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Transformation of microcystin-LR and olefinic compounds by ferrate(VI): Oxidative cleavage of olefinic double bonds as the primary reaction pathway.
Water Res. 2018 Sep 15; 141:268-278.WR

Abstract

The presence of toxic microcystins in algal-impacted surface waters is a concern for drinking water quality management. In this study, the potential of ferrate(VI) to eliminate microcystins during drinking water treatment was assessed by investigating reaction kinetics, reaction sites, transformation products, and toxicity changes for the oxidation of microcystin-LR (MC-LR) as a representative microsystin. The investigations also included several substructural model compounds of MC-LR, such as cinnamic acid and sorbic acid, to elucidate the major transformation products and pathways of MC-LR and olefinic compounds. Second-order rate constants were determined in the pH range 6-10.4 for the reaction of ferrate(VI) with MC-LR and the model compounds. The kinetic data revealed that the olefinic double bonds in the Adda and Mdha residues of MC-LR were the primary ferrate(VI) reaction sites, while the phenyl or guanidine moiety was not the reaction site. This finding was supported by detection and identification of the MC-LR transformation products of double bond cleavage, with high peak abundance in the liquid chromatography-mass spectrometry. Furthermore, the reaction of ferrate(VI) with cinnamic and sorbic acids formed the corresponding aldehydes and organic acids with near complete carbon mass balance, indicating the oxidative cleavage of the double bonds as the primary reaction pathway. A quantitative protein phosphatase 2A (PP2A) binding assay for ferrate(VI)-treated MC-LR solutions showed that the MC-LR transformation products exhibited negligible PP2A binding activity compared to that of the parent MC-LR. Oxidation experiments in a filtered river water matrix spiked with MC-LR demonstrated the efficient elimination of MC-LR during water treatment with ferrate(VI).

Authors+Show Affiliations

School of Earth Sciences and Environmental Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju, 61005, Republic of Korea.School of Earth Sciences and Environmental Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju, 61005, Republic of Korea.School of Earth Sciences and Environmental Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju, 61005, Republic of Korea.School of Earth Sciences and Environmental Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju, 61005, Republic of Korea.School of Earth Sciences and Environmental Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju, 61005, Republic of Korea.School of Earth Sciences and Environmental Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju, 61005, Republic of Korea. Electronic address: yhlee42@gist.ac.kr.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

29800835

Citation

Islam, Ananna, et al. "Transformation of microcystin-LR and Olefinic Compounds By ferrate(VI): Oxidative Cleavage of Olefinic Double Bonds as the Primary Reaction Pathway." Water Research, vol. 141, 2018, pp. 268-278.
Islam A, Jeon D, Ra J, et al. Transformation of microcystin-LR and olefinic compounds by ferrate(VI): Oxidative cleavage of olefinic double bonds as the primary reaction pathway. Water Res. 2018;141:268-278.
Islam, A., Jeon, D., Ra, J., Shin, J., Kim, T. Y., & Lee, Y. (2018). Transformation of microcystin-LR and olefinic compounds by ferrate(VI): Oxidative cleavage of olefinic double bonds as the primary reaction pathway. Water Research, 141, 268-278. https://doi.org/10.1016/j.watres.2018.05.009
Islam A, et al. Transformation of microcystin-LR and Olefinic Compounds By ferrate(VI): Oxidative Cleavage of Olefinic Double Bonds as the Primary Reaction Pathway. Water Res. 2018 Sep 15;141:268-278. PubMed PMID: 29800835.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Transformation of microcystin-LR and olefinic compounds by ferrate(VI): Oxidative cleavage of olefinic double bonds as the primary reaction pathway. AU - Islam,Ananna, AU - Jeon,Dahee, AU - Ra,Jiwoon, AU - Shin,Jaedon, AU - Kim,Tae-Young, AU - Lee,Yunho, Y1 - 2018/05/09/ PY - 2018/01/31/received PY - 2018/05/01/revised PY - 2018/05/06/accepted PY - 2018/5/26/pubmed PY - 2018/10/4/medline PY - 2018/5/26/entrez KW - Algal toxin KW - Cinnamic acid KW - Ferrate(VI) KW - Microcystin-LR KW - Olefin KW - Sorbic acid SP - 268 EP - 278 JF - Water research JO - Water Res. VL - 141 N2 - The presence of toxic microcystins in algal-impacted surface waters is a concern for drinking water quality management. In this study, the potential of ferrate(VI) to eliminate microcystins during drinking water treatment was assessed by investigating reaction kinetics, reaction sites, transformation products, and toxicity changes for the oxidation of microcystin-LR (MC-LR) as a representative microsystin. The investigations also included several substructural model compounds of MC-LR, such as cinnamic acid and sorbic acid, to elucidate the major transformation products and pathways of MC-LR and olefinic compounds. Second-order rate constants were determined in the pH range 6-10.4 for the reaction of ferrate(VI) with MC-LR and the model compounds. The kinetic data revealed that the olefinic double bonds in the Adda and Mdha residues of MC-LR were the primary ferrate(VI) reaction sites, while the phenyl or guanidine moiety was not the reaction site. This finding was supported by detection and identification of the MC-LR transformation products of double bond cleavage, with high peak abundance in the liquid chromatography-mass spectrometry. Furthermore, the reaction of ferrate(VI) with cinnamic and sorbic acids formed the corresponding aldehydes and organic acids with near complete carbon mass balance, indicating the oxidative cleavage of the double bonds as the primary reaction pathway. A quantitative protein phosphatase 2A (PP2A) binding assay for ferrate(VI)-treated MC-LR solutions showed that the MC-LR transformation products exhibited negligible PP2A binding activity compared to that of the parent MC-LR. Oxidation experiments in a filtered river water matrix spiked with MC-LR demonstrated the efficient elimination of MC-LR during water treatment with ferrate(VI). SN - 1879-2448 UR - https://www.unboundmedicine.com/medline/citation/29800835/Transformation_of_microcystin_LR_and_olefinic_compounds_by_ferrate_VI_:_Oxidative_cleavage_of_olefinic_double_bonds_as_the_primary_reaction_pathway_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0043-1354(18)30371-3 DB - PRIME DP - Unbound Medicine ER -