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Autore: Grafiati

Pubblicato: 22 giugno 2024

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1

Lamas, J. Pablo, Fabiola Arévalo, Ángeles Moroño, Jorge Correa, Susana Muñíz e Juan Blanco. "Detection and Spatio-Temporal Distribution of Pinnatoxins in Shellfish from the Atlantic and Cantabrian Coasts of Spain". Toxins 11, n. 6 (14 giugno 2019): 340. http://dx.doi.org/10.3390/toxins11060340.

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For the first time, pinnatoxins have been detected in shellfish from the Atlantic and Cantabrian coasts of Spain. High sensitivity LC-MS/MS systems were used to monitor all the currently known pinnatoxins (A–H). Pinnatoxin G (PnTX G) was the most prevalent toxin of the group, but its metabolite PnTX A has also been found at much lower levels. No trend in PnTX G concentration was found in the area, but a hotspot in the Ría de Camariñas has been identified. The maximum concentrations found did not exceed 15 µg·kg−1, being, in most cases, below 3 µg·kg−1. The highest concentrations were found in wild (intertidal) populations of mussels which attained much higher levels than raft-cultured ones, suggesting that the toxin-producer organisms preferentially develop in shallow areas. Other bivalve species had, in general, lower concentrations. The incidence of PnTX G followed a seasonal pattern in which the maximum concentrations took place in winter months. PnTX G was found to be partially esterified but the esterification percentage was not high (lower than 30%).

2

Hort, Vincent, Isabel Bastardo-Fernández e Marina Nicolas. "Exploration of Vulcanodinium rugosum Toxins and their Metabolism Products in Mussels from the Ingril Lagoon Hotspot in France". Marine Drugs 21, n. 8 (29 luglio 2023): 429. http://dx.doi.org/10.3390/md21080429.

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Over the year 2018, we assessed toxin contamination of shellfish collected on a monthly basis in Ingril Lagoon, France, a site known as a hotspot for Vulcanodinium rugosum growth. This short time-series study gave an overview of the presence and seasonal variability of pinnatoxins, pteriatoxins, portimines and kabirimine, all associated with V. rugosum, in shellfish. Suspect screening and targeted analysis approaches were implemented by means of liquid chromatography coupled to both low- and high-resolution mass spectrometry. We detected pinnatoxin-A and pinnatoxin-G throughout the year, with maximum levels for each one observed in June (6.7 µg/kg for pinnatoxin-A; 467.5 µg/kg for pinnatoxin-G), whereas portimine-A was detected between May and September (maximum level = 75.6 µg/kg). One of the main findings was the identification of a series of fatty acid esters of pinnatoxin-G (n = 13) although the levels detected were low. The profile was dominated by the palmitic acid conjugation of pinnatoxin-G. The other 12 fatty acid esters had not been reported in European shellfish to date. In addition, after thorough investigations, two compounds were detected, with one being probably identified as portimine-B, and the other one putatively attributed to pteriatoxins. If available, reference materials would have ensured full identification. Monitoring of these V. rugosum emerging toxins and their biotransformation products will contribute towards filling the data gaps pointed out in risk assessments and in particular the need for more contamination data for shellfish.

3

Finch, Sarah C., D. Tim Harwood, Michael J. Boundy e Andrew I. Selwood. "A Review of Cyclic Imines in Shellfish: Worldwide Occurrence, Toxicity and Assessment of the Risk to Consumers". Marine Drugs 22, n. 3 (11 marzo 2024): 129. http://dx.doi.org/10.3390/md22030129.

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Cyclic imines are a class of lipophilic shellfish toxins comprising gymnodimines, spirolides, pinnatoxins, portimines, pteriatoxins, prorocentrolides, spiro-prorocentrimine, symbiomines and kabirimine. They are structurally diverse, but all share an imine moiety as part of a bicyclic ring system. These compounds are produced by marine microalgal species and are characterized by the rapid death that they induce when injected into mice. Cyclic imines have been detected in a range of shellfish species collected from all over the world, which raises the question as to whether they present a food safety risk. The European Food Safety Authority (EFSA) considers them to be an emerging food safety issue, and in this review, the risk posed by these toxins to shellfish consumers is assessed by collating all available occurrence and toxicity data. Except for pinnatoxins, the risk posed to human health by the cyclic imines appears low, although this is based on only a limited dataset. For pinnatoxins, two different health-based guidance values have been proposed at which the concentration should not be exceeded in shellfish (268 and 23 µg PnTX/kg shellfish flesh), with the discrepancy caused by the application of different uncertainty factors. Pinnatoxins have been recorded globally in multiple shellfish species at concentrations of up to 54 times higher than the lower guidance figure. Despite this observation, pinnatoxins have not been associated with recorded human illness, so it appears that the lower guidance value may be conservative. However, there is insufficient data to generate a more robust guidance value, so additional occurrence data and toxicity information are needed.

4

Araoz, Romulo, Denis Servent, Jordi Molgó, Bogdan I. Iorga, Carole Fruchart-Gaillard, Evelyne Benoit, Zhenhua Gu, Craig Stivala e Armen Zakarian. "Total Synthesis of Pinnatoxins A and G and Revision of the Mode of Action of Pinnatoxin A". Journal of the American Chemical Society 133, n. 27 (13 luglio 2011): 10499–511. http://dx.doi.org/10.1021/ja201254c.

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5

Tamele, Isidro José, Ilário Timba, Vitor Vasconcelos e Pedro Reis Costa. "First Report of Pinnatoxins in Bivalve Molluscs from Inhaca Island (South of Mozambique)—South of the Indian Ocean". Journal of Marine Science and Engineering 10, n. 9 (31 agosto 2022): 1215. http://dx.doi.org/10.3390/jmse10091215.

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The objective of this work was to screen the EU-regulated lipophilic and cyclic imine toxins in four bivalve species (Atrina vexillum, Pinctada imbricata, Anadara antiquata, and Saccostrea Cucculata) from the Mozambican coast in the Indian Ocean. Toxins were extracted and analyzed according to the EU reference method for the determination of lipophilic toxins in shellfish via LC–MS/MS, but no regulated toxins were found in the analyzed species. However, pinnatoxins (PnTX G, E, and F) were detected in A. vexillum, P. imbricata, and A. antiquata. Higher levels of the PnTX G were determined for A. vexillum (7.7 and 14.3 µg·kg−1) than for P. imbricata (1.6 and 2.4 µg·kg−1), and for A. antiquata (4.5 and 5.9 µg·kg−1) with both hydrolyzed and non-hydrolyzed extracts, respectively. The higher levels of PnTX G determined in the hydrolyzed extracts indicate the high potential of this species to esterify pinnatoxins, in particular PnTX G.

6

Takada, Noboru, Naoyoshi Umemura, Kiyotake Suenaga, Tong Chou, Akito Nagatsu, Takeharu Haino, Kaoru Yamada e Daisuke Uemura. "Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata". Tetrahedron Letters 42, n. 20 (maggio 2001): 3491–94. http://dx.doi.org/10.1016/s0040-4039(01)00480-4.

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7

Pelc, Matthew J., e Armen Zakarian. "An Approach to the Imine Ring System of Pinnatoxins". Organic Letters 7, n. 8 (aprile 2005): 1629–31. http://dx.doi.org/10.1021/ol050321l.

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8

Stivala, Craig E., e Armen Zakarian. "Studies toward the synthesis of pinnatoxins: the spiroimine fragment". Tetrahedron Letters 48, n. 39 (settembre 2007): 6845–48. http://dx.doi.org/10.1016/j.tetlet.2007.07.182.

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9

Arnich, Nathalie, Eric Abadie, Nicolas Delcourt, Valérie Fessard, Jean-Marc Fremy, Vincent Hort, Emmeline Lagrange et al. "Health risk assessment related to pinnatoxins in French shellfish". Toxicon 180 (giugno 2020): 1–10. http://dx.doi.org/10.1016/j.toxicon.2020.03.007.

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10

Rundberget, Thomas, John A. Bunæs Aasen, Andrew I. Selwood e Christopher O. Miles. "Pinnatoxins and spirolides in Norwegian blue mussels and seawater". Toxicon 58, n. 8 (dicembre 2011): 700–711. http://dx.doi.org/10.1016/j.toxicon.2011.08.008.

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11

Hellyer, Shane D., Andrew I. Selwood, Lesley Rhodes e D. Steven Kerr. "Neuromuscular blocking activity of pinnatoxins E, F and G". Toxicon 76 (dicembre 2013): 214–20. http://dx.doi.org/10.1016/j.toxicon.2013.10.009.

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12

Matsuura, Fumiyoshi, Junliang Hao, Reinhard Reents e Yoshito Kishi. "Total Synthesis and Stereochemistry of Pinnatoxins B and C". Organic Letters 8, n. 15 (luglio 2006): 3327–30. http://dx.doi.org/10.1021/ol0611548.

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13

Otero, Paz, Carmen Vale, Andrea Boente-Juncal, Celia Costas, M. Carmen Louzao e Luis M. Botana. "Detection of Cyclic Imine Toxins in Dietary Supplements of Green Lipped Mussels (Perna canaliculus) and in Shellfish Mytilus chilensis". Toxins 12, n. 10 (24 settembre 2020): 613. http://dx.doi.org/10.3390/toxins12100613.

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Seafood represents a significant part of the human staple diet. In the recent years, the identification of emerging lipophilic marine toxins has increased, leading to the potential for consumers to be intoxicated by these toxins. In the present work, we investigate the presence of lipophilic marine toxins (both regulated and emerging) in commercial seafood products from non-European locations, including mussels Mytilus chilensis from Chile, clams Tawerea gayi and Metetrix lyrate from the Southeast Pacific and Vietnam, and food supplements based on mussels formulations of Perna canaliculus from New Zealand. All these products were purchased from European Union markets and they were analyzed by UPLC-MS/MS. Results showed the presence of the emerging pinnatoxin-G in mussels Mytilus chilensis at levels up to 5.2 µg/kg and azaspiracid-2 and pectenotoxin-2 in clams Tawera gayi up to 4.33 µg/kg and 10.88 µg/kg, respectively. This study confirms the presence of pinnatoxins in Chile, one of the major mussel producers worldwide. Chromatograms showed the presence of 13-desmethyl spirolide C in dietary supplements in the range of 33.2–97.9 µg/kg after an extraction with water and methanol from 0.39 g of the green lipped mussels powder. As far as we know, this constitutes the first time that an emerging cyclic imine toxin in dietary supplements is reported. Identifying new matrix, locations, and understanding emerging toxin distribution area are important for preventing the risks of spreading and contamination linked to these compounds.

14

Barreiro-Crespo, Lourdes, Margarita Fernández-Tejedor, Jorge Diogène e Maria Rambla-Alegre. "The Temporal Distribution of Cyclic Imines in Shellfish in the Bays of Fangar and Alfacs, Northwestern Mediterranean Region". Toxins 16, n. 1 (23 dicembre 2023): 10. http://dx.doi.org/10.3390/toxins16010010.

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Spirolides (SPXs), gymnodimines (GYMs), and pinnatoxins (PnTXs) have been detected in shellfish from the northwestern Mediterranean coast of Spain. Several samples of bivalves were collected from Fangar Bay and Alfacs Bay in Catalonia over a period of over 7 years (from 2015 to 2021). Shellfish samples were analyzed for cyclic imines (CIs) on an LC1200 Agilent and 3200 QTrap triple–quadrupole mass spectrometer. In shellfish, SPX-1 was detected in two cases (of 26.5 µg/kg and 34 µg/kg), and GYM-A was only detected in trace levels in thirteen samples. Pinnatoxin G (PnTX-G) was detected in 44.6% of the samples, with its concentrations ranging from 2 µg/kg to 38.4 µg/kg. Statistical analyses revealed that seawater temperature influenced the presence or absence of these toxins. PnTX-G showed an extremely significant presence/temperature relationship in both bays in comparison to SPX-1 and GYM-A. The prevalence of these toxins in different bivalve mollusks was evaluated. A seasonal pattern was observed, in which the maximum concentrations were found in the winter months for SPX-1 and GYM-A but in the summer months for PnTX-G. The obtained results indicate that it is unlikely that CIs in the studied area pose a potential health risk through the consumption of a seafood diet. However, further toxicological information about CIs is necessary in order to perform a conclusive risk assessment.

15

Amzil, Zouher, Amélie Derrien, Aouregan Terre Terrillon, Véronique Savar, Thomas Bertin, Marion Peyrat, Audrey Duval et al. "Five Years Monitoring the Emergence of Unregulated Toxins in Shellfish in France (EMERGTOX 2018–2022)". Marine Drugs 21, n. 8 (31 luglio 2023): 435. http://dx.doi.org/10.3390/md21080435.

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Shellfish accumulate microalgal toxins, which can make them unsafe for human consumption. In France, in accordance with EU regulations, three groups of marine toxins are currently under official monitoring: lipophilic toxins, saxitoxins, and domoic acid. Other unregulated toxin groups are also present in European shellfish, including emerging lipophilic and hydrophilic marine toxins (e.g., pinnatoxins, brevetoxins) and the neurotoxin β-N-methylamino-L-alanine (BMAA). To acquire data on emerging toxins in France, the monitoring program EMERGTOX was set up along the French coasts in 2018. Three new broad-spectrum LC-MS/MS methods were developed to quantify regulated and unregulated lipophilic and hydrophilic toxins and the BMAA group in shellfish (bivalve mollusks and gastropods). A single-laboratory validation of each of these methods was performed. Additionally, these specific, reliable, and sensitive operating procedures allowed the detection of groups of EU unregulated toxins in shellfish samples from French coasts: spirolides (SPX-13-DesMeC, SPX-DesMeD), pinnatoxins (PnTX-G, PnTX-A), gymnodimines (GYM-A), brevetoxins (BTX-2, BTX-3), microcystins (dmMC-RR, MC-RR), anatoxin, cylindrospermopsin and BMAA/DAB. Here, we present essentially the results of the unregulated toxins obtained from the French EMERGTOX monitoring plan during the past five years (2018–2022). Based on our findings, we outline future needs for monitoring to protect consumers from emerging unregulated toxins.

16

Takada, Noboru, Naoyoshi Umemura, Kiyotake Suenaga, Tong Chou, Akito Nagatsu, Takeharu Haino, Kaoru Yamada e Daisuke Uemura. "ChemInform Abstract: Pinnatoxins B (Ia) and C (Ib), the Most Toxic Components in the Pinnatoxin Series from the Okinawan bivalve Pinna muricata." ChemInform 32, n. 32 (25 maggio 2010): no. http://dx.doi.org/10.1002/chin.200132233.

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17

Sosa, Silvio, Marco Pelin, Federica Cavion, Fabienne Hervé, Philipp Hess e Aurelia Tubaro. "Acute Oral Toxicity of Pinnatoxin G in Mice". Toxins 12, n. 2 (28 gennaio 2020): 87. http://dx.doi.org/10.3390/toxins12020087.

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Pinnatoxin G (PnTx-G) is a marine cyclic imine toxin produced by the dinoflagellate Vulcanodinium rugosum, frequently detected in edible shellfish from Ingril Lagoon (France). As other pinnatoxins, to date, no human poisonings ascribed to consumption of PnTx-G contaminated seafood have been reported, despite its potent antagonism at nicotinic acetylcholine receptors and its high and fast-acting toxicity after intraperitoneal or oral administration in mice. The hazard characterization of PnTx-G by oral exposure is limited to a single acute toxicity study recording lethality and clinical signs in non-fasted mice treated by gavage or through voluntary food ingestion, which showed differences in PnTx-G toxic potency. Thus, an acute toxicity study was carried out using 3 h-fasted CD-1 female mice, administered by gavage with PnTx-G (8–450 µg kg−1). At the dose of 220 µg kg−1 and above, the toxin induced a rapid onset of clinical signs (piloerection, prostration, hypothermia, abdominal breathing, paralysis of the hind limbs, and cyanosis), leading to the death of mice within 30 min. Except for moderate mucosal degeneration in the small intestine recorded at doses of 300 µg kg−1, the toxin did not induce significant morphological changes in the other main organs and tissues, or alterations in blood chemistry parameters. This acute oral toxicity study allowed to calculate an oral LD50 for PnTx-G equal to 208 μg kg−1 (95% confidence limits: 155–281 µg kg−1) and to estimate a provisional NOEL of 120 µg kg−1.

18

Hellyer, Shane D., Dinesh Indurthi, Thomas Balle, Vanda Runder-Varga, Andrew I. Selwood, Joel D. A. Tyndall, Mary Chebib, Lesley Rhodes e D. Steven Kerr. "Pinnatoxins E, F and G target multiple nicotinic receptor subtypes". Journal of Neurochemistry 135, n. 3 (3 agosto 2015): 479–91. http://dx.doi.org/10.1111/jnc.13245.

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19

Ishihara, Jun, Shingo Tojo, Akio Kamikawa e Akio Murai. "One-step assembling reaction to the pentacyclic acetal of pinnatoxins". Chemical Communications, n. 15 (2001): 1392–93. http://dx.doi.org/10.1039/b104200a.

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20

Munday, Rex, Andrew I. Selwood e Lesley Rhodes. "Acute toxicity of pinnatoxins E, F and G to mice". Toxicon 60, n. 6 (novembre 2012): 995–99. http://dx.doi.org/10.1016/j.toxicon.2012.07.002.

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21

Couesnon, A., J. Lindovsky, A. Zakarian, S. Creuzet e J. Molgó. "28. Pinnatoxins block skeletal neuromuscular junction activity and affect embryo development". Toxicon 91 (dicembre 2014): 175–76. http://dx.doi.org/10.1016/j.toxicon.2014.08.036.

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22

Delcourt, Nicolas, Emmeline Lagrange, Eric Abadie, Valérie Fessard, Jean-Marc Frémy, Jean-Paul Vernoux, Marie-Bénédicte Peyrat et al. "Pinnatoxins’ Deleterious Effects on Cholinergic Networks: From Experimental Models to Human Health". Marine Drugs 17, n. 7 (20 luglio 2019): 425. http://dx.doi.org/10.3390/md17070425.

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Abstract (sommario):

Pinnatoxins (PnTXs) are emerging neurotoxins that were discovered about 30 years ago. They are solely produced by the marine dinoflagellate Vulcanodinium rugosum, and may be transferred into the food chain, as they have been found in various marine invertebrates, including bivalves. No human intoxication has been reported to date although acute toxicity was induced by PnTxs in rodents. LD50 values have been estimated for the different PnTXs through the oral route. At sublethal doses, all symptoms are reversible, and no neurological sequelae are visible. These symptoms are consistent with impairment of central and peripheral cholinergic network functions. In fact, PnTXs are high-affinity competitive antagonists of nicotinic acetylcholine receptors (nAChRs). Moreover, their lethal effects are consistent with the inhibition of muscle nAChRs, inducing respiratory distress and paralysis. Human intoxication by ingestion of PnTXs could result in various symptoms observed in episodes of poisoning with natural nAChR antagonists. This review updates the available data on PnTX toxicity with a focus on their mode of action on cholinergic networks and suggests the effects that could be extrapolated on human physiology.

23

Sugimoto, Tetsuya, Jun Ishihara e Akio Murai. "Synthesis of the B,C,D,E,F-Ring Fragment of Pinnatoxins". Synlett 1999, n. 5 (maggio 1999): 541–44. http://dx.doi.org/10.1055/s-1999-2689.

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24

Selwood, Andrew I., Christopher O. Miles, Alistair L. Wilkins, Roel van Ginkel, Rex Munday, Frode Rise e Paul McNabb. "Isolation, Structural Determination and Acute Toxicity of Pinnatoxins E, F and G". Journal of Agricultural and Food Chemistry 58, n. 10 (26 maggio 2010): 6532–42. http://dx.doi.org/10.1021/jf100267a.

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25

Lu, Chong-Dao, e Armen Zakarian. "Studies toward the Synthesis of Pinnatoxins: The B,C,D-Dispiroketal Fragment". Organic Letters 9, n. 16 (agosto 2007): 3161–63. http://dx.doi.org/10.1021/ol071266e.

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26

Rhodes, L., K. Smith, A. Selwood, P. McNabb, R. van Ginkel, P. Holland e R. Munday. "Production of pinnatoxins by a peridinoid dinoflagellate isolated from Northland, New Zealand". Harmful Algae 9, n. 4 (maggio 2010): 384–89. http://dx.doi.org/10.1016/j.hal.2010.01.008.

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27

Ishihara, Jun, Shingo Tojo, Akio Kamikawa e Akio Murai. "ChemInform Abstract: One-Step Assembling Reaction to the Pentacyclic Acetal of Pinnatoxins." ChemInform 32, n. 45 (23 maggio 2010): no. http://dx.doi.org/10.1002/chin.200145249.

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28

Otero, Paz, e Marisa Silva. "Emerging Marine Biotoxins in European Waters: Potential Risks and Analytical Challenges". Marine Drugs 20, n. 3 (8 marzo 2022): 199. http://dx.doi.org/10.3390/md20030199.

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Harmful algal blooms pose a challenge regarding food safety due to their erratic nature and forming circumstances which are yet to be disclosed. The best strategy to protect human consumers is through legislation and monitoring strategies. Global warming and anthropological intervention aided the migration and establishment of emerging toxin producers into Europe’s temperate waters, creating a new threat to human public health. The lack of information, standards, and reference materials delay effective solutions, being a matter of urgent resolution. In this work, the recent findings of the presence of emerging azaspiracids, spirolildes, pinnatoxins, gymnodimines, palitoxins, ciguatoxins, brevetoxins, and tetrodotoxins on European Coasts are addressed. The information concerning emerging toxins such as new matrices, locations, and toxicity assays is paramount to set the risk assessment guidelines, regulatory levels, and analytical methodology that would protect the consumers.

29

Sugimoto, Tetsuya, Jun Ishihara e Akio Murai. "ChemInform Abstract: Synthesis of the B,C,D,E,F-Ring Fragment of Pinnatoxins." ChemInform 30, n. 33 (14 giugno 2010): no. http://dx.doi.org/10.1002/chin.199933286.

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30

Kim, Young-Sang, Hyun-Joo An, Jaeseong Kim e You-Jin Jeon. "Current Situation of Palytoxins and Cyclic Imines in Asia-Pacific Countries: Causative Phytoplankton Species and Seafood Poisoning". International Journal of Environmental Research and Public Health 19, n. 8 (18 aprile 2022): 4921. http://dx.doi.org/10.3390/ijerph19084921.

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Among marine biotoxins, palytoxins (PlTXs) and cyclic imines (CIs), including spirolides, pinnatoxins, pteriatoxins, and gymnodimines, are not managed in many countries, such as the USA, European nations, and South Korea, because there are not enough poisoning cases or data for the limits on these biotoxins. In this article, we review unregulated marine biotoxins (e.g., PlTXs and CIs), their toxicity, causative phytoplankton species, and toxin extraction and detection protocols. Due to global warming, the habitat of the causative phytoplankton has expanded to the Asia-Pacific region. When ingested by humans, shellfish that accumulated toxins can cause various symptoms (muscle pain or diarrhea) and even death. There are no systematic reports on the occurrence of these toxins; however, it is important to continuously monitor causative phytoplankton and poisoning of accumulating shellfish by PlTXs and CI toxins because of the high risk of toxicity in human consumers.

31

Hellyer, Shane D., Andrew I. Selwood, Lesley Rhodes e D. Steven Kerr. "Marine algal pinnatoxins E and F cause neuromuscular block in an in vitro hemidiaphragm preparation". Toxicon 58, n. 8 (dicembre 2011): 693–99. http://dx.doi.org/10.1016/j.toxicon.2011.09.006.

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32

Bouquet, Aurélien, Marie Anaïs Perdrau, Mohamed Laabir, Elodie Foucault, Nicolas Chomérat, Jean Luc Rolland e Eric Abadie. "Liza ramada Juveniles after Exposure to the Toxic Dinoflagellate Vulcanodinium rugosum: Effects on Fish Viability, Tissue Contamination and Microalgae Survival after Gut Passage". Toxins 14, n. 6 (10 giugno 2022): 401. http://dx.doi.org/10.3390/toxins14060401.

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Pinnatoxins (PnTX) and Portimines (Prtn), two toxins produced by the benthic dinoflagellate Vulcanodinium rugosum, are known to be lethal to mice after intraperitoneal or oral administration. They are also known to accumulate in shellfish such as mussels and clams, but their effect on fish and the upper food chain remains unknown. In this work, juveniles of the fish Liza ramada (Mullet) were exposed to a strain of V. rugosum producing PnTX G and Prtn A. The fishes’ viability and contamination were recorded at times interval. Results showed that L. ramada juveniles were able to feed on V. rugosum and that their tissues could be contaminated by PnTX G and Prtn A without impact on fish viability. Furthermore, the microalgae temporary cysts survived and germinated after fish gut passage. This study showed the potential of L. ramada to transfer PnTX and Prtn toxins to the upper food chain and to disseminate V. rugosum in environment.

33

Rhodes, Lesley, Kirsty Smith, Andrew Selwood, Paul McNabb, Rex Munday, Shoichiro Suda, Sam Molenaar e Gustaaf Hallegraeff. "Dinoflagellate Vulcanodinium rugosum identified as the causative organism of pinnatoxins in Australia, New Zealand and Japan". Phycologia 50, n. 6 (novembre 2011): 624–28. http://dx.doi.org/10.2216/11-19.1.

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34

Benoit, Evelyne, Aurélie Couesnon, Jiri Lindovsky, Bogdan I. Iorga, Rómulo Aráoz, Denis Servent, Armen Zakarian e Jordi Molgó. "Synthetic Pinnatoxins A and G Reversibly Block Mouse Skeletal Neuromuscular Transmission In Vivo and In Vitro". Marine Drugs 17, n. 5 (24 maggio 2019): 306. http://dx.doi.org/10.3390/md17050306.

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Pinnatoxins (PnTXs) A-H constitute an emerging family belonging to the cyclic imine group of phycotoxins. Interest has been focused on these fast-acting and highly-potent toxins because they are widely found in contaminated shellfish. Despite their highly complex molecular structure, PnTXs have been chemically synthetized and demonstrated to act on various nicotinic acetylcholine receptor (nAChR) subtypes. In the present work, PnTX-A, PnTX-G and analogue, obtained by chemical synthesis with a high degree of purity (>98%), have been studied in vivo and in vitro on adult mouse and isolated nerve-muscle preparations expressing the mature muscle-type (α1)2β1δε nAChR. The results show that PnTX-A and G acted on the neuromuscular system of anesthetized mice and blocked the compound muscle action potential (CMAP) in a dose- and time-dependent manner, using a minimally invasive electrophysiological method. The CMAP block produced by both toxins in vivo was reversible within 6–8 h. PnTX-A and G, applied to isolated extensor digitorum longus nerve-muscle preparations, blocked reversibly isometric twitches evoked by nerve stimulation. The action of PnTX-A was reversed by 3,4-diaminopyridine. Both toxins exerted no direct action on muscle fibers, as revealed by direct muscle stimulation. PnTX-A and G blocked synaptic transmission at mouse neuromuscular junctions and PnTX-A amino ketone analogue (containing an open form of the imine ring) had no effect on neuromuscular transmission. These results indicate the importance of the cyclic imine for interacting with the adult mammalian muscle-type nAChR. Modeling and docking studies revealed molecular determinants responsible for the interaction of PnTXs with the muscle-type nAChR.

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Rhodes, L., K. Smith, A. Selwood, P. McNabb, S. Molenaar, R. Munday, C. Wilkinson e G. Hallegraeff. "Production of pinnatoxins E, F and G by scrippsielloid dinoflagellates isolated from Franklin Harbour, South Australia". New Zealand Journal of Marine and Freshwater Research 45, n. 4 (dicembre 2011): 703–9. http://dx.doi.org/10.1080/00288330.2011.586041.

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36

Sugimoto, Tetsuya, Jun Ishihara e Akio Murai. "The first construction of the B,C,D-ring fragment of pinnatoxins via highly stereocontrolled acetallization". Tetrahedron Letters 38, n. 42 (ottobre 1997): 7379–82. http://dx.doi.org/10.1016/s0040-4039(97)01725-5.

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37

McNabb, P. S., D. J. McCoubrey, L. Rhodes, K. Smith, A. I. Selwood, R. van Ginkel, A. L. MacKenzie, R. Munday e P. T. Holland. "New perspectives on biotoxin detection in Rangaunu Harbour, New Zealand arising from the discovery of pinnatoxins". Harmful Algae 13 (gennaio 2012): 34–39. http://dx.doi.org/10.1016/j.hal.2011.09.013.

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38

Bouquet, Aurélien, Christine Felix, Estelle Masseret, Coralie Reymond, Eric Abadie, Mohamed Laabir e Jean Luc Rolland. "Artificial Substrates Coupled with qPCR (AS-qPCR) Assay for the Detection of the Toxic Benthopelagic Dinoflagellate Vulcanodinium rugosum". Toxins 15, n. 3 (11 marzo 2023): 217. http://dx.doi.org/10.3390/toxins15030217.

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Abstract (sommario):

Vulcanodinium rugosum is an emerging benthopelagic neuro-toxic dinoflagellate species responsible for seasonal Pinnatoxins and Portimines contaminations of shellfish and marine animals. This species is challenging to detect in the environment, as it is present in low abundance and difficult to be identified using light microscopy. In this work, we developed a method using artificial substrates coupled with qPCR (AS-qPCR) to detect V. rugosum in a marine environment. This sensitive, specific and easy-to-standardize alternative to current techniques does not require specialized expertise in taxonomy. After determining the limits and specificity of the qPCR, we searched for the presence of V. rugosum in four French Mediterranean lagoons using artificial substrates collected every two weeks for one year. The AS-qPCR method revealed its occurrences in summer 2021 in every studied lagoon and detected cells in more samples than light microscopy. As V. rugosum development induces shellfish contamination even at low microalga densities, the AS-qPCR method is accurate and relevant for monitoring V. rugosum in a marine environment.

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CHATZIANASTASIOU (Μ. ΧΑΤΖΗΑΝΑΣΤΑΣΙΟΥ), M., M. KATIKOU (Μ. ΚΑΤΙΚΟΥ), Th ZACHARAKI (Θ. ΖΑΧΑΡΑΚΗ), A. PAPAZACHARIOU (Α. ΠΑΠΑΖΑΧΑΡΙΟΥ) e A. McKEVITT. "Cyclic imines, as emerging marine toxins: Chemical properties, distribution, toxicological aspects and detection methods". Journal of the Hellenic Veterinary Medical Society 62, n. 3 (10 novembre 2017): 240. http://dx.doi.org/10.12681/jhvms.14856.

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Shellfish and, specifically, bivalve molluscs are a food commodity of great nterest for both commercial and public health reasons. They consume microalgae from surrounding waters, which are generally beneficial for aquaculture, but they comprise certain toxin-producing species. These species produce marine toxins which, via the filter-feeding mechanism of bivalve molluscs, accumulate in their tissues. This accumulation is more intense andmore dangerous for public health during the so-called periods of Harmful Algal Blooms (HABs) when the microalgal population grows. According to their chemical structure, marine toxins are classified into 8 groups, one of which is the cyclic imines. These lipophilic toxins were accidentally discovered during routine bioassays for the detection of other lipophilic marine toxins due to the induction of neurological symptoms and acute death in mice. They include the following subgroups: Spirolides (SPX), gymnodimines (GYM), pinnatoxins (PnTX), pteriatoxins (PtTX), prorocentrolides and spiro-prorocentrimines. The European Union (EU) is more concerned about the first three subgroups, because, in contrast with the latter three, they have already been detected in Europe or there is strong evidence supporting their presence. Spirolides are produced by the dmof\a.ge\\ate Alexandrìum ostenfeldii/peruvianum, gymnodimines by the dinoflagellate Karenia selliformis and pinnatoxins by a peridinoid dinoflagellate recently described in the new genus Vulcanodinium spp.. Although there is insufficient information regarding the geographical distribution of cyclic imines, the fact that they have been detected on multiple occasions in European waters, in combination with their aforementioned acute toxicity in mice after intraperitoneal injection, has established them, at least within the EU, as a topic of profound scientific research. In spite of their acute toxicity in mice, no incident of human intoxication has been attributed to cyclic imines. Presently, the EU has neither set any Maximum Permissible Limits for the concentration of cyclic imines in shellfish nor appointed any reference method for their detection and quantification. Currently, the methods applied are biological, biochemical and chemical. The biological method is a bioassay, which is conducted via the intraperitoneal injection of mice with an extract containing the compound under examination and it detects total toxicity. This properly is essential for the detection of unknown toxins, but the use of laboratory animals raises serious ethical concerns and animal welfare issues. The biochemical method is based on competition between cyclic imines and a fluorescently labelled compound for binding to receptors of the electric ray Torpedo marmorata. Finally, in respect of chemical methods, liquid chromatography with tandem mass spectrometry detection (LC-MS/MS) is the most significant method because it is fast, of high repeatability and specificity.

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Ishihara, Jun, Tetsuya Sugimoto e Akio Murai. "Studies on the Stability of 1,7,9-Trioxadispiro[5.1.5.2]pentadecane System: The Common Tricyclic Acetal Moiety in Pinnatoxins". Synlett 1998, n. 6 (giugno 1998): 603–6. http://dx.doi.org/10.1055/s-1998-1742.

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Pelc, Matthew J., e Armen Zakarian. "Synthesis of the A,G-spiroimine of pinnatoxins by a microwave-assisted tandem Claisen–Mislow–Evans rearrangement". Tetrahedron Letters 47, n. 43 (ottobre 2006): 7519–23. http://dx.doi.org/10.1016/j.tetlet.2006.08.083.

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McCarron, Pearse, Wade A. Rourke, William Hardstaff, Brandy Pooley e Michael A. Quilliam. "Identification of Pinnatoxins and Discovery of Their Fatty Acid Ester Metabolites in Mussels (Mytilus edulis) from Eastern Canada". Journal of Agricultural and Food Chemistry 60, n. 6 (31 gennaio 2012): 1437–46. http://dx.doi.org/10.1021/jf204824s.

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43

SUGIMOTO, T., J. ISHIHARA e A. MURAI. "ChemInform Abstract: The First Construction of the B,C,D-Ring Fragment of Pinnatoxins via Highly Stereocontrolled Acetalization." ChemInform 29, n. 5 (24 giugno 2010): no. http://dx.doi.org/10.1002/chin.199805238.

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44

Rossignoli, Araceli E., Carmen Mariño, Helena Martín e Juan Blanco. "Development of a Fast Liquid Chromatography Coupled to Mass Spectrometry Method (LC-MS/MS) to Determine Fourteen Lipophilic Shellfish Toxins Based on Fused–Core Technology: In-House Validation". Marine Drugs 19, n. 11 (24 ottobre 2021): 603. http://dx.doi.org/10.3390/md19110603.

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Abstract (sommario):

Prevalence and incidence of the marine toxins (paralytic, amnesic, and lipophilic toxins) including the so-called emerging toxins (these are, gymnodimines, pinnatoxins, or spirolides among others) have increased in recent years all over the world. Climate change, which is affecting the distribution of their producing phytoplankton species, is probably one of the main causes. Early detection of the toxins present in a particular area, and linking the toxins to their causative phytoplankton species are key tools to minimize the risk they pose for human consumers. The development of both types of studies requires fast and highly sensitive analytical methods. In the present work, we have developed a highly sensitive liquid chromatography-mass spectrometry methodology (LC-MS/MS), using a column with fused-core particle technology, for the determination of fourteen lipophilic toxins in a single run of 3.6 min. The performance of the method was evaluated for specificity, linearity, precision (repeatability and reproducibility) and accuracy by analysing spiked and naturally contaminated samples. The in-house validation was successful, and the limit of detection (LOD) and quantification (LOQ) for all the toxins were far below their regulatory action limits. The method is suitable to be considered in monitoring systems of bivalves for food control.

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Bacchiocchi, Simone, Melania Siracusa, Debora Campacci, Martina Ciriaci, Alessandra Dubbini, Tamara Tavoloni, Arianna Stramenga, Stefania Gorbi e Arianna Piersanti. "Cyclic Imines (CIs) in Mussels from North-Central Adriatic Sea: First Evidence of Gymnodimine A in Italy". Toxins 12, n. 6 (4 giugno 2020): 370. http://dx.doi.org/10.3390/toxins12060370.

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Cyclic imines (CIs) are emerging marine lipophilic toxins (MLTs) occurring in microalgae and shellfish worldwide. The present research aimed to study CIs in mussels farmed in the Adriatic Sea (Italy) during the period 2014–2015. Twenty-eight different compounds belonging to spirolides (SPXs), gymnodimines (GYMs), pinnatoxins (PnTXs) and pteriatoxins (PtTXs) were analyzed by the official method for MLTs in 139 mussel samples collected along the Marche coast. Compounds including 13-desmethyl spirolide C (13-desMe SPX C) and 13,19-didesmethyl spirolide C (13,19-didesMe SPX C) were detected in 86% of the samples. The highest levels were generally reported in the first half of the year reaching 29.2 µg kg−1 in January/March with a decreasing trend until June. GYM A, for the first time reported in Italian mussels, was found in 84% of the samples, reaching the highest concentration in summer (12.1 µg kg−1). GYM A and SPXs, submitted to tissue distribution studies, showed the tendency to accumulate mostly in mussel digestive glands. Even if SPX levels in mussels were largely below the European Food Safety Authority (EFSA) reference of 400 μg SPXs kg−1, most of the samples contained CIs for the large part of the year. Since chronic toxicity data are still missing, monitoring is surely recommended.

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ISHIHARA, J., T. SUGIMOTO e A. MURAI. "ChemInform Abstract: Studies on the Stability of 1,7,9-Trioxadispiro[5.1.5.2]pentadecane System: The Common Tricyclic Acetal Moiety in Pinnatoxins." ChemInform 29, n. 39 (19 giugno 2010): no. http://dx.doi.org/10.1002/chin.199839284.

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Bourne, Yves, Gerlind Sulzenbacher, Zoran Radić, Rómulo Aráoz, Morgane Reynaud, Evelyne Benoit, Armen Zakarian et al. "Marine Macrocyclic Imines, Pinnatoxins A and G: Structural Determinants and Functional Properties to Distinguish Neuronal α7 from Muscle α12βγδ nAChRs". Structure 23, n. 6 (giugno 2015): 1106–15. http://dx.doi.org/10.1016/j.str.2015.04.009.

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McCarron, Pearse, Elliott Wright e Michael A. Quilliam. "Liquid Chromatography/Mass Spectrometry of Domoic Acid and Lipophilic Shellfish Toxins with Selected Reaction Monitoring and Optional Confirmation by Library Searching of Product Ion Spectra". Journal of AOAC INTERNATIONAL 97, n. 2 (1 marzo 2014): 316–24. http://dx.doi.org/10.5740/jaoacint.sgemccarron.

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Abstract LC/MS methodology for the analysis of domoic acidand lipophilic toxins in shellfish was developed using a hybrid triple quadrupole linear ion trap mass spectrometer. For routine quantitation a scheduled selected reaction monitoring (SRM) method for the analysis of domoic acid, okadaic acid, dinophysistoxins,azaspiracids, pectenotoxins, yessotoxins, gymnodimines, spirolides, and pinnatoxins was developed and validated. The method performed well in terms of LOD, linearity, precision, and trueness. Taking advantageof the high instrument sensitivity, matrix effects were mitigated by reducing the amount of sample introduced to the mass spectrometer. Optionally, samples can be analyzed using information dependent acquisition (IDA) methods, either in positive or negative mode, which can provide an extra level of confirmationby matching the full product ion spectra acquired for a sample with those from a specially constructedspectral library. Methods were applied to the analysisof a new certified reference material and Canadian mussels (Mytilus edulis) implicated in a 2011 diarrhetic shellfish poisoning (DSP) incident. The scheduled SRM method enabled the screening and quantitation of multiple phycotoxins. As DSPhad not previously been observed in this area of Canada,positive identification of putative toxins was accomplished using the IDA and spectral search method. Analysis of the 2011 toxic mussel samples revealed thepresence of high levels of dinophysistoxin-1, which explained the DSP symptoms, as well as pectenotoxins, yessotoxins, and variety of cyclic imines.

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Servent, Denis, Sophie Creuzet, Carole Malgorn, Vincent Dive, Armen Zakarian e Jordi Molgó. "Pinnatoxins, an emergent class of marine toxins interacting with nAChRs. Pharmacological characterization, biodistribution and musculo-skeletal effect of these neurotoxic agents". Toxicon 177 (aprile 2020): S3. http://dx.doi.org/10.1016/j.toxicon.2019.10.015.

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Moreiras, Guillermo, José Manuel Leão e Ana Gago-Martínez. "Analysis of Cyclic Imines in Mussels (Mytilus galloprovincialis) from Galicia (NW Spain) by LC-MS/MS". International Journal of Environmental Research and Public Health 17, n. 1 (31 dicembre 2019): 281. http://dx.doi.org/10.3390/ijerph17010281.

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Abstract (sommario):

Cyclic imines (CIs) are being considered as emerging toxins in the European Union, and a scientific opinion has been published by the European Food Safety Authority (EFSA) in which an assessment of the risks to human health related to their consumption has been carried out. Recommendations on the EFSA opinion include the search for data occurrence of CIs in shellfish and using confirmatory methods by liquid chromatography-tandem mass spectrometry (LC-MS/MS), which need to be developed and optimized. The aim of this work is the application of LC-MS/MS to the analysis of gymnodimines (GYMs), spirolides (SPXs), pinnatoxins (PnTXs), and pteriatoxins (PtTXs) in mussels from Galician Rias, northwest Spain, the main production area in Europe, and therefore a representative emplacement for their evaluation. Conditions were adjusted using commercially available certified reference standards of GYM-A, SPX-1, and PnTX-G and evaluated through quality control studies. The EU-Harmonised Standard Operating Procedure for determination of lipophilic marine biotoxins in molluscs by LC-MS/MS was followed, and the results obtained from the analysis of eighteen samples from three different locations that showed the presence of PnTXs and SPXs are presented and discussed. Concentrations of PnTX-G and SPX-1 ranged from 1.8 to 3.1 µg/kg and 1.2 to 6.9 µg/kg, respectively, and PnTX-A was detected in the group of samples with higher levels of PnTX-G after a solid phase extraction (SPE) step used for the concentration of extracts.