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Christopher O. Miles
Biotoxin Metrology, National Research Council, 1411 Oxford St., Halifax, NS B3H 3Z1, Canada

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Journal article
Published: 21 July 2021 in Toxins
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Two high-mass polar compounds were observed in aqueous side-fractions from the purification of okadaic acid (1) and dinophysistoxin-2 (2) from Dinophysis blooms in Spain and Norway. These were isolated and shown to be 24-O-β-d-glucosides of 1 and 2 (4 and 5, respectively) by nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and enzymatic hydrolysis. These, together with standards of 1, 2, dinophysistoxin-1 (3), and a synthetic specimen of 7-deoxy-1 (7), combined with an understanding of their mass spectrometric fragmentation patterns, were then used to identify 1–5, the 24-O-β-d-glucoside of dinophysistoxin-1 (6), 7, 7-deoxy-2 (8), and 7-deoxy-3 (9) in a range of extracts from Dinophysis blooms, Dinophysis cultures, and contaminated shellfish from Spain, Norway, Ireland, Canada, and New Zealand. A range of Prorocentrumlima cultures was also examined by liquid chromatography–high resolution tandem mass spectrometry (LC–HRMS/MS) and was found to contain 1, 3, 7, and 9. However, although 4–6 were not detected in these cultures, low levels of putative glycosides with the same exact masses as 4 and 6 were present. The potential implications of these findings for the toxicology, metabolism, and biosynthesis of the okadaic acid group of marine biotoxins are briefly discussed.

ACS Style

Alistair L. Wilkins; Thomas Rundberget; Morten Sandvik; Frode Rise; Brent K. Knudsen; Jane Kilcoyne; Beatriz Reguera; Pilar Rial; Elliott J. Wright; Sabrina D. Giddings; Michael J. Boundy; Cheryl Rafuse; Christopher O. Miles. Identification of 24-O-β-d-Glycosides and 7-Deoxy-Analogues of Okadaic Acid and Dinophysistoxin-1 and -2 in Extracts from Dinophysis Blooms, Dinophysis and Prorocentrum Cultures, and Shellfish in Europe, North America and Australasia. Toxins 2021, 13, 510 .

AMA Style

Alistair L. Wilkins, Thomas Rundberget, Morten Sandvik, Frode Rise, Brent K. Knudsen, Jane Kilcoyne, Beatriz Reguera, Pilar Rial, Elliott J. Wright, Sabrina D. Giddings, Michael J. Boundy, Cheryl Rafuse, Christopher O. Miles. Identification of 24-O-β-d-Glycosides and 7-Deoxy-Analogues of Okadaic Acid and Dinophysistoxin-1 and -2 in Extracts from Dinophysis Blooms, Dinophysis and Prorocentrum Cultures, and Shellfish in Europe, North America and Australasia. Toxins. 2021; 13 (8):510.

Chicago/Turabian Style

Alistair L. Wilkins; Thomas Rundberget; Morten Sandvik; Frode Rise; Brent K. Knudsen; Jane Kilcoyne; Beatriz Reguera; Pilar Rial; Elliott J. Wright; Sabrina D. Giddings; Michael J. Boundy; Cheryl Rafuse; Christopher O. Miles. 2021. "Identification of 24-O-β-d-Glycosides and 7-Deoxy-Analogues of Okadaic Acid and Dinophysistoxin-1 and -2 in Extracts from Dinophysis Blooms, Dinophysis and Prorocentrum Cultures, and Shellfish in Europe, North America and Australasia." Toxins 13, no. 8: 510.

Journal article
Published: 16 December 2020 in Marine Drugs
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Okadaic acid (OA) group toxins may accumulate in shellfish and can result in diarrhetic shellfish poisoning when consumed by humans, and are therefore regulated. Purified toxins are required for the production of certified reference materials used to accurately quantitate toxin levels in shellfish and water samples, and for other research purposes. An improved procedure was developed for the isolation of dinophysistoxin-2 (DTX2) from shellfish (M. edulis), reducing the number of purification steps from eight to five, thereby increasing recoveries to ~68%, compared to ~40% in a previously reported method, and a purity of >95%. Cell densities and toxin production were monitored in cultures of Prorocentrum lima, that produced OA, DTX1, and their esters, over ~1.5 years with maximum cell densities of ~70,000 cells mL−1 observed. Toxin accumulation progressively increased over the study period, to ~0.7 and 2.1 mg L−1 of OA and DTX1 (including their esters), respectively, providing information on appropriate harvesting times. A procedure for the purification of OA and DTX1 from the harvested biomass was developed employing four purification steps, with recoveries of ~76% and purities of >95% being achieved. Purities were confirmed by LC-HRMS, LC-UV, and NMR spectroscopy. Additional stability observations led to a better understanding of the chemistry of these toxins.

ACS Style

Jane Kilcoyne; Stephen Burrell; Cíara Nulty; Rafael Salas; Elliott J. Wright; Isabelle Rajotte; Christopher O. Miles. Improved Isolation Procedures for Okadaic Acid Group Toxins from Shellfish (Mytilus edulis) and Microalgae (Prorocentrum lima). Marine Drugs 2020, 18, 647 .

AMA Style

Jane Kilcoyne, Stephen Burrell, Cíara Nulty, Rafael Salas, Elliott J. Wright, Isabelle Rajotte, Christopher O. Miles. Improved Isolation Procedures for Okadaic Acid Group Toxins from Shellfish (Mytilus edulis) and Microalgae (Prorocentrum lima). Marine Drugs. 2020; 18 (12):647.

Chicago/Turabian Style

Jane Kilcoyne; Stephen Burrell; Cíara Nulty; Rafael Salas; Elliott J. Wright; Isabelle Rajotte; Christopher O. Miles. 2020. "Improved Isolation Procedures for Okadaic Acid Group Toxins from Shellfish (Mytilus edulis) and Microalgae (Prorocentrum lima)." Marine Drugs 18, no. 12: 647.

Journal article
Published: 05 May 2020 in Toxins
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Lake Steinsfjorden, an important Norwegian location for noble crayfish (Astacus astacus), is often affected by cyanobacterial blooms caused by microcystin (MC)-producing Planktothrix spp. The impact of MCs on noble crayfish as a food source and crayfish health is largely unknown. We investigated the quantities and correlations of MCs in noble crayfish and lake water during and after a cyanobacterial bloom peaking in June–July 2015. Noble crayfish and water samples were collected monthly from June to October 2015 and in October 2016. The content of MCs was analysed by ELISA from tail muscle, intestine, stomach and hepatopancreas. PCR analysis for Planktothrix gene markers was performed on crayfish stomach content. Water samples were analysed for phytoplankton composition, biomass and MCs. PCR-positive stomach contents indicated Planktothrix to be part of the noble crayfish diet. Concentrations of MCs were highest in the hepatopancreas, stomach and intestine, peaking in August–September. Tail muscle contained low concentrations of MCs. Similar levels of MCs were found in crayfish from 2016. Except in September 2015, a normal portion of boiled noble crayfish tails was below the tolerable daily intake (TDI) for MCs for humans. Removing the intestine more than halved the content of MCs and seems a reasonable precautionary measure for noble crayfish consumers.

ACS Style

Ingunn Anita Samdal; David Allan Strand; Andreas Ballot; Johannes Christopher Rusch; Sigrid Haande; Kjersti Liv Eriksen Løvberg; Christopher Owen Miles; Trude Vrålstad. Microcystins in European Noble Crayfish Astacus astacus in Lake Steinsfjorden, a Planktothrix-Dominated Lake. Toxins 2020, 12, 298 .

AMA Style

Ingunn Anita Samdal, David Allan Strand, Andreas Ballot, Johannes Christopher Rusch, Sigrid Haande, Kjersti Liv Eriksen Løvberg, Christopher Owen Miles, Trude Vrålstad. Microcystins in European Noble Crayfish Astacus astacus in Lake Steinsfjorden, a Planktothrix-Dominated Lake. Toxins. 2020; 12 (5):298.

Chicago/Turabian Style

Ingunn Anita Samdal; David Allan Strand; Andreas Ballot; Johannes Christopher Rusch; Sigrid Haande; Kjersti Liv Eriksen Løvberg; Christopher Owen Miles; Trude Vrålstad. 2020. "Microcystins in European Noble Crayfish Astacus astacus in Lake Steinsfjorden, a Planktothrix-Dominated Lake." Toxins 12, no. 5: 298.

Preprint content
Published: 16 April 2020
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Cyanobacteria form harmful mass blooms in freshwater and marine environments around the world. A range of secondary metabolites has been identified from cultures of cyanobacteria and biomass collected from cyanobacterial bloom events. A comprehensive database is necessary to correctly identify cyanobacterial metabolites and advance research on their abundance, persistence and toxicity in natural environments. We consolidated open access databases and manually curated missing information from the literature published between 1970 and March 2020. The result is the database CyanoMetDB, which includes more than 2000 entries based on more than 750 literature references. This effort has more than doubled the total number of entries with complete literature metadata and structural composition (SMILES codes) compared to publicly available databases to this date. Over the past decade, more than one hundred additional secondary metabolites have been identified yearly. We organized all entries into structural classes and conducted substructure searches of the provided SMILES codes. This approach demonstrated, for example, that 65% of the compounds carry at least one peptide bond, 57% are cyclic compounds, and 30% carry at least one halogen atom. Structural searches by SMILES code can be further specified to identify structural motifs that are relevant for analytical approaches, research on biosynthetic pathways, bioactivity-guided analysis, or to facilitate predictive science and modeling efforts on cyanobacterial metabolites. This database facilitates rapid identification of cyanobacterial metabolites from toxic blooms, research on the biosynthesis of cyanobacterial natural products, and the identification of novel natural products from cyanobacteria.

ACS Style

Martin R. Jones; Ernani Pinto; Mariana A. Torres; Fabiane Doerr; Hanna Mazur-Marzec; Karolina Szubert; Luciana Tartaglione; Carmela Dell’Aversano; Christopher O. Miles; Daniel G. Beach; Pearse McCarron; Kaarina Sivonen; David P. Fewer; Jouni Jokela; Elisabeth M.-L. Janssen. Comprehensive database of secondary metabolites from cyanobacteria. 2020, 1 .

AMA Style

Martin R. Jones, Ernani Pinto, Mariana A. Torres, Fabiane Doerr, Hanna Mazur-Marzec, Karolina Szubert, Luciana Tartaglione, Carmela Dell’Aversano, Christopher O. Miles, Daniel G. Beach, Pearse McCarron, Kaarina Sivonen, David P. Fewer, Jouni Jokela, Elisabeth M.-L. Janssen. Comprehensive database of secondary metabolites from cyanobacteria. . 2020; ():1.

Chicago/Turabian Style

Martin R. Jones; Ernani Pinto; Mariana A. Torres; Fabiane Doerr; Hanna Mazur-Marzec; Karolina Szubert; Luciana Tartaglione; Carmela Dell’Aversano; Christopher O. Miles; Daniel G. Beach; Pearse McCarron; Kaarina Sivonen; David P. Fewer; Jouni Jokela; Elisabeth M.-L. Janssen. 2020. "Comprehensive database of secondary metabolites from cyanobacteria." , no. : 1.

Journal article
Published: 07 April 2020 in Toxins
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Meiktila Lake is a shallow reservoir located close to Meiktila city in central Myanmar. Its water is used for irrigation, domestic purposes and drinking water. No detailed study of the presence of cyanobacteria and their potential toxin production has been conducted so far. To ascertain the cyanobacterial composition and presence of cyanobacterial toxins in Meiktila Lake, water samples were collected in March and November 2017 and investigated for physico-chemical and biological parameters. Phytoplankton composition and biomass determination revealed that most of the samples were dominated by the cyanobacterium Raphidiopsis raciborskii. In a polyphasic approach, seven isolated cyanobacterial strains were classified morphologically and phylogenetically as R. raciborskii, and Microcystis spp. and tested for microcystins (MCs), cylindrospermopsins (CYNs), saxitoxins and anatoxins by enzyme-linked immunosorbent assay (ELISA) and liquid chromatography–mass spectrometry (LC–MS). ELISA and LC–MS analyses confirmed CYNs in three of the five Raphidiopsis strains between 1.8 and 9.8 μg mg−1 fresh weight. Both Microcystis strains produced MCs, one strain 52 congeners and the other strain 20 congeners, including 22 previously unreported variants. Due to the presence of CYN- and MC-producing cyanobacteria, harmful effects on humans, domestic and wild animals cannot be excluded in Meiktila Lake.

ACS Style

Andreas Ballot; Thida Swe; Marit Mjelde; Leonardo Cerasino; Vladyslava Hostyeva; Christopher O. Miles. Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar. Toxins 2020, 12, 232 .

AMA Style

Andreas Ballot, Thida Swe, Marit Mjelde, Leonardo Cerasino, Vladyslava Hostyeva, Christopher O. Miles. Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar. Toxins. 2020; 12 (4):232.

Chicago/Turabian Style

Andreas Ballot; Thida Swe; Marit Mjelde; Leonardo Cerasino; Vladyslava Hostyeva; Christopher O. Miles. 2020. "Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar." Toxins 12, no. 4: 232.

Journal article
Published: 31 March 2020 in Marine Drugs
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Ciguatera poisoning is linked to the ingestion of seafood that is contaminated with ciguatoxins (CTXs). The structural variability of these polyether toxins in nature remains poorly understood due to the low concentrations present even in highly toxic fish, which makes isolation and chemical characterization difficult. We studied the mass spectrometric fragmentation of Caribbean CTXs, i.e., the epimers C-CTX-1 and -2 (1 and 2), using a sensitive UHPLC–HRMS/MS approach in order to identify product ions of diagnostic value. We found that the fragmentation of the ladder-frame backbone follows a characteristic pattern and propose a generalized nomenclature for the ions formed. These data were applied to the structural characterization of a pair of so far poorly characterized isomers, C-CTX-3 and -4 (3 and 4), which we found to be reduced at C-56 relative to 1 and 2. Furthermore, we tested and applied reduction and oxidation reactions, monitored by LC–HRMS, in order to confirm the structures of 3 and 4. Reduction of 1 and 2 with NaBH4 afforded 3 and 4, thereby unambiguously confirming the identities of 3 and 4. In summary, this work provides a foundation for mass spectrometry-based characterization of new C-CTXs, including a suite of simple chemical reactions to assist the examination of structural modifications.

ACS Style

Fedor Kryuchkov; Alison Robertson; Christopher O. Miles; Elizabeth M. Mudge; Silvio Uhlig. LC–HRMS and Chemical Derivatization Strategies for the Structure Elucidation of Caribbean Ciguatoxins: Identification of C-CTX-3 and -4. Marine Drugs 2020, 18, 182 .

AMA Style

Fedor Kryuchkov, Alison Robertson, Christopher O. Miles, Elizabeth M. Mudge, Silvio Uhlig. LC–HRMS and Chemical Derivatization Strategies for the Structure Elucidation of Caribbean Ciguatoxins: Identification of C-CTX-3 and -4. Marine Drugs. 2020; 18 (4):182.

Chicago/Turabian Style

Fedor Kryuchkov; Alison Robertson; Christopher O. Miles; Elizabeth M. Mudge; Silvio Uhlig. 2020. "LC–HRMS and Chemical Derivatization Strategies for the Structure Elucidation of Caribbean Ciguatoxins: Identification of C-CTX-3 and -4." Marine Drugs 18, no. 4: 182.

Journal article
Published: 23 January 2020 in Toxins
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[D-Leu1]MC-LY (1) ([M + H]+ m/z 1044.5673, Δ 2.0 ppm), a new microcystin, was isolated from Microcystis aeruginosa strain CPCC-464. The compound was characterized by 1H and 13C NMR spectroscopy, liquid chromatography–high resolution tandem mass spectrometry (LC–HRMS/MS) and UV spectroscopy. A calibration reference material was produced after quantitation by 1H NMR spectroscopy and LC with chemiluminescence nitrogen detection. The potency of 1 in a protein phosphatase 2A inhibition assay was essentially the same as for MC-LR (2). Related microcystins, [D-Leu1]MC-LR (3) ([M + H]+ m/z 1037.6041, Δ 1.0 ppm), [D-Leu1]MC-M(O)R (6) ([M + H]+ m/z 1071.5565, Δ 2.0 ppm) and [D-Leu1]MC-MR (7) ([M + H]+ m/z 1055.5617, Δ 2.2 ppm), were also identified in culture extracts, along with traces of [D-Leu1]MC-M(O2)R (8) ([M + H]+ m/z 1087.5510, Δ 1.6 ppm), by a combination of chemical derivatization and LC–HRMS/MS experiments. The relative abundances of 1, 3, 6, 7 and 8 in a freshly extracted culture in the positive ionization mode LC–HRMS were ca. 84, 100, 3.0, 11 and 0.05, respectively. These and other results indicate that [D-Leu1]-containing MCs may be more common in cyanobacterial blooms than is generally appreciated but are easily overlooked with standard targeted LC–MS/MS screening methods.

ACS Style

Patricia Leblanc; Nadine Merkley; Krista Thomas; Nancy I. Lewis; Khalida Békri; Susan LeBlanc Renaud; Frances R. Pick; Pearse McCarron; Christopher O. Miles; Michael A. Quilliam. Isolation and Characterization of [D-Leu1]microcystin-LY from Microcystis aeruginosa CPCC-464. Toxins 2020, 12, 77 .

AMA Style

Patricia Leblanc, Nadine Merkley, Krista Thomas, Nancy I. Lewis, Khalida Békri, Susan LeBlanc Renaud, Frances R. Pick, Pearse McCarron, Christopher O. Miles, Michael A. Quilliam. Isolation and Characterization of [D-Leu1]microcystin-LY from Microcystis aeruginosa CPCC-464. Toxins. 2020; 12 (2):77.

Chicago/Turabian Style

Patricia Leblanc; Nadine Merkley; Krista Thomas; Nancy I. Lewis; Khalida Békri; Susan LeBlanc Renaud; Frances R. Pick; Pearse McCarron; Christopher O. Miles; Michael A. Quilliam. 2020. "Isolation and Characterization of [D-Leu1]microcystin-LY from Microcystis aeruginosa CPCC-464." Toxins 12, no. 2: 77.

Review
Published: 07 December 2019 in Toxins
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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.

ACS Style

Noureddine Bouaïcha; Christopher Miles; Daniel Beach; Zineb Labidi; Amina Djabri; Naila Benayache; Tri Nguyen-Quang. Structural Diversity, Characterization and Toxicology of Microcystins. Toxins 2019, 11, 714 .

AMA Style

Noureddine Bouaïcha, Christopher Miles, Daniel Beach, Zineb Labidi, Amina Djabri, Naila Benayache, Tri Nguyen-Quang. Structural Diversity, Characterization and Toxicology of Microcystins. Toxins. 2019; 11 (12):714.

Chicago/Turabian Style

Noureddine Bouaïcha; Christopher Miles; Daniel Beach; Zineb Labidi; Amina Djabri; Naila Benayache; Tri Nguyen-Quang. 2019. "Structural Diversity, Characterization and Toxicology of Microcystins." Toxins 11, no. 12: 714.

Journal article
Published: 15 November 2019 in Marine Drugs
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Microcystins are cyclic heptapeptides from cyanobacteria that are potent inhibitors of protein phosphatases and are toxic to animals and humans. At present, more than 250 microcystin variants are known, with variants reported for all seven peptide moieties. While d-glutamic acid (d-Glu) is highly-conserved at position-6 of microcystins, there has been only one report of a cyanobacterium (Anabaena) producing microcystins containing l-Glu at the variable 2- and 4-positions. Liquid chromatography–mass spectrometry analyses of extracts from Planktothrix prolifica NIVA-CYA 544 led to the tentative identification of two new Glu-containing microcystins, [d-Asp3]MC-ER (12) and [d-Asp3]MC-EE (13). Structure determination was aided by thiol derivatization of the Mdha7-moiety and esterification of the carboxylic acid groups, while 15N-labeling of the culture and isotopic profile analysis assisted the determination of the number of nitrogen atoms present and the elemental composition of molecular and product-ions. The major microcystin analog in the extracts was [d-Asp3]MC-RR (1). A microcystin with an unprecedented high-molecular-mass (2116 Da) was also detected and tentatively identified as a sulfide-linked conjugate of [d-Asp3]MC-RR (15) by LC–HRMS/MS and sulfide oxidation, together with its sulfoxide (16) produced via autoxidation. Low levels of [d-Asp3]MC-RW (14), [d-Asp3]MC-LR (4), [d-Asp3,Mser7]MC-RR (11), [d-Asp3]MC-RY (17), [d-Asp3]MC-RF (18), [d-Asp3]MC-RR–glutathione conjugate (19), and [d-Asp3]MC-RCit (20), the first reported microcystin containing citrulline, were also identified in the extract, and an oxidized derivative of [d-Asp3]MC-RR and the cysteine conjugate of 1 were partially characterized.

ACS Style

Vittoria Mallia; Silvio Uhlig; Cheryl Rafuse; Juris Meija; Christopher O. Miles. Novel Microcystins from Planktothrix prolifica NIVA-CYA 544 Identified by LC-MS/MS, Functional Group Derivatization and 15N-labeling. Marine Drugs 2019, 17, 643 .

AMA Style

Vittoria Mallia, Silvio Uhlig, Cheryl Rafuse, Juris Meija, Christopher O. Miles. Novel Microcystins from Planktothrix prolifica NIVA-CYA 544 Identified by LC-MS/MS, Functional Group Derivatization and 15N-labeling. Marine Drugs. 2019; 17 (11):643.

Chicago/Turabian Style

Vittoria Mallia; Silvio Uhlig; Cheryl Rafuse; Juris Meija; Christopher O. Miles. 2019. "Novel Microcystins from Planktothrix prolifica NIVA-CYA 544 Identified by LC-MS/MS, Functional Group Derivatization and 15N-labeling." Marine Drugs 17, no. 11: 643.

Preprint
Published: 03 October 2019
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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 269 MCs have been reported. Among these, about 20% (54 of 269) 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 cyanobacterial, 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.

ACS Style

Noureddine Bouaïcha; Christopher O. Miles; Daniel G. Beach; Zineb Labidi; Amina Djabri; Naila Yasmine Benayache; Tri Nguyen-Quang. Structural Diversity, Characterization and Toxicology of Microcystins. 2019, 1 .

AMA Style

Noureddine Bouaïcha, Christopher O. Miles, Daniel G. Beach, Zineb Labidi, Amina Djabri, Naila Yasmine Benayache, Tri Nguyen-Quang. Structural Diversity, Characterization and Toxicology of Microcystins. . 2019; ():1.

Chicago/Turabian Style

Noureddine Bouaïcha; Christopher O. Miles; Daniel G. Beach; Zineb Labidi; Amina Djabri; Naila Yasmine Benayache; Tri Nguyen-Quang. 2019. "Structural Diversity, Characterization and Toxicology of Microcystins." , no. : 1.

Journal article
Published: 07 June 2019 in Toxicon
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Microcystins (MCs) are hepatotoxic and potentially carcinogenic cyanotoxins. They exhibit high structural variability, with nearly 250 variants described to date. This variability can result in incomplete detection of MC variants during lake surveys due to the frequent use of targeted analytical methods and a lack of standards available for identification and quantitation. In this study, Lake Uluabat in Turkey was sampled during the summer of 2015. Phylogenetic analysis of the environmental mcyA sequences suggested Microcystis spp. were the major MC contributors. A combination of liquid chromatography-tandem mass spectrometry (LC-MS/MS), liquid chromatography with UV detection and mass spectrometry (LC-UV-MS), and a novel liquid chromatography-high resolution mass spectrometry (LC-HRMS) method, together with thiol and periodate reactivity, revealed more than 36 MC variants in the lake samples and a strain of M. aeruginosa (AQUAMEB-24) isolated from Lake Uluabat. Only MCs containing arginine at position-4 were detected in the culture, while MC-LA, -LY, -LW and -LF were also detected in the lake samples, suggesting the presence of other MC producers in the lake. The previously unreported MCs MC-(H2)YR (dihydrotyrosine at position-2) (17), [epoxyAdda5]MC-LR, [DMAdda5]MC-RR (1) and [Mser7]MC-RR (8) were detected in the culture and/or field samples. This study is a good example of how commonly used targeted LC-MS methods can underestimate the diversity of MCs in freshwater lakes and cyanobacteria cultures and how untargeted LC-MS methods can be used to comprehensively assess MC diversity present in a new system.

ACS Style

Mete Yilmaz; Amanda J. Foss; Christopher O. Miles; Mihriban Özen; Nilsun Demir; Muharrem Balcı; Daniel G. Beach. Comprehensive multi-technique approach reveals the high diversity of microcystins in field collections and an associated isolate of Microcystis aeruginosa from a Turkish lake. Toxicon 2019, 167, 87 -100.

AMA Style

Mete Yilmaz, Amanda J. Foss, Christopher O. Miles, Mihriban Özen, Nilsun Demir, Muharrem Balcı, Daniel G. Beach. Comprehensive multi-technique approach reveals the high diversity of microcystins in field collections and an associated isolate of Microcystis aeruginosa from a Turkish lake. Toxicon. 2019; 167 ():87-100.

Chicago/Turabian Style

Mete Yilmaz; Amanda J. Foss; Christopher O. Miles; Mihriban Özen; Nilsun Demir; Muharrem Balcı; Daniel G. Beach. 2019. "Comprehensive multi-technique approach reveals the high diversity of microcystins in field collections and an associated isolate of Microcystis aeruginosa from a Turkish lake." Toxicon 167, no. : 87-100.

Evaluation study
Published: 06 February 2019 in Journal of Agricultural and Food Chemistry
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Azaspiracids (AZAs) are a group of biotoxins that appear periodically in shellfish and can cause food poisoning in humans. Current methods for quantifying the regulated AZAs are restricted to LC-MS but are not well suited to detecting novel and unregulated AZAs. An ELISA method for total AZAs in shellfish was reported recently, but unfortunately, it used relatively large amounts of the AZA-1-containing plate-coating conjugate, consuming significant amounts of pure AZA-1 per assay. Therefore, a new plate-coater, OVA–cdiAZA1 was produced, resulting in an ELISA with a working range of 0.30–4.1 ng/mL and a limit of quantification of 37 μg/kg for AZA-1 in shellfish. This ELISA was nearly twice as sensitive as the previous ELISA while using 5-fold less plate-coater. The new ELISA displayed broad cross-reactivity toward AZAs, detecting all available quantitative AZA reference materials as well as the precursors to AZA-3 and AZA-6, and results from shellfish analyzed with the new ELISA showed excellent correlation (R2 = 0.99) with total AZA-1–10 by LC-MS. The results suggest that the new ELISA is suitable for screening samples for total AZAs, even in cases where novel AZAs are present and regulated AZAs are absent, such as was reported recently from Puget Sound and the Bay of Naples.

ACS Style

Ingunn A. Samdal; Kjersti E. Løvberg; Anja B. Kristoffersen; Lyn R. Briggs; Jane Kilcoyne; Craig J. Forsyth; Christopher O. Miles. A Practical ELISA for Azaspiracids in Shellfish via Development of a New Plate-Coating Antigen. Journal of Agricultural and Food Chemistry 2019, 67, 2369 -2376.

AMA Style

Ingunn A. Samdal, Kjersti E. Løvberg, Anja B. Kristoffersen, Lyn R. Briggs, Jane Kilcoyne, Craig J. Forsyth, Christopher O. Miles. A Practical ELISA for Azaspiracids in Shellfish via Development of a New Plate-Coating Antigen. Journal of Agricultural and Food Chemistry. 2019; 67 (8):2369-2376.

Chicago/Turabian Style

Ingunn A. Samdal; Kjersti E. Løvberg; Anja B. Kristoffersen; Lyn R. Briggs; Jane Kilcoyne; Craig J. Forsyth; Christopher O. Miles. 2019. "A Practical ELISA for Azaspiracids in Shellfish via Development of a New Plate-Coating Antigen." Journal of Agricultural and Food Chemistry 67, no. 8: 2369-2376.

Research article
Published: 28 November 2018 in Journal of Agricultural and Food Chemistry
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New compounds, 11,12-epoxyjanthitrem B, 1, and 11,12-epoxyjanthitrem C, 4, were isolated from Penicillium janthinellum, and given the trivial names janthitrem A and janthitrem D, respectively. The known compounds janthitrem B, 2, and janthitrem C, 3, were also isolated and NMR assignments made for all 4 compounds. This showed that the previously published NMR assignments for 3 needed considerable revision. 1 and 2 were used as model compounds for the more complex, and highly unstable, epoxyjanthitrems that have been isolated from perennial ryegrass infected with the AR37 endophyte and which contain an epoxide group analogous to that of 1. Both 1 and 2 induced tremors in mice and reduced weight gain and food consumption of porina (Wiseana cervinata) larvae although 1 showed greater potency. This shows the importance of the epoxy group and suggests that epoxyjanthitrems are likely to be involved in the observed effects of the AR37 endophyte on livestock and insects.

ACS Style

Jacob V. Babu; Alison J. Popay; Christopher O. Miles; Alistair L. Wilkins; Margaret E. di Menna; Sarah C. Finch. Identification and Structure Elucidation of Janthitrems A and D from Penicillium janthinellum and Determination of the Tremorgenic and Anti-Insect Activity of Janthitrems A and B. Journal of Agricultural and Food Chemistry 2018, 66, 13116 -13125.

AMA Style

Jacob V. Babu, Alison J. Popay, Christopher O. Miles, Alistair L. Wilkins, Margaret E. di Menna, Sarah C. Finch. Identification and Structure Elucidation of Janthitrems A and D from Penicillium janthinellum and Determination of the Tremorgenic and Anti-Insect Activity of Janthitrems A and B. Journal of Agricultural and Food Chemistry. 2018; 66 (50):13116-13125.

Chicago/Turabian Style

Jacob V. Babu; Alison J. Popay; Christopher O. Miles; Alistair L. Wilkins; Margaret E. di Menna; Sarah C. Finch. 2018. "Identification and Structure Elucidation of Janthitrems A and D from Penicillium janthinellum and Determination of the Tremorgenic and Anti-Insect Activity of Janthitrems A and B." Journal of Agricultural and Food Chemistry 66, no. 50: 13116-13125.

Research article
Published: 04 March 2018 in Journal of Agricultural and Food Chemistry
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Azaspiracids (AZAs) belong to a family of more than 50 polyether toxins originating from marine dinoflagellates such as Azadinium spinosum. All of the AZAs reported thus far contain a 21,22-dihydroxy group. Boric acid gel (BAG) can bind selectively to compounds containing vic-diols or α-hydroxycarboxylic acids via formation of reversible boronate complexes. Here we report use of BAG to selectively capture and release AZAs from extracts of blue mussels. Analysis of the extracts and BAG fractions by LC–MS showed that this procedure resulted in an excellent clean-up of the AZAs in the extract. Analysis by ELISA and LC–MS indicated that most AZA analogues were recovered in good yield by this procedure. The capacity of BAG for AZAs was at least 50 μg/g, making this procedure suitable for use in the early stages of preparative purification of AZAs. In addition to its potential for concentration of dilute samples, the extensive clean-up provided by BAG fractionation of AZAs in mussel samples almost eliminated matrix effects during subsequent LC–MS, and could be expected to reduce matrix effects during ELISA analysis. The method may therefore prove useful for quantitative analysis of AZAs as part of monitoring programs. Although LC-MS data showed that okadaic acid analogues also bound to BAG, this was much less efficient than for AZAs under the conditions used. The BAG methodology is potentially applicable to other important groups of natural toxins containing diols, including ciguatoxins, palytoxins, pectenotoxins,karlotoxins, tetrodotoxin, trichothecenes, and toxin glycosides.

ACS Style

Christopher O. Miles; Jane Kilcoyne; Pearse McCarron; Sabrina D. Giddings; Thor Waaler; Thomas Rundberget; Ingunn A. Samdal; Kjersti E. Løvberg. Selective Extraction and Purification of Azaspiracids from Blue Mussels (Mytilus edulis) Using Boric Acid Gel. Journal of Agricultural and Food Chemistry 2018, 66, 2962 -2969.

AMA Style

Christopher O. Miles, Jane Kilcoyne, Pearse McCarron, Sabrina D. Giddings, Thor Waaler, Thomas Rundberget, Ingunn A. Samdal, Kjersti E. Løvberg. Selective Extraction and Purification of Azaspiracids from Blue Mussels (Mytilus edulis) Using Boric Acid Gel. Journal of Agricultural and Food Chemistry. 2018; 66 (11):2962-2969.

Chicago/Turabian Style

Christopher O. Miles; Jane Kilcoyne; Pearse McCarron; Sabrina D. Giddings; Thor Waaler; Thomas Rundberget; Ingunn A. Samdal; Kjersti E. Løvberg. 2018. "Selective Extraction and Purification of Azaspiracids from Blue Mussels (Mytilus edulis) Using Boric Acid Gel." Journal of Agricultural and Food Chemistry 66, no. 11: 2962-2969.

Journal article
Published: 01 February 2018 in Environmental Research
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Cyclic imines constitute a quite recently discovered group of marine biotoxins that act on neural receptors and that bioaccumulate in seafood. They are grouped together due to the imino group functioning as their common pharmacore, responsible for acute neurotoxicity in mice. Cyclic imines (CIs) have not been linked yet to human poisoning and are not regulated in the European Union (EU), although the European Food Safety Authority (EFSA) requires more data to perform conclusive risk assessment for consumers. Several commercial samples of bivalves including raw and processed samples from eight countries (Italy, Portugal, Slovenia, Spain, Ireland, Norway, The Netherlands and Denmark) were obtained over 2 years. Emerging cyclic imine concentrations in all the samples were analysed on a LC-3200QTRAP and LC-HRMS QExactive mass spectrometer. In shellfish, two CIs, pinnatoxin G (PnTX-G) and 13-desmethylspirolide C (SPX-1) were found at low concentrations (0.1-12µg/kg PnTX-G and 26-66µg/kg SPX-1), while gymnodimines and pteriatoxins were not detected in commercial (raw and processed) samples. In summary, SPX-1 (n: 47) and PnTX-G (n: 96) were detected in 9.4% and 4.2% of the samples, respectively, at concentrations higher than the limit of quantification (LOQ), and in 7.3% and 31.2% of the samples at concentrations lower than the LOQ (25µg/kg for SPX-1 and 3µg/kg for PnTX-G), respectively. For the detected cyclic imines, the average exposure and the 95th percentile were calculated. The results obtained indicate that it is unlikely that a potential health risk exists through the seafood diet for CIs in the EU. However, further information about CIs is necessary in order to perform a conclusive risk assessment.

ACS Style

Maria Rambla-Alegre; Christopher O. Miles; Pablo de la Iglesia; Margarita Fernandez-Tejedor; Silke Jacobs; Isabelle Sioen; Wim Verbeke; Ingunn Anita Samdal; Morten Sandvik; Vera Liane Barbosa; Alice Tediosi; Eneko Madorran; Kit Granby; Michiel Kotterman; Tanja Calis; Jorge Diogène. Occurrence of cyclic imines in European commercial seafood and consumers risk assessment. Environmental Research 2018, 161, 392 -398.

AMA Style

Maria Rambla-Alegre, Christopher O. Miles, Pablo de la Iglesia, Margarita Fernandez-Tejedor, Silke Jacobs, Isabelle Sioen, Wim Verbeke, Ingunn Anita Samdal, Morten Sandvik, Vera Liane Barbosa, Alice Tediosi, Eneko Madorran, Kit Granby, Michiel Kotterman, Tanja Calis, Jorge Diogène. Occurrence of cyclic imines in European commercial seafood and consumers risk assessment. Environmental Research. 2018; 161 ():392-398.

Chicago/Turabian Style

Maria Rambla-Alegre; Christopher O. Miles; Pablo de la Iglesia; Margarita Fernandez-Tejedor; Silke Jacobs; Isabelle Sioen; Wim Verbeke; Ingunn Anita Samdal; Morten Sandvik; Vera Liane Barbosa; Alice Tediosi; Eneko Madorran; Kit Granby; Michiel Kotterman; Tanja Calis; Jorge Diogène. 2018. "Occurrence of cyclic imines in European commercial seafood and consumers risk assessment." Environmental Research 161, no. : 392-398.

Article
Published: 15 January 2018 in Angewandte Chemie International Edition
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A convergent and stereoselective total synthesis of the previously assigned structure of azaspiracid-3 has been achieved via a late stage NHK coupling to form the C21‒C22 bond with the C20 configuration unambiguously established from L-(+)-tartaric acid. Post-coupling steps involved oxidation to an ynone, modified Stryker reduction of the alkyne, global deprotection, and oxidation of the primary alcohol to the carboxylic acid. The synthetic product matched naturally occurring azaspiracid-3 by mass spectrometry, but differed both chromatographically and spectroscopically.

ACS Style

Nathaniel T. Kenton; Daniel Adu-Ampratwum; Antony A. Okumu; Zhigao Zhang; Yong Chen; Son Nguyen; Jianyan Xu; Yue Ding; Pearse McCarron; Jane Kilcoyne; Frode Rise; Alistair L. Wilkins; Christopher O. Miles; Craig J. Forsyth. Total Synthesis of (6 R ,10 R ,13 R ,14 R ,16 R ,17 R ,19 S ,20 R ,21 R ,24 S , 25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 Reveals Non‐Identity with the Natural Product. Angewandte Chemie International Edition 2018, 57, 805 -809.

AMA Style

Nathaniel T. Kenton, Daniel Adu-Ampratwum, Antony A. Okumu, Zhigao Zhang, Yong Chen, Son Nguyen, Jianyan Xu, Yue Ding, Pearse McCarron, Jane Kilcoyne, Frode Rise, Alistair L. Wilkins, Christopher O. Miles, Craig J. Forsyth. Total Synthesis of (6 R ,10 R ,13 R ,14 R ,16 R ,17 R ,19 S ,20 R ,21 R ,24 S , 25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 Reveals Non‐Identity with the Natural Product. Angewandte Chemie International Edition. 2018; 57 (3):805-809.

Chicago/Turabian Style

Nathaniel T. Kenton; Daniel Adu-Ampratwum; Antony A. Okumu; Zhigao Zhang; Yong Chen; Son Nguyen; Jianyan Xu; Yue Ding; Pearse McCarron; Jane Kilcoyne; Frode Rise; Alistair L. Wilkins; Christopher O. Miles; Craig J. Forsyth. 2018. "Total Synthesis of (6 R ,10 R ,13 R ,14 R ,16 R ,17 R ,19 S ,20 R ,21 R ,24 S , 25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 Reveals Non‐Identity with the Natural Product." Angewandte Chemie International Edition 57, no. 3: 805-809.

Article
Published: 15 December 2017 in Angewandte Chemie
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The previously accepted structure of the marine toxin azaspiracid-3 is revised based upon an original convergent and stereoselective total synthesis of the natural product. The development of a structural revision hypothesis, its testing, and corroboration are reported. Synthetic (6R,10R,13R,14R,16R,17R, 19S,20S,21R,24S,25S,28S,30S,32R,33R,34R,36S,37S,39R)-azaspiracid-3 chromatographically and spectroscopically matched naturally occurring azaspiracid-3, whereas the previously assigned (20R)-epimer did not.

ACS Style

Nathaniel T. Kenton; Daniel Adu-Ampratwum; Antony A. Okumu; Pearse McCarron; Jane Kilcoyne; Frode Rise; Alistair L. Wilkins; Christopher O. Miles; Craig J. Forsyth. Stereochemical Definition of the Natural Product (6 R ,10 R ,13 R , 14 R ,16 R ,17 R ,19 S ,20 S ,21 R ,24 S ,25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 by Total Synthesis and Comparative Analyses. Angewandte Chemie 2017, 130, 818 -821.

AMA Style

Nathaniel T. Kenton, Daniel Adu-Ampratwum, Antony A. Okumu, Pearse McCarron, Jane Kilcoyne, Frode Rise, Alistair L. Wilkins, Christopher O. Miles, Craig J. Forsyth. Stereochemical Definition of the Natural Product (6 R ,10 R ,13 R , 14 R ,16 R ,17 R ,19 S ,20 S ,21 R ,24 S ,25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 by Total Synthesis and Comparative Analyses. Angewandte Chemie. 2017; 130 (3):818-821.

Chicago/Turabian Style

Nathaniel T. Kenton; Daniel Adu-Ampratwum; Antony A. Okumu; Pearse McCarron; Jane Kilcoyne; Frode Rise; Alistair L. Wilkins; Christopher O. Miles; Craig J. Forsyth. 2017. "Stereochemical Definition of the Natural Product (6 R ,10 R ,13 R , 14 R ,16 R ,17 R ,19 S ,20 S ,21 R ,24 S ,25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 by Total Synthesis and Comparative Analyses." Angewandte Chemie 130, no. 3: 818-821.

Communication
Published: 28 November 2017 in Angewandte Chemie International Edition
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The previously accepted structure of the marine toxin azaspiracid‐3 is revised based upon an original convergent and stereoselective total synthesis of the natural product. The development of a structural revision hypothesis, its testing, and corroboration are reported. Synthetic (6R,10R,13R,14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R, 33R,34R,36S,37S,39R)‐azaspiracid‐3 chromatographically and spectroscopically matched naturally occurring azaspiracid‐3, whereas the previously assigned 20R epimer did not.

ACS Style

Nathaniel T. Kenton; Daniel Adu-Ampratwum; Antony A. Okumu; Pearse McCarron; Jane Kilcoyne; Dr. Frode Rise; Dr. Alistair L. Wilkins; Christopher O. Miles; Dr. Craig J. Forsyth. Stereochemical Definition of the Natural Product (6 R ,10 R ,13 R , 14 R ,16 R ,17 R ,19 S ,20 S ,21 R ,24 S ,25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 by Total Synthesis and Comparative Analyses. Angewandte Chemie International Edition 2017, 57, 810 -813.

AMA Style

Nathaniel T. Kenton, Daniel Adu-Ampratwum, Antony A. Okumu, Pearse McCarron, Jane Kilcoyne, Dr. Frode Rise, Dr. Alistair L. Wilkins, Christopher O. Miles, Dr. Craig J. Forsyth. Stereochemical Definition of the Natural Product (6 R ,10 R ,13 R , 14 R ,16 R ,17 R ,19 S ,20 S ,21 R ,24 S ,25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 by Total Synthesis and Comparative Analyses. Angewandte Chemie International Edition. 2017; 57 (3):810-813.

Chicago/Turabian Style

Nathaniel T. Kenton; Daniel Adu-Ampratwum; Antony A. Okumu; Pearse McCarron; Jane Kilcoyne; Dr. Frode Rise; Dr. Alistair L. Wilkins; Christopher O. Miles; Dr. Craig J. Forsyth. 2017. "Stereochemical Definition of the Natural Product (6 R ,10 R ,13 R , 14 R ,16 R ,17 R ,19 S ,20 S ,21 R ,24 S ,25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 by Total Synthesis and Comparative Analyses." Angewandte Chemie International Edition 57, no. 3: 810-813.

Zuschrift
Published: 28 November 2017 in Angewandte Chemie
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A convergent and stereoselective total synthesis of the previously assigned structure of azaspiracid‐3 has been achieved by a late‐stage Nozaki–Hiyama–Kishi coupling to form the C21−C22 bond with the C20 configuration unambiguously established from l‐(+)‐tartaric acid. Postcoupling steps involved oxidation to an ynone, modified Stryker reduction of the alkyne, global deprotection, and oxidation of the resulting C1 primary alcohol to the carboxylic acid. The synthetic product matched naturally occurring azaspiracid‐3 by mass spectrometry, but differed both chromatographically and spectroscopically.

ACS Style

Nathaniel T. Kenton; Daniel Adu-Ampratwum; Antony A. Okumu; Zhigao Zhang; Yong Chen; Son Nguyen; Jianyan Xu; Yue Ding; Pearse McCarron; Jane Kilcoyne; Dr. Frode Rise; Dr. Alistair L. Wilkins; Christopher O. Miles; Dr. Craig J. Forsyth. Total Synthesis of (6 R ,10 R ,13 R ,14 R ,16 R ,17 R ,19 S ,20 R ,21 R ,24 S , 25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 Reveals Non‐Identity with the Natural Product. Angewandte Chemie 2017, 130, 813 -817.

AMA Style

Nathaniel T. Kenton, Daniel Adu-Ampratwum, Antony A. Okumu, Zhigao Zhang, Yong Chen, Son Nguyen, Jianyan Xu, Yue Ding, Pearse McCarron, Jane Kilcoyne, Dr. Frode Rise, Dr. Alistair L. Wilkins, Christopher O. Miles, Dr. Craig J. Forsyth. Total Synthesis of (6 R ,10 R ,13 R ,14 R ,16 R ,17 R ,19 S ,20 R ,21 R ,24 S , 25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 Reveals Non‐Identity with the Natural Product. Angewandte Chemie. 2017; 130 (3):813-817.

Chicago/Turabian Style

Nathaniel T. Kenton; Daniel Adu-Ampratwum; Antony A. Okumu; Zhigao Zhang; Yong Chen; Son Nguyen; Jianyan Xu; Yue Ding; Pearse McCarron; Jane Kilcoyne; Dr. Frode Rise; Dr. Alistair L. Wilkins; Christopher O. Miles; Dr. Craig J. Forsyth. 2017. "Total Synthesis of (6 R ,10 R ,13 R ,14 R ,16 R ,17 R ,19 S ,20 R ,21 R ,24 S , 25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 Reveals Non‐Identity with the Natural Product." Angewandte Chemie 130, no. 3: 813-817.

Journal article
Published: 01 September 2017 in Journal of Chromatography B
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Commercial immunoaffinity columns (IACs) are today available for all major mycotoxins. However, manufacturers give usually no or very limited information on the epitope, i.e. the specific part of the toxin molecule that binds to the antibody. 4-Deoxynivalenol (DON) is a trichothecene mycotoxin that is produced by plant pathogenic field fungi and is regulated in many countries worldwide. DON was shown to be biotransformed via different metabolic pathways, and thus many different biotransformation products may be found in different products or organisms. In addition, several structurally similar mycotoxins may co-occur with DON. We compared five commercial IACs for their retention of a range of DON derivatives modified in the C-3, C-8, C-10, C-13 or C-15 positions, as well as nivalenol (NIV) and T-2 tetraol. The DON-derivatives were deepoxy-DON, DON 3-, 8- and 15-O-β-d-glucuronides, 3- and 15-O-acetyl-DON, DON-3-O-β-d-glucoside, 10- and 13-cysteinyl-adducts of DON, and the 13-mercaptoethanol and 10,13-dimercaptoethanol adducts of DON. The C-3 derivatives and deepoxy-DON were retained by most of the columns. Only one of the five IACs retained C-15 and C-8 derivatives, but it did not retain C-3 derivatives or deepoxy-DON. The antibodies in two of the IACs bound C-10 conjugates, but C-13 derivatives were not retained by any of the columns. This study shows that all of the antibodies in commercial IACs bind a range of DON derivatives, especially those that are modified at C-3. NIV was retained by three of the columns, and T-2 tetraol was partially retained by one IAC.

ACS Style

Silvio Uhlig; Ana Stanic; Fozia Hussain; Christopher O. Miles. Selectivity of commercial immunoaffinity columns for modified forms of the mycotoxin 4-deoxynivalenol (DON). Journal of Chromatography B 2017, 1061-1062, 322 -326.

AMA Style

Silvio Uhlig, Ana Stanic, Fozia Hussain, Christopher O. Miles. Selectivity of commercial immunoaffinity columns for modified forms of the mycotoxin 4-deoxynivalenol (DON). Journal of Chromatography B. 2017; 1061-1062 ():322-326.

Chicago/Turabian Style

Silvio Uhlig; Ana Stanic; Fozia Hussain; Christopher O. Miles. 2017. "Selectivity of commercial immunoaffinity columns for modified forms of the mycotoxin 4-deoxynivalenol (DON)." Journal of Chromatography B 1061-1062, no. : 322-326.