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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Labdane</span></h1>
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<td colspan="2" class="hintergrundfarbe6"><b>Labdan</b><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>S 1<span class="cite-bracket">]</span></a></sup>
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<td class="hintergrundfarbe5" align="left"><a href="Strukturformel" title="Strukturformel">Strukturformel</a>
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<td><span class="mw-default-size" typeof="mw:File"></span>
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<td class="hintergrundfarbe5" align="left"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
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<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=561-90-0">561-90-0</a><span class="editoronly" style="display:none;"></span>
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<td class="hintergrundfarbe5" align="left"><a href="PubChem" title="PubChem">PubChem</a>
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<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/9548711">9548711</a>
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<td class="hintergrundfarbe5" align="left"><a href="Summenformel" title="Summenformel">Summenformel</a>
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<td>C<sub>20</sub>H<sub>38</sub>
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<td class="hintergrundfarbe5" align="left"><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
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<td>278,5 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
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<p>Die <b>Labdane</b>, oder auch <i>Labdan-Diterpene</i>, sind eine Stoffgruppe <a href="Organische_Chemie" title="Organische Chemie">organisch</a>-<a href="Chemische_Verbindung" title="Chemische Verbindung">chemischer Verbindungen</a>, aufgebaut aus natürlichen, <a href="Bicyclen" title="Bicyclen">bicyclischen</a> <a href="Diterpene" title="Diterpene">Diterpenen</a>. Ihr Grundgerüst, das <b>Labdan</b>, kommt in einer großen Vielfalt an <a href="Pflanzen" class="mw-redirect" title="Pflanzen">Pflanzen</a> vor, darunter in <i><a href="Salbei" title="Salbei">Salvia</a> sp.</i>,<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <i><a href="Plectranthus" class="mw-redirect" title="Plectranthus">Plectranthus</a> sp.</i><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> und <i><a href="Andrographis_paniculata" class="mw-redirect" title="Andrographis paniculata">Andrographis paniculata</a></i>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
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<p> Labdane bestehen aus einem <a href="Decalin" title="Decalin">Decalingerüst</a>, mit vier Methylgruppen und einem 3-Methylpentylrest. Sie sind nach der ersten gefundenen chemischen Verbindung ihrer Klasse benannt, dem Labdan, welches aus <a href="Labdanum" class="mw-redirect" title="Labdanum">Labdanum</a>, einem Harz der <a href="Lack-Zistrose" title="Lack-Zistrose">Lack-Zistrose</a> (<i>Cistus ladanifer</i>), gewonnen werden kann.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Labdane weisen eine Vielzahl an biologischen Aktivitäten auf, unter anderem <a href="Antibakteriell" class="mw-redirect" title="Antibakteriell">antibakterielle</a>, <a href="Antifungal" class="mw-redirect" title="Antifungal">antifungale</a> und <a href="Protozoen" title="Protozoen">antiprotozoale</a> Aktivität. Sie können zudem <a href="Entz%C3%BCndungshemmung" title="Entzündungshemmung">entzündungshemmend</a> wirken<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> und sind oft auch Duftstoffe.
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<div class="mw-heading mw-heading2"><h2 id="Beispiele_von_Labdanen">Beispiele von Labdanen</h2></div>
<ul><li><a href="Ambrein" title="Ambrein">Ambrein</a></li>
<li><a href="Abienol" class="mw-redirect" title="Abienol">Abienol</a></li>
<li><a href="Forskolin" title="Forskolin">Forskolin</a></li>
<li><a href="Sclareol" title="Sclareol">Sclareol</a></li></ul>
<div class="mw-heading mw-heading2"><h2 id="Literatur">Literatur</h2></div>
<ul><li>J. R. Hanson: <i>Diterpenoids of terrestrial origin.</i> In: <i>Natural product reports.</i> Band 34, Nummer 10, Oktober 2017, S. 1233–1243, <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/c7np00040e">10.1039/c7np00040e</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/28875214?dopt=Abstract">PMID 28875214</a>.</li></ul>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">M. Akaberi, S. Mehri, M. Iranshahi: <i>Multiple pro-apoptotic targets of abietane diterpenoids from Salvia species.</i> In: <i>Fitoterapia.</i> Band 100, Januar 2015, S. 118–132, <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/j.fitote.2014.11.008">10.1016/j.fitote.2014.11.008</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/25447154?dopt=Abstract">PMID 25447154</a>.</span>
</li>
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">S. Waldia, B. C. Joshi, U. Pathak, M. C. Joshi: <i>The genus Plectranthus in India and its chemistry.</i> In: <i>Chemistry & biodiversity.</i> Band 8, Nummer 2, Februar 2011, S. 244–252, <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/cbdv.201000048">10.1002/cbdv.201000048</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/21337498?dopt=Abstract">PMID 21337498</a>.</span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">L. S. Chua: <i>Review on liver inflammation and antiinflammatory activity of Andrographis paniculata for hepatoprotection.</i> In: <i>Phytotherapy research : PTR.</i> Band 28, Nummer 11, November 2014, S. 1589–1598, <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/ptr.5193">10.1002/ptr.5193</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/25043965?dopt=Abstract">PMID 25043965</a>.</span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">J. D. Cocker, T. G. Halsall, A. Bowers: <cite style="font-style:italic">The chemistry of gum labdanum. I. Some acidic constituents</cite>. In: <cite style="font-style:italic">Journal of the Chemical Society</cite>. 1956, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>4259–4262</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/JR9560004259">10.1039/JR9560004259</a></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:Labdane&rft.atitle=The+chemistry+of+gum+labdanum.+I.+Some+acidic+constituents&rft.au=J.+D.+Cocker%2C+T.+G.+Halsall%2C+A.+Bowers&rft.btitle=Journal+of+the+Chemical+Society&rft.date=1956&rft.doi=10.1039%2FJR9560004259&rft.genre=book&rft.pages=4259-4262" 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">J. D. Cocker, T. G. Halsall: <cite style="font-style:italic">The chemistry of gum labdanum. II. The structure of labdanolic acid</cite>. In: <cite style="font-style:italic">Journal of the Chemical Society</cite>. 1956, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>4262–4271</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/JR9560004262">10.1039/JR9560004262</a></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:Labdane&rft.atitle=The+chemistry+of+gum+labdanum.+II.+The+structure+of+labdanolic+acid&rft.au=J.+D.+Cocker%2C+T.+G.+Halsall&rft.btitle=Journal+of+the+Chemical+Society&rft.date=1956&rft.doi=10.1039%2FJR9560004262&rft.genre=book&rft.pages=4262-4271" style="display:none"> </span></span>
</li>
<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">A.-U. Rahman: <cite style="font-style:italic">Studies in Natural Product Chemistry : Bioactive Natural Products, Part F</cite>. ISBN 978-0-08-044001-9.<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:Labdane&rft.au=A.-U.+Rahman&rft.btitle=Studies+in+Natural+Product+Chemistry+%3A+Bioactive+Natural+Products%2C+Part+F&rft.genre=book&rft.isbn=9780080440019" style="display:none"> </span></span>
</li>
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<div class="mw-heading mw-heading2"><h2 id="Externe_Links_zu_erwähnten_Verbindungen"><span id="Externe_Links_zu_erw.C3.A4hnten_Verbindungen"></span>Externe Links zu erwähnten Verbindungen</h2></div>
<ol class="references" data-mw-group="S">
<li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a></span> <span class="reference-text">Externe Identifikatoren von bzw. Datenbank-Links zu <span style="font-style:italic">Labdan</span>: <a href="CAS-Nummer" title="CAS-Nummer">CAS-Nr.</a>: <span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=561-90-0">561-90-0</a><span class="editoronly" style="display:none;"></span>, <a href="PubChem" title="PubChem">PubChem</a>: <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/9548711">9548711</a>, <a href="ChemSpider" title="ChemSpider">ChemSpider</a>: <a rel="nofollow" class="external text" href="http://www.chemspider.com/Chemical-Structure.7827634.html"><span class="wikidata-content">7827634</span></a><span style="display:none;"></span>, <a href="Wikidata" title="Wikidata">Wikidata</a>: <a href="https://www.wikidata.org/wiki/Q8214660" class="extiw external" title="d:Q8214660">Q8214660</a>.<span class="editoronly" style="display:none;"></span></span>
</li>
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