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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Senecionin</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
<tbody><tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
</th></tr>
<tr>
<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>Senecionin
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<p>(15<i>Z</i>)-12-Hydroxysenecionan-11,16-dion
</p>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>18</sub>H<sub>25</sub>NO<sub>5</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>farb- und geruchsloser Feststoff<sup id="cite_ref-SDS_1-0" class="reference"><a href="#cite_note-SDS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
</th></tr>
<tr>
<td colspan="2" style="padding:0;">
<table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);">
<tbody><tr>
<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=130-01-8">130-01-8 </a><span class="editoronly" style="display:none;"></span>
</td>
<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
<tr>
<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a> (<a href="EG-Nummer#Listennummern" title="EG-Nummer">Listennummer</a>)
</td>
<td colspan="2">603-379-6
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.125.118">100.125.118</a>
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5280906">5280906</a>
</td></tr>
<tr>
<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.10254883.html">10254883</a>
</td></tr>
<tr>
<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q2083871" class="extiw external" title="d:Q2083871">Q2083871</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>335,4 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>fest<sup id="cite_ref-SDS_1-1" class="reference"><a href="#cite_note-SDS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>235–240 °C<sup id="cite_ref-SDS_1-2" class="reference"><a href="#cite_note-SDS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
<tbody><tr>
<td colspan="2" style="text-align:center"><b><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-SDS_1-3" class="reference"><a href="#cite_note-SDS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><span typeof="mw:File"><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien#Übersicht:_EU-Gefahrensymbole,_UN/GHS-Gefahrenpiktogramme,_UN/ADR-Gefahrensymbole" title="06 – Giftig oder sehr giftig"></a></span>
</td></tr></tbody></table>
<p><b>Gefahr</b>
</p>
</td></tr>
<tr>
<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>
</td>
<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Giftig bei Verschlucken.">301</span></span></a>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Bei Gebrauch nicht essen, trinken oder rauchen.">270</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Bei Verschlucken: Sofort Giftinformationszentrum, Arzt oder … anrufen.">301+310</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Mund ausspülen.">330</span></span></a><sup id="cite_ref-SDS_1-4" class="reference"><a href="#cite_note-SDS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td></tr>
</tbody></table>
</td></tr>
<tr>
<td><a href="Toxizit%C3%A4t" title="Toxizität">Toxikologische Daten</a>
</td>
<td>
<p>85 mg·kg<sup>−1</sup> (<a href="Letale_Dosis" title="Letale Dosis">LD<sub>50</sub></a>, <a href="Ratten" title="Ratten">Ratte</a>, <a href="Peroral" title="Peroral">oral</a>)<sup id="cite_ref-SDS_1-5" class="reference"><a href="#cite_note-SDS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><span class="editoronly" style="display:none;"></span>
</p>
</td></tr>
<tr>
<td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Senecionin</b> ist ein giftiges, <a href="Hepatotoxizit%C3%A4t" title="Hepatotoxizität">hepatotoxisches</a> <a href="Pyrrolizidinalkaloide" title="Pyrrolizidinalkaloide">Pyrrolizidinalkaloid</a>, welches in verschiedenen Pflanzen vorkommt. Es ist nach der Gattung <i><a href="Greiskr%C3%A4uter" title="Greiskräuter">Senecio</a></i> benannt, deren
Vertreter es enthalten.
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Wie am Namen erkennbar kommt Senecionin hauptsächlich in Vertretern der Gattung <i>Senecio</i> vor, zum Beispiel in <i><a href="Senecio_vulgaris" class="mw-redirect" title="Senecio vulgaris">Senecio vulgaris</a></i>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Auch das bekannte <a href="Jakobskreuzkraut" class="mw-redirect" title="Jakobskreuzkraut">Jakobskreuzkraut</a> (<i>Jacobaea vulgaris</i>) enthält neben anderen Pyrrolizidinalkaloiden Senecionin.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Toxikologie">Toxikologie</h2></div>
<p>Senecionin wird nach der Aufnahme relativ schnell in der <a href="Leber" title="Leber">Leber</a> verstoffwechselt. <i>In vivo</i> konnte eine <a href="Zytotoxizit%C3%A4t" title="Zytotoxizität">Zytotoxizität</a> gegenüber <a href="Hepatozyt" title="Hepatozyt">Hepatozyten</a> gezeigt 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> In einer Studie an trächtigen Ratten wurde sowohl eine fruchtbarkeitshemmende, wie auch eine <a href="Teratogen" title="Teratogen">teratogene</a> Wirkung von Senecionin gezeigt.<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>
<div class="mw-heading mw-heading2"><h2 id="Biosynthese">Biosynthese</h2></div>
<p>In Pflanzen der Gattung <i>Senecio</i> beginnt die Biosynthese mit der Aminosäure <i>(S)</i>-<a href="Arginin" title="Arginin">Arginin</a>, manchmal auch mit <i>(S)</i>-<a href="Ornithin" title="Ornithin">Ornithin</a>. Daraus wird zuerst <a href="Putrescin" title="Putrescin">Putrescin</a> gebildet.
Dieses reagiert unter Katalyse des Enzyms Homospermidinsynthase (HSS) und <a href="NAD%2B" class="mw-redirect" title="NAD+">NAD<sup>+</sup></a> mit <a href="Spermidin" title="Spermidin">Spermidin</a> zu Homospermidin. Dieses reagiert
katalysiert durch das kupferhaltige Enzym Diaminoxidase zu 4,4'-Iminodibutanal. Danach findet eine <a href="Cyclisierung" title="Cyclisierung">Cyclisierung</a> zu Pyrrolizidin-1-carbaldehyd durch eine <a href="Mannich-Reaktion" title="Mannich-Reaktion">Mannich-Reaktion</a> statt.
Durch eine Reduktion zum Alkohol, vermutlich mit <a href="Alkoholdehydrogenase" title="Alkoholdehydrogenase">Alkoholdehydrogenase</a>, entsteht <a href="Trachelanthamidin" title="Trachelanthamidin">Trachelanthamidin</a>. Dieses spaltet an der C1/C2-Bindung Wasserstoff ab, anschließend wird es
an der C7-Bindung zu <a href="Retronecin" title="Retronecin">Retronecin</a> hydroxyliert. Dann wird das Retronecin mit Senecinsäure, welche aus zwei Äquivalenten <i>(S)</i>-<a href="Isoleucin" title="Isoleucin">Isoleucin</a> gebildet wurde, <a href="Acetylierung" title="Acetylierung">acetyliert</a>.
Zuletzt wird das entstandene Produkt Senecionin-<i>N</i>-oxid zum Endprodukt Senecionin reduziert.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-SDS-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-SDS_1-0">a</a></sup> <sup><a href="#cite_ref-SDS_1-1">b</a></sup> <sup><a href="#cite_ref-SDS_1-2">c</a></sup> <sup><a href="#cite_ref-SDS_1-3">d</a></sup> <sup><a href="#cite_ref-SDS_1-4">e</a></sup> <sup><a href="#cite_ref-SDS_1-5">f</a></sup></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.carlroth.com/downloads/sdb/de/2/SDB_2261_DE_DE.pdf">Senecionin</a></span> (PDF) bei <a href="Carl_Roth_(Unternehmen)" title="Carl Roth (Unternehmen)">Carl Roth</a>, abgerufen am 29. Juni 2022.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">L. A. C. Pieters, A. J. Vlietinck: <cite style="font-style:italic">Quantitative analysis of pyrrolizidine alkaloid mixtures from Senecio vulgaris by carbon-13 nuclear magnetic resonance spectroscopy</cite>. In: <cite style="font-style:italic">Magnetic Resonance in Chemistry</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>25</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, Januar 1987, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>8–10</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/10.1002/mrc.1260250103">10.1002/mrc.1260250103</a></span>.<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:Senecionin&rft.atitle=Quantitative+analysis+of+pyrrolizidine+alkaloid+mixtures+from+Senecio+vulgaris+by+carbon-13+nuclear+magnetic+resonance+spectroscopy&rft.au=L.+A.+C.+Pieters%2C+A.+J.+Vlietinck&rft.date=1987-01&rft.doi=10.1002%2Fmrc.1260250103&rft.genre=journal&rft.issue=1&rft.jtitle=Magnetic+Resonance+in+Chemistry&rft.pages=8-10&rft.volume=25" style="display:none"> </span></span>
</li>
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">Lotte Joosten, Patrick P. J. Mulder, Klaas Vrieling, Johannes A. van Veen, Peter G. L. Klinkhamer: <cite style="font-style:italic">The analysis of pyrrolizidine alkaloids in Jacobaea vulgaris; a comparison of extraction and detection methods</cite>. In: <cite style="font-style:italic">Pythochemical Analysis</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>21</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>2</span>, 11. November 2009, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>197–204</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/10.1002/pca.1183">10.1002/pca.1183</a></span>.<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:Senecionin&rft.atitle=The+analysis+of+pyrrolizidine+alkaloids+in+Jacobaea+vulgaris%3B+a+comparison+of+extraction+and+detection+methods&rft.au=Lotte+Joosten%2C+Patrick+P.+J.+Mulder%2C+Klaas+Vrieling%2C+...&rft.date=2009-11-11&rft.doi=10.1002%2Fpca.1183&rft.genre=journal&rft.issue=2&rft.jtitle=Pythochemical+Analysis&rft.pages=197-204&rft.volume=21" style="display:none"> </span></span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">Carol E. Green, H. J. Segall, James L. Byard: <cite style="font-style:italic">Metabolism, cytotoxicity, and genotoxicity of the pyrrolizidine alkaloid senecionine in primary cultures of rat hepatocytes</cite>. In: <cite style="font-style:italic">Toxicology and Applied Pharmacology</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>60</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>2</span>, 15. September 1981, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>176–185</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/10.1016/0041-008X%2891%2990221-Y">10.1016/0041-008X(91)90221-Y</a></span>.<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:Senecionin&rft.atitle=Metabolism%2C+cytotoxicity%2C+and+genotoxicity+of+the+pyrrolizidine+alkaloid+senecionine+in+primary+cultures+of+rat+hepatocytes&rft.au=Carol+E.+Green%2C+H.+J.+Segall%2C+James+L.+Byard&rft.date=1981-09-15&rft.doi=10.1016%2F0041-008X%2891%2990221-Y&rft.genre=journal&rft.issue=2&rft.jtitle=Toxicology+and+Applied+Pharmacology&rft.pages=176-185&rft.volume=60" style="display:none"> </span></span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">Zhi-Ben Tu, Chohachi Konno, D. Doel Soejarto, Donald P. Waller, Audrey S. Bingel, Russell J. Molyneux, John A. Edgar, Geoffrey A. Cordell, Harry H. S. Fong: <cite style="font-style:italic">Identification of senecionine and senecionine N-oxide as antifertility constituents in Senecio vulgaris</cite>. In: <cite style="font-style:italic"><a href="Journal_of_Pharmaceutical_Sciences" title="Journal of Pharmaceutical Sciences">Journal of Pharmaceutical Sciences</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>77</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>5</span>, Mai 1988, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>461–463</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/10.1002/jps.2600770522">10.1002/jps.2600770522</a></span>.<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:Senecionin&rft.atitle=Identification+of+senecionine+and+senecionine+N-oxide+as+antifertility+constituents+in+Senecio+vulgaris&rft.au=Zhi-Ben+Tu%2C+Chohachi+Konno%2C+D.+Doel+Soejarto%2C+...&rft.date=1988-05&rft.doi=10.1002%2Fjps.2600770522&rft.genre=journal&rft.issue=5&rft.jtitle=Journal+of+Pharmaceutical+Sciences&rft.pages=461-463&rft.volume=77" style="display:none"> </span></span>
</li>
<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">Sebastian Schramm, Nikolai Köhler and Wilfried Rozhon: <cite style="font-style:italic">Pyrrolizidine Alkaloids: Biosynthesis, Biological Activities and Occurrence in Crop Plants</cite>. 24. Februar 2019, <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/10.3390/molecules24030498">10.3390/molecules24030498</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/30704105?dopt=Abstract">PMID 30704105</a>, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385001/">PMC 6385001</a> (freier Volltext).<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:Senecionin&rft.au=Sebastian+Schramm%2C+Nikolai+K%C3%B6hler+and+Wilfried+Rozhon&rft.btitle=Pyrrolizidine+Alkaloids%3A+Biosynthesis%2C+Biological+Activities+and+Occurrence+in+Crop+Plants&rft.date=2019-02-24&rft.doi=10.3390%2Fmolecules24030498&rft.genre=book&rft.pmc=6385001&rft.pmid=30704105" style="display:none"> </span></span>
</li>
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