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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Histrionicotoxine</span></h1>
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<p>Die <b>Histrionicotoxine</b> sind eine Gruppe von <a href="Alkaloide" title="Alkaloide">Alkaloiden</a>, welche in der Haut von <a href="Baumsteigerfr%C3%B6sche" title="Baumsteigerfrösche">Baumsteigerfröschen</a> vorkommen. Es handelt sich um <a href="Spiroverbindung" title="Spiroverbindung">Spiroverbindungen</a> aus einem <a href="Cyclohexan" title="Cyclohexan">Cyclohexan</a>- und einem <a href="Piperidin" title="Piperidin">Piperidin</a>-Ring.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
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<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Die Histrionicotoxine wurden in dem <a href="Harlekin-Baumsteiger" title="Harlekin-Baumsteiger">Harlekin-Baumsteiger</a> (Dendrobates histrionicus), selten auch Gepunkteter Pfeilgiftfrosch genannt, gefunden.<sup id="cite_ref-Natur_2-0" class="reference"><a href="#cite_note-Natur-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
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<div class="mw-heading mw-heading2"><h2 id="Vertreter">Vertreter</h2></div>
<p>Zu den Hauptvertretern zählen u. a. <a href="Histrionicotoxin" class="mw-redirect" title="Histrionicotoxin">Histrionicotoxin</a> (283A), Allodihydro-Histrionicotoxin (285C) und Isodihydro-Histrionicotoxin (285A).<sup id="cite_ref-Römpp_3-0" class="reference"><a href="#cite_note-Römpp-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
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<div class="gallerytext">(–)-Histrionicotoxin (283A)</div>
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<li class="gallerybox" style="width: 285px">
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<div class="gallerytext">(–)-Histrionicotoxin (285C)</div>
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<div class="gallerytext">(–)-Histrionicotoxin (285A)</div>
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<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Histrionicotoxine sind potente Antagonisten des <a href="Nikotinischer_Acetylcholinrezeptor" title="Nikotinischer Acetylcholinrezeptor">nikotinischen Acetylcholinrezeptors</a>. Der Wirkmechanismus ist komplex und beinhaltet paradoxerweise eine positive <a href="Allosterischer_Modulator" title="Allosterischer Modulator">allosterische Modulation</a> der postsynaptischen Rezeptoren, wodurch die <a href="Motorische_Endplatte" title="Motorische Endplatte">motorischen Endplatten</a> anfälliger für einen Depolarisationsblock werden.<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><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
</p><p>Aus chemischer Sicht sind diese Substanzen durch die terminalen <a href="Alkine" title="Alkine">Alkingruppen</a> (C≡C-Dreifachbindung) interessant.
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<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a></span> <span class="reference-text">A. Sinclair, R. A. Stockman: <cite style="font-style:italic">Thirty-five years of synthetic studies directed towards the histrionicotoxin family of alkaloids</cite>. In: <cite style="font-style:italic"><a href="Natural_Product_Reports" title="Natural Product Reports">Natural Product Reports</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>24</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>2</span>, 2007, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>298–326</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1039/b604203c">10.1039/b604203c</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/17389999?dopt=Abstract">PMID 17389999</a>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Histrionicotoxine&rft.atitle=Thirty-five+years+of+synthetic+studies+directed+towards+the+histrionicotoxin+family+of+alkaloids&rft.au=A.+Sinclair%2C+R.+A.+Stockman&rft.date=2007&rft.doi=10.1039%2Fb604203c&rft.genre=journal&rft.issue=2&rft.jtitle=Natural+Product+Reports&rft.pages=298-326&rft.pmid=17389999&rft.volume=24" style="display:none"> </span></span>
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<li id="cite_note-Natur-2"><span class="mw-cite-backlink"><a href="#cite_ref-Natur_2-0">↑</a></span> <span class="reference-text">G. Habermehl, P. Hammann, H. Krebs: <cite style="font-style:italic">Naturstoffchemie</cite>. 3. Auflage. Springer-Verlag, Berlin Heidelberg 2008, ISBN 978-3-540-73732-2, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>157</span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:Histrionicotoxine&rft.au=G.+Habermehl%2C+P.+Hammann%2C+H.+Krebs&rft.btitle=Naturstoffchemie&rft.date=2008&rft.edition=3&rft.genre=book&rft.isbn=9783540737322&rft.pages=157&rft.place=Berlin+Heidelberg&rft.pub=Springer-Verlag" style="display:none"> </span></span>
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<li id="cite_note-Römpp-3"><span class="mw-cite-backlink"><a href="#cite_ref-Römpp_3-0">↑</a></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://roempp.thieme.de/lexicon/RD-08-01399"><i>Histrionicotoxine</i></a>. In: <i><a href="R%C3%B6mpp_Online" class="mw-redirect" title="Römpp Online">Römpp Online</a>.</i> Georg Thieme Verlag, abgerufen am 29. Mai 2020.<span class="editoronly" style="display:none;"></span></span>
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<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">W. Burgermeister, W. A. Catterall, B. Witkop: <i>Histrionicotoxin enhances agonist-induced desensitization of acetylcholine receptor.</i> In: <i><a href="Proceedings_of_the_National_Academy_of_Sciences" class="mw-redirect" title="Proceedings of the National Academy of Sciences">Proceedings of the National Academy of Sciences</a>.</i> Band 74, Nummer 12, Dezember 1977, S. 5754–5758, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/272000?dopt=Abstract">PMID 272000</a>, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC431872/">PMC 431872</a> (freier Volltext).</span>
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<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">Eva Bartels-Bernal, Edgar Diaz, Rosalina Cadena, Jorge Ramos, John W. Daly: <i>Effect of histrionicotoxin on ion channels in synaptic and conducting membranes of electroplax of Electrophorus electricus.</i> In: <i>Cellular and Molecular Neurobiology.</i> 3, 1983, S. 203, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1007/BF00710947">10.1007/BF00710947</a></span>.</span>
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