalgae-Mediated Transformation of Metoprolol by MS/MS Spectrum Based Networking |
title_fullStr | Identification of Enantiomeric Byproducts During Microalgae-Mediated Transformation of Metoprolol by MS/MS Spectrum Based Networking |
title_full_unstemmed | Identification of Enantiomeric Byproducts During Microalgae-Mediated Transformation of Metoprolol by MS/MS Spectrum Based Networking |
title_short | Identification of Enantiomeric Byproducts During Microalgae-Mediated Transformation of Metoprolol by MS/MS Spectrum Based Networking |
title_sort | identification of enantiomeric byproducts during microalgae-mediated transformation of metoprolol by ms/ms spectrum based networking |
topic | Microbiology |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6137207/ https://www.ncbi.nlm.nih.gov/pubmed/30245676 http://dx.doi.org/10.3389/fmicb.2018.02115 |
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