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Journal articles on the topic 'Azaspiracidi'

Author: Grafiati

Published: 1 April 2023

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

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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4

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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5

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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6

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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7

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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8

OFUJI, Katsuya, Masayuki SATAKE, Terry MCMAHON, et al. "Structures of Azaspiracid Analogs, Azaspiracid-4 and Azaspiracid-5, Causative Toxins of Azaspiracid Poisoning in Europe." Bioscience, Biotechnology, and Biochemistry 65, no. 3 (2001): 740–42. http://dx.doi.org/10.1271/bbb.65.740.

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9

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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10

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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11

Nguyen Tuan, Anh, Trac Nguyen Duc Anh, Thien Nguyen Quang, and Nhan Le Cong. "Determination of lipophilic marine biotoxins in aquatic products by liquid chromatography coupled with triple quadrupole mass spectrometry." Heavy metals and arsenic concentrations in water, agricultural soil, and rice in Ngan Son district, Bac Kan province, Vietnam 6, no. 2 (2023): 42–57. http://dx.doi.org/10.47866/2615-9252/vjfc.4073.

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Lipophilic marine biotoxins include Azaspiracid-1 (AZA-1), Azaspiracid-2 (AZA-2), Azaspiracid-3 (AZA-3), Pectenotoxin-2 (PTX 2), Okadaic acid (OA), Dinophysistoxin-2 (DTX-2), Dinophysistoxin-1 (DTX-1), Yessotoxin (YTX), and 1-Homoyessotoxin (Homo-YTX) were extracted with methanol, followed by cleaning up with solid phase extraction technique (SPE). Lipophilic toxins were confirmed and quantified by liquid chromatography coupled with triple quadrupole mass spectrometry (LC/MS/MS) using calibration curves on the solvent. The quantification limits of this method satisfied the requirements of the

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12

Li, Jialiang, Xiaohua Li, and David R. Mootoo. "Synthetic and Computational Studies on the ABC Trioxadispiroketal Subunit of the Marine Biotoxin Azaspiracid-1." Natural Product Communications 3, no. 11 (2008): 1934578X0800301. http://dx.doi.org/10.1177/1934578x0800301106.

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The trioxadispiroketal residue in the marine biotoxin azaspiracid-1, which exists in a configuration capable of exhibiting a double anomeric effect, is believed to be the thermodynamically most stable bis-spiroketal diastereomer. In order to get insight into how structural factors affect this equilibrium, a simplified ABC trioxadispiroketal analog of azaspiracid-1 was synthesized and subjected to equilbration and computational studies. Compound 7, which represents a double anomeric effect was obtained as the major isomer, together with diastereomers 14 and 15, in a respective ratio of 62:22:16

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13

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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14

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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15

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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16

Nicolaou, K. C., Michael O. Frederick, Goran Petrovic, Kevin P. Cole, and Eriketi Z. Loizidou. "Total Synthesis and Confirmation of the Revised Structures of Azaspiracid-2 and Azaspiracid-3." Angewandte Chemie 118, no. 16 (2006): 2671–77. http://dx.doi.org/10.1002/ange.200600295.

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17

Brombacher, Stephan, Suzanne Edmonds, and Dietrich A. Volmer. "Studies on azaspiracid biotoxins. II. Mass spectral behavior and structural elucidation of azaspiracid analogs." Rapid Communications in Mass Spectrometry 16, no. 24 (2002): 2306–16. http://dx.doi.org/10.1002/rcm.863.

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18

Nicolaou, K. C., Michael O. Frederick, Goran Petrovic, Kevin P. Cole, and Eriketi Z. Loizidou. "Total Synthesis and Confirmation of the Revised Structures of Azaspiracid-2 and Azaspiracid-3." Angewandte Chemie International Edition 45, no. 16 (2006): 2609–15. http://dx.doi.org/10.1002/anie.200600295.

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19

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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20

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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21

Nicolaou, K. C., and Jason S. Chen. "Total synthesis of complex heterocyclic natural products." Pure and Applied Chemistry 80, no. 4 (2008): 727–42. http://dx.doi.org/10.1351/pac200880040727.

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Total synthesis campaigns toward complex heterocyclic natural products are a prime source of inspiration for the design and execution of complex cascade sequences, powerful reactions, and efficient synthetic strategies. We highlight selected examples of such innovations in the course of our total syntheses of diazonamide A, azaspiracid-1, thiostrepton, 2,2'-epi-cytoskyrin A and rugulosin, abyssomycin C, platensimycin, and uncialamycin.

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22

Geisler, Lisa K., Son Nguyen, and Craig J. Forsyth. "Synthesis of the Azaspiracid-1 Trioxadispiroketal." Organic Letters 6, no. 23 (2004): 4159–62. http://dx.doi.org/10.1021/ol048581a.

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23

Frederick, Michael O., Sandra De Lamo Marin, Kim D. Janda, K. C. Nicolaou, and Tobin J. Dickerson. "Monoclonal Antibodies with Orthogonal Azaspiracid Epitopes." ChemBioChem 10, no. 10 (2009): 1625–29. http://dx.doi.org/10.1002/cbic.200900201.

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24

Tillmann, Urban, C. Marcela Borel, Facundo Barrera, et al. "Azadinium poporum from the Argentine Continental Shelf, Southwestern Atlantic, produces azaspiracid-2 and azaspiracid-2 phosphate." Harmful Algae 51 (January 2016): 40–55. http://dx.doi.org/10.1016/j.hal.2015.11.001.

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25

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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26

Oikawa, Masato, and Makoto Sasaki. "Synthetic Studies on Shellfish Toxin Azaspiracid-1." Journal of Synthetic Organic Chemistry, Japan 66, no. 9 (2008): 836–45. http://dx.doi.org/10.5059/yukigoseikyokaishi.66.836.

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27

Nguyen, Son, Jianyan Xu, and Craig J. Forsyth. "Facile biomimetic syntheses of the azaspiracid spiroaminal." Tetrahedron 62, no. 22 (2006): 5338–46. http://dx.doi.org/10.1016/j.tet.2006.01.112.

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28

Nicolaou, K., T. Koftis, S. Vyskocil, et al. "Synthesis and Structural Elucidation of Azaspiracid-1." Synfacts 2006, no. 8 (2006): 0748. http://dx.doi.org/10.1055/s-2006-941937.

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29

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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30

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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31

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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32

Klontz, Karl C. "Mussel-Associated Azaspiracid Intoxication in the United States." Annals of Internal Medicine 150, no. 5 (2009): 361. http://dx.doi.org/10.7326/0003-4819-150-5-200903030-00023.

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33

Flanagan, Andrew F., John Donlon, Roy Palmer, and Marian Kane. "Bioanalytical detection of azaspiracid, a newly discovered phycotoxin." Biochemical Society Transactions 28, no. 1 (2000): A46. http://dx.doi.org/10.1042/bst028a046a.

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34

Nzoughet, K. J., J. T. G. Hamilton, S. D. Floyd, et al. "Azaspiracid: First evidence of protein binding in shellfish." Toxicon 51, no. 7 (2008): 1255–63. http://dx.doi.org/10.1016/j.toxicon.2008.02.016.

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35

OZAWA, MAYU. "7. Study on azaspiracid shellfish poisoning in Japan." NIPPON SUISAN GAKKAISHI 88, no. 6 (2022): 541. http://dx.doi.org/10.2331/suisan.wa2980-7.

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36

Nicolaou, K. C., Petri M. Pihko, Nicole Diedrichs, Ning Zou, and Federico Bernal. "Synthesis of the FGHI Ring System of Azaspiracid." Angewandte Chemie 113, no. 7 (2001): 1302–5. http://dx.doi.org/10.1002/1521-3757(20010401)113:7<1302::aid-ange1302>3.0.co;2-s.

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37

Nicolaou, K. C., Petri M. Pihko, Nicole Diedrichs, Ning Zou, and Federico Bernal. "Synthesis of the FGHI Ring System of Azaspiracid." Angewandte Chemie 113, no. 9 (2001): 1621. http://dx.doi.org/10.1002/1521-3757(20010504)113:9<1621::aid-ange16213>3.0.co;2-k.

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38

Nicolaou, K. C., Wenyuan Qian, Federico Bernal, Noriaki Uesaka, Petri M. Pihko, and Jürgen Hinrichs. "Synthesis of the ABCD Ring System of Azaspiracid." Angewandte Chemie 113, no. 21 (2001): 4192–95. http://dx.doi.org/10.1002/1521-3757(20011105)113:21<4192::aid-ange4192>3.0.co;2-0.

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39

Nicolaou, K. C., Petri M. Pihko, Nicole Diedrichs, Ning Zou, and Federico Bernal. "Synthesis of the FGHI Ring System of Azaspiracid." Angewandte Chemie International Edition 40, no. 7 (2001): 1262–65. http://dx.doi.org/10.1002/1521-3773(20010401)40:7<1262::aid-anie1262>3.0.co;2-9.

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40

Nicolaou, K. C., Petri M. Pihko, Nicole Diedrichs, Ning Zou, and Federico Bernal. "Synthesis of the FGHI Ring System of Azaspiracid." Angewandte Chemie International Edition 40, no. 9 (2001): 1573. http://dx.doi.org/10.1002/1521-3773(20010504)40:9<1573::aid-anie15733>3.0.co;2-d.

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41

Tillmann, Urban, and Alfred Wegener. "Neu entdeckte Giftalge ist Ursache der Azaspiracid-Muschelvergiftung." Biologie in unserer Zeit 39, no. 3 (2009): 152–53. http://dx.doi.org/10.1002/biuz.200990040.

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42

Nicolaou, K. C., Theocharis V. Koftis, Stepan Vyskocil, et al. "Total Synthesis and Structural Elucidation of Azaspiracid-1. Final Assignment and Total Synthesis of the Correct Structure of Azaspiracid-1." Journal of the American Chemical Society 128, no. 9 (2006): 2859–72. http://dx.doi.org/10.1021/ja054750q.

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43

Vale, Carmen, Carolina Wandscheer, K. C. Nicolaou, et al. "Cytotoxic effect of azaspiracid-2 and azaspiracid-2-methyl ester in cultured neurons: Involvement of the c-Jun N-terminal kinase." Journal of Neuroscience Research 86, no. 13 (2008): 2952–62. http://dx.doi.org/10.1002/jnr.21731.

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44

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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45

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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46

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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47

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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48

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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49

Okumu, Antony A., and Craig J. Forsyth. "Synthesis of the C1–C19 Domain of Azaspiracid-34." Organic Letters 21, no. 2 (2019): 356–59. http://dx.doi.org/10.1021/acs.orglett.8b03451.

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50

Kellmann, Ralf, Carlos A. M. Schaffner, Toril A. Grønset, Masayuki Satake, Mathias Ziegler, and Kari E. Fladmark. "Proteomic response of human neuroblastoma cells to azaspiracid-1." Journal of Proteomics 72, no. 4 (2009): 695–707. http://dx.doi.org/10.1016/j.jprot.2009.02.008.

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