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<title>Oleanane</title>

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<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Oleanane</span></span>

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<caption>18β-Oleanane

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names

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<td colspan="2" style="text-align:left;"><a href="Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a>

<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Oleanane<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></div>

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<td colspan="2" style="text-align:left;"><a href="Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a>

<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(4a<i>R</i>,6a<i>R</i>,6b<i>R</i>,8a<i>S</i>,12a<i>S</i>,12b<i>R</i>,14a<i>R</i>,14b<i>S</i>)-2,2,4a,6a,6b,9,9,12a-Octamethyldocosahydropicene</div></div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div>

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</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=471-67-0">471-67-0</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">N</span></sup></li></ul></div>

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<td><a href="ChEBI" title="ChEBI">ChEBI</a>

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<td><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=36481">CHEBI:36481</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div>

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<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div>

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<td><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID00872582">DTXSID00872582</a> </span></li></ul></div>

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<div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div>

<ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C30H52/c1-25(2)16-17-27(5)18-19-29(7)21(22(27)20-25)10-11-24-28(6)14-9-13-26(3,4)23(28)12-15-30(24,29)8/h21-24H,9-20H2,1-8H3/t21-,22+,23+,24-,27-,28+,29-,30-/m1/s1<sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: VCNKUCWWHVTTBY-KQCVGMHHSA-N<sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C30H52/c1-25(2)16-17-27(5)18-19-29(7)21(22(27)20-25)10-11-24-28(6)14-9-13-26(3,4)23(28)12-15-30(24,29)8/h21-24H,9-20H2,1-8H3/t21-,22+,23+,24-,27-,28+,29-,30-/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: VCNKUCWWHVTTBY-KQCVGMHHBI</div></div></li></ul>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="Chemical_formula" title="Chemical formula">Chemical formula</a></div>

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<td><a href="Molar_mass" title="Molar mass">Molar mass</a>

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<td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div>

<div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span></span></span><span style="display:none">N</span> <span class="reflink nourlexpansion"><a class="external text external" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=459444041&page2=Oleanane">verify</a></span> (what is <sup><span typeof="mw:File"><span></span></span><span style="display:none">Y</span><span typeof="mw:File"><span></span></span><span style="display:none">N</span></sup> ?)

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<div style="margin-top: 0.3em; text-align: center;">Infobox references</div>

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<p><b>Oleanane</b> is a natural <a href="Triterpenoid" class="mw-redirect" title="Triterpenoid">triterpenoid</a>. It is commonly found in woody angiosperms and as a result is often used as an indicator of these plants in the fossil record. It is a member of the oleanoid series, which consists of pentacyclic triterpenoids (such as beta-<a href="Amyrin" title="Amyrin">amyrin</a> and <a href="Taraxerol" title="Taraxerol">taraxerol</a>) where all rings are six-membered.

</p>

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

<p>Oleanane is a pentacyclic triterpenoid, a class of molecules made up of six connected isoprene units. The naming of both the ring structures and individual carbon atoms in oleanane is the same as in <a href="Steroid" title="Steroid">steroids</a>. As such, it consists of a A, B, C, D, and E ring, all of which are six-membered rings.<sup id="cite_ref-:0_2-0" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>

</p><p>The structure of oleanane contains a number of different methyl groups, that vary in orientation between different oleananes. For example, in 18-alpha-oleanane contains a downward facing methyl group for the 18th carbon atom, while 18-beta-oleanane contains an upward facing methyl group at the same position.

</p><p>A and B rings of the oleanane structure are identical to that of <a href="Hopane" title="Hopane">hopane</a>. As a result, both molecules produce a fragment of m/z 191. Because this fragment is often used to identify hopanes, oleanane can be mis-identified in hopane analysis.

</p>

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

<p>Like other triterpenoids, are formed from six combined isoprene units.<sup id="cite_ref-:0_2-1" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> These isoprene units can be combined via a number of different pathways. In eukaryotes (including plants), this pathway is the mevalonate (MVA) pathway. For the formation of steroids and other triterpenoids the isoprenoids are combined into a precursor known as squalene, which then undergoes enzymatic cyclization to produce the various different triterpenoids, including oleanane.<sup id="cite_ref-:0_2-2" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>

</p><p>Once the oleananes have been transported into rocks or sediments they will undergo further alteration before they are measured.

</p>

<div class="mw-heading mw-heading2"><h2 id="Measurement_in_Rock_Samples">Measurement in Rock Samples</h2></div>

<p>Oleananes can be identified in extracts from rock samples (or plants) using GC/MS. A GC/MS is a gas chromatograph coupled with a mass spectrometer. The sample is first injected into the system, then run through as chromatographic column. How fast a material moves through a chromatographic column depends on how long it spends in each of the two stages there. Compounds that partition more into the mobile phase will move faster as opposed to compounds that partition more into the stationary phase. The result of this is a separation of different organic molecules based on their retention time in the GC.

</p><p>After being separated by the GC, the compounds can then be analyzed by a mass spectrometer. Each compound will contain a characteristic mass spectrum, based on the fragments it splits into during ionization in the mass spectrometer. This means that the GC can not only separate different types of molecules, it can also identify them.

</p><p>As mentioned above, they have a characteristic mass fragment at m/z = 191, and thus will appear in the same selected ion chromatograph (SIC) as hopanes. This can help one identify them in GC/MS datasets.

</p>

<div class="mw-heading mw-heading3"><h3 id="As_a_biomarker">As a biomarker</h3></div>

<p>Oleanane has been identified as a compound in modern day angiosperms.<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><p>Because of this, its presence is the fossil record has also been used to trace angiosperms through the fossil record. For example, the ratio of 18-alpha-oleanane + 18-beta-oleanane:17-alpha-hopane in rock extracts (and associated petroleums/oils) has been found to correlate (at least broadly) to the presence of angiosperms in the fossil record.<sup id="cite_ref-:2_4-0" class="reference"><a href="#cite_note-:2-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In this study, the combination of alpha and beta-oleanane were used as indicators for the presence of angiosperms. They are normalized to hopanes, which are broadly present in almost all rock extracts coming from petroleum. Furthermore, because of the structural similarities between hopanes and oleananes, it is assumed that they will react similarly to the various weathering processes that degrade the biomarkers present. As such, the ratio of hopanes to oleananes should be similar to the initial ratio, and unaffected by processes occurring in the rock after fossilization.

</p><p>There is some delay in the accepted increases in taxonomic diversification of angiosperms (which occurred during the mid-Cretaceous period) and the increase of oleanane concentrations in the fossil record (which occurred in the late-Cretaceous or even after). This could be due to a number of factors, one being that the early angiosperms were more herbaceous than woody and that woody angiosperms only appeared after further taxonomic diversification.<sup id="cite_ref-:2_4-1" class="reference"><a href="#cite_note-:2-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>

</p><p>Lastly, the study introduced the idea of an "oleanane parameter," which could be used in assessing angiosperm input to petroleum sources. This, in turn, gives some idea of the age of said petroleum sources.<sup id="cite_ref-:2_4-2" class="reference"><a href="#cite_note-:2-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>

</p><p>That being said, the presence of angiosperms may not be the only thing affecting the oleanane content of sediments, rock extracts and petroleum. For example, there is evidence that contact with seawater during early sedimentation processes can increase the concentration of oleananes in the mature sediment.<sup id="cite_ref-:1_5-0" class="reference"><a href="#cite_note-:1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> This evidence comes from the fact that various indicators of marine influence (C27/C29 sterane ratios, changes in elemental composition in the downstream direction that are indicative of the infiltration of water into the system and the homophane index). Despite this, it is still unclear as to how marine influence enhances the expression of oleananes (thus increasing observed concentration). Some ideas include the changes in pH, Eh and the microbial environment that come with the interaction with seawater.<sup id="cite_ref-:1_5-1" class="reference"><a href="#cite_note-:1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>

</p>

<ul><li><a href="Oleanolic_acid" title="Oleanolic acid">Oleanolic acid</a></li></ul>

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

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</style><cite id="CITEREFInternational_Union_of_Pure_and_Applied_Chemistry2014" class="citation book cs1"><a href="International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> (2014). <i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013</i>. <a href="Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. p. 1538. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069">10.1039/9781849733069</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-85404-182-4</bdi>.</cite></span>

</li>

<li id="cite_note-:0-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:0_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://sites.google.com/site/killopsiog/">"killopsiog"</a>. <i>sites.google.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2019-05-15</span></span>.</cite></span>

</li>

<li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><cite id="CITEREFBaas1985" class="citation journal cs1">Baas, Wim J. (January 1985). "Naturally occurring seco-ring-A-triterpenoids and their possible biological significance". <i>Phytochemistry</i>. <b>24</b> (9): <span class="nowrap">1875–</span>1889. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1985PChem..24.1875B">1985PChem..24.1875B</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0031-9422%2800%2983085-x">10.1016/s0031-9422(00)83085-x</a>.</cite></span>

</li>

<li id="cite_note-:2-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-:2_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:2_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:2_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFTaylorPeakmanHickeyFago1994" class="citation journal cs1">Taylor, David Winship; Peakman, Torren M.; Hickey, Leo J.; Fago, Frederick J.; Huizinga, Bradley J.; Dahl, Jeremy; Moldowan, J. Michael (1994-08-05). "The Molecular Fossil Record of Oleanane and Its Relation to Angiosperms". <i>Science</i>. <b>265</b> (5173): <span class="nowrap">768–</span>771. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1994Sci...265..768M">1994Sci...265..768M</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.265.5173.768">10.1126/science.265.5173.768</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0036-8075">0036-8075</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17736275">17736275</a>.</cite></span>

</li>

<li id="cite_note-:1-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.researchgate.net/publication/223465178">"Oleananes in oils and sediments: Evidence of marine influence during early diagenesis? | Request PDF"</a>. <i>ResearchGate</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2019-05-15</span></span>.</cite></span>

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</ol></div></div>

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</style><div id="Saponin_Glycosides65" style="font-size:114%;margin:0 4em"><a href="Saponin" title="Saponin">Saponin</a> <a href="Glycoside" title="Glycoside">Glycosides</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Sapogenin" title="Sapogenin">Sapogenin</a> (<a href="Aglycone" title="Aglycone">aglycone</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Steroidal<br> (C<sub>27</sub> skeleton)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Diosgenin" title="Diosgenin">Diosgenin</a></li>

<li><a href="Yamogenin" title="Yamogenin">Yamogenin</a></li>

<li><a href="Sarsasapogenin" title="Sarsasapogenin">Sarsasapogenin</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Triterpene<br> (C<sub>30</sub> skeleton)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Tetracyclic</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Lanostane" title="Lanostane">Lanostane</a></li>

<li><a href="Dammarane" title="Dammarane">Dammarane</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pentacyclic</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Lupane_triterpene" class="mw-redirect" title="Lupane triterpene">Lupane</a></li>

<li>

<ul><li><a href="Hederagenin" title="Hederagenin">Hederagenin</a></li>

<li><a href="Enoxolone" title="Enoxolone">Enoxolone</a></li>

<li><a href="Maslinic_acid" title="Maslinic acid">Maslinic acid</a></li></ul></li>

<li>Ursane</li>

<li><a href="Hopane" title="Hopane">Hopane</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Glycone" class="mw-redirect" title="Glycone">Glycone</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Monosaccharide" title="Monosaccharide">Monosaccharide</a></li>

<li><a href="Oligosaccharide" title="Oligosaccharide">Oligosaccharide</a></li></ul>

</div></td></tr></tbody></table></div></div><div><div class="zim-footer">

This article is issued from <a class="external text" title="Last edited on 2025-01-12" href="https://en.wikipedia.org/wiki/?title=Oleanane&oldid=1268917566">Wikipedia</a>. The text is available under <a class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">Creative Commons Attribution-Share Alike 4.0</a> unless otherwise noted. Additional terms may apply for the media files.

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