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Journal articles on the topic 'Dinophysistoxin'

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Published: 1 April 2023

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1

GARCêA, Carlos, Dominique TRUAN, Marcelo LAGOS, Juan Pablo SANTELICES, Juan Carlos DêAZ, and NŽstor LAGOS. "METABOLIC TRANSFORMATION OF DINOPHYSISTOXIN-3 INTO DINOPHYSISTOXIN-1 CAUSES HUMAN INTOXICATION BY CONSUMPTION OF O-ACYL-DERIVATIVES DINOPHYSISTOXINS CONTAMINATED SHELLFISH." Journal of Toxicological Sciences 30, no. 4 (2005): 287–96. http://dx.doi.org/10.2131/jts.30.287.

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2

Chin, Julia D., Michael A. Quilliam, J. Marc Fremy, Sushil K. Mohapatra, and Hanna M. Skorska. "Screening for Okadaic Acid by Immunoassay." Journal of AOAC INTERNATIONAL 78, no. 2 (March 1, 1995): 508–13. http://dx.doi.org/10.1093/jaoac/78.2.508.

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Abstract Increasing incidences of phytoplankton blooms with the potential danger of toxin release into the food chain have necessitated the search for new diagnostic methods that can detect toxins quickly and reliably. A competitive enzymelinked immunosorbent assay (ELISA) was developed to quantitate okadaic acid in shellfish and phytoplankton extracts. To determine the specificity of the assay, a number of toxins, such as calyculin A, brevetoxin-1, and dinophysistoxins-1, -2, and -3 were analyzed. Both dinophysistoxins-2 and -1 could be detected by the assay but in concentration ranges 10- and 20-fold higher than that for okadaic acid, respectively. Dinophysistoxin-3, calyculin A, or brevetoxin-1 could not be detected with this assay. To validate the accuracy of the method, 18 mussel and 7 phytoplankton extracts were analyzed in parallel for okadaic acid content by ELISA and liquid chromatography combined with either fluorescence or mass spectrometric detection. Very high correlation between the results was found.

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3

Suzuki, Toshiyuki, Hiroto Ota, and Makoto Yamasaki. "Direct evidence of transformation of dinophysistoxin-1 to 7-O-acyl-dinophysistoxin-1 (dinophysistoxin-3) in the scallop Patinopecten yessoensis." Toxicon 37, no. 1 (January 1999): 187–98. http://dx.doi.org/10.1016/s0041-0101(98)00182-2.

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4

Suzuki, T., and T. Mitsuya. "Comparison of dinophysistoxin-1 and esterified dinophysistoxin-1 (dinophysistoxin-3) contents in the scallop Patinopecten yessoensis and the mussel Mytilus galloprovincialis." Toxicon 39, no. 6 (June 2001): 905–8. http://dx.doi.org/10.1016/s0041-0101(00)00205-1.

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5

Pang, Yucheng, Chao Fang, Michael J. Twiner, Christopher O. Miles, and Craig J. Forsyth. "Total Synthesis of Dinophysistoxin-2 and 2-epi-Dinophysistoxin-2 and Their PPase Inhibition." Angewandte Chemie 123, no. 33 (July 1, 2011): 7773–77. http://dx.doi.org/10.1002/ange.201101741.

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6

Pang, Yucheng, Chao Fang, Michael J. Twiner, Christopher O. Miles, and Craig J. Forsyth. "Total Synthesis of Dinophysistoxin-2 and 2-epi-Dinophysistoxin-2 and Their PPase Inhibition." Angewandte Chemie International Edition 50, no. 33 (July 1, 2011): 7631–35. http://dx.doi.org/10.1002/anie.201101741.

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7

Lee, Sang Yoo, So Young Woo, Fei Tian, Jong Bin Park, Kwang-Sik Choi, and Hyang Sook Chun. "Simultaneous determination of okadaic acid, dinophysistoxin-1, dinophysistoxin-2, and dinophysistoxin-3 using liquid chromatography-tandem mass spectrometry in raw and cooked food matrices." Food Control 139 (September 2022): 109068. http://dx.doi.org/10.1016/j.foodcont.2022.109068.

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8

Wilkins, Alistair L., Thomas Rundberget, Morten Sandvik, Frode Rise, Brent K. Knudsen, Jane Kilcoyne, Beatriz Reguera, et al. "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 (July 21, 2021): 510. http://dx.doi.org/10.3390/toxins13080510.

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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 Prorocentrum lima 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.

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9

Rawn, Dorothea F. K., Cathie Ménard, Barbara Niedzwiadek, David Lewis, Benjamin P. Y. Lau, Nathalie Delauney-Bertoncini, Marie Claire Hennion, and James F. Lawrence. "Confirmation of okadaic acid, dinophysistoxin-1 and dinophysistoxin-2 in shellfish as their anthrylmethyl derivatives using UV radiation." Journal of Chromatography A 1080, no. 2 (July 2005): 148–56. http://dx.doi.org/10.1016/j.chroma.2005.05.035.

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10

Li, Zhen, Bo Hu, Rong Zhou, Xiaojuan Zhang, Ruizhe Wang, Yun Gao, Mingjuan Sun, Binghua Jiao, and Lianghua Wang. "Selection and application of aptamers with high-affinity and high-specificity against dinophysistoxin-1." RSC Advances 10, no. 14 (2020): 8181–89. http://dx.doi.org/10.1039/c9ra10600f.

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For the first time, the aptamer of dinophysistoxin-1 was successfully obtained with high affinity and specificity by SELEX, and an aptasensor with a detection range from 40 to 600 nM was developed by biolayer interferometry.

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11

Abal, Paula, M. Carmen Louzao, Toshiyuki Suzuki, Ryuichi Watanabe, Natalia Vilariño, Cristina Carrera, Ana M. Botana, Mercedes R. Vieytes, and Luis M. Botana. "Toxic Action Reevaluation of Okadaic Acid, Dinophysistoxin-1 and Dinophysistoxin-2: Toxicity Equivalency Factors Based on the Oral Toxicity Study." Cellular Physiology and Biochemistry 49, no. 2 (2018): 743–57. http://dx.doi.org/10.1159/000493039.

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Background/Aims: Okadaic acid (OA) and the structurally related compounds dinophysistoxin-1 (DTX1) and dinophysistoxin-2 (DTX2) are marine phycotoxins that cause diarrheic shellfish poisoning (DSP) in humans due to ingestion of contaminated shellfish. In order to guarantee consumer protection, the regulatory authorities have defined the maximum level of DSP toxins as 160 µg OA equivalent kg-1 shellfish meat. For risk assessment and overall toxicity determination, knowledge of the relative toxicities of each analogue is required. In absence of enough information from human intoxications, oral toxicity in mice is the most reliable data for establishing Toxicity Equivalence Factors (TEFs). Methods: Toxins were administered to mice by gavage, after that the symptomatology and mice mortality was registered over a period of 24 h. Organ damage data were collected at necropsy and transmission electron microscopy (TEM) was used for ultrastructural studies. Toxins in urine, feces and blood were analyzed by HPLC-MS/MS. The evaluation of in vitro potencies of OA, DTX1 and DTX2 was performed by the protein phosphatase 2A (PP2A) inhibition assay. Results: Mice that received DSP toxins by gavage showed diarrhea as the main symptom. Those toxins caused similar gastrointestinal alterations as well as intestine ultrastructural changes. However, DSP toxins did not modify tight junctions to trigger diarrhea. They had different toxicokinetics and toxic potency. The lethal dose 50 (LD50) was 487 µg kg-1 bw for DTX1, 760 µg kg-1 bw for OA and 2262 µg kg-1 bw for DTX2. Therefore, the oral TEF values are: OA = 1, DTX1 = 1.5 and DTX2 = 0.3. Conclusion: This is the first comparative study of DSP toxins performed with accurate well-characterized standards and based on acute toxicity data. Results confirmed that DTX1 is more toxic than OA by oral route while DTX2 is less toxic. Hence, the current TEFs based on intraperitoneal toxicity should be modified. Also, the generally accepted toxic mode of action of this group of toxins needs to be reevaluated.

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12

Soliño, Lucia, Francesc X. Sureda, and Jorge Diogène. "Evaluation of okadaic acid, dinophysistoxin-1 and dinophysistoxin-2 toxicity on Neuro-2a, NG108-15 and MCF-7 cell lines." Toxicology in Vitro 29, no. 1 (February 2015): 59–62. http://dx.doi.org/10.1016/j.tiv.2014.09.002.

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13

Larsen, Kristofer, Dirk Petersen, Alistair L. Wilkins, Ingunn A. Samdal, Morten Sandvik, Thomas Rundberget, David Goldstone, et al. "Clarification of the C-35 Stereochemistries of Dinophysistoxin-1 and Dinophysistoxin-2 and Its Consequences for Binding to Protein Phosphatase." Chemical Research in Toxicology 20, no. 6 (June 2007): 868–75. http://dx.doi.org/10.1021/tx700016m.

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14

Larsen, Kristofer, Dirk Petersen, Alistair L. Wilkins, Ingunn A. Samdal, Morten Sandvik, Thomas Rundberget, David Goldstone, et al. "Clarification of the C-35 Stereochemistries of Dinophysistoxin-1 and Dinophysistoxin-2 and Its Consequences for Binding to Protein Phosphatase." Chemical Research in Toxicology 20, no. 12 (December 2007): 2020. http://dx.doi.org/10.1021/tx700358s.

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15

Thi Thanh Tong, Vuong, Chi Dinh LE, and Hao Thi Hong LE. "Simultaneous detection of three biotoxins causing diarrhetic shellfish poisoning (okadaic acid, dinophysistoxin-1, dinophysistoxin-2) in oyster by LC-MS/MS." Pharmaceutical Sciences Asia 45, no. 3 (2018): 161–73. http://dx.doi.org/10.29090/psa.2018.03.161.

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16

McCarron, Pearse, Elliott Wright, and 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, no. 2 (March 1, 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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17

Carmody, Eoin P., Kevin J. James, and Seán S. Kelly. "Dinophysistoxin-2: The predominant diarrhoetic shellfish toxin in Ireland." Toxicon 34, no. 3 (March 1996): 351–59. http://dx.doi.org/10.1016/0041-0101(95)00141-7.

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18

Louzao, M. Carmen, Paula Abal, Celia Costas, Toshiyuki Suzuki, Ryuichi Watanabe, Natalia Vilariño, Ana M. Botana, Mercedes R. Vieytes, and Luis M. Botana. "DSP Toxin Distribution across Organs in Mice after Acute Oral Administration." Marine Drugs 19, no. 1 (January 8, 2021): 23. http://dx.doi.org/10.3390/md19010023.

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Okadaic acid (OA) and its main structural analogs dinophysistoxin-1 (DTX1) and dinophysistoxin-2 (DTX2) are marine lipophilic phycotoxins distributed worldwide that can be accumulated by edible shellfish and can cause diarrheic shellfish poisoning (DSP). In order to study their toxicokinetics, mice were treated with different doses of OA, DTX1, or DTX2 and signs of toxicity were recorded up to 24 h. Toxin distribution in the main organs from the gastrointestinal tract was assessed by liquid chromatography-mass spectrometry (LC/MS/MS) analysis. Our results indicate a dose-dependency in gastrointestinal absorption of these toxins. Twenty-four hours post-administration, the highest concentration of toxin was detected in the stomach and, in descending order, in the large intestine, small intestine, and liver. There was also a different toxicokinetic pathway between OA, DTX1, and DTX2. When the same toxin doses are compared, more OA than DTX1 is detected in the small intestine. OA and DTX1 showed similar concentrations in the stomach, liver, and large intestine tissues, but the amount of DTX2 is much lower in all these organs, providing information on DSP toxicokinetics for human safety assessment.

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19

Louzao, M. Carmen, Paula Abal, Celia Costas, Toshiyuki Suzuki, Ryuichi Watanabe, Natalia Vilariño, Ana M. Botana, Mercedes R. Vieytes, and Luis M. Botana. "DSP Toxin Distribution across Organs in Mice after Acute Oral Administration." Marine Drugs 19, no. 1 (January 8, 2021): 23. http://dx.doi.org/10.3390/md19010023.

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Okadaic acid (OA) and its main structural analogs dinophysistoxin-1 (DTX1) and dinophysistoxin-2 (DTX2) are marine lipophilic phycotoxins distributed worldwide that can be accumulated by edible shellfish and can cause diarrheic shellfish poisoning (DSP). In order to study their toxicokinetics, mice were treated with different doses of OA, DTX1, or DTX2 and signs of toxicity were recorded up to 24 h. Toxin distribution in the main organs from the gastrointestinal tract was assessed by liquid chromatography-mass spectrometry (LC/MS/MS) analysis. Our results indicate a dose-dependency in gastrointestinal absorption of these toxins. Twenty-four hours post-administration, the highest concentration of toxin was detected in the stomach and, in descending order, in the large intestine, small intestine, and liver. There was also a different toxicokinetic pathway between OA, DTX1, and DTX2. When the same toxin doses are compared, more OA than DTX1 is detected in the small intestine. OA and DTX1 showed similar concentrations in the stomach, liver, and large intestine tissues, but the amount of DTX2 is much lower in all these organs, providing information on DSP toxicokinetics for human safety assessment.

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20

Rodríguez, Inés, Amparo Alfonso, Alvaro Antelo, Mercedes Alvarez, and Luis Botana. "Evaluation of the Impact of Mild Steaming and Heat Treatment on the Concentration of Okadaic Acid, Dinophysistoxin-2 and Dinophysistoxin-3 in Mussels." Toxins 8, no. 6 (June 6, 2016): 175. http://dx.doi.org/10.3390/toxins8060175.

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21

Lawrence, J. E., A. D. Cembella, N. W. Ross, and J. L. C. Wright. "Cross-reactivity of an anti-okadaic acid antibody to dinophysistoxin-4 (DTX-4), dinophysistoxin-5 (DTX-5), and an okadaic acid diol ester." Toxicon 36, no. 8 (August 1998): 1193–96. http://dx.doi.org/10.1016/s0041-0101(98)00005-1.

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22

Ikehara, Tsuyoshi, Kazuya Chikanishi, and Naomasa Oshiro. "Specification of the Okadaic Acid Equivalent for Okadaic Acid, Dinophysistoxin-1, and Dinophysistoxin-2 Based on Protein Phosphatase 2A Inhibition and Cytotoxicity Assays Using Neuro 2A Cell Line." Journal of Marine Science and Engineering 9, no. 10 (October 17, 2021): 1140. http://dx.doi.org/10.3390/jmse9101140.

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Diarrhetic shellfish poisoning (DSP) is a globally occurring disease threatening public health and trade. The causative toxins, okadaic acid (OA), dinophysistoxin-1 (DTX1), and dinophysistoxin-2 (DTX2) are collectively called OAs, and are quantified using the LC-MS/MS method. The hazardous effect of total OAs is expressed as the sum of OA equivalents defined for respective OAs based on mouse lethality, produced by either intraperitoneal (OAip) or oral administration (OAor). OAs are potent inhibitors of protein phosphatase 2A (PP2A) and are cytotoxic, necessitating expansion of the concept of OA equivalents to all relevant bioactivities. In this study, we determined OA equivalents for respective OA members in PP2A inhibition and cytotoxicity assays. To secure result credibility, we used certified OAs, reference materials, and PP2A produced using genetic engineering. The relative ratio of the OA equivalents determined by PP2A inhibition assays for OA, DTX1, and DTX2 were 1.0:1.6:0.3, while the ratio determined using the cytotoxicity assays indicated 1.0:1.5:0.5. OA equivalents showed a similar tendency in the PP2A inhibition and cytotoxicity assays, and matched better with oral toxicity data than intraperitoneal toxicity in mice. The PP2A inhibition assay, which measures the core activity of the OAs, suggested a higher OA equivalent for DTX1 than that currently used.

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23

Jiménez-Cárcamo, Danae, Carlos García, and Héctor R. Contreras. "Toxins of Okadaic Acid-Group Increase Malignant Properties in Cells of Colon Cancer." Toxins 12, no. 3 (March 13, 2020): 179. http://dx.doi.org/10.3390/toxins12030179.

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Diarrhetic shellfish poisoning (DSP) is a syndrome caused by the intake of shellfish contaminated with a group of lipophilic and thermostable toxins, which consists of okadaic acid (OA), dinophysistoxin-1 (DTX-1) and dinophysistoxin-2 (DTX-2). These toxins are potent protein Ser/Thr phosphatase inhibitors, mainly type 1 protein phosphatase (PP1) and type 2A protein phosphatase (PP2A). Different effects have been reported at the cellular, molecular and genetic levels. In this study, changes in cell survival and cell mobility induced by OA, DTX-1 and DTX-2 were determined in epithelial cell lines of the colon and colon cancer. The cell viability results showed that tumoral cell lines were more resistant to toxins than the nontumoral cell line. The results of the functional assays for testing cell migration, evaluation of cell death and the expression of proteins associated with cell adhesion showed a dual effect of toxins since in the nontumoral cell line, a greater induction of cell death, presumably by anoikis, was detected. In the tumoral cell lines, there was an induction of a more aggressive phenotype characterized by increased resistance to toxins, increased migration and increased FAK activation. In tumoral cell lines of colon cancer, OA, DTX-1/DTX-2 induce a more aggressive phenotype.

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24

Huhn, Jason, Philip D. Jeffrey, Kristofer Larsen, Thomas Rundberget, Frode Rise, Neil R. Cox, Vickery Arcus, Yigong Shi, and Christopher O. Miles. "A Structural Basis for the Reduced Toxicity of Dinophysistoxin-2." Chemical Research in Toxicology 22, no. 11 (November 16, 2009): 1782–86. http://dx.doi.org/10.1021/tx9001622.

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25

Vale, Paulo, and M. A. de M. Sampayo. "Dinophysistoxin-2: a rare diarrhoeic toxin associated with Dinophysis acuta." Toxicon 38, no. 11 (November 2000): 1599–606. http://dx.doi.org/10.1016/s0041-0101(00)00079-9.

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26

SUZUKI, Hodaka, and Yumiko OKADA. "Comparative toxicity of dinophysistoxin-1 and okadaic acid in mice." Journal of Veterinary Medical Science 80, no. 4 (2018): 616–19. http://dx.doi.org/10.1292/jvms.17-0377.

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27

Draisci, Rosa, Luca Lucentini, Luigi Giannetti, Pierpaolo Boria, Kevin J. James, Ambrose Furey, Marion Gillman, and Séan S. Kelly. "Determination of Diarrheic Shellfish Toxins in Mussels b Microliquid Chromatography-Tandem Mass Spectrometry." Journal of AOAC INTERNATIONAL 81, no. 2 (March 1, 1998): 441–47. http://dx.doi.org/10.1093/jaoac/81.2.441.

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abstract A fast, sensitive, and specific procedure for determining toxins that cause diarrheic shellfish poisoning (DSP) using microliquid chromatography coupled with tandem mass spectrometry (micro-LC-MS-MS) is reported. The lipophylic polyether acidic toxins okadaic acid (OA), its isomer dinophysistoxin-2 (DTX-2), the 35-methylokadaic acid dinophysistoxin-1 (DTX-1), and the novel toxin dinophysistoxin-2B (DTX-2B; recently isolated from Irish mussels) were extracted from shellfish tissues with acetone and chromatographed by isocratic elution at 10 ixL/min with CH3CN-H20, 80 + 20 (v/v), containing 0.1% trifluoroacetic acid, through a C18 reversed-phase column (1.0 mm id). The chromatograph is coupled via an ion spray interface to an atmospheric pressure ionization source. Collision-induced-dissociation (CID) ion mass spectra of the protonated molecule, [M + H]+, at m/z 805 for OA, DTX-2, and DTX-2B and at m/z 819 for DTX-1, were obtained in MS-MS experiments to identify 2 diagnostic fragment ions for each analyte that could be used for selected-reaction-monitoring (SRM) micro-LC-MS-MS analysis. The CID spectrum of DTX-2B confirmed it to be a new OA isomer, like DTX-2. Standard curves obtained by SRM micro-LC-MS-MS were linear (r2 μ 0.9992) over the range 0.05-1.00 μg/mL (i.e., 0.10-2.00 μg toxin/g hepatopancreas), and a detection limit of 15 pg/injection was obtained for each DSP toxin. Average recoveries ranged from 95 to 101%, and coefficients of variation ranged from 1.8 to 3.4%. This novel SRM micro-LC-MS-MS method was used to confirm acidic DSP toxins in Irish and Italian toxic mussels. It offers a high degree of specificity because analyte confirmation is based on retention time, molecular weight, structural information obtained from the presence of 2 diag-nostic fragments for each analyte, and ion ratios. OA was found in both Irish (< 0.7 μg/g hepatopancreas) and Italian (<1.5 μg/g hepatopancreas) mussels. DTX-1 was found only in Italian mussels (<0.3 μg/g hepatopancreas). DTX-2 (<6.1 μg/g hepatopancreas) and DTX-2B (<0.08 μg/g hepatopancreas) were unique to Irish shellfish.

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Huguet, Antoine, Olivia Drapeau, Fanny Rousselet, Hélène Quenault, and Valérie Fessard. "Differences in Toxic Response Induced by Three Variants of the Diarrheic Shellfish Poisoning Phycotoxins in Human Intestinal Epithelial Caco-2 Cells." Toxins 12, no. 12 (December 8, 2020): 783. http://dx.doi.org/10.3390/toxins12120783.

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Diarrheic shellfish poisoning (DSP) is caused by the consumption of shellfish contaminated with a group of phycotoxins that includes okadaic acid (OA), dinophysistoxin-1 (DTX-1), and dinophysistoxin-2 (DTX-2). These toxins are inhibitors of serine/threonine protein phosphatases 1 (PP1) and 2A (PP2A), but show distinct levels of toxicity. Aside from a difference in protein phosphatases (PP) inhibition potency that would explain these differences in toxicity, others mechanisms of action are thought to be involved. Therefore, we investigated and compared which mechanisms are involved in the toxicity of these three analogues. As the intestine is one of the target organs, we studied the transcriptomic profiles of human intestinal epithelial Caco-2 cells exposed to OA, DTX-1, and DTX-2. The pathways specifically affected by each toxin treatment were further confirmed through the expression of key genes and markers of toxicity. Our results did not identify any distinct biological mechanism for OA and DTX-2. However, only DTX-1 induced up-regulation of the MAPK transduction signalling pathway, and down-regulation of gene products involved in the regulation of DNA repair. As a consequence, based on transcriptomic results, we demonstrated that the higher toxicity of DTX-1 compared to OA and DTX-2 was consistent with certain specific pathways involved in intestinal cell response.

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29

Swan, Sarah, Andrew Turner, Eileen Bresnan, Callum Whyte, Ruth Paterson, Sharon McNeill, Elaine Mitchell, and Keith Davidson. "Dinophysis acuta in Scottish Coastal Waters and Its Influence on Diarrhetic Shellfish Toxin Profiles." Toxins 10, no. 10 (September 28, 2018): 399. http://dx.doi.org/10.3390/toxins10100399.

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Diarrhetic shellfish toxins produced by the dinoflagellate genus Dinophysis are a major problem for the shellfish industry worldwide. Separate species of the genus have been associated with the production of different analogues of the okadaic acid group of toxins. To evaluate the spatial and temporal variability of Dinophysis species and toxins in the important shellfish-harvesting region of the Scottish west coast, we analysed data collected from 1996 to 2017 in two contrasting locations: Loch Ewe and the Clyde Sea. Seasonal studies were also undertaken, in Loch Ewe in both 2001 and 2002, and in the Clyde in 2015. Dinophysis acuminata was present throughout the growing season during every year of the study, with blooms typically occurring between May and September at both locations. The appearance of D. acuta was interannually sporadic and, when present, was most abundant in the late summer and autumn. The Clyde field study in 2015 indicated the importance of a temperature front in the formation of a D. acuta bloom. A shift in toxin profiles of common mussels (Mytilus edulis) tested during regulatory monitoring was evident, with a proportional decrease in okadaic acid (OA) and dinophysistoxin-1 (DTX1) and an increase in dinophysistoxin-2 (DTX2) occurring when D. acuta became dominant. Routine enumeration of Dinophysis to species level could provide early warning of potential contamination of shellfish with DTX2 and thus determine the choice of the most suitable kit for effective end-product testing.

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30

Boundy, Michael J., D. Tim Harwood, Andreas Kiermeier, Cath McLeod, Jeane Nicolas, and Sarah Finch. "Risk Assessment of Pectenotoxins in New Zealand Bivalve Molluscan Shellfish, 2009–2019." Toxins 12, no. 12 (December 6, 2020): 776. http://dx.doi.org/10.3390/toxins12120776.

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Pectenotoxins (PTXs) are produced by Dinophysis spp., along with okadaic acid, dinophysistoxin 1, and dinophysistoxin 2. The okadaic acid group toxins cause diarrhetic shellfish poisoning (DSP), so are therefore regulated. New Zealand currently includes pectenotoxins within the DSP regulations. To determine the impact of this decision, shellfish biotoxin data collected between 2009 and 2019 were examined. They showed that 85 samples exceeded the DSP regulatory limit (0.45%) and that excluding pectenotoxins would have reduced this by 10% to 76 samples. The incidence (1.3%) and maximum concentrations of pectenotoxins (0.079 mg/kg) were also found to be low, well below the current European Food Safety Authority (EFSA) safe limit of 0.12 mg/kg. Inclusion within the DSP regulations is scientifically flawed, as pectenotoxins and okadaic acid have a different mechanism of action, meaning that their toxicities are not additive, which is the fundamental principle of grouping toxins. Furthermore, evaluation of the available toxicity data suggests that pectenotoxins have very low oral toxicity, with recent studies showing no oral toxicity in mice dosed with the PTX analogue PTX2 at 5000 µg/kg. No known human illnesses have been reported due to exposure to pectenotoxins in shellfish, a fact which combined with the toxicity data indicates that they pose negligible risk to humans. Regulatory policies should be commensurate with the level of risk, thus deregulation of PTXs ought to be considered, a stance already adopted by some countries.

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31

Garibo, Diana, Pablo de la Iglesia, Jorge Diogène, and Mònica Campàs. "Inhibition Equivalency Factors for Dinophysistoxin-1 and Dinophysistoxin-2 in Protein Phosphatase Assays: Applicability to the Analysis of Shellfish Samples and Comparison with LC-MS/MS." Journal of Agricultural and Food Chemistry 61, no. 10 (February 27, 2013): 2572–79. http://dx.doi.org/10.1021/jf305334n.

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32

Twiner, Michael, Gregory Doucette, Yucheng Pang, Chao Fang, Craig Forsyth, and Christopher Miles. "Structure–Activity Relationship Studies Using Natural and Synthetic Okadaic Acid/Dinophysistoxin Toxins." Marine Drugs 14, no. 11 (November 4, 2016): 207. http://dx.doi.org/10.3390/md14110207.

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33

Deeds, Jonathan R., Whitney L. Stutts, Mary Dawn Celiz, Jill MacLeod, Amy E. Hamilton, Bryant J. Lewis, David W. Miller, et al. "Dihydrodinophysistoxin-1 Produced by Dinophysis norvegica in the Gulf of Maine, USA and Its Accumulation in Shellfish." Toxins 12, no. 9 (August 20, 2020): 533. http://dx.doi.org/10.3390/toxins12090533.

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Dihydrodinophysistoxin-1 (dihydro-DTX1, (M-H)−m/z 819.5), described previously from a marine sponge but never identified as to its biological source or described in shellfish, was detected in multiple species of commercial shellfish collected from the central coast of the Gulf of Maine, USA in 2016 and in 2018 during blooms of the dinoflagellate Dinophysis norvegica. Toxin screening by protein phosphatase inhibition (PPIA) first detected the presence of diarrhetic shellfish poisoning-like bioactivity; however, confirmatory analysis using liquid chromatography-tandem mass spectrometry (LC-MS/MS) failed to detect okadaic acid (OA, (M-H)−m/z 803.5), dinophysistoxin-1 (DTX1, (M-H)−m/z 817.5), or dinophysistoxin-2 (DTX2, (M-H)−m/z 803.5) in samples collected during the bloom. Bioactivity-guided fractionation followed by liquid chromatography-high resolution mass spectrometry (LC-HRMS) tentatively identified dihydro-DTX1 in the PPIA active fraction. LC-MS/MS measurements showed an absence of OA, DTX1, and DTX2, but confirmed the presence of dihydro-DTX1 in shellfish during blooms of D. norvegica in both years, with results correlating well with PPIA testing. Two laboratory cultures of D. norvegica isolated from the 2018 bloom were found to produce dihydro-DTX1 as the sole DSP toxin, confirming the source of this compound in shellfish. Estimated concentrations of dihydro-DTX1 were >0.16 ppm in multiple shellfish species (max. 1.1 ppm) during the blooms in 2016 and 2018. Assuming an equivalent potency and molar response to DTX1, the authority initiated precautionary shellfish harvesting closures in both years. To date, no illnesses have been associated with the presence of dihydro-DTX1 in shellfish in the Gulf of Maine region and studies are underway to determine the potency of this new toxin relative to the currently regulated DSP toxins in order to develop appropriate management guidance.

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34

YANAGI, Toshihiko, Michio MURATA, Koichiro TORIGOE, and Takeshi YASUMOTO. "Biological activities of semisynthetic analogs of dinophysistoxin-3, the major diarrhetic shellfish toxin." Agricultural and Biological Chemistry 53, no. 2 (1989): 525–29. http://dx.doi.org/10.1271/bbb1961.53.525.

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35

Yanagi, Toshihiko, Michio Murata, Koichiro Torigoe, and Takeshi Yasumoto. "Biological Activities of Semisynthetic Analogs of Dinophysistoxin-3, the Major Diarrhetic Shellfish Toxin." Agricultural and Biological Chemistry 53, no. 2 (February 1989): 525–29. http://dx.doi.org/10.1080/00021369.1989.10869308.

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36

Norte, Manuel, Agustín Padilla, and José J. Fernández. "Studies on the biosynthesis of the polyether marine toxin dinophysistoxin-1 (DTX-1)." Tetrahedron Letters 35, no. 9 (February 1994): 1441–44. http://dx.doi.org/10.1016/s0040-4039(00)76241-1.

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37

Fujiki, Hirota, Masami Suganuma, Hiroko Suguri, Shigeru Yoshizawa, Kanji Takagi, Naoto Uda, Kazumasa Wakamatsu, et al. "Diarrhetic Shellfish Toxin, Dinophysistoxin-1, Is a Potent Tumor Promoter on Mouse Skin." Japanese Journal of Cancer Research 79, no. 10 (October 1988): 1089–93. http://dx.doi.org/10.1111/j.1349-7006.1988.tb01531.x.

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38

James, Kevin J., Alan G. Bishop, Brendan M. Healy, Cilian Roden, Ian R. Sherlock, Marian Twohig, Rosa Draisci, Luigi Giannetti, and Luca Lucentini. "Efficient isolation of the rare diarrhoeic shellfish toxin, dinophysistoxin-2, from marine phytoplankton." Toxicon 37, no. 2 (February 1999): 343–57. http://dx.doi.org/10.1016/s0041-0101(98)00184-6.

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39

Vale, Paulo, Maria Antónia, and M. Sampayo. "Esters of okadaic acid and dinophysistoxin-2 in Portuguese bivalves related to human poisonings." Toxicon 37, no. 8 (August 1999): 1109–21. http://dx.doi.org/10.1016/s0041-0101(98)00247-5.

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40

Forsyth, Craig J., and Ce Wang. "Synthesis and stereochemistry of the terminal spiroketal domain of the phosphatase inhibitor dinophysistoxin-2." Bioorganic & Medicinal Chemistry Letters 18, no. 10 (May 2008): 3043–46. http://dx.doi.org/10.1016/j.bmcl.2008.01.002.

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41

Kamiyama, Takashi, and Toshiyuki Suzuki. "Production of dinophysistoxin-1 and pectenotoxin-2 by a culture of Dinophysis acuminata (Dinophyceae)." Harmful Algae 8, no. 2 (January 2009): 312–17. http://dx.doi.org/10.1016/j.hal.2008.07.003.

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42

Perez-Gomez, A. "The Marine Toxin Dinophysistoxin-2 Induces Differential Apoptotic Death of Rat Cerebellar Neurons and Astrocytes." Toxicological Sciences 80, no. 1 (March 10, 2004): 74–82. http://dx.doi.org/10.1093/toxsci/kfh139.

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43

Pan, Lei, Junhui Chen, Xiuping He, Tianrong Zhan, and Huihui Shen. "Aqueous photodegradation of okadaic acid and dinophysistoxin-1: Persistence, kinetics, photoproducts, pathways, and toxicity evaluation." Science of The Total Environment 743 (November 2020): 140593. http://dx.doi.org/10.1016/j.scitotenv.2020.140593.

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44

Fernández, Diego, M. Louzao, María Fraga, Natalia Vilariño, Mercedes Vieytes, and Luis Botana. "Experimental Basis for the High Oral Toxicity of Dinophysistoxin 1: A Comparative Study of DSP." Toxins 6, no. 1 (January 3, 2014): 211–28. http://dx.doi.org/10.3390/toxins6010211.

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45

Kuuppo, Pirjo, Pauliina Uronen, Anika Petermann, Timo Tamminen, and Edna Granéli. "Pectenotoxin-2 and dinophysistoxin-1 in suspended and sedimenting organic matter in the Baltic Sea." Limnology and Oceanography 51, no. 5 (September 2006): 2300–2307. http://dx.doi.org/10.4319/lo.2006.51.5.2300.

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46

Lee, Sangbum, Buyng Su Hwang, Hyung Seop Kim, Wonho Yih, Eun Ju Jeong, and Jung-Rae Rho. "A New Diol Ester Derivative of Dinophysistoxin-1 from Cultures ofProrocentrum limaCollected in South Korea." Bulletin of the Korean Chemical Society 36, no. 1 (January 2015): 395–98. http://dx.doi.org/10.1002/bkcs.10031.

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47

LEE, KA JEONG, JONG SOO MOK, KI CHEOL SONG, HONGSIK YU, JEE HYUNG JUNG, and JI HOE KIM. "Geographical and Annual Variation in Lipophilic Shellfish Toxins from Oysters and Mussels along the South Coast of Korea." Journal of Food Protection 74, no. 12 (December 1, 2011): 2127–33. http://dx.doi.org/10.4315/0362-028x.jfp-11-148.

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To better understand critical aspects of diarrhetic shellfish poisoning (DSP) occurrence in a chief producing region of bivalves in Korea, the geographical and annual variation of DSP toxins and other lipophilic toxins in mussels (Mytilus galloprovincialis) and oysters (Crassostrea gigas) were investigated by liquid chromatography–tandem mass spectrometry in an area on the south coast of Korea from 2007 to 2009. The total lipophilic shellfish toxin (LST) levels in bivalves showed geographical and annual variations. LSTs were detected mostly in the hepatopancreas of mussels from Jinhae Bay throughout the entire year, except in November and December of 2007, but were almost undetectable in all samples during the entire year in 2009. The peak DSP toxin (okadaic acid plus dinophysistoxin 1) levels in the hepatopancreas of mussels from Jinhae Bay and the Tongyeong region were 945.3 and 37.6 ng/g, respectively. The DSP toxin content was about 10 times higher in mussels than in oysters collected from the same region. The major toxins in bivalves were okadaic acid and dinophysistoxin 1; however, pectenotoxin 2 or yessotoxin was occasionally detected as a major component. The results of a quantitative analysis of phytoplankton showed that Dinophysis acuminata was the most probable source of the LSTs, with the exception of yessotoxin. When the highest DSP toxin level was measured (945.3 ng/g in the hepatopancreas of mussels from Jinhae Bay), the toxin concentration in whole mussel tissue was calculated to be 114.0 ng/g. The calculated highest DSP toxin level in whole oyster tissue from both regions was 15.0 ng/g. The calculated maximum toxicities in whole mussel and oyster tissues were lower than the regulatory limit (160 to 200 ng/g) in Korea, the European Union, and the United States. Korean oysters (242 samples) and mussels (214 samples) were thus deemed safe for consumption. But because such variation was detected in a relatively small area of the coast, it is possible that at some locations or during a specific period LST levels could exceed the standard and a few consumers could be at risk of experiencing DSP.

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48

Ikehara, Tsuyoshi, Shihoko Imamura, Atsushi Yoshino, and Takeshi Yasumoto. "PP2A Inhibition Assay Using Recombinant Enzyme for Rapid Detection of Okadaic Acid and Its Analogs in Shellfish." Toxins 2, no. 1 (January 25, 2010): 195–204. http://dx.doi.org/10.3390/toxins2010195.

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Okadaic acid and its analogs (OAs) responsible for diarrhetic shellfish poisoning (DSP) strongly inhibit protein phosphatase 2A (PP2A) and thus are quantifiable by measuring the extent of the enzyme inhibition. In this study, we evaluated the suitability of the catalytic subunit of recombinant human PP2A (rhPP2Ac) for use in a microplate OA assay. OA, dinophysistoxin-1(DTX1), and hydrolyzate of 7-O-palmitoyl-OA strongly inhibited rhPP2Ac activity with IC50 values of 0.095, 0.104, and 0.135 nM, respectively. The limits of detection and quantitation for OA in the digestive gland of scallops and mussels were 0.0348 μg/g and 0.0611 μg/g respectively, and, when converted to the whole meat basis, are well below the regulation level proposed by EU (0.16 μg/g whole meat). A good correlation with LC-MS data was demonstrated, the correlation coefficient being 0.996 with the regression slope of 1.097.

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Lawrence, James F., Sonia Roussel, and Cathie Ménard. "Liquid chromatographic determination of okadaic acid and dinophysistoxin-1 in shellfish after derivatization with 9-chloromethylanthracene." Journal of Chromatography A 721, no. 2 (January 1996): 359–64. http://dx.doi.org/10.1016/0021-9673(95)00808-x.

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50

Abal, Paula, M. Carmen Louzao, José Manuel Cifuentes, Natalia Vilariño, Ines Rodriguez, Amparo Alfonso, Mercedes R. Vieytes, and Luis M. Botana. "Characterization of the dinophysistoxin-2 acute oral toxicity in mice to define the Toxicity Equivalency Factor." Food and Chemical Toxicology 102 (April 2017): 166–75. http://dx.doi.org/10.1016/j.fct.2017.02.023.

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