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class="vector-toc-numb">3.2.3</span> <span>Chromatographic methods</span> </div> </a> <ul id="toc-Chromatographic_methods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Capillary_electrophoresis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Capillary_electrophoresis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2.4</span> <span>Capillary electrophoresis</span> </div> </a> <ul id="toc-Capillary_electrophoresis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" 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mw-list-item"><a href="https://de.wikipedia.org/wiki/Yessotoxin" title="Yessotoxin – German" lang="de" hreflang="de" data-title="Yessotoxin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DB%8C%D8%B3%D9%88%D8%AA%D9%88%DA%A9%D8%B3%DB%8C%D9%86" title="یسوتوکسین – Persian" lang="fa" hreflang="fa" data-title="یسوتوکسین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Yessotoxine" title="Yessotoxine – French" lang="fr" hreflang="fr" data-title="Yessotoxine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Jesotoksin" title="Jesotoksin – Serbian" lang="sr" hreflang="sr" data-title="Jesotoksin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Jesotoksin" title="Jesotoksin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Jesotoksin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%99%BE%E5%A4%B7%E6%89%87%E8%B4%9D%E6%AF%92%E7%B4%A0" title="虾夷扇贝毒素 – Chinese" lang="zh" hreflang="zh" data-title="虾夷扇贝毒素" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div 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For the defunct airport in British Columbia, see <a href="/wiki/Telegraph_Creek_Airport" title="Telegraph Creek Airport">Telegraph Creek Airport</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Yessotoxin </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Yessotoxin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Yessotoxin.svg/300px-Yessotoxin.svg.png" decoding="async" width="300" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Yessotoxin.svg/450px-Yessotoxin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Yessotoxin.svg/600px-Yessotoxin.svg.png 2x" data-file-width="663" data-file-height="297" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(2<i>S</i>,4a<i>S</i>,5a<i>R</i>,6<i>R</i>,6a<i>S</i>,7a<i>R</i>,8<i>S</i>,10a<i>S</i>,11a<i>R</i>,13a<i>S</i>,14a<i>R</i>,15a<i>S</i>,16a<i>R</i>,18<i>S</i>,19<i>R</i>,20a<i>S</i>,21a<i>R</i>,22a<i>S</i>,23a<i>R</i>,24a<i>S</i>,25a<i>R</i>,26a<i>S</i>,27a<i>R</i>,28a<i>S</i>,29a<i>R</i>)-6-Hydroxy-2-[(2<i>R</i>,3<i>E</i>)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-5a,8,10a,11a,19-pentamethyl-3-methylidene-19-[2-(sulfooxy)ethyl]octatriacontahydropyrano[2<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>,3<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>:5<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>,6<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>]pyrano[2<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>,3<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>:5<span class="nowrap" style="padding-left:0.15em;">′</span>,6<span class="nowrap" style="padding-left:0.15em;">′</span>]pyrano[2<span class="nowrap" style="padding-left:0.15em;">′</span>,3<span class="nowrap" style="padding-left:0.15em;">′</span>:5,6]pyrano[3,2-<i>b</i>]pyrano[2<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>,3<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>:5<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>,6<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>]pyrano[2<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>,3<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>:5<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>,6<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>]pyrano[2<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>,3<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>:5<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>,6<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>]pyrano[2<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>,3<span class="nowrap" style="padding-left:0.15em;">′</span><span class="nowrap" style="padding-left:0.15em;">′</span>:6<span class="nowrap" style="padding-left:0.15em;">′</span>,7<span class="nowrap" style="padding-left:0.15em;">′</span>]oxepino[2<span class="nowrap" style="padding-left:0.15em;">′</span>,3<span class="nowrap" style="padding-left:0.15em;">′</span>:5,6]pyrano[2,3-<i>g</i>]oxocin-18-yl hydrogen sulfate</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=112514-54-2">112514-54-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DS%28%3DO%29%28O%29O%5BC%40H%5D4C%5BC%40H%5D5O%5BC%40H%5D6C%5BC%40H%5D7O%5BC%40H%5D8CC%5BC%40%5D9%28O%5BC%40%40%5D%2510%28C%29CC%5BC%40H%5D%28C%29%5BC%40H%5D%2511O%5BC%40%40H%5D1%5BC%40H%5D%28O%5BC%40H%5D2C%5BC%40H%5D3O%5BC%40%40H%5D%28C%28%3DC%29%5CC%5BC%40%40H%5D3O%5BC%40%5D2%28C%29%5BC%40%40H%5D1O%29%5BC%40%5D%28O%29%28%5CC%3DC%5CC%28%3DC%29C%5CC%3DC%29C%29C%5BC%40%40H%5D%2511O%5BC%40%40H%5D%2510C%5BC%40%40H%5D9O%5BC%40%40H%5D8C%5BC%40%40H%5D7O%5BC%40%40H%5D6C%5BC%40%40H%5D5O%5BC%40%5D4%28C%29CCOS%28%3DO%29%28%3DO%29O%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1269577">ChEMBL1269577</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4945067.html">4945067</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6440821">6440821</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/P6M9FM2L2G">P6M9FM2L2G</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID20880023">DTXSID20880023</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q8052934#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C55H82O21S2/c1-10-11-28(2)12-15-51(5,57)50-30(4)20-39-38(71-50)26-46-55(9,74-39)49(56)48-42(70-46)24-41-47(72-48)29(3)13-16-53(7)44(69-41)27-43-54(8,76-53)17-14-31-32(68-43)21-34-33(65-31)22-35-36(66-34)23-40-37(67-35)25-45(75-78(61,62)63)52(6,73-40)18-19-64-77(58,59)60/h10,12,15,29,31-50,56-57H,1-2,4,11,13-14,16-27H2,3,5-9H3,(H,58,59,60)(H,61,62,63)/b15-12+/t29-,31-,32+,33+,34-,35-,36+,37+,38+,39-,40-,41-,42+,43-,44+,45-,46-,47+,48+,49+,50-,51+,52+,53-,54+,55-/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: HCYDZFJGUKMTQB-AVHIVUAZSA-N</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C55H82O21S2/c1-10-11-28(2)12-15-51(5,57)50-30(4)20-39-38(71-50)26-46-55(9,74-39)49(56)48-42(70-46)24-41-47(72-48)29(3)13-16-53(7)44(69-41)27-43-54(8,76-53)17-14-31-32(68-43)21-34-33(65-31)22-35-36(66-34)23-40-37(67-35)25-45(75-78(61,62)63)52(6,73-40)18-19-64-77(58,59)60/h10,12,15,29,31-50,56-57H,1-2,4,11,13-14,16-27H2,3,5-9H3,(H,58,59,60)(H,61,62,63)/b15-12+/t29-,31-,32+,33+,34-,35-,36+,37+,38+,39-,40-,41-,42+,43-,44+,45-,46-,47+,48+,49+,50-,51+,52+,53-,54+,55-/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: HCYDZFJGUKMTQB-AVHIVUAZBJ</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=S(=O)(O)O[C@H]4C[C@H]5O[C@H]6C[C@H]7O[C@H]8CC[C@]9(O[C@@]%10(C)CC[C@H](C)[C@H]%11O[C@@H]1[C@H](O[C@H]2C[C@H]3O[C@@H](C(=C)\C[C@@H]3O[C@]2(C)[C@@H]1O)[C@](O)(\C=C\C(=C)C\C=C)C)C[C@@H]%11O[C@@H]%10C[C@@H]9O[C@@H]8C[C@@H]7O[C@@H]6C[C@@H]5O[C@]4(C)CCOS(=O)(=O)O)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>55</sub><span title="Hydrogen">H</span><sub>82</sub><span title="Oxygen">O</span><sub>21</sub><span title="Sulfur">S</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7003114335999999999♠"></span>1<span style="margin-left:.25em;">143</span>.36</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Yessotoxins</b> are a group of <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a>, <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> bearing <a href="/wiki/Polyether" class="mw-redirect" title="Polyether">polyether</a> <a href="/wiki/Toxin" title="Toxin">toxins</a> that are related to <a href="/wiki/Ciguatoxins" class="mw-redirect" title="Ciguatoxins">ciguatoxins</a>.<sup id="cite_ref-tubaro_1-0" class="reference"><a href="#cite_note-tubaro-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They are produced by a variety of <a href="/wiki/Dinoflagellates" class="mw-redirect" title="Dinoflagellates">dinoflagellates</a>, most notably <i><a href="/wiki/Lingulodinium_polyedrum" class="mw-redirect" title="Lingulodinium polyedrum">Lingulodinium polyedrum</a></i> and <i><a href="/w/index.php?title=Gonyaulax_spinifera&action=edit&redlink=1" class="new" title="Gonyaulax spinifera (page does not exist)">Gonyaulax spinifera</a></i>.<sup id="cite_ref-howard_2-0" class="reference"><a href="#cite_note-howard-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>When the environmental conditions encourage the growth of YTX producing <a href="/wiki/Dinoflagellates" class="mw-redirect" title="Dinoflagellates">dinoflagellates</a>, the toxin(s) <a href="/wiki/Bioaccumulate" class="mw-redirect" title="Bioaccumulate">bioaccumulate</a> in edible tissues of <a href="/wiki/Bivalve_molluscs" class="mw-redirect" title="Bivalve molluscs">bivalve molluscs</a>, including <a href="/wiki/Mussels" class="mw-redirect" title="Mussels">mussels</a>, <a href="/wiki/Scallops" class="mw-redirect" title="Scallops">scallops</a>, and <a href="/wiki/Clams" class="mw-redirect" title="Clams">clams</a>, thus allowing entry of YTX into the <a href="/wiki/Food_chain" title="Food chain">food chain</a>.<sup id="cite_ref-efsa_3-0" class="reference"><a href="#cite_note-efsa-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first YTX analog discovered, yessotoxin, was initially found in the <a href="/wiki/Scallop" title="Scallop">scallop</a> species <i><a href="/wiki/Patinopecten_yessoensis" class="mw-redirect" title="Patinopecten yessoensis">Patinopecten yessoensis</a></i> in the 1960s.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Since then, numerous yessotoxin analogs have been isolated from <a href="/wiki/Shellfish" title="Shellfish">shellfish</a> and marine algae (including 45-hydroxyyessotoxin and carboxyyessotoxin).<sup id="cite_ref-tubaro_1-1" class="reference"><a href="#cite_note-tubaro-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Initially, scientists wrongly classified YTXs in the group of diarrhetic shellfish poisoning (DSP) toxins along the lines of <a href="/wiki/Okadaic_acid" title="Okadaic acid">okadaic acid</a> and <a href="/wiki/Azaspiracid" title="Azaspiracid">azaspiracids</a>. These type of toxins can cause extreme gastrointestinal upset and accelerate cancer growth. Once scientists realized YTXs did not have the same toxicological mechanism of action as the other toxins (<a href="/wiki/Protein_phosphatase" title="Protein phosphatase">protein phosphatase</a> inhibitors), they were given their own classification.<sup id="cite_ref-iglesia_5-0" class="reference"><a href="#cite_note-iglesia-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=2" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A large number of studies have been conducted to assess the potential toxicity of YTXs. To date none of these studies has highlighted any toxic effects of YTXs when they are present in humans. They have, however, found YTXs to have toxic effects in mice when the YTX had been administered by an <a href="/wiki/Intraperitoneal" class="mw-redirect" title="Intraperitoneal">intraperitoneal</a> injection into the animal. The toxicological effects encountered are similar to those seen for paralytic shellfish toxins, and include <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>, <a href="/wiki/Cardiotoxicity" title="Cardiotoxicity">cardiotoxicity</a>, and <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxicity</a>, with a YTX level of 100 μg/kg causing toxic effects. Limited toxic effects have been seen after oral administration of the toxin to animals. The mechanism by which YTX exerts a toxic effect is unknown and is currently being studied by a number of research groups. However, some recent studies suggest the mode of action may have something to do with altering <a href="/wiki/Calcium" title="Calcium">calcium</a> <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a>.<sup id="cite_ref-paz_6-0" class="reference"><a href="#cite_note-paz-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Genotoxicity has been newly reported and confirmed. <sup id="cite_ref-Korsnes_and_Korsnes,_2017_7-0" class="reference"><a href="#cite_note-Korsnes_and_Korsnes,_2017-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> <sup id="cite_ref-Korsnes_and_Korsnes,_2018_8-0" class="reference"><a href="#cite_note-Korsnes_and_Korsnes,_2018-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Although no data illustrate the direct association of YTXs and toxicity in humans, issues with regards to the potential health risks of YTXs still stand due to the significant animal toxicity observed, and like other algal <a href="/wiki/Toxins" class="mw-redirect" title="Toxins">toxins</a> present within <a href="/wiki/Shellfish" title="Shellfish">shellfish</a>, YTKs are not destroyed by heating or freezing.<sup id="cite_ref-efsa_3-1" class="reference"><a href="#cite_note-efsa-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> As a result, several countries, including New Zealand, Japan, and those in Europe, regulate the levels of YTXs in shellfish. In 2002, the <a href="/wiki/European_Commission" title="European Commission">European Commission</a> placed the regulatory level at 1 μg of YTXs per g (1 mg/kg) of <a href="/wiki/Shellfish" title="Shellfish">shellfish</a> meat intended for human consumption (Directive 20012/225/EC).<sup id="cite_ref-howard_2-1" class="reference"><a href="#cite_note-howard-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Recently, it was shown that yessotoxins can trigger ribotoxic stress.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Analysis">Analysis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=3" title="Edit section: Analysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The analysis of YTXs is necessary because of the possible health risks and the limits put in place by the European Commission directive. It is complex due to the large number of YTX analogues that can be present in the sample. Analysis is also problematic because YTXs have similar properties to other <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> <a href="/wiki/Toxins" class="mw-redirect" title="Toxins">toxins</a> present in the samples, so methods can be subject to false negative or false positive results due to sample interferences. </p><p>Several experimental techniques have been developed to detect YTXs, each offering varying levels of <a href="/wiki/Functional_selectivity" title="Functional selectivity">selectivity</a> and <a href="/wiki/Sensitivity_and_specificity" title="Sensitivity and specificity">sensitivity</a>, whilst having numerous advantages and disadvantages. </p> <div class="mw-heading mw-heading3"><h3 id="Extraction_methods">Extraction methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=4" title="Edit section: Extraction methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Prior to analysis, YTXs must be isolated from the sample medium whether this is the digestive gland of a <a href="/wiki/Shellfish" title="Shellfish">shellfish</a>, a water sample, or a growth-culture medium. This can be achieved by several methods: </p> <div class="mw-heading mw-heading4"><h4 id="Liquid–liquid_or_solvent_extraction"><span id="Liquid.E2.80.93liquid_or_solvent_extraction"></span>Liquid–liquid or solvent extraction</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=5" title="Edit section: Liquid–liquid or solvent extraction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Liquid%E2%80%93liquid_extraction" title="Liquid–liquid extraction">Liquid–liquid extraction</a> or <a href="/wiki/Solvent_extraction" class="mw-redirect" title="Solvent extraction">solvent extraction</a> can be used to isolate YTXs from the sample medium. <a href="/wiki/Methanol" title="Methanol">Methanol</a> is normally the solvent of choice, but other solvents can also be used including <a href="/wiki/Acetone" title="Acetone">acetone</a> and <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>. The drawback of using the <a href="/wiki/Solvent_extraction" class="mw-redirect" title="Solvent extraction">solvent extraction</a> method is the levels of analyte recovery can be poor, so any results obtained from the <a href="/wiki/Quantitative_data" class="mw-redirect" title="Quantitative data">quantification</a> processes may not be representative of the sample.<sup id="cite_ref-paz_6-1" class="reference"><a href="#cite_note-paz-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-these_10-0" class="reference"><a href="#cite_note-these-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Solid_phase_extraction">Solid phase extraction</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=6" title="Edit section: Solid phase extraction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Solid_phase_extraction" class="mw-redirect" title="Solid phase extraction">Solid phase extraction</a> also can be used to isolate YTXs from the sample medium. This technique separates the components of a mixture by using their different chemical and physical properties. This method is robust and extremely useful when small sample volumes are being analysed. It is advantageous over <a href="/wiki/Solvent" title="Solvent">solvent</a> extraction, as it concentrates (can give sample enrichment up to the power of 10) and can purify the sample by the removal of <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> and <a href="/wiki/Non-polar" class="mw-redirect" title="Non-polar">nonpolar</a> substances which can interfere with the final analysis. This technique is also beneficial because it gives good levels of YTX recovery — ranging from 40 to 50%.<sup id="cite_ref-paz_6-2" class="reference"><a href="#cite_note-paz-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-these_10-1" class="reference"><a href="#cite_note-these-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Analytical_techniques">Analytical techniques</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=7" title="Edit section: Analytical techniques"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A range of analytical methods can be used to identify and quantify YTXs. </p> <div class="mw-heading mw-heading4"><h4 id="Mouse_bioassay">Mouse bioassay</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=8" title="Edit section: Mouse bioassay"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The mouse bioassay (MBA) procedure developed by Yasumoto <i>et al.</i> is the official reference method used to analyse for YTX and <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> toxins including okadaic acid, <a href="/w/index.php?title=Dinophysistoxin&action=edit&redlink=1" class="new" title="Dinophysistoxin (page does not exist)">dinophysistoxins</a> (DSPs), azaspiracids, and pectenotoxins. </p><p>The MBA involves injecting the extracted toxin into a mouse and monitoring the mouse survival rate; the toxicity of the sample can be subsequently deduced and the analyte concentration determined. This calculation is made on the basis that one <a href="/wiki/Mouse_unit" title="Mouse unit">mouse unit</a> (MU) is the minimum quantity of toxin needed to kill a mouse in 24hours. The MU is set by regulating bodies at 0.05 MU/g of animal. </p><p>The original Yasumoto MBA is subject to interferences from paralytic shellfish toxins and free <a href="/wiki/Fatty_acids" class="mw-redirect" title="Fatty acids">fatty acids</a> in solution, which cause false positive results. Several modifications to the MBA can be made to allow the test to be performed without these errors. </p><p>The MBA, however, still has many drawbacks; </p> <ul><li>The method is a nonspecific <a href="/wiki/Assay" title="Assay">assay</a>- it is unable to differentiate between YTX and other sample components, including DSP toxins</li> <li>The method has economic and social issues with regards to testing on animals.</li> <li>The results produced are not very reproducible.</li> <li>The method has insufficient detection capabilities.</li></ul> <p>The method, though, is quick and inexpensive. Due to these factors, the other, more recently developed, techniques are being preferred for analysis of YTX.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (May 2013)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="Enzyme-linked_immunosorbent_assay">Enzyme-linked immunosorbent assay</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=9" title="Edit section: Enzyme-linked immunosorbent assay"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Enzyme-linked_immunosorbent_assay" class="mw-redirect" title="Enzyme-linked immunosorbent assay">enzyme-linked immunosorbent assay</a> (ELISA) technique used for the analysis of YTXs is a recently developed method by Briggs <i>et al.</i><sup id="cite_ref-paz_6-3" class="reference"><a href="#cite_note-paz-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> This competitive, indirect <a href="/wiki/Immunoassay" title="Immunoassay">immunoassay</a> uses <a href="/wiki/Polyclonal_antibodies" title="Polyclonal antibodies">polyclonal antibodies</a> against YTX to determine its concentration in the sample. The assay is commercially available, and is a rapid technique for the analysis of YTXs in <a href="/wiki/Shellfish" title="Shellfish">shellfish</a>, algal cells, and culture samples. </p><p>ELISA has several advantages: it is very sensitive, has a <a href="/wiki/Limit_of_quantification" class="mw-redirect" title="Limit of quantification">limit of quantification</a> of 75 μg/kg,<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> is relatively cheap, and is easy to carry out. The major disadvantage to this method is it cannot differentiate between the different YTX analogues and takes a long time to generate results.<sup id="cite_ref-paz_6-4" class="reference"><a href="#cite_note-paz-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Chromatographic_methods">Chromatographic methods</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=10" title="Edit section: Chromatographic methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A variety of chromatographic methods can be used to analyse YTXs. This includes chromatographic techniques coupled to <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> and <a href="/wiki/Fluorescence" title="Fluorescence">fluorescence</a> detectors. All of the chromatographic techniques require a <a href="/wiki/Calibration" title="Calibration">calibration</a> step prior to sample analysis. </p> <dl><dt>Chromatographic methods with <a href="/wiki/Fluorescence" title="Fluorescence">fluorescence</a> detection</dt></dl> <p><a href="/wiki/Liquid_chromatography" class="mw-redirect" title="Liquid chromatography">Liquid chromatography</a> with fluorescence detection (LC-FLD) provides a selective, relatively cheap, reproducible method for the <a href="/wiki/Qualitative_research" title="Qualitative research">qualitative</a> and <a href="/wiki/Quantitative_data" class="mw-redirect" title="Quantitative data">quantitative</a> analysis of YTX for shellfish and algae samples.<sup id="cite_ref-paz_6-5" class="reference"><a href="#cite_note-paz-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> This method requires an additional sample preparation step after the analyte extraction procedure has been completed (in this case SPE is preferentially used so common interferences can be removed from the sample). This additional step involves the <a href="/wiki/Derivatization" title="Derivatization">derivatization</a> of the YTXs with a <a href="/wiki/Fluorescent" class="mw-redirect" title="Fluorescent">fluorescent</a> dienophile <a href="/wiki/Reagent" title="Reagent">reagent</a> — dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalinyl)ethyl]-1,2,4-triazoline-3,5-dione, which facilitates analyte detection. This additional sample preparation step can make LC-FLD analysis extremely time-consuming and is a major disadvantage of the technique.<sup id="cite_ref-iglesia_5-1" class="reference"><a href="#cite_note-iglesia-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <dl><dt>Chromatographic methods coupled to mass spectrometry</dt></dl> <p>This technique is extremely useful for the analysis of multiple toxins. It has numerous advantages over the other techniques used. It is a sensitive and selective analytical method, making it ideal for the analysis of complex samples and those with low analyte concentrations. The method is also beneficial in that it provides important structural information on the analyte which is helpful for aiding analyte identification and when unknown analytes are present in the sample. The technique has benefits over LC-FLD as the derivatisation and purification extraction steps are not necessary. YTX analysis limits of detection of 30 mg/g of shellfish tissue for chromatographic methods coupled to mass spectrometry have been recorded.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>The major drawback to LC-MS is that the equipment is very expensive.<sup id="cite_ref-paz_6-6" class="reference"><a href="#cite_note-paz-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Capillary_electrophoresis">Capillary electrophoresis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=11" title="Edit section: Capillary electrophoresis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Capillary_electrophoresis" title="Capillary electrophoresis">Capillary electrophoresis</a> (CE)is emerging as the preferred analytical method for YTX analysis, as it has significant advantages over the other analytical techniques used, including high efficiency, a fast and simple separation procedure, a small sample volume required, and minimal reagent is required. </p><p>The techniques used for YTX analysis include: CE with <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> (UV) detection and CE coupled to <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> (MS). CEUV is a good method for YTX analysis, as its selectivity can easily differentiate between YTXs and DSP toxins. The <a href="/wiki/Sensitivity_and_specificity" title="Sensitivity and specificity">sensitivity</a> of these techniques can, however, be poor due to the low <a href="/wiki/Molar_absorptivity" class="mw-redirect" title="Molar absorptivity">molar absorptivity</a> of the analytes. The technique gives a limit of detection (LOD) of 0.3 μg/ml and a limit of quantification (LOQ)of 0.9 μg/ml. The sensitivity of conventional CEUV can be improved by using micellar electrokinetic chromatography (MEKC). </p><p>CEMS has the added advantage over CEUV of being able to give molecular weight and/or structural information about the analyte. This enables the user to carry out unequivocal confirmations of the analytes present in the sample. The LOD and the LOQ have been calculated as 0.02 μg/ml and 0.08 μg/ml, respectively, again meeting the <a href="/wiki/European_Commission" title="European Commission">European Commission</a> directive.<sup id="cite_ref-iglesia_5-2" class="reference"><a href="#cite_note-iglesia-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Canadian_Reference_Materials" title="Canadian Reference Materials">Canadian Reference Materials</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-tubaro-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-tubaro_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-tubaro_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFA._TubaroV._Dell'OvoS._SosaC._Florio2010" class="citation journal cs1">A. 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"Liquid chromatography with electrospray ion-trap mass spectrometry for the determination of yessotoxins in shellfish". <i>Journal of Chromatography A</i>. <b>976</b> (<span class="nowrap">1–</span>2): <span class="nowrap">329–</span>334. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9673%2802%2900946-9">10.1016/S0021-9673(02)00946-9</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12462625">12462625</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chromatography+A&rft.atitle=Liquid+chromatography+with+electrospray+ion-trap+mass+spectrometry+for+the+determination+of+yessotoxins+in+shellfish&rft.volume=976&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E329-%3C%2Fspan%3E334&rft.date=2002&rft_id=info%3Adoi%2F10.1016%2FS0021-9673%2802%2900946-9&rft_id=info%3Apmid%2F12462625&rft.au=M.+Fern%C3%A1ndez+Amandi&rft.au=A.+Furey&rft.au=M.+Lehane&rft.au=H.+Ramstad&rft.au=K.+J.+James&rfr_id=info%3Asid%2Fen.wikipedia.org%3AYessotoxin" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Yessotoxin&action=edit&section=14" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJ._AasenI._A._SamdalC._O._MilesE._Dahl2005" class="citation journal cs1">J. Aasen; I. A. Samdal; C. O. Miles; E. Dahl; L. R. Briggs; T. Aune (2005). "Yessotoxins in Norwegian blue mussels (<i>Mytilus edulis</i>): Uptake from <i>Protoceratium reticulatum</i>, metabolism and depuration". <i>Toxicon</i>. <b>45</b> (3): <span class="nowrap">265–</span>272. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.toxicon.2004.10.012">10.1016/j.toxicon.2004.10.012</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15683864">15683864</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicon&rft.atitle=Yessotoxins+in+Norwegian+blue+mussels+%28Mytilus+edulis%29%3A+Uptake+from+Protoceratium+reticulatum%2C+metabolism+and+depuration&rft.volume=45&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E265-%3C%2Fspan%3E272&rft.date=2005&rft_id=info%3Adoi%2F10.1016%2Fj.toxicon.2004.10.012&rft_id=info%3Apmid%2F15683864&rft.au=J.+Aasen&rft.au=I.+A.+Samdal&rft.au=C.+O.+Miles&rft.au=E.+Dahl&rft.au=L.+R.+Briggs&rft.au=T.+Aune&rfr_id=info%3Asid%2Fen.wikipedia.org%3AYessotoxin" class="Z3988"></span></li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Yessotoxin&oldid=1276048270">https://en.wikipedia.org/w/index.php?title=Yessotoxin&oldid=1276048270</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Phycotoxins" title="Category:Phycotoxins">Phycotoxins</a></li><li><a href="/wiki/Category:Polyether_toxins" title="Category:Polyether toxins">Polyether toxins</a></li><li><a href="/wiki/Category:Alkene_derivatives" title="Category:Alkene derivatives">Alkene derivatives</a></li><li><a href="/wiki/Category:Organic_sodium_salts" title="Category:Organic sodium salts">Organic sodium salts</a></li><li><a href="/wiki/Category:Marine_neurotoxins" title="Category:Marine neurotoxins">Marine neurotoxins</a></li><li><a href="/wiki/Category:Sulfate_esters" title="Category:Sulfate esters">Sulfate esters</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_without_KEGG_source" title="Category:Articles without KEGG source">Articles without KEGG source</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li><li><a href="/wiki/Category:Chembox_image_size_set" title="Category:Chembox image size set">Chembox image size set</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_May_2013" title="Category:Articles with unsourced statements from May 2013">Articles with unsourced statements from May 2013</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 16 February 2025, at 16:03<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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