LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment
The discovery of various sartans, which are among the most used antihypertensive drugs in the world, is increasingly frequent not only in wastewater but also in surface water and, in some cases, even in drinking or groundwater. In this paper, the degradation pathway of olmesartan acid, one of the mo...
Main Authors: | , , , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2021-03-01
|
Series: | Molecules |
Subjects: | |
Online Access: | https://www.mdpi.com/1420-3049/26/6/1769 |
_version_ | 1797540516517117952 |
---|---|
author | Giovanni Luongo Antonietta Siciliano Giovanni Libralato Sara Serafini Lorenzo Saviano Lucio Previtera Giovanni Di Fabio Armando Zarrelli |
author_facet | Giovanni Luongo Antonietta Siciliano Giovanni Libralato Sara Serafini Lorenzo Saviano Lucio Previtera Giovanni Di Fabio Armando Zarrelli |
author_sort | Giovanni Luongo |
collection | DOAJ |
description | The discovery of various sartans, which are among the most used antihypertensive drugs in the world, is increasingly frequent not only in wastewater but also in surface water and, in some cases, even in drinking or groundwater. In this paper, the degradation pathway of olmesartan acid, one of the most used sartans, was investigated by simulating the chlorination process normally used in a wastewater treatment plant to reduce similar emerging pollutants. The structures of nine isolated degradation byproducts (DPs), eight of which were isolated for the first time, were separated via chromatography column and HPLC methods, identified by combining nuclear magnetic resonance and mass spectrometry, and justified by a proposed mechanism of formation beginning from the parent drug. Ecotoxicity tests on olmesartan acid and its nine DPs showed that 50% of the investigated byproducts inhibited the target species <i>Aliivibrio fischeri</i> and <i>Raphidocelis subcapitata</i>, causing functional decreases of 18% and 53%, respectively. |
first_indexed | 2024-03-10T13:01:43Z |
format | Article |
id | doaj.art-c4b6f5fb700e4b02b2079085bfc2ec84 |
institution | Directory Open Access Journal |
issn | 1420-3049 |
language | English |
last_indexed | 2024-03-10T13:01:43Z |
publishDate | 2021-03-01 |
publisher | MDPI AG |
record_format | Article |
series | Molecules |
spelling | doaj.art-c4b6f5fb700e4b02b2079085bfc2ec842023-11-21T11:27:38ZengMDPI AGMolecules1420-30492021-03-01266176910.3390/molecules26061769LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity AssessmentGiovanni Luongo0Antonietta Siciliano1Giovanni Libralato2Sara Serafini3Lorenzo Saviano4Lucio Previtera5Giovanni Di Fabio6Armando Zarrelli7Department of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyDepartment of Biology, University of Naples Federico II, 80126 Naples, ItalyDepartment of Biology, University of Naples Federico II, 80126 Naples, ItalyDepartment of Biology, University of Naples Federico II, 80126 Naples, ItalyDepartment of Biology, University of Naples Federico II, 80126 Naples, ItalyAssociazione Italiana per la Promozione delle Ricerche su Ambiente e Salute Umana, 82030 Dugenta, ItalyDepartment of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyThe discovery of various sartans, which are among the most used antihypertensive drugs in the world, is increasingly frequent not only in wastewater but also in surface water and, in some cases, even in drinking or groundwater. In this paper, the degradation pathway of olmesartan acid, one of the most used sartans, was investigated by simulating the chlorination process normally used in a wastewater treatment plant to reduce similar emerging pollutants. The structures of nine isolated degradation byproducts (DPs), eight of which were isolated for the first time, were separated via chromatography column and HPLC methods, identified by combining nuclear magnetic resonance and mass spectrometry, and justified by a proposed mechanism of formation beginning from the parent drug. Ecotoxicity tests on olmesartan acid and its nine DPs showed that 50% of the investigated byproducts inhibited the target species <i>Aliivibrio fischeri</i> and <i>Raphidocelis subcapitata</i>, causing functional decreases of 18% and 53%, respectively.https://www.mdpi.com/1420-3049/26/6/1769olmesartan acidchlorinationhypochloritedegradation byproductswater treatment<i>Aliivibrio fischeri</i> |
spellingShingle | Giovanni Luongo Antonietta Siciliano Giovanni Libralato Sara Serafini Lorenzo Saviano Lucio Previtera Giovanni Di Fabio Armando Zarrelli LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment Molecules olmesartan acid chlorination hypochlorite degradation byproducts water treatment <i>Aliivibrio fischeri</i> |
title | LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment |
title_full | LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment |
title_fullStr | LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment |
title_full_unstemmed | LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment |
title_short | LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment |
title_sort | lc and nmr studies for identification and characterization of degradation byproducts of olmesartan acid elucidation of their degradation pathway and ecotoxicity assessment |
topic | olmesartan acid chlorination hypochlorite degradation byproducts water treatment <i>Aliivibrio fischeri</i> |
url | https://www.mdpi.com/1420-3049/26/6/1769 |
work_keys_str_mv | AT giovanniluongo lcandnmrstudiesforidentificationandcharacterizationofdegradationbyproductsofolmesartanacidelucidationoftheirdegradationpathwayandecotoxicityassessment AT antoniettasiciliano lcandnmrstudiesforidentificationandcharacterizationofdegradationbyproductsofolmesartanacidelucidationoftheirdegradationpathwayandecotoxicityassessment AT giovannilibralato lcandnmrstudiesforidentificationandcharacterizationofdegradationbyproductsofolmesartanacidelucidationoftheirdegradationpathwayandecotoxicityassessment AT saraserafini lcandnmrstudiesforidentificationandcharacterizationofdegradationbyproductsofolmesartanacidelucidationoftheirdegradationpathwayandecotoxicityassessment AT lorenzosaviano lcandnmrstudiesforidentificationandcharacterizationofdegradationbyproductsofolmesartanacidelucidationoftheirdegradationpathwayandecotoxicityassessment AT lucioprevitera lcandnmrstudiesforidentificationandcharacterizationofdegradationbyproductsofolmesartanacidelucidationoftheirdegradationpathwayandecotoxicityassessment AT giovannidifabio lcandnmrstudiesforidentificationandcharacterizationofdegradationbyproductsofolmesartanacidelucidationoftheirdegradationpathwayandecotoxicityassessment AT armandozarrelli lcandnmrstudiesforidentificationandcharacterizationofdegradationbyproductsofolmesartanacidelucidationoftheirdegradationpathwayandecotoxicityassessment |