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Journal articles on the topic 'Azaspiracids'

Author: Grafiati
Published: 2 June 2025
Last updated: 31 July 2025

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1

Hamilton, Brett, Mónica Díaz Sierra, Mary Lehane, Ambrose Furey, and Kevin J. James. "The fragmentation pathways of azaspiracids elucidated using positive nanospray hybrid quadrupole time-of-flight (QqTOF) mass spectrometry." Spectroscopy 18, no. 2 (2004): 355–62. http://dx.doi.org/10.1155/2004/949018.

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The azaspiracids, AZA1, AZA2 and AZA3, are the predominant shellfish toxins responsible for the human toxic syndrome, azaspiracid poisoning. Collision induced dissociation (CID) mass spectra were generated for azaspiracids using nano-electrospray ionisation (ESI) with a hybrid quadrupole time-of-flight (QqTOF) mass spectrometer in positive mode. Six main backbone fragmentations of the polyether skeleton of azaspiracids were observed as well as multiple neutral losses of water molecules from the parent and product ions. The characteristic charge-remote fragmentation of the carbon skeleton of az
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2

Yang, Jiaping, Xinhao Li, Weiqin Sun, et al. "High Affinity Aptamers and Their Specificity for Azaspiracid-2 Using Capture-SELEX." Marine Drugs 23, no. 5 (2025): 183. https://doi.org/10.3390/md23050183.

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Azaspiracids are a type of polyether toxin. Currently, the existing detection methods for azaspiracids all have certain drawbacks. Aptamers offer a cost-effective and convenient approach for the detection of azaspiracids. By employing the Capture-SELEX (Systematic evolution of ligands by exponential enrichment) method to screen aptamers specific to azaspiracid-2, a high-affinity aptamer can be identified for toxin detection. The bin ding affinity of the toxin is verified using biolayer interferometry (BLI) technology. Additionally, computer simulations are utilized to explore the binding sites
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3

Alfonso, Carmen, Amparo Alfonso, Paz Otero, et al. "Purification of five azaspiracids from mussel samples contaminated with DSP toxins and azaspiracids." Journal of Chromatography B 865, no. 1-2 (2008): 133–40. http://dx.doi.org/10.1016/j.jchromb.2008.02.020.

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4

Krock, Bernd, Urban Tillmann, Daniela Voß, et al. "New azaspiracids in Amphidomataceae (Dinophyceae)." Toxicon 60, no. 5 (2012): 830–39. http://dx.doi.org/10.1016/j.toxicon.2012.05.007.

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5

Yang, Jiaping, Weiqin Sun, Mingjuan Sun, Yunyi Cui, and Lianghua Wang. "Current Research Status of Azaspiracids." Marine Drugs 22, no. 2 (2024): 79. http://dx.doi.org/10.3390/md22020079.

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The presence and impact of toxins have been detected in various regions worldwide ever since the discovery of azaspiracids (AZAs) in 1995. These toxins have had detrimental effects on marine resource utilization, marine environmental protection, and fishery production. Over the course of more than two decades of research and development, scientists from all over the world have conducted comprehensive studies on the in vivo metabolism, in vitro synthesis methods, pathogenic mechanisms, and toxicology of these toxins. This paper aims to provide a systematic introduction to the discovery, distrib
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6

Kilcoyne, Jane, Adela Keogh, Ger Clancy, et al. "Improved Isolation Procedure for Azaspiracids from Shellfish, Structural Elucidation of Azaspiracid-6, and Stability Studies." Journal of Agricultural and Food Chemistry 60, no. 10 (2012): 2447–55. http://dx.doi.org/10.1021/jf2048788.

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7

Vilariño, Natalia. "Marine toxins and the cytoskeleton: azaspiracids." FEBS Journal 275, no. 24 (2008): 6075–81. http://dx.doi.org/10.1111/j.1742-4658.2008.06713.x.

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8

Krock, Bernd, Urban Tillmann, Jan Tebben, Nicole Trefault, and Haifeng Gu. "Two novel azaspiracids from Azadinium poporum, and a comprehensive compilation of azaspiracids produced by Amphidomataceae, (Dinophyceae)." Harmful Algae 82 (February 2019): 1–8. http://dx.doi.org/10.1016/j.hal.2018.12.005.

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9

Kilcoyne, Jane, Pearse McCarron, Michael J. Twiner, et al. "Epimers of Azaspiracids: Isolation, Structural Elucidation, Relative LC-MS Response, andin VitroToxicity of 37-epi-Azaspiracid-1." Chemical Research in Toxicology 27, no. 4 (2014): 587–600. http://dx.doi.org/10.1021/tx400434b.

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10

Abal, Paula, M. Carmen Louzao, María Fraga, et al. "Absorption and Effect of Azaspiracid-1 Over the Human Intestinal Barrier." Cellular Physiology and Biochemistry 43, no. 1 (2017): 136–46. http://dx.doi.org/10.1159/000480331.

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Background: Azaspiracids (AZAs) are marine biotoxins produced by the dinoflagellates genera Azadinium and Amphidoma. These toxins cause azaspiracid poisoning (AZP), characterized by severe gastrointestinal illness in humans after the consumption of bivalve molluscs contaminated with AZAs. The main aim of the present study was to examine the consequences of human exposure to AZA1 by the study of absorption and effects of the toxin on Caco-2 cells, a reliable model of the human intestine. Methods: The ability of AZA1 to cross the human intestinal epithelium has been evaluated by the Caco-2 trans
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11

WU, Haiyan, Qingyun LI, Xiaofei BING, et al. "Metabolic regulation of azaspiracids in Chlamys farreri." Journal of Fishery Sciences of China 24, no. 6 (2017): 1298. http://dx.doi.org/10.3724/sp.j.1118.2017.17025.

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12

Krock, Bernd, Urban Tillmann, Uwe John, and Allan D. Cembella. "Characterization of azaspiracids in plankton size-fractions and isolation of an azaspiracid-producing dinoflagellate from the North Sea." Harmful Algae 8, no. 2 (2009): 254–63. http://dx.doi.org/10.1016/j.hal.2008.06.003.

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13

Trainer, Vera L., and Teri L. King. "SoundToxins: A Research and Monitoring Partnership for Harmful Phytoplankton in Washington State." Toxins 15, no. 3 (2023): 189. http://dx.doi.org/10.3390/toxins15030189.

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The more frequent occurrence of marine harmful algal blooms (HABs) and recent problems with newly-described toxins in Puget Sound have increased the risk for illness and have negatively impacted sustainable access to shellfish in Washington State. Marine toxins that affect safe shellfish harvest because of their impact on human health are the saxitoxins that cause paralytic shellfish poisoning (PSP), domoic acid that causes amnesic shellfish poisoning (ASP), diarrhetic shellfish toxins that cause diarrhetic shellfish poisoning (DSP) and the recent measurement of azaspiracids, known to cause az
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14

Alfonso, Amparo, Mercedes R. Vieytes, Katsuya Ofuji, et al. "Azaspiracids modulate intracellular pH levels in human lymphocytes." Biochemical and Biophysical Research Communications 346, no. 3 (2006): 1091–99. http://dx.doi.org/10.1016/j.bbrc.2006.06.019.

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15

Rodríguez, Laura P., Natalia Vilariño, M. Carmen Louzao, et al. "Microsphere-based immunoassay for the detection of azaspiracids." Analytical Biochemistry 447 (February 2014): 58–63. http://dx.doi.org/10.1016/j.ab.2013.10.035.

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16

Jauffrais, Thierry, Christine Herrenknecht, Véronique Séchet, et al. "Quantitative analysis of azaspiracids in Azadinium spinosum cultures." Analytical and Bioanalytical Chemistry 403, no. 3 (2012): 833–46. http://dx.doi.org/10.1007/s00216-012-5849-2.

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17

Yadav, J. S., Sipak Joyasawal, S. K. Dutta, and A. C. Kunwar. "Stereoselective synthesis of the ABCD ring framework of azaspiracids." Tetrahedron Letters 48, no. 30 (2007): 5335–40. http://dx.doi.org/10.1016/j.tetlet.2007.05.021.

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18

Blanco, Juan, Fabiola Arévalo, Ángeles Moroño, et al. "Presence of azaspiracids in bivalve molluscs from Northern Spain." Toxicon 137 (October 2017): 135–43. http://dx.doi.org/10.1016/j.toxicon.2017.07.025.

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19

Zhang, Zhigao, Yong Chen, Daniel Adu-Ampratwum, Antony Akura Okumu, Nathaniel T. Kenton, and Craig J. Forsyth. "Synthesis of the C22–C40 Domain of the Azaspiracids." Organic Letters 18, no. 8 (2016): 1824–27. http://dx.doi.org/10.1021/acs.orglett.6b00557.

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20

Geraghty, J., C. Duffy, J. A. Aasen Bunæs, P. Hess, and B. Foley. "20. In vivo study of azaspiracids in mini pigs." Toxicon 91 (December 2014): 172–73. http://dx.doi.org/10.1016/j.toxicon.2014.08.028.

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21

Samdal, Ingunn A., Kjersti E. Løvberg, Lyn R. Briggs, et al. "Development of an ELISA for the Detection of Azaspiracids." Journal of Agricultural and Food Chemistry 63, no. 35 (2015): 7855–61. http://dx.doi.org/10.1021/acs.jafc.5b02513.

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22

Rossi, Rachele, Carmela Dell’Aversano, Bernd Krock, et al. "Mediterranean Azadinium dexteroporum (Dinophyceae) produces six novel azaspiracids and azaspiracid-35: a structural study by a multi-platform mass spectrometry approach." Analytical and Bioanalytical Chemistry 409, no. 4 (2016): 1121–34. http://dx.doi.org/10.1007/s00216-016-0037-4.

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23

Zhao, Liye, Jiangbing Qiu, Jingrui Zhang, Aifeng Li, and Guixiang Wang. "Apoptosis and Oxidative Stress in Human Intestinal Epithelial Caco-2 Cells Caused by Marine Phycotoxin Azaspiracid-2." Toxins 16, no. 9 (2024): 381. http://dx.doi.org/10.3390/toxins16090381.

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When humans consume seafood contaminated by lipophilic polyether phycotoxins, such as azaspiracids (AZAs), the toxins are mainly leached and absorbed in the small intestine, potentially causing intestinal damage. In this study, human intestinal epithelial Caco-2 cells were used to investigate the adverse effects of azaspiracid-2 (AZA-2) on human intestinal epithelial cells. Cell viability, apoptosis, oxidative damage and mitochondrial ultrastructure were investigated, and ribonucleic acid sequence (RNA-seq) analysis was applied to explore the potential mechanisms of AZA-2 toxicity to Caco-2 ce
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24

Triantafyllakis, Myron, Maria Tofi, Tamsyn Montagnon, Antonia Kouridaki, and Georgios Vassilikogiannakis. "Singlet Oxygen-Mediated Synthesis of Bis-spiroketals Found in Azaspiracids." Organic Letters 16, no. 11 (2014): 3150–53. http://dx.doi.org/10.1021/ol501301w.

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25

Dounay, Amy B., and Craig J. Forsyth. "Synthetic Studies toward the C5−C20 Domain of the Azaspiracids." Organic Letters 3, no. 7 (2001): 975–78. http://dx.doi.org/10.1021/ol015570y.

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26

Nicolaou, K. C., Michael O Frederick, Eriketi Z Loizidou, et al. "Second-Generation Total Synthesis of Azaspiracids-1, -2, and -3." Chemistry – An Asian Journal 1, no. 1-2 (2006): 245–63. http://dx.doi.org/10.1002/asia.200600059.

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27

Kilcoyne, Jane, Pearse McCarron, Philipp Hess, and Christopher O. Miles. "Effects of Heating on Proportions of Azaspiracids 1–10 in Mussels (Mytilus edulis) and Identification of Carboxylated Precursors for Azaspiracids 5, 10, 13, and 15." Journal of Agricultural and Food Chemistry 63, no. 51 (2015): 10980–87. http://dx.doi.org/10.1021/acs.jafc.5b04609.

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28

WU, Haiyan, Mengmeng GUO, Chunxia ZHAO, et al. "Liquid chromatography-tandem mass spectrometry analysis for azaspiracids and their metabolites." Chinese Journal of Chromatography 34, no. 4 (2016): 401. http://dx.doi.org/10.3724/sp.j.1123.2015.11043.

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29

Forsyth, Craig J., Jianyan Xu, Son T. Nguyen, et al. "Antibodies with Broad Specificity to Azaspiracids by Use of Synthetic Haptens." Journal of the American Chemical Society 128, no. 47 (2006): 15114–16. http://dx.doi.org/10.1021/ja066971h.

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30

Magdalena, Ana Braña, Mary Lehane, Sophie Krys, Mariá Luisa Fernández, Ambrose Furey, and Kevin J. James. "The first identification of azaspiracids in shellfish from France and Spain." Toxicon 42, no. 1 (2003): 105–8. http://dx.doi.org/10.1016/s0041-0101(03)00105-3.

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31

Aiguade, Josep, Junliang Hao, and Craig J. Forsyth. "Biomimetic studies towards the C28–C40 polycyclic domain of the azaspiracids." Tetrahedron Letters 42, no. 5 (2001): 817–20. http://dx.doi.org/10.1016/s0040-4039(00)02156-0.

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32

Jauffrais, Thierry, Jane Kilcoyne, Christine Herrenknecht, et al. "Dissolved azaspiracids are absorbed and metabolized by blue mussels (Mytilus edulis)." Toxicon 65 (April 2013): 81–89. http://dx.doi.org/10.1016/j.toxicon.2013.01.010.

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33

Kilcoyne, J., C. Nulty, P. McCarron, et al. "19. Isolation of minor and novel azaspiracids – Structure elucidation and toxicology." Toxicon 91 (December 2014): 172. http://dx.doi.org/10.1016/j.toxicon.2014.08.027.

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34

Zhang, Zhigao, Yue Ding, Jianyan Xu, Yong Chen, and Craig J. Forsyth. "Synthesis of the C1–C21 Domain of Azaspiracids-1 and −3." Organic Letters 15, no. 10 (2013): 2338–41. http://dx.doi.org/10.1021/ol400487e.

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35

Tillmann, Urban, Bente Edvardsen, Bernd Krock, Kirsty F. Smith, Ruth F. Paterson, and Daniela Voß. "Diversity, distribution, and azaspiracids of Amphidomataceae (Dinophyceae) along the Norwegian coast." Harmful Algae 80 (December 2018): 15–34. http://dx.doi.org/10.1016/j.hal.2018.08.011.

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36

Torgersen, Trine, Nanna Bruun Bremnes, Thomas Rundberget, and Tore Aune. "Structural confirmation and occurrence of azaspiracids in Scandinavian brown crabs (Cancer pagurus)." Toxicon 51, no. 1 (2008): 93–101. http://dx.doi.org/10.1016/j.toxicon.2007.08.008.

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37

Furey, Ambrose, Cian Moroney, Ana Braña Magdalena, Maria José Fidalgo Saez, Mary Lehane, and Kevin J. James. "Geographical, Temporal, and Species Variation of the Polyether Toxins, Azaspiracids, in Shellfish." Environmental Science & Technology 37, no. 14 (2003): 3078–84. http://dx.doi.org/10.1021/es020246z.

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38

Román, Yolanda, Amparo Alfonso, Mercedes R. Vieytes, et al. "Effects of Azaspiracids 2 and 3 on Intracellular cAMP, [Ca2+], and pH." Chemical Research in Toxicology 17, no. 10 (2004): 1338–49. http://dx.doi.org/10.1021/tx0341862.

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39

Furey, Ambrose, Ana Braña-Magdalena, Mary Lehane, et al. "Determination of azaspiracids in shellfish using liquid chromatography/tandem electrospray mass spectrometry." Rapid Communications in Mass Spectrometry 16, no. 3 (2002): 238–42. http://dx.doi.org/10.1002/rcm.560.

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40

Triantafyllakis, Myron, Maria Tofi, Tamsyn Montagnon, Antonia Kouridaki, and Georgios Vassilikogiannakis. "ChemInform Abstract: Singlet Oxygen-Mediated Synthesis of Bis-spiroketals Found in Azaspiracids." ChemInform 45, no. 48 (2014): no. http://dx.doi.org/10.1002/chin.201448104.

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41

Dounay, Amy B., and Craig J. Forsyth. "ChemInform Abstract: Synthetic Studies Toward the C5-C20 Domain of the Azaspiracids." ChemInform 32, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.200129192.

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42

Abouabdellaha, Rachid, Asmae Bennouna, Jaouad El Attar, et al. "Diarrhetic shellfish poisoning toxin profile of shellfish from Southern Atlantic coasts of Morocco." South Asian Journal of Experimental Biology 1, no. 2 (2011): 101–6. http://dx.doi.org/10.38150/sajeb.1(2).p101-106.

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During the monitoring program of phycotoxins conducted in 2005 and 2006, lipophilic shell fish toxins (LSTs) are involved in shellfish toxicity phenomena in the South Atlantic Moroccan coasts (Dakhla region). Toxicity was assessed by the traditional mouse bioassay (MBA); the content and the nature of the toxic components were established through Liquid chromatography (LC) coupled with mass spectrometry (MS). The ‘traditional’ DSP toxins group, okadaic acid (OA) and dinophysitoxins (DTXs) and their associated esters were exclusives contaminants of Dakhla’s shellfish (muss
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43

Otero, Paz, and Marisa Silva. "Emerging Marine Biotoxins in European Waters: Potential Risks and Analytical Challenges." Marine Drugs 20, no. 3 (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 pre
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44

Pelin, Marco, Jane Kilcoyne, Chiara Florio, Philipp Hess, Aurelia Tubaro, and Silvio Sosa. "Azaspiracids Increase Mitochondrial Dehydrogenases Activity in Hepatocytes: Involvement of Potassium and Chloride Ions." Marine Drugs 17, no. 5 (2019): 276. http://dx.doi.org/10.3390/md17050276.

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Background: Azaspiracids (AZAs) are marine toxins that are produced by Azadinium and Amphidoma dinoflagellates that can contaminate edible shellfish inducing a foodborne poisoning in humans, which is characterized by gastrointestinal symptoms. Among these, AZA1, -2, and -3 are regulated in the European Union, being the most important in terms of occurrence and toxicity. In vivo studies in mice showed that, in addition to gastrointestinal effects, AZA1 induces liver alterations that are visible as a swollen organ, with the presence of hepatocellular fat droplets and vacuoles. Hence, an in vitro
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45

Boente-Juncal, Andrea, Sandra Raposo-García, Celia Costas, M. Carmen Louzao, Carmen Vale, and Luis M. Botana. "Partial Blockade of Human Voltage-Dependent Sodium Channels by the Marine Toxins Azaspiracids." Chemical Research in Toxicology 33, no. 10 (2020): 2593–604. http://dx.doi.org/10.1021/acs.chemrestox.0c00216.

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46

Sasaki, Makoto, Yuko Iwamuro, Jyunichi Nemoto, and Masato Oikawa. "Studies toward the total synthesis of azaspiracids: synthesis of the FGHI ring domain." Tetrahedron Letters 44, no. 33 (2003): 6199–201. http://dx.doi.org/10.1016/s0040-4039(03)01553-3.

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47

McCarron, Pearse, Sabrina D. Giddings, Kelley L. Reeves, Philipp Hess, and Michael A. Quilliam. "A mussel (Mytilus edulis) tissue certified reference material for the marine biotoxins azaspiracids." Analytical and Bioanalytical Chemistry 407, no. 11 (2014): 2985–96. http://dx.doi.org/10.1007/s00216-014-8250-5.

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48

Ofuji, Katsuya, Masayuki Satake, Yasukatsu Oshima, Terry McMahon, Kevin J. James, and Takeshi Yasumoto. "A sensitive and specific determination method for azaspiracids by liquid chromatography mass spectrometry." Natural Toxins 7, no. 6 (1999): 247–50. http://dx.doi.org/10.1002/1522-7189(199911/12)7:6<247::aid-nt68>3.0.co;2-t.

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49

Aiguade, Josep, Junliang Hao, and Craig J. Forsyth. "ChemInform Abstract: Biomimetic Studies Towards the C28-C40 Polycyclic Domain of the Azaspiracids." ChemInform 32, no. 19 (2001): no. http://dx.doi.org/10.1002/chin.200119200.

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50

Murphy, Elliot, Rafael Salas, Urban Tillmann, Jane Kilcoyne, Bernd Krock, and Olivier P. Thomas. "Bioaccumulations and biotransformations of azaspiracids from Amphidoma languida in the mussel Mytilus edulis." Chemosphere 384 (September 2025): 144502. https://doi.org/10.1016/j.chemosphere.2025.144502.

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