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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Maslinsäure</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>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
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<td style="width:33%;">Name
</td>
<td>Maslinsäure
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>(4a<i>S</i>,6a<i>R</i>,6a<i>S</i>,6b<i>R</i>,8a<i>R</i>,10<i>R</i>,11<i>R</i>,12a<i>R</i>,14b<i>S</i>)-10,11-Dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-4a-carbonsäure <small>(<a href="IUPAC-Nomenklatur" class="mw-redirect" title="IUPAC-Nomenklatur">IUPAC</a>)</small></li>
<li>2<i>α</i>-Hydroxyoleanolsäure</li>
<li>2<i>α</i>,3<i>β</i>-Dihydroxyolean-12-en-28-carbonsäure</li>
<li>Crataegolsäure<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></li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>30</sub>H<sub>48</sub>O<sub>4</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>farblose Kristalle<sup id="cite_ref-Sigma_2-0" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<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);">
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<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=4373-41-5">4373-41-5</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">610-137-3
</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/100.128.873">100.128.873</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/73659">73659</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.66312.html">66312</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/Q1907191" class="extiw external" title="d:Q1907191">Q1907191</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>472,70 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
</p>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<ul><li>schlecht in Wasser (0,3 g/l bei 25 °C)<sup id="cite_ref-Sigma_2-1" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li>
<li>gut in DMSO (20 g/l)<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></li></ul>
</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-Sigma_2-2" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<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><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table>
<p>
</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><i>keine H-Sätze</i>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i><sup id="cite_ref-Sigma_2-3" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td></tr>
</tbody></table>
</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>Maslinsäure</b> ist ein <a href="Terpene#Pentacyclische" title="Terpene">pentazyklisches Triterpen</a>, das aus fünf <a href="Cyclohexan" title="Cyclohexan">Cyclohexanringen</a> aufgebaut ist. Maslinsäure ist ein natürlicher Bestandteil des <a href="Oliven%C3%B6l" title="Olivenöl">Olivenöls</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Maslinsäure findet sich als wachsartige Schutzschicht auf den Blättern und den Früchten des <a href="Olivenbaum" title="Olivenbaum">Olivenbaums</a>.<sup id="cite_ref-PMID21524306_4-0" class="reference"><a href="#cite_note-PMID21524306-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In Oliven liegt der Gehalt an Maslinsäure zwischen etwa 700 und 1000 mg pro kg. Mit zunehmender Reifung nimmt der Gehalt ab.<sup id="cite_ref-PMID20712364_5-0" class="reference"><a href="#cite_note-PMID20712364-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Pro Kilogramm nativem Olivenöl können bis zu 250 mg Maslinsäure enthalten sein. In <a href="Raffination" title="Raffination">raffiniertem</a> Öl ist der Gehalt an Maslinsäure erheblich niedriger. Die Press- und Zentrifugenrückstände von der Olivenölherstellung sind eine wichtige Quelle zur Gewinnung von Maslinsäure und anderen verwandten pentacyclischen Triterpenen, wie beispielsweise <a href="Oleanols%C3%A4ure" title="Oleanolsäure">Oleanolsäure</a>. Aus diesen Rückständen lassen sich die Triterpene durch <a href="Extraktion_(Verfahrenstechnik)" class="mw-redirect" title="Extraktion (Verfahrenstechnik)">Extraktion</a> mit <a href="L%C3%B6sungsmittel" title="Lösungsmittel">Lösungsmitteln</a> gewinnen.<sup id="cite_ref-Schmandke_6-0" class="reference"><a href="#cite_note-Schmandke-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PMID20151391_7-0" class="reference"><a href="#cite_note-PMID20151391-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>
</p><p>Auch in der Japanischen Nelkenwurz (<i>Geum japonicum</i>)<sup id="cite_ref-PMID8759159_8-0" class="reference"><a href="#cite_note-PMID8759159-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>, der <a href="K%C3%B6niginblume" title="Königinblume">Königinblume</a> (<i>Lagerstroemia speciosa</i>)<sup id="cite_ref-PMID19107840_9-0" class="reference"><a href="#cite_note-PMID19107840-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> der <a href="Kleine_Braunelle" title="Kleine Braunelle">Kleinen Braunelle</a> (<i>Prunella vulgaris</i>),<sup id="cite_ref-PMID19099227_10-0" class="reference"><a href="#cite_note-PMID19099227-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> dem <a href="Asiatischer_Bl%C3%BCten-Hartriegel" title="Asiatischer Blüten-Hartriegel">Asiatischen Blüten-Hartriegel</a> (<i>Cornus kousa</i>),<sup id="cite_ref-PMID17661332_11-0" class="reference"><a href="#cite_note-PMID17661332-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> der <a href="Sibirische_Ulme" title="Sibirische Ulme">Sibirischen Ulme</a> (<i>Ulmus pumila</i>),<sup id="cite_ref-PMID16755042_12-0" class="reference"><a href="#cite_note-PMID16755042-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> im <a href="Ramie" title="Ramie">Chinagras</a> (<i>Boehmeria nivea</i>)<sup id="cite_ref-PMID20069903_13-0" class="reference"><a href="#cite_note-PMID20069903-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> und einer Reihe anderer Pflanzen konnte Maslinsäure nachgewiesen und isoliert werden.
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften_und_pharmakologisches_Potenzial">Eigenschaften und pharmakologisches Potenzial</h2></div>
<p>Maslinsäure ist <a href="Zytotoxizit%C3%A4t" title="Zytotoxizität">zytotoxisch</a>. Sie ist zwar nicht in der Lage <a href="Radikale_(Chemie)" class="mw-redirect" title="Radikale (Chemie)">freie Radikale</a> abzufangen, bewirkt aber einen Schutz der <a href="Desoxyribonukleins%C3%A4ure" title="Desoxyribonukleinsäure">DNA</a> gegen <a href="Oxidation" title="Oxidation">Oxidation</a>.<sup id="cite_ref-PMID21142067_14-0" class="reference"><a href="#cite_note-PMID21142067-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup>
In <a href="In_vitro" title="In vitro">In-vitro</a>-Versuchen konnte eine <a href="Zellproliferation" title="Zellproliferation">antiproliferative</a> und <a href="Apoptose" title="Apoptose">apoptoseauslösende</a> Wirkung der Maslinsäure nachgewiesen werden.<sup id="cite_ref-PMID21524306_4-1" class="reference"><a href="#cite_note-PMID21524306-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Maslinsäure aktiviert <a href="Caspasen" title="Caspasen">Caspase-3</a>,<sup id="cite_ref-PMID18298868_15-0" class="reference"><a href="#cite_note-PMID18298868-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> ein für die Apoptose wichtiges <a href="Enzym" title="Enzym">Enzym</a>. Die Verbindung scheint darüber hinaus die Gefäßneubildung (<a href="Angiogenese" title="Angiogenese">Angiogenese</a>)<sup id="cite_ref-PMID21175131_16-0" class="reference"><a href="#cite_note-PMID21175131-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> sowie das Enzym <a href="Cyclooxygenase-2" title="Cyclooxygenase-2">Cyclooxygenase-2</a> (COX-2) zu inhibieren.<sup id="cite_ref-PMID20669087_17-0" class="reference"><a href="#cite_note-PMID20669087-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Eine <a href="Diabetes_mellitus" title="Diabetes mellitus">anti-diabetische</a> Wirkung konnte in <a href="Modellorganismus" title="Modellorganismus">Modellorganismen</a> nachgewiesen werden.<sup id="cite_ref-PMID17978478_18-0" class="reference"><a href="#cite_note-PMID17978478-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup>
</p><p>An verschiedenen <a href="Krebs_(Medizin)" title="Krebs (Medizin)">Krebszelllinien</a> – insbesondere an <a href="Kolorektales_Karzinom" title="Kolorektales Karzinom">Dickdarmkrebszellen</a> – wurde eine anti-<a href="Karzinogene" class="mw-redirect" title="Karzinogene">karzinogene</a> Wirkung nachgewiesen. Es wird vermutet, dass das aus <a href="Epidemiologie" title="Epidemiologie">epidemiologischen</a> Daten her bekannte, vergleichsweise niedrige Dickdarmrisiko der <a href="Mittelmeer" title="Mittelmeer">mediterranen</a> Bevölkerung mit dem vergleichsweise hohen Verzehr an Olivenöl und Oliven zusammenhängt und eine der Ursachen der Olivenbestandteil Maslinsäure ist. Pro Person und Tag liegt dort die Aufnahme an Maslinsäure bei etwa 62 mg.<sup id="cite_ref-Schmandke_6-1" class="reference"><a href="#cite_note-Schmandke-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Darüber hinaus konnten kardioprotektive Eigenschaften der Maslinsäure nachgewiesen werden.<sup id="cite_ref-PMID20650302_19-0" class="reference"><a href="#cite_note-PMID20650302-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup>
</p><p>Gegenüber <a href="Parasit" class="mw-redirect" title="Parasit">parasitären</a> Krankheitserregern, wie beispielsweise <a href="Plasmodien" title="Plasmodien">Plasmodien</a> (<i><a href="Plasmodium_falciparum" title="Plasmodium falciparum">Plasmodium falciparum</a></i><sup id="cite_ref-PMID21477369_20-0" class="reference"><a href="#cite_note-PMID21477369-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PMID21518429_21-0" class="reference"><a href="#cite_note-PMID21518429-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> oder <i><a href="Toxoplasma_gondii" title="Toxoplasma gondii">Toxoplasma gondii</a></i><sup id="cite_ref-PMID20441162_22-0" class="reference"><a href="#cite_note-PMID20441162-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup>) oder Protozoen wie <i>Eimeria tenella</i>,<sup id="cite_ref-PMID20499099_23-0" class="reference"><a href="#cite_note-PMID20499099-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> zeigt Maslinsäure eine anti-<a href="Parasit" class="mw-redirect" title="Parasit">parasitäre</a> Wirkung.
</p><p>Maslinsäure hemmt Enzyme, die das <a href="Humanes_Immundefizienz-Virus" class="mw-redirect" title="Humanes Immundefizienz-Virus">HI-Virus</a> benötigt.<sup id="cite_ref-PMID8759159_8-1" class="reference"><a href="#cite_note-PMID8759159-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Weiterführende_Literatur"><span id="Weiterf.C3.BChrende_Literatur"></span>Weiterführende Literatur</h2></div>
<ul><li>X. Wen, H. Sun, J. Liu, K. Cheng, P. Zhang, L. Zhang, J. Hao, L. Zhang, P. Ni, u. a.: <i>Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies.</i> In: <i><a href="Journal_of_Medicinal_Chemistry" title="Journal of Medicinal Chemistry">Journal of Medicinal Chemistry</a></i> Band 51, Nummer 12, Juni 2008, S. 3540–3554, <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/10.1021/jm8000949">10.1021/jm8000949</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/18517260?dopt=Abstract">PMID 18517260</a>.</li>
<li>C. Li, Z. Yang, Z. Li, Y. Ma, L. Zhang, C. Zheng, W. Qiu, X. Wu, u. a.: <i>Maslinic acid suppresses osteoclastogenesis and prevents ovariectomy-induced bone loss by regulating RANKL-mediated NF-κB and MAPK signaling pathways.</i> In: <i><a href="Journal_of_Bone_and_Mineral_Research" title="Journal of Bone and Mineral Research">Journal of Bone and Mineral Research</a></i> Band 26, Nummer 3, März 2011, S. 644–656, <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/jbmr.242">10.1002/jbmr.242</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/20814972?dopt=Abstract">PMID 20814972</a>.</li>
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<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
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<li id="cite_note-PMID20441162-22"><span class="mw-cite-backlink"><a href="#cite_ref-PMID20441162_22-0">↑</a></span> <span class="reference-text">L. M. De Pablos, G. González, R. Rodrigues, A. García Granados, A. Parra, A. Osuna: <i>Action of a pentacyclic triterpenoid, maslinic acid, against Toxoplasma gondii.</i> In: <i>Journal of natural products</i> Band 73, Nummer 5, Mai 2010, S. 831–834, <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/10.1021/np900749b">10.1021/np900749b</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/20441162?dopt=Abstract">PMID 20441162</a>.</span>
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<li id="cite_note-PMID20499099-23"><span class="mw-cite-backlink"><a href="#cite_ref-PMID20499099_23-0">↑</a></span> <span class="reference-text">L. M. De Pablos, M. F. dos Santos, E. Montero, A. Garcia-Granados, A. Parra, A. Osuna: <i>Anticoccidial activity of maslinic acid against infection with Eimeria tenella in chickens.</i> In: <i>Parasitology research</i> Band 107, Nummer 3, August 2010, S. 601–604, <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/s00436-010-1901-3">10.1007/s00436-010-1901-3</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/20499099?dopt=Abstract">PMID 20499099</a>. </span>
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<li id="cite_note-24"><span class="mw-cite-backlink"><a href="#cite_ref-24">↑</a></span> <span class="reference-text">J. Zittlau: <a rel="nofollow" class="external text" href="https://www.welt.de/wissenschaft/article1590908/Olivenoel-kann-die-Blutgefaesse-beschaedigen.html"><i>Olivenöl kann die Blutgefäße beschädigen.</i></a> In: <i>Die Welt</i> vom 24. Januar 2008.</span>
</li>
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<div class="mw-heading mw-heading2"><h2 id="Weblinks">Weblinks</h2></div>
<ul><li><a rel="nofollow" class="external text" href="https://www.aerztezeitung.de/Medizin/Substanz-aus-Olivenoel-hemmt-HIV-Freisetzung-396699.html">Substanz aus Olivenöl hemmt HIV-Freisetzung</a> Ärzte Zeitung vom 11. Juli 2007</li></ul></div><!--htdig_noindex--><div><div class="zim-footer">
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