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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Oleanolsäure</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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<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>Oleanolsäure
</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>S</i>,12a<i>R</i>,14b<i>S</i>)-10-Hydroxy-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 (<a href="IUPAC-Nomenklatur" class="mw-redirect" title="IUPAC-Nomenklatur">IUPAC</a>)</li>
<li><small>OLEANOLIC ACID</small> (<a href="Internationale_Nomenklatur_f%C3%BCr_kosmetische_Inhaltsstoffe" title="Internationale Nomenklatur für kosmetische Inhaltsstoffe">INCI</a>)<sup id="cite_ref-CosIng_1-0" class="reference"><a href="#cite_note-CosIng-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><span class="editoronly" style="display:none;"></span></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>3</sub>
</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=508-02-1">508-02-1</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>
</td>
<td colspan="2">208-081-6
</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/100.007.347">100.007.347</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/10494">10494</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.10062.html">10062</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/Q418628" class="extiw external" title="d:Q418628">Q418628</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>456,71 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="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>306–308 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-muehle_2-0" class="reference"><a href="#cite_note-muehle-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>








<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<p>nahezu unlöslich in Wasser, gut löslich in Methanol<sup id="cite_ref-muehle_2-1" class="reference"><a href="#cite_note-muehle-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;">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_3-0" class="reference"><a href="#cite_note-Sigma-3"><span class="cite-bracket">[</span>3<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="07 – Achtung"></a></span>
</td></tr></tbody></table>
<p><b>Achtung</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="Verursacht Hautreizungen.">315</span></span></a>​‐​<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="Verursacht schwere Augenreizung.">319</span></span></a>​‐​<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="Kann die Atemwege reizen.">335</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="Einatmen von Staub / Rauch / Gas / Nebel / Dampf / Aerosol vermeiden.">261</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 Kontakt mit den Augen:">305</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="Einige Minuten lang behutsam mit Wasser ausspülen.">351</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="Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter ausspülen.">338</span></span></a><sup id="cite_ref-Sigma_3-1" class="reference"><a href="#cite_note-Sigma-3"><span class="cite-bracket">[</span>3<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>&gt; 2000 mg·kg<sup>−1</sup> (<a href="Letale_Dosis" title="Letale Dosis">LD<sub>50</sub></a>,&nbsp;<a href="Ratten" title="Ratten">Ratte</a>,&nbsp;<a href="Peroral" title="Peroral">oral</a>)<sup id="cite_ref-Sigma_3-2" class="reference"><a href="#cite_note-Sigma-3"><span class="cite-bracket">[</span>3<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&nbsp;hPa).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Oleanolsäure</b> ist ein <a href="Terpene#Pentacyclische" title="Terpene">pentacyclisches Triterpen</a>, das aus fünf <a href="Cyclohexan" title="Cyclohexan">Cyclohexanringen</a> aufgebaut ist. Das <a href="Sapogenine" title="Sapogenine">Sapogenin</a> Oleanolsäure ist ein natürlicher Bestandteil einer Reihe von Pflanzen.
</p>

<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>

<p>Oleanolsäure ist als <a href="Naturstoff" title="Naturstoff">Naturstoff</a> in einer Vielzahl von Pflanzen enthalten. Beispielsweise kann sie aus <a href="Salbei" title="Salbei">Salbei</a> (<i>Salvia officinalis</i>), <a href="Rosmarin" title="Rosmarin">Rosmarin</a> (<i>Salvia rosmarinus</i>)<sup id="cite_ref-Dr._P.N._Ravindran_4-0" class="reference"><a href="#cite_note-Dr._P.N._Ravindran-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>, <a href="Gemeiner_Efeu" title="Gemeiner Efeu">Gemeinem Efeu</a> (<i>Hedera helix</i>),<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> <a href="Zuckerr%C3%BCbe" title="Zuckerrübe">Zuckerrüben</a> (<i>Beta vulgaris</i>), <a href="Ginseng" title="Ginseng">Ginseng</a> (<i>Panax ginseng</i>), <a href="Breitwegerich" title="Breitwegerich">Breitwegerich</a> (<i>Plantago major</i>), <i><a href="Syzygium_cumini" title="Syzygium cumini">Syzygium cumini</a></i>, <a href="Pistazie" title="Pistazie">Pistazien</a> (<i>Pistazia vera</i>), <a href="Trester_(Pressr%C3%BCckst%C3%A4nde)" title="Trester (Pressrückstände)">Trester</a> von <a href="Olivenbaum" title="Olivenbaum">Oliven</a> (<i>Olea europaea</i>)<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> besonders konzentriert und <a href="Wei%C3%9Fbeerige_Mistel" title="Weißbeerige Mistel">Weißbeerigen Misteln</a> (<i>Viscum album</i>)<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> gewonnen werden.
</p>
<div class="mw-heading mw-heading2"><h2 id="Pharmakologische_Eigenschaften">Pharmakologische Eigenschaften</h2></div>
<p>Oleanolsäure ist schwach <a href="Zytotoxizit%C3%A4t" title="Zytotoxizität">zytotoxisch</a> und weist nur ein geringes <a href="Antioxidans" title="Antioxidans">anti-oxidatives</a> Potenzial auf. Da die pharmakologisch interessanten Eigenschaften nur relativ schwach ausgeprägt sind, wurden verschiedene <a href="Derivat_(Chemie)" title="Derivat (Chemie)">Derivate</a> der Oleanolsäure hergestellt, die eine erheblich höhere Potenz haben.<sup id="cite_ref-PMID21196213_8-0" class="reference"><a href="#cite_note-PMID21196213-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Ein Derivat mit deutlich höherem Potenzial ist <a href="Bardoxolon" class="mw-redirect" title="Bardoxolon">Bardoxolon</a> (2-Cyan-3,12-dioxo-l,9-dien-28-oleanolsäure, CDDO), beziehungsweise dessen Methylester (Bardoxolon-Methyl). Bardoxolon ist eine vielversprechende <a href="Krebspr%C3%A4vention#Chemoprävention_–_Arzneimittel_zur_Krebsvorbeugung" title="Krebsprävention">chemopräventive</a> und <a href="Zytostatikum" title="Zytostatikum">zytostatische</a> Substanz, die <a href="Zellproliferation" title="Zellproliferation">anti-proliferativ</a> und <a href="Apoptose" title="Apoptose">pro-apoptotisch</a> wirkt.<sup id="cite_ref-PMID21325633_9-0" class="reference"><a href="#cite_note-PMID21325633-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Die Verbindung befindet sich in der <a href="Klinische_Studie" title="Klinische Studie">klinischen Erprobung</a> (Phase I/II).<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PMID21035854_11-0" class="reference"><a href="#cite_note-PMID21035854-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Zur Behandlung von <a href="Chronisches_Nierenversagen" title="Chronisches Nierenversagen">chronischer Niereninsuffizienz</a> ist Bardoxolon-Methyl in der klinischen Phase III.<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>Seit 1977 wird Oleanolsäure in <a href="China" title="China">China</a> und <a href="Japan" title="Japan">Japan</a> bei <a href="Leber" title="Leber">Lebererkrankungen</a> als orales <a href="Arzneimittel" title="Arzneimittel">Therapeutikum</a> verwendet. Seit 1986 gegen <a href="Hyperlipoprotein%C3%A4mie" title="Hyperlipoproteinämie">Hyperlipidämie</a> und nichtlymphatische <a href="Leuk%C3%A4mie" title="Leukämie">Leukämie</a>. In Japan ist seit 1990 eine oleanolhaltige Creme zum Schutz vor <a href="Hautkrebs" title="Hautkrebs">Hautkrebs</a> im Handel.<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>
</p>
<div class="mw-heading mw-heading2"><h2 id="Siehe_auch">Siehe auch</h2></div>
<ul><li><a href="Maslins%C3%A4ure" title="Maslinsäure">Maslinsäure</a></li>
<li><a href="Ursols%C3%A4ure" title="Ursolsäure">Ursolsäure</a></li></ul>
<div class="mw-heading mw-heading2"><h2 id="Weiterführende_Literatur"><span id="Weiterf.C3.BChrende_Literatur"></span>Weiterführende Literatur</h2></div>
<ul><li>A. Bishayee, S. Ahmed, N. Brankov, M. Perloff: <i>Triterpenoids as potential agents for the chemoprevention and therapy of breast cancer.</i> In: <i>Frontiers in bioscience</i> Band 16, 2011, S.&nbsp;980–996, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/21196213?dopt=Abstract">PMID 21196213</a>. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3057757/">PMC&nbsp;3057757</a> (freier Volltext). (Review).</li>
<li>M. B. Sporn, K. T. Liby, M. M. Yore, L. Fu, J. M. Lopchuk, G. W. Gribble: <i>New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress.</i> In: <i><a href="Journal_of_Natural_Products" title="Journal of Natural Products">Journal of Natural Products</a></i> Band 74, Nummer 3, März 2011, S.&nbsp;537–545, <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/np100826q">10.1021/np100826q</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/21309592?dopt=Abstract">PMID 21309592</a>. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3064114/">PMC&nbsp;3064114</a> (freier Volltext). (Review).</li>
<li>J. L. Ríos: <i>Effects of triterpenes on the immune system.</i> In: <i><a href="Journal_of_ethnopharmacology" class="mw-redirect" title="Journal of ethnopharmacology">Journal of ethnopharmacology</a></i> Band 128, Nummer 1, März 2010, S.&nbsp;1–14, <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.jep.2009.12.045">10.1016/j.jep.2009.12.045</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/20079412?dopt=Abstract">PMID 20079412</a>. (Review).</li>
<li>I. Sogno, N. Vannini, G. Lorusso, R. Cammarota, D. M. Noonan, L. Generoso, M. B. Sporn, A. Albini: <i>Anti-angiogenic activity of a novel class of chemopreventive compounds: oleanic acid terpenoids.</i> In: <i>Recent results in cancer research. Fortschritte der Krebsforschung. Progrès dans les recherches sur le cancer</i> Band 181, 2009, S.&nbsp;209–212, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/19213570?dopt=Abstract">PMID 19213570</a>. (Review).</li>
<li>A. Petronelli, G. Pannitteri, U. Testa: <i>Triterpenoids as new promising anticancer drugs.</i> In: <i><a href="Anti-Cancer_Drugs" title="Anti-Cancer Drugs">Anti-Cancer Drugs</a></i> Band 20, Nummer 10, November 2009, S.&nbsp;880–892, <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/10.1097/CAD.0b013e328330fd90">10.1097/CAD.0b013e328330fd90</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/19745720?dopt=Abstract">PMID 19745720</a>. (Review).</li>
<li>M. N. Laszczyk: <i>Pentacyclic triterpenes of the lupane, oleanane and ursane group as tools in cancer therapy.</i> In: <i><a href="Planta_Medica" title="Planta Medica">Planta Medica</a></i> Band 75, Nummer 15, Dezember 2009, S.&nbsp;1549–1560, <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/10.1055/s-0029-1186102">10.1055/s-0029-1186102</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/19742422?dopt=Abstract">PMID 19742422</a>. (Review).</li>
<li>B. Yu, J. Sun: <i>Current synthesis of triterpene saponins.</i> In: <i>Chemistry, an Asian journal</i> Band 4, Nummer 5, Mai 2009, S.&nbsp;642–654, <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/asia.200800462">10.1002/asia.200800462</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/19294723?dopt=Abstract">PMID 19294723</a>. (Review).</li>
<li>N. Sultana, A. Ata: <i>Oleanolic acid and related derivatives as medicinally important compounds.</i> In: <i><a href="Journal_of_Enzyme_Inhibition_and_Medicinal_Chemistry" title="Journal of Enzyme Inhibition and Medicinal Chemistry">Journal of Enzyme Inhibition and Medicinal Chemistry</a></i> Band 23, Nummer 6, Dezember 2008, S.&nbsp;739–756, <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/10.1080/14756360701633187">10.1080/14756360701633187</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/18618318?dopt=Abstract">PMID 18618318</a>.</li>
<li>J. Liu: <i>Oleanolic acid and ursolic acid: research perspectives.</i> In: <i>Journal of ethnopharmacology</i> Band 100, Nummer 1–2, August 2005, S.&nbsp;92–94, <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.jep.2005.05.024">10.1016/j.jep.2005.05.024</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/15994040?dopt=Abstract">PMID 15994040</a>. (Review).</li>
<li>Z. Ovesná, A. Vachálková, K. Horváthová, D. Tóthová: <i>Pentacyclic triterpenoic acids: new chemoprotective compounds. Minireview.</i> In: <i>Neoplasma</i> Band 51, Nummer 5, 2004, S.&nbsp;327–333, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/15640935?dopt=Abstract">PMID 15640935</a>. (Review).</li></ul>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-CosIng-1"><span class="mw-cite-backlink"><a href="#cite_ref-CosIng_1-0">↑</a></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://ec.europa.eu/growth/tools-databases/cosing/details/57708"><i><small>OLEANOLIC ACID</small></i></a> in der <a href="CosIng-Datenbank" title="CosIng-Datenbank">CosIng-Datenbank</a> der EU-Kommission, abgerufen am 18.&nbsp;Mai 2020.</span>
</li>
<li id="cite_note-muehle-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-muehle_2-0">a</a></sup> <sup><a href="#cite_ref-muehle_2-1">b</a></sup></span> <span class="reference-text">T. Mühle: <i>Trennung der Positionsisomere Oleanolsäure und Ursolsäure.</i> Diplomica Verlag, 2009, ISBN 3-836-67870-5, S.&nbsp;7 (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=Z_TfUOBWhUYC&amp;pg=PA7#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).</span>
</li>
<li id="cite_note-Sigma-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_3-0">a</a></sup> <sup><a href="#cite_ref-Sigma_3-1">b</a></sup> <sup><a href="#cite_ref-Sigma_3-2">c</a></sup></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/ALDRICH/O5504">Oleanolic acid</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 24.&nbsp;April 2011 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/O5504?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Dr._P.N._Ravindran-4"><span class="mw-cite-backlink"><a href="#cite_ref-Dr._P.N._Ravindran_4-0">↑</a></span> <span class="reference-text">Dr. P.N. Ravindran: <a rel="nofollow" class="external text" href="https://books.google.de/books?id=6pJNDwAAQBAJ&amp;pg=PA812&amp;lpg=PA812&amp;dq=Senorans+et+al.,+2000;+Okamura+et+al.,+1994+rosemary&amp;source=bl&amp;ots=L9aXSpt8fP&amp;sig=ACfU3U1tBoV56frrirNQ77Qvny-pV-uHVg&amp;hl=de&amp;sa=X&amp;ved=2ahUKEwiCjd-MlbnoAhXhXRUIHQp1DSgQ6AEwAXoECAsQAQ#v=onepage&amp;q=Rosmary%20oleanolic%20acid%2010%25&amp;f=false"><i>The Encyclopedia of Herbs and Spices</i></a> (Inhaltsstoffe, Triterpene in der Arzneidroge) In: <i>Google Books</i>, 2017, S. 812.</span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.fh-muenster.de/hochschule/downloads/publikationen/FHocus/FHocus_08/fhocus_08_s26-39.pdf"><i>Salbei konzentriert – Wirkstoff der alten Heilpflanze effektiv gewinnen.</i></a><span style="display:none"><a rel="nofollow" class="external text" href="http://deadurl.invalid/https://www.fh-muenster.de/hochschule/downloads/publikationen/FHocus/FHocus_08/fhocus_08_s26-39.pdf">@1</a></span><span style="display:none"><a rel="nofollow" class="external text" href="https://www.fh-muenster.de/hochschule/downloads/publikationen/FHocus/FHocus_08/fhocus_08_s26-39.pdf">@2</a></span><span style="display:none">Vorlage:Toter Link/www.fh-muenster.de</span> <small>(Seite dauerhaft nicht mehr abrufbar, festgestellt im Mai 2019. <a rel="nofollow" class="external text" href="http://timetravel.mementoweb.org/list/2010/https://www.fh-muenster.de/hochschule/downloads/publikationen/FHocus/FHocus_08/fhocus_08_s26-39.pdf">Suche in Webarchiven</a>)</small> (PDF; 851&nbsp;kB) Fachhochschule Münster, S.&nbsp;26–27.</span>
</li>
<li id="cite_note-Schmandke-6"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Schmandke_6-0">a</a></sup> <sup><a href="#cite_ref-Schmandke_6-1">b</a></sup></span> <span class="reference-text"><a href="Horst_Schmandke" title="Horst Schmandke">H. Schmandke</a>: <a rel="nofollow" class="external text" href="https://www.ernaehrungs-umschau.de/fileadmin/Ernaehrungs-Umschau/pdfs/pfd_2009/02_09/EU02_92_95.qxd.pdf"><i>Triterpenoide in Oliven.</i></a> (PDF; 283&nbsp;kB) In: <i>Ernährungs Umschau</i> 2, 2009, S.&nbsp;92–95.</span>
</li>
<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">S. Jäger, A. Scheffler, H. Schmellenkamp: <a rel="nofollow" class="external text" href="https://www.pharmazeutische-zeitung.de/index.php?id=1354"><i>Pharmakologie ausgewählter Terpene.</i></a> In: <i>Pharmazeutische Zeitung</i> 22, 2006.</span>
</li>
<li id="cite_note-PMID21196213-8"><span class="mw-cite-backlink"><a href="#cite_ref-PMID21196213_8-0">↑</a></span> <span class="reference-text">A. Bishayee, S. Ahmed, N. Brankov, M. Perloff: <i>Triterpenoids as potential agents for the chemoprevention and therapy of breast cancer.</i> In: <i>Frontiers in bioscience</i> Band 16, 2011, S.&nbsp;980–996, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/21196213?dopt=Abstract">PMID 21196213</a>. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3057757/">PMC&nbsp;3057757</a> (freier Volltext). (Review).</span>
</li>
<li id="cite_note-PMID21325633-9"><span class="mw-cite-backlink"><a href="#cite_ref-PMID21325633_9-0">↑</a></span> <span class="reference-text">D. Deeb, X. Gao, Y. Liu, D. Jiang, G. W. Divine, A. S. Arbab, S. A. Dulchavsky, S. C. Gautam: <i>Synthetic triterpenoid CDDO prevents the progression and metastasis of prostate cancer in TRAMP mice by inhibiting survival signaling.</i> In: <i><a href="Carcinogenesis" title="Carcinogenesis">Carcinogenesis</a></i> Band 32, Nummer 5, Mai 2011, S.&nbsp;757–764, <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/10.1093/carcin%2Fbgr030">10.1093/carcin/bgr030</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/21325633?dopt=Abstract">PMID 21325633</a>. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3086702/">PMC&nbsp;3086702</a> (freier Volltext).</span>
</li>
<li id="cite_note-10"><span class="mw-cite-backlink"><a href="#cite_ref-10">↑</a></span> <span class="reference-text">
<a href="Klinische_Studie" title="Klinische Studie">Klinische Studie</a> (Phase I/II): <a rel="nofollow" class="external text" href="https://www.clinicaltrials.gov/ct2/show/NCT00352040"><i>CDDO in Treating Patients With Metastatic or Unresectable Solid Tumors or Lymphoma</i></a> bei <span lang="en">Clinicaltrials.gov der <a href="National_Institutes_of_Health" title="National Institutes of Health">NIH</a></span></span>
</li>
<li id="cite_note-PMID21035854-11"><span class="mw-cite-backlink"><a href="#cite_ref-PMID21035854_11-0">↑</a></span> <span class="reference-text">A. Petronelli, E. Pelosi, S. Santoro, E. Saulle, A. M. Cerio, G. Mariani, C. Labbaye, U. Testa: <i>CDDO-Im is a stimulator of megakaryocytic differentiation.</i> In: <i><a href="Leukemia_Research" title="Leukemia Research">Leukemia Research</a></i> Band 35, Nummer 4, April 2011, S.&nbsp;534–544, <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.leukres.2010.09.013">10.1016/j.leukres.2010.09.013</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/21035854?dopt=Abstract">PMID 21035854</a>.</span>
</li>
<li id="cite_note-12"><span class="mw-cite-backlink"><a href="#cite_ref-12">↑</a></span> <span class="reference-text"><a href="Klinische_Studie" title="Klinische Studie">Klinische Studie</a> (Phase III): <a rel="nofollow" class="external text" href="https://www.clinicaltrials.gov/ct2/show/NCT01351675"><i>Bardoxolone Methyl Evaluation in Patients With Chronic Kidney Disease and Type 2 Diabetes (BEACON)</i></a> bei <span lang="en">Clinicaltrials.gov der <a href="National_Institutes_of_Health" title="National Institutes of Health">NIH</a></span></span>
</li>
</ol>
<div class="mw-heading mw-heading2"><h2 id="Weblinks">Weblinks</h2></div>
<ul><li><a rel="nofollow" class="external text" href="https://www.pharmazeutische-zeitung.de/index.php?id=1354">Pharmakologie ausgewählter Terpene.</a> Pharmazeutische Zeitung</li></ul>
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Normdaten&nbsp;(Sachbegriff): <a href="Gemeinsame_Normdatei" title="Gemeinsame Normdatei">GND</a>: <span class="-print"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4698695-9">4698695-9</a></span> </div>
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