An integrated strategy for rapid and accurate determination of free and cell-bound microcystins and related peptides in natural blooms by liquid chromatography–electrospray-high resolution mass spectrometry and matrix-assisted laser desorption/ionization time-of-flight/time-of-flight mass spectrometry using both positive and negative ionization modes

Flores, Cintia; Caixach, Josep

doi:10.1016/j.chroma.2015.06.022

Cited by 27 publications

(21 citation statements)

References 54 publications

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“…The MS/MS dissociation of MCs has been studied extensively in both positive [102,103], and negative [104,105] ionization modes. In most cases, MCs fragment to produce sensitive class-characteristic fragments at m/z 135.0804 originating from the Adda 5 -residue in positive mode, and m/z 128.0353 originating from the Glu 6 -residue in negative mode [82,105,106]. Since MCs are cyclic peptides, a large body of previous work on the collision induced dissociation (CID) of non-microcystin peptides also exists [107] that can be useful in interpretation of microcystin MS/MS spectra.…”

Section: Mass Spectrometry For Structural Elucidationmentioning

confidence: 99%

Structural Diversity, Characterization and Toxicology of Microcystins

Bouaı̈cha

Miles

Beach

et al. 2019

Toxins

313

192

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Hepatotoxic microcystins (MCs) are the most widespread class of cyanotoxins and the one that has most often been implicated in cyanobacterial toxicosis. One of the main challenges in studying and monitoring MCs is the great structural diversity within the class. The full chemical structure of the first MC was elucidated in the early 1980s and since then, the number of reported structural analogues has grown steadily and continues to do so, thanks largely to advances in analytical methodology. The structures of some of these analogues have been definitively elucidated after chemical isolation using a combination of techniques including nuclear magnetic resonance, amino acid analysis, and tandem mass spectrometry (MS/MS). Others have only been tentatively identified using liquid chromatography-MS/MS without chemical isolation. An understanding of the structural diversity of MCs, the genetic and environmental controls for this diversity and the impact of structure on toxicity are all essential to the ongoing study of MCs across several scientific disciplines. However, because of the diversity of MCs and the range of approaches that have been taken for characterizing them, comprehensive information on the state of knowledge in each of these areas can be challenging to gather. We have conducted an in-depth review of the literature surrounding the identification and toxicity of known MCs and present here a concise review of these topics. At present, at least 279 MCs have been reported and are tabulated here. Among these, about 20% (55 of 279) appear to be the result of chemical or biochemical transformations of MCs that can occur in the environment or during sample handling and extraction of cyanobacteria, including oxidation products, methyl esters, or post-biosynthetic metabolites. The toxicity of many MCs has also been studied using a range of different approaches and a great deal of variability can be observed between reported toxicities, even for the same congener. This review will help clarify the current state of knowledge on the structural diversity of MCs as a class and the impacts of structure on toxicity, as well as to identify gaps in knowledge that should be addressed in future research.

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Section: Mass Spectrometry For Structural Elucidationmentioning

confidence: 99%

Structural Diversity, Characterization and Toxicology of Microcystins

Bouaı̈cha

Miles

Beach

et al. 2019

Toxins

313

192

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“…Some studies have also explored the possibility of using high-resolution MS to quantify known cyanotoxins and identify unknown cyanopeptide variants using LC-QTOF or LC-Orbitrap. 35,40,41,44 HRMS is increasingly used as a powerful tool to perform targeted analysis, with the further advantage of allowing suspect-target and non-target screening when certied standards are not available.…”

Section: Introductionmentioning

confidence: 99%

Analysis of multiclass cyanotoxins (microcystins, anabaenopeptins, cylindrospermopsin and anatoxins) in lake waters using on-line SPE liquid chromatography high-resolution Orbitrap mass spectrometry

et al. 2019

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“…The methanolic extract was analyzed in an Exactive/Orbitrap mass spectrometer equipped with an electrospray ionization (ESI) source (Thermo Fisher Scientific, Bremen, Germany). LC/ESI-HRMS (liquid chromatography electrospray ionization high-resolution mass spectrometry) analysis was performed to confirm the identity of microcystins present in the liver tissue [ 35 ].…”

Section: Methodsmentioning

confidence: 99%

Recreational Exposure during Algal Bloom in Carrasco Beach, Uruguay: A Liver Failure Case Report

Vidal

Sedán

D’Agostino

et al. 2017

Toxins

Self Cite

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In January 2015, a 20-month-old child and her family took part in recreational activities at Carrasco and Malvín beaches (Montevideo, Uruguay). An intense harmful algae bloom (HAB) was developing along the coast at that time. A few hours after the last recreational exposure episode, the family suffered gastrointestinal symptoms which were self-limited except in the child’s case, who was admitted to hospital in Uruguay with diarrhea, vomiting, fatigue, and jaundice. The patient had increased serum levels of liver enzymes and bilirubin and five days later presented acute liver failure. She was referred to the Italian Hospital in Buenos Aires, being admitted with grade II–III encephalopathy and hepatomegaly and requiring mechanical respiratory assistance. Serology tests for hepatitis A, B, and C, Epstein-Barr virus, and cytomegalovirus were negative. Laboratory features showed anemia, coagulopathy, and increased serum levels of ammonium, alanine aminotransferase (ALT), aspartate aminotransferase (AST), and bilirubin. Autoimmune Hepatitis Type-II (AH-II) was the initial diagnosis based on a liver kidney microsomal type 1 antibodies (LKM-1) positive result, and twenty days later a liver transplant was performed. The liver histopathology had indicated hemorrhagic necrosis in zone 3, and cholestasis and nodular regeneration, which were not characteristic of AH-II. LC/ESI-HRMS (liquid chromatography electrospray ionization high-resolution mass spectrometry) analysis of MCs in the explanted liver revealed the presence of Microsytin-LR (MC-LR) (2.4 ng·gr−1 tissue) and [D-Leu1]MC-LR (75.4 ng·gr−1 tissue), which constitute a toxicological nexus and indicate a preponderant role of microcystins in the development of fulminant hepatitis.

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Cited by 27 publications

References 54 publications

Structural Diversity, Characterization and Toxicology of Microcystins

Structural Diversity, Characterization and Toxicology of Microcystins

Analysis of multiclass cyanotoxins (microcystins, anabaenopeptins, cylindrospermopsin and anatoxins) in lake waters using on-line SPE liquid chromatography high-resolution Orbitrap mass spectrometry

Recreational Exposure during Algal Bloom in Carrasco Beach, Uruguay: A Liver Failure Case Report

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