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class="vector-toc-numb">2</span> <span>Dietary phytosterols</span> </div> </a> <ul id="toc-Dietary_phytosterols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Health_claims" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Health_claims"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Health claims</span> </div> </a> <button aria-controls="toc-Health_claims-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Health claims subsection</span> </button> <ul id="toc-Health_claims-sublist" class="vector-toc-list"> <li id="toc-EFSA" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#EFSA"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>EFSA</span> </div> </a> <ul id="toc-EFSA-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-FDA" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#FDA"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>FDA</span> </div> </a> <ul id="toc-FDA-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Health_Canada" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Health_Canada"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Health Canada</span> </div> </a> <ul id="toc-Health_Canada-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Cholesterol_lowering" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Cholesterol_lowering"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Cholesterol lowering</span> </div> </a> <ul id="toc-Cholesterol_lowering-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" 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href="#Functions_in_plants"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Functions in plants</span> </div> </a> <ul id="toc-Functions_in_plants-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" 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Available in 30 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-30" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">30 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D8%A7%D9%8A%D8%AA%D9%88%D8%B3%D8%AA%D9%8A%D8%B1%D9%88%D9%84" title="فايتوستيرول – Arabic" lang="ar" hreflang="ar" data-title="فايتوستيرول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Fitosterol" title="Fitosterol – Bosnian" lang="bs" hreflang="bs" data-title="Fitosterol" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fitosterol" title="Fitosterol – Catalan" lang="ca" hreflang="ca" data-title="Fitosterol" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Fytosterol" title="Fytosterol – Czech" lang="cs" hreflang="cs" data-title="Fytosterol" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phytosterine" title="Phytosterine – German" lang="de" hreflang="de" data-title="Phytosterine" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Fitoesterol" title="Fitoesterol – Spanish" lang="es" hreflang="es" data-title="Fitoesterol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Fitosterol" title="Fitosterol – Basque" lang="eu" hreflang="eu" data-title="Fitosterol" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%DB%8C%D8%AA%D9%88%D8%A7%D8%B3%D8%AA%D8%B1%D9%88%D9%84" title="فیتواسترول – Persian" lang="fa" hreflang="fa" data-title="فیتواسترول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Phytost%C3%A9rol" title="Phytostérol – French" lang="fr" hreflang="fr" data-title="Phytostérol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Fitosterol" title="Fitosterol – Galician" lang="gl" hreflang="gl" data-title="Fitosterol" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%94%BC%ED%86%A0%EC%8A%A4%ED%85%8C%EB%A1%A4" title="피토스테롤 – Korean" lang="ko" hreflang="ko" data-title="피토스테롤" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AB%E0%A4%BE%E0%A4%87%E0%A4%9F%E0%A5%8B%E0%A4%B8%E0%A5%8D%E0%A4%9F%E0%A5%87%E0%A4%B0%E0%A5%89%E0%A4%B2" title="फाइटोस्टेरॉल – Hindi" lang="hi" hreflang="hi" data-title="फाइटोस्टेरॉल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Fitosterol" title="Fitosterol – Indonesian" lang="id" hreflang="id" data-title="Fitosterol" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Fitosteroli" title="Fitosteroli – Italian" lang="it" hreflang="it" data-title="Fitosteroli" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Fitosterol" title="Fitosterol – Malay" lang="ms" hreflang="ms" data-title="Fitosterol" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Plantensterolen" title="Plantensterolen – Dutch" lang="nl" hreflang="nl" data-title="Plantensterolen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A3%E3%83%88%E3%82%B9%E3%83%86%E3%83%AD%E3%83%BC%E3%83%AB" title="フィトステロール – Japanese" lang="ja" hreflang="ja" data-title="フィトステロール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Fytosterol" title="Fytosterol – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Fytosterol" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Fytosterol" title="Fytosterol – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Fytosterol" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fitosterole" title="Fitosterole – Polish" lang="pl" hreflang="pl" data-title="Fitosterole" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Fitoesterol" title="Fitoesterol – Portuguese" lang="pt" hreflang="pt" data-title="Fitoesterol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Fitosterol" title="Fitosterol – Romanian" lang="ro" hreflang="ro" data-title="Fitosterol" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%B8%D1%82%D0%BE%D1%81%D1%82%D0%B5%D1%80%D0%B8%D0%BD%D1%8B" title="Фитостерины – Russian" lang="ru" hreflang="ru" data-title="Фитостерины" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Fitosterol" title="Fitosterol – Slovenian" lang="sl" hreflang="sl" data-title="Fitosterol" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Fitosterol" title="Fitosterol – Serbian" lang="sr" hreflang="sr" data-title="Fitosterol" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-fi badge-Q70893996 mw-list-item" title=""><a href="https://fi.wikipedia.org/wiki/Kasvisterolit" title="Kasvisterolit – Finnish" lang="fi" hreflang="fi" data-title="Kasvisterolit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Fitosterol" title="Fitosterol – Turkish" lang="tr" hreflang="tr" data-title="Fitosterol" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D1%96%D1%82%D0%BE%D1%81%D1%82%D0%B5%D1%80%D0%B8%D0%BD%D0%B8" title="Фітостерини – Ukrainian" 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src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Sitosterol_structure.svg/220px-Sitosterol_structure.svg.png" decoding="async" width="220" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Sitosterol_structure.svg/330px-Sitosterol_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Sitosterol_structure.svg/440px-Sitosterol_structure.svg.png 2x" data-file-width="1220" data-file-height="720" /></a><figcaption><a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, a prototypical phytosterol</figcaption></figure> <p><b>Phytosterols</b> are <a href="/wiki/Phytosteroid" title="Phytosteroid">phytosteroids</a>, similar to <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>, that serve as structural components of biological membranes of <a href="/wiki/Plant" title="Plant">plants</a>.<sup id="cite_ref-moreau_1-0" class="reference"><a href="#cite_note-moreau-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They encompass plant <a href="/wiki/Sterol" title="Sterol">sterols</a> and <a href="/wiki/Stanol_ester" title="Stanol ester">stanols</a>.<sup id="cite_ref-moreau_1-1" class="reference"><a href="#cite_note-moreau-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> More than 250 sterols and related compounds have been identified.<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> Free phytosterols extracted from oils are insoluble in water, relatively insoluble in oil, and soluble in alcohols. </p><p>Phytosterol-enriched foods and <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplements</a> have been marketed for decades.<sup id="cite_ref-aafc_3-0" class="reference"><a href="#cite_note-aafc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Despite well-documented <a href="/wiki/LDL_cholesterol" class="mw-redirect" title="LDL cholesterol">LDL cholesterol</a>-lowering effects from long-term consumption of phytosterols, there is insufficient evidence for an effect on <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular diseases</a>, <a href="/wiki/Fasting_blood_sugar" class="mw-redirect" title="Fasting blood sugar">fasting blood sugar</a>, <a href="/wiki/Glycated_hemoglobin" title="Glycated hemoglobin">glycated hemoglobin</a>, or overall <a href="/wiki/Mortality_rate" title="Mortality rate">mortality rate</a>.<sup id="cite_ref-Genser_2012_4-0" class="reference"><a href="#cite_note-Genser_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><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> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=1" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Steroid_numbering.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Steroid_numbering.svg/275px-Steroid_numbering.svg.png" decoding="async" width="275" height="177" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Steroid_numbering.svg/413px-Steroid_numbering.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Steroid_numbering.svg/550px-Steroid_numbering.svg.png 2x" data-file-width="512" data-file-height="330" /></a><figcaption>Nomenclature of the structure of a tetracyclic damarane triterpene</figcaption></figure> <p>They have a fused polycyclic structure and vary in carbon side chains and / or presence or absence of a <a href="/wiki/Double_bond" title="Double bond">double bond</a> (saturation).<sup id="cite_ref-aafc_3-1" class="reference"><a href="#cite_note-aafc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> They<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="None of the example phytosterols given here have a 4-methyl group, so what are "they" and what are some examples of natural ones with such a group? Lupeol does not count. (April 2022)">clarification needed</span></a></i>]</sup> are divided into 4,4-dimethyl phytosterols, 4-monomethyl phytosterols, and 4-desmethyl phytosterols based on the location of methyl groups at the carbon-4 position.<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> Stanols are <a href="/wiki/Saturated_fat" title="Saturated fat">saturated</a> sterols, having no double bonds in the sterol ring structure. </p><p>The molecule in the article lead is <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>. The nomenclature is shown on the right. </p> <ul><li>By removing carbon 24<sup>2</sup>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a> is obtained.</li> <li>By removing carbons 24<sup>1</sup> and 24<sup>2</sup>, <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> is obtained.</li> <li>Removing a hydrogen from carbons 22 and 23 yields <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a> (stigmasta-5,22-dien-3β-ol).</li> <li>By hydrogenating the double bond between carbons 5 and 6, β-<a href="/wiki/Sitostanol" class="mw-redirect" title="Sitostanol">sitostanol</a> (Stigmastanol) is obtained.</li> <li>By hydrogenating the double bond between carbons 5 and 6 and removing carbon 24<sup>2</sup>, <a href="/wiki/Campestanol" title="Campestanol">campestanol</a> is obtained.</li> <li>Removing carbon 24<sup>2</sup> and hydrogens from carbons 22 and 23, and inverting the stereochemistry at C-24 yields <a href="/wiki/Brassicasterol" title="Brassicasterol">brassicasterol</a> (ergosta-5,22-dien-3β-ol).</li> <li>Further removal of hydrogens from carbons 7 and 8 from brassicasterol yields <a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a> (ergosta-5,7,22-trien-3β-ol). Important: Ergosterol is not a plant sterol. Ergosterol is a component of fungal cell membranes, serving the same function in fungi that cholesterol serves in animal cells.</li></ul> <p>In addition: </p> <ul><li>Esterification of the hydroxyl group at carbon 3 with fatty/organic acids or carbohydrates results in plant <a href="/wiki/Sterol_ester" title="Sterol ester">sterol esters</a>, i.e. oleates, ferulates and (acyl) glycosides.</li></ul> <ul class="gallery mw-gallery-nolines"> <li class="gallerycaption">Structures of some common phytosterols</li> <li class="gallerybox" style="width: 125px"> <div class="thumb" style="width: 120px;"><span typeof="mw:File"><a href="/wiki/File:Sitosterol_structure.svg" class="mw-file-description" title="β-sitosterol"><img alt="β-sitosterol" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Sitosterol_structure.svg/120px-Sitosterol_structure.svg.png" decoding="async" width="120" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Sitosterol_structure.svg/180px-Sitosterol_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Sitosterol_structure.svg/240px-Sitosterol_structure.svg.png 2x" data-file-width="1220" data-file-height="720" /></a></span></div> <div class="gallerytext"><a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a></div> </li> <li class="gallerybox" style="width: 125px"> <div class="thumb" style="width: 120px;"><span typeof="mw:File"><a href="/wiki/File:Campesterol.svg" class="mw-file-description" title="Campesterol"><img alt="Campesterol" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Campesterol.svg/120px-Campesterol.svg.png" decoding="async" width="120" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Campesterol.svg/180px-Campesterol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Campesterol.svg/240px-Campesterol.svg.png 2x" data-file-width="1575" data-file-height="1165" /></a></span></div> <div class="gallerytext"><a href="/wiki/Campesterol" title="Campesterol">Campesterol</a></div> </li> <li class="gallerybox" style="width: 125px"> <div class="thumb" style="width: 120px;"><span typeof="mw:File"><a href="/wiki/File:Stigmasterin.svg" class="mw-file-description" title="Stigmasterol"><img alt="Stigmasterol" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Stigmasterin.svg/120px-Stigmasterin.svg.png" decoding="async" width="120" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Stigmasterin.svg/180px-Stigmasterin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Stigmasterin.svg/240px-Stigmasterin.svg.png 2x" data-file-width="441" data-file-height="261" /></a></span></div> <div class="gallerytext"><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a></div> </li> <li class="gallerybox" style="width: 125px"> <div class="thumb" style="width: 120px;"><span typeof="mw:File"><a href="/wiki/File:Stigmastanol.svg" class="mw-file-description" title="Stigmastanol"><img alt="Stigmastanol" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Stigmastanol.svg/120px-Stigmastanol.svg.png" decoding="async" width="120" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Stigmastanol.svg/180px-Stigmastanol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Stigmastanol.svg/240px-Stigmastanol.svg.png 2x" data-file-width="512" data-file-height="311" /></a></span></div> <div class="gallerytext"><a href="/wiki/Stigmastanol" title="Stigmastanol">Stigmastanol</a></div> </li> <li class="gallerybox" style="width: 125px"> <div class="thumb" style="width: 120px;"><span typeof="mw:File"><a href="/wiki/File:Campestanol.svg" class="mw-file-description" title="Campestanol"><img alt="Campestanol" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Campestanol.svg/120px-Campestanol.svg.png" decoding="async" width="120" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Campestanol.svg/180px-Campestanol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Campestanol.svg/240px-Campestanol.svg.png 2x" data-file-width="343" data-file-height="180" /></a></span></div> <div class="gallerytext"><a href="/wiki/Campestanol" title="Campestanol">Campestanol</a></div> </li> <li class="gallerybox" style="width: 125px"> <div class="thumb" style="width: 120px;"><span typeof="mw:File"><a href="/wiki/File:Brassicasterol.svg" class="mw-file-description" title="Brassicasterol"><img alt="Brassicasterol" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Brassicasterol.svg/120px-Brassicasterol.svg.png" decoding="async" width="120" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Brassicasterol.svg/180px-Brassicasterol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Brassicasterol.svg/240px-Brassicasterol.svg.png 2x" data-file-width="512" data-file-height="367" /></a></span></div> <div class="gallerytext"><a href="/wiki/Brassicasterol" title="Brassicasterol">Brassicasterol</a></div> </li> <li class="gallerybox" style="width: 125px"> <div class="thumb" style="width: 120px;"><span typeof="mw:File"><a href="/wiki/File:Cycloartenol.svg" class="mw-file-description" title="Cycloartenol"><img alt="Cycloartenol" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Cycloartenol.svg/120px-Cycloartenol.svg.png" decoding="async" width="120" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Cycloartenol.svg/180px-Cycloartenol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Cycloartenol.svg/240px-Cycloartenol.svg.png 2x" data-file-width="324" data-file-height="171" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cycloartenol" title="Cycloartenol">Cycloartenol</a></div> </li> </ul> <ul class="gallery mw-gallery-nolines"> <li class="gallerycaption">Structures of some common sterols, for comparison</li> <li class="gallerybox" style="width: 125px"> <div class="thumb" style="width: 120px;"><span typeof="mw:File"><a href="/wiki/File:Cholesterol.svg" class="mw-file-description" title="Cholesterol"><img alt="Cholesterol" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Cholesterol.svg/120px-Cholesterol.svg.png" decoding="async" width="120" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Cholesterol.svg/180px-Cholesterol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Cholesterol.svg/240px-Cholesterol.svg.png 2x" data-file-width="613" data-file-height="390" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></div> </li> <li class="gallerybox" style="width: 125px"> <div class="thumb" style="width: 120px;"><span typeof="mw:File"><a href="/wiki/File:Ergosterol.svg" class="mw-file-description" title="Ergosterol"><img alt="Ergosterol" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Ergosterol.svg/120px-Ergosterol.svg.png" decoding="async" width="120" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Ergosterol.svg/180px-Ergosterol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Ergosterol.svg/240px-Ergosterol.svg.png 2x" data-file-width="1708" data-file-height="1128" /></a></span></div> <div class="gallerytext"><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Dietary_phytosterols">Dietary phytosterols</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=2" title="Edit section: Dietary phytosterols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The richest naturally occurring sources of phytosterols are vegetable oils and products made from them. Sterols can be present in the free form and as <a href="/wiki/Fatty_acid_ester" title="Fatty acid ester">fatty acid esters</a> and <a href="/wiki/Glycolipids" class="mw-redirect" title="Glycolipids">glycolipids</a>. The bound form is usually hydrolyzed in the small intestines by <a href="/wiki/Pancreatic_enzyme" class="mw-redirect" title="Pancreatic enzyme">pancreatic enzymes</a>.<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> Some of the sterols are removed during the deodorization step of <a href="/wiki/Hydrotreated_vegetable_oil" title="Hydrotreated vegetable oil">refining oils</a> and fats, without, however, changing their relative composition. Sterols are therefore a useful tool in checking authenticity. </p><p>As common sources of phytosterols, <a href="/wiki/Vegetable_oil" title="Vegetable oil">vegetable oils</a> have been developed as <a href="/wiki/Margarine" title="Margarine">margarine</a> products highlighting phytosterol content.<sup id="cite_ref-aafc_3-2" class="reference"><a href="#cite_note-aafc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Cereal products, vegetables, fruit and berries, which are not as rich in phytosterols, may also be significant sources of phytosterols due to their higher intakes.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>The intake of naturally occurring phytosterols ranges between ~200–300 mg/day depending on eating habits.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Specially designed vegetarian experimental diets have been produced yielding upwards of 700 mg/day.<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> The most commonly occurring phytosterols in the human diet are β-sitosterol, campesterol and stigmasterol,<sup id="cite_ref-aafc_3-3" class="reference"><a href="#cite_note-aafc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> which account for about 65%, 30% and 3% of diet contents, respectively.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The most common plant <i>stanols</i> in the human diet are sitostanol and campestanol, which combined make up about 5% of dietary phytosterol.<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> <table class="wikitable"> <caption>Sterol composition in crude oils (as percentage of total sterol fraction)<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th> </th> <th><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> </th> <th><a href="/wiki/Brassicasterol" title="Brassicasterol">Brassicasterol</a> </th> <th><a href="/wiki/Campesterol" title="Campesterol">Campesterol</a> </th> <th><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a> </th> <th><a href="/wiki/%CE%92-Sitosterol" title="Β-Sitosterol">β-Sitosterol</a> </th> <th>∆5-<a href="/wiki/Avenasterol" title="Avenasterol">Avenasterol</a> </th> <th><a href="/wiki/Isofucosterol" title="Isofucosterol">∆7-Avenasterol</a> </th> <th>∆7-<a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a> </th></tr> <tr> <td><a href="/wiki/Coconut_oil" title="Coconut oil">Coconut oil</a> </td> <td>0.6 – 2 </td> <td>0 – 0.9 </td> <td>7 – 10 </td> <td>12 – 18 </td> <td>50 – 70 </td> <td>5 – 16 </td> <td>0.6 – 2 </td> <td>2 – 8 </td></tr> <tr> <td><a href="/wiki/Corn_oil" title="Corn oil">Corn oil</a> </td> <td>0.2 – 0.6 </td> <td>0 – 0.2 </td> <td>18 – 24 </td> <td>4 – 8 </td> <td>55 – 67 </td> <td>4 – 8 </td> <td>1 – 3 </td> <td>1 – 4 </td></tr> <tr> <td><a href="/wiki/Cottonseed_oil" title="Cottonseed oil">Cottonseed oil</a> </td> <td>0.7 – 2.3 </td> <td>0.1 – 0.9 </td> <td>7.2 – 8.4 </td> <td>1.2 – 1.8 </td> <td>80 – 90 </td> <td>1.9 – 3.8 </td> <td>1.4 – 3.3 </td> <td>0.7 – 1.4 </td></tr> <tr> <td><a href="/wiki/Olive_oil" title="Olive oil">Olive oil</a> </td> <td>0 – 0.5 </td> <td> </td> <td>2.3 – 3.6 </td> <td>0.6 – 2 </td> <td>75.6 – 90 </td> <td>3.1 – 14 </td> <td> </td> <td>0 – 4 </td></tr> <tr> <td><a href="/wiki/Palm_oil" title="Palm oil">Palm oil</a> </td> <td>2.2 – 6.7 </td> <td> </td> <td>18.7 – 29.1 </td> <td>8.9 – 13.9 </td> <td>50.2 – 62.1 </td> <td>0 – 2.8 </td> <td>0 – 5.1 </td> <td>0.2 – 2.4 </td></tr> <tr> <td><a href="/wiki/Palm_kernel_oil" title="Palm kernel oil">Palm kernel oil</a> </td> <td>1 – 3.7 </td> <td>0 – 0.3 </td> <td>8.4 – 12.7 </td> <td>12.3 – 16.1 </td> <td>62.6 – 70.4 </td> <td>4 – 9 </td> <td>0 – 1.4 </td> <td>0 – 2.1 </td></tr> <tr> <td><a href="/wiki/Peanut_oil" title="Peanut oil">Peanut oil</a> </td> <td>0.6 – 3.8 </td> <td>0 – 0.2 </td> <td>12 – 20 </td> <td>5 – 13 </td> <td>48 – 65 </td> <td>7 – 9 </td> <td>0 – 5 </td> <td>0 – 5 </td></tr> <tr> <td><a href="/wiki/Rapeseed_oil" title="Rapeseed oil">Rapeseed oil</a> </td> <td>0.4 – 2 </td> <td>5 – 13 </td> <td>18 – 39 </td> <td>0 – 0.7 </td> <td>45 – 58 </td> <td>0 – 6.6 </td> <td>0 – 0.8 </td> <td>0 – 5 </td></tr> <tr> <td><a href="/wiki/Soybean_oil" title="Soybean oil">Soybean oil</a> </td> <td>0.6 – 1.4 </td> <td>0 – 0.3 </td> <td>16 – 24 </td> <td>16 – 19 </td> <td>52 – 58 </td> <td>2 – 4 </td> <td>1 – 4.5 </td> <td>1.5 – 5 </td></tr> <tr> <td><a href="/wiki/Sunflower_oil" title="Sunflower oil">Sunflower oil</a> </td> <td>0.2 – 1.3 </td> <td>0 – 0.2 </td> <td>7 – 13 </td> <td>8 – 11 </td> <td>56 – 63 </td> <td>2 – 7 </td> <td>7 – 13 </td> <td>3 – 6 </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Health_claims">Health claims</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=3" title="Edit section: Health claims"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="EFSA">EFSA</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=4" title="Edit section: EFSA"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The European Foods Safety Authority (EFSA) concluded that <a href="/wiki/Blood_cholesterol" class="mw-redirect" title="Blood cholesterol">blood cholesterol</a> can be reduced on average by 7 to 10.5% if a person consumes 1.5 to 2.4 grams of plant sterols and stanols per day, an effect usually established within 2–3 weeks. Longer-term studies extending up to 85 weeks showed that the cholesterol-lowering effect could be sustained.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Based on this and other efficacy data, the EFSA scientific panel provided the following health advisory: "Plant sterols have been shown to lower/reduce blood cholesterol. Blood cholesterol lowering may reduce the risk of <a href="/wiki/Coronary_artery_disease" title="Coronary artery disease">coronary heart disease</a>".<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="FDA">FDA</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=5" title="Edit section: FDA"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">FDA</a> has approved the following claim for phytosterols: <i>For plant <a href="/wiki/Sterol_ester" title="Sterol ester">sterol esters</a></i>: (i) Foods containing at least 0.65 g per serving of plant sterol esters, eaten twice a day with meals for a daily total intake of at least 1.3 g, as part of a diet low in saturated fat and cholesterol, may reduce the risk of heart disease. A serving of [name of the food] supplies ___grams of vegetable oil sterol esters.<sup id="cite_ref-fda_16-0" class="reference"><a href="#cite_note-fda-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> <i>For plant stanol esters</i>: (i) Foods containing at least 1.7 g per serving of plant stanol esters, eaten twice a day with meals for a total daily intake of at least 3.4 g, as part of a diet low in saturated fat and cholesterol, may reduce the risk of heart disease. A serving of [name of the food] supplies ___grams of plant stanol esters.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Reviewing clinical trials involving phytosterol supplementation, the FDA concluded that when consumed in the range of 1 to 3 grams in enriched foods, phytosterols resulted in statistically significant (5-15%) reductions in blood LDL cholesterol levels relative to placebo. The FDA also concluded that a daily dietary intake of 2 grams a day of phytosterols (expressed as non-esterified phytosterols) is required to demonstrate a relationship between phytosterol consumption and cholesterol lowering for reduced CVD risk.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Health_Canada">Health Canada</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=6" title="Edit section: Health Canada"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a> reviewed the evidence of 84 randomized controlled trials published between 1994 and 2007 involving phytosterol supplementation. An average 8.8% reduction in LDL-cholesterol was observed at a mean intake of 2 grams per day.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Health Canada concluded that sufficient scientific evidence exists to support a relationship between phytosterol consumption and blood cholesterol lowering. Based on this evidence, Health Canada approved the following statements for qualifying foods intended for <a href="/wiki/Hypercholesterolemia" title="Hypercholesterolemia">hypercholesterolemic</a> individuals: Primary statement: "[serving size from Nutrition Facts table in metric and common household measures] of [naming the product] provides X% of the daily amount* of plant sterols shown to help reduce/lower cholesterol in adults." Two additional statements that could be used in combination or alone, adjacent to the primary statement, without any intervening printed, written or graphic material: "Plant sterols help reduce [or help lower] cholesterol." This statement when used, shall be shown in letters up to twice the size and prominence as those of the primary statement. "High cholesterol is a risk factor for heart disease." This statement when used, shall be shown in letters up to the same size and prominence as those of the primary statement. </p> <div class="mw-heading mw-heading2"><h2 id="Cholesterol_lowering">Cholesterol lowering</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=7" title="Edit section: Cholesterol lowering"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The ability of phytosterols to reduce <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> levels was first demonstrated in humans in 1953.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> From 1954 to 1982, phytosterols were subsequently marketed as a pharmaceutical under the name Cytellin as a treatment for elevated cholesterol.<sup id="cite_ref-Jones2007_22-0" class="reference"><a href="#cite_note-Jones2007-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Unlike the <a href="/wiki/Statin" title="Statin">statins</a>, where cholesterol lowering has been proven to reduce risk of <a href="/wiki/Cardiovascular_diseases" class="mw-redirect" title="Cardiovascular diseases">cardiovascular diseases</a> (CVD) and overall mortality under well-defined circumstances, the evidence has been inconsistent for phytosterol-enriched foods or supplements to lower risk of CVD, with two reviews indicating no or marginal effect,<sup id="cite_ref-Weingaertner_2008_23-0" class="reference"><a href="#cite_note-Weingaertner_2008-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Genser_2012_4-1" class="reference"><a href="#cite_note-Genser_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and another review showing evidence for use of dietary phytosterols to attain a cholesterol-lowering effect.<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><p>Coadministration of statins with phytosterol-enriched foods increases the cholesterol-lowering effect of phytosterols, again without any proof of clinical benefit and with anecdotal evidence of potential <a href="/wiki/Adverse_effects" class="mw-redirect" title="Adverse effects">adverse effects</a>.<sup id="cite_ref-Weingaertner_2008_23-1" class="reference"><a href="#cite_note-Weingaertner_2008-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Statins work by reducing cholesterol synthesis via inhibition of the rate-limiting <a href="/wiki/HMG-CoA_reductase" title="HMG-CoA reductase">HMG-CoA reductase</a> <a href="/wiki/Enzyme" title="Enzyme">enzyme</a>. Phytosterols reduce cholesterol levels by competing with cholesterol absorption in the gut via one or several possible mechanisms,<sup id="cite_ref-nguyen_25-0" class="reference"><a href="#cite_note-nguyen-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> an effect that complements statins. Phytosterols further reduce cholesterol levels by about 9% to 17% in statin users.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> The type or dose of statin does not appear to affect the cholesterol-lowering efficacy of phytosterols.<sup id="cite_ref-Katan2003_29-0" class="reference"><a href="#cite_note-Katan2003-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>Because of their cholesterol reducing properties, some manufacturers are using sterols or stanols as a food additive.<sup id="cite_ref-aafc_3-4" class="reference"><a href="#cite_note-aafc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=8" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phytosterols have a long history of safe use,<sup id="cite_ref-aafc_3-5" class="reference"><a href="#cite_note-aafc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> dating back to Cytellin, the pharmaceutical preparation of phytosterols marketed in the US from 1954 to 1982.<sup id="cite_ref-Jones2007_22-1" class="reference"><a href="#cite_note-Jones2007-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Phytosterol esters have <a href="/wiki/Generally_recognized_as_safe" title="Generally recognized as safe">generally recognized as safe</a> (GRAS) status in the US.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Phytosterol-containing <a href="/wiki/Functional_food" title="Functional food">functional foods</a> were subject to postlaunch monitoring after being introduced to the EU market in 2000, and no unpredicted side effects were reported.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>A potential safety concern regarding phytosterol consumption is in patients with <a href="/wiki/Sitosterolemia" title="Sitosterolemia">phytosterolaemia</a>, a rare genetic disorder which results in a 50- to 100-fold increase in blood plant sterol levels and is associated with rapid development of coronary atherosclerosis. Phytosterolaemia has been linked to mutations in the ABCG5/G8 proteins which pump plant sterols out of enterocytes and hepatocytes into the lumen and bile ducts, respectively. Plant sterol levels in the blood have been shown to be positively, negatively or not associated with CVD risk, depending on the study population investigated.<sup id="cite_ref-Silbernagel2009_33-0" class="reference"><a href="#cite_note-Silbernagel2009-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rajaratnam2000_37-0" class="reference"><a href="#cite_note-Rajaratnam2000-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Assmann2006_38-0" class="reference"><a href="#cite_note-Assmann2006-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sudhop2002_39-0" class="reference"><a href="#cite_note-Sudhop2002-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>The link between plant sterols and CVD or CHD risk is complicated because phytosterol levels reflect cholesterol absorption. (See <a href="#Phytosterols_as_a_marker_for_cholesterol_absorption">Phytosterols as a marker for cholesterol absorption</a>).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2012)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Sterol_vs_stanol">Sterol vs stanol</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=9" title="Edit section: Sterol vs stanol"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The equivalent ability and safety of plant sterols and plant <a href="/wiki/Stanol" class="mw-redirect" title="Stanol">stanols</a> to lower cholesterol continues to be a hotly debated topic. Plant sterols and stanols, when compared head-to-head in clinical trials, have been shown to equally reduce cholesterol levels.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> A meta-analysis of 14 randomized, controlled trials comparing plant sterols to plant stanols directly at doses of 0.6 to 2.5 g/day showed no difference between the two forms on total cholesterol, LDL cholesterol, HDL cholesterol, or triglyceride levels.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> Trials looking at high doses (> 4 g/day) of plant sterols or stanols are very limited, and none have yet to be completed comparing the same high dose of plant sterol to plant stanol. </p><p>The debate regarding sterol vs. stanol safety is centered on their differing intestinal absorption and resulting plasma concentrations. Phytostanols have a lower estimated intestinal absorption rate (0.02 - 0.3%) than phytosterols (0.4 - 5%) and consequently blood phytostanol concentration is generally lower than phytosterol concentration.<sup id="cite_ref-Weingaertner_2008_23-2" class="reference"><a href="#cite_note-Weingaertner_2008-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Functions_in_plants">Functions in plants</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=10" title="Edit section: Functions in plants"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sterols are essential for all <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a>. In contrast to animal and <a href="/wiki/Fungus" title="Fungus">fungal</a> cells, which contain only one major sterol, plant cells synthesize an array of sterol mixtures in which <a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">sitosterol</a> and <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a> predominate.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Sitosterol regulates membrane fluidity and permeability in a similar manner to cholesterol in mammalian cell membranes.<sup id="cite_ref-mnfr_46-0" class="reference"><a href="#cite_note-mnfr-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Plant sterols can also modulate the activity of membrane-bound enzymes.<sup id="cite_ref-mnfr_46-1" class="reference"><a href="#cite_note-mnfr-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Phytosterols are also linked to plant adaptation to temperature and plant immunity against pathogens.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytosterol&action=edit&section=11" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output 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"Plant sterols and the membrane environment". <i>Trends in Plant Science</i>. <b>3</b> (5): <span class="nowrap">170–</span>175. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS1360-1385%2898%2901233-3">10.1016/S1360-1385(98)01233-3</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Trends+in+Plant+Science&rft.atitle=Plant+sterols+and+the+membrane+environment&rft.volume=3&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E170-%3C%2Fspan%3E175&rft.date=1998&rft_id=info%3Adoi%2F10.1016%2FS1360-1385%2898%2901233-3&rft.aulast=Hartmann&rft.aufirst=Marie-Andr%C3%A9e&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhytosterol" class="Z3988"></span></span> </li> <li id="cite_note-mnfr-46"><span class="mw-cite-backlink">^ <a href="#cite_ref-mnfr_46-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-mnfr_46-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDe_SmetMensinkPlat2012" class="citation journal cs1">De Smet, E; Mensink, R. P; Plat, J (2012). "Effects of plant sterols and stanols on intestinal cholesterol metabolism: Suggested mechanisms from past to present". <i>Molecular Nutrition & Food Research</i>. <b>56</b> (7): <span class="nowrap">1058–</span>72. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fmnfr.201100722">10.1002/mnfr.201100722</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22623436">22623436</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Nutrition+%26+Food+Research&rft.atitle=Effects+of+plant+sterols+and+stanols+on+intestinal+cholesterol+metabolism%3A+Suggested+mechanisms+from+past+to+present&rft.volume=56&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1058-%3C%2Fspan%3E72&rft.date=2012&rft_id=info%3Adoi%2F10.1002%2Fmnfr.201100722&rft_id=info%3Apmid%2F22623436&rft.aulast=De+Smet&rft.aufirst=E&rft.au=Mensink%2C+R.+P&rft.au=Plat%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhytosterol" class="Z3988"></span></span> </li> <li id="cite_note-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-47">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDe_BruyneHöfteDe_Vleesschauwer2014" class="citation journal cs1">De Bruyne, L; Höfte, M; De Vleesschauwer, D (2014). <a rel="nofollow" class="external text" href="http://www.cell.com/molecular-plant/fulltext/S1674-2052(14)60799-1">"Connecting growth and defense: The emerging roles of brassinosteroids and gibberellins in plant innate immunity"</a>. <i>Molecular Plant</i>. <b>7</b> (6): <span class="nowrap">943–</span>59. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fmp%2Fssu050">10.1093/mp/ssu050</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24777987">24777987</a>.</cite><span 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class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phytochemicals" title="Template:Phytochemicals"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phytochemicals" title="Template talk:Phytochemicals"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phytochemicals" title="Special:EditPage/Template:Phytochemicals"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_phytochemicals153" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Phytochemical" title="Phytochemical">phytochemicals</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Terpenoid" title="Terpenoid">Terpenoids</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 class="navbox-styles"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_terpenes_and_terpenoids_(#_of_isoprene_units)435" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Terpenoids" title="Template:Terpenoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Terpenoids" title="Template talk:Terpenoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Terpenoids" title="Special:EditPage/Template:Terpenoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_terpenes_and_terpenoids_(#_of_isoprene_units)435" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Terpene" title="Terpene">terpenes</a> and <a href="/wiki/Terpenoid" title="Terpenoid">terpenoids</a> (# of <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> units)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Basic forms:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Acyclic (linear, <i>cis</i> and <i>trans</i> forms)</li> <li>Monocyclic (single ring)</li> <li>Bicyclic (2 rings)</li> <li><a href="/wiki/Iridoid" title="Iridoid">Iridoids</a> (cyclopentane ring)</li> <li>Iridoid glycosides (iridoids bound to a sugar)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroids</a> (4 rings)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hemiterpenoid" class="mw-redirect" title="Hemiterpenoid">Hemiterpenoids</a> (1)</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="/wiki/Isoprene" title="Isoprene">Isoprene</a> (C<sub>5</sub>H<sub>8</sub>)</li> <li><a href="/wiki/Prenol" title="Prenol">Prenol</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monoterpene" title="Monoterpene">Monoterpenes</a> <br />(C<sub>10</sub>H<sub>16</sub>)(2)</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%">Acyclic</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="/wiki/Ocimene" title="Ocimene">Ocimene</a></li> <li><a href="/wiki/Myrcene" title="Myrcene">Myrcenes</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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="/wiki/Limonene" title="Limonene">Limonene</a></li> <li><a href="/wiki/Terpinene" title="Terpinene">Terpinene</a></li> <li><a href="/wiki/Phellandrene" title="Phellandrene">Phellandrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</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="/wiki/Pinene" title="Pinene">Pinene</a> (<a href="/wiki/Alpha-Pinene" class="mw-redirect" title="Alpha-Pinene">α</a> and <a href="/wiki/Beta-Pinene" class="mw-redirect" title="Beta-Pinene">β</a>)</li> <li><a href="/wiki/Camphene" title="Camphene">Camphene</a></li> <li><a href="/wiki/Thujene" title="Thujene">Thujene</a></li> <li><a href="/wiki/Sabinene" title="Sabinene">Sabinene</a></li> <li><a href="/wiki/Carene" class="mw-redirect" title="Carene">Carene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monoterpenoids <br />(2,modified)</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%">Acyclic</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="/wiki/Citronellal" title="Citronellal">Citronellal</a></li> <li><a href="/wiki/Citral" title="Citral">Citral</a></li> <li><a href="/wiki/Citronellol" title="Citronellol">Citronellol</a></li> <li><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a></li> <li><a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Halomon" title="Halomon">Halomon</a></li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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="/wiki/Grapefruit_mercaptan" title="Grapefruit mercaptan">Grapefruit mercaptan</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene">p-Cymene</a></li> <li><a href="/wiki/Thujaplicin" title="Thujaplicin">Thujaplicins</a> (<a href="/wiki/Hinokitiol" title="Hinokitiol">Hinokitiol</a>)</li> <li><a href="/wiki/Thymol" title="Thymol">Thymol</a></li> <li><a href="/wiki/Perillyl_alcohol" title="Perillyl alcohol">Perillyl alcohol</a></li> <li><a href="/wiki/Carvacrol" title="Carvacrol">Carvacrol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</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="/wiki/Camphor" title="Camphor">Camphor</a></li> <li><a href="/wiki/Borneol" title="Borneol">Borneol</a></li> <li><a href="/wiki/Bornyl_acetate" title="Bornyl acetate">Bornyl acetate</a></li> <li><a href="/wiki/Eucalyptol" title="Eucalyptol">Eucalyptol</a></li> <li><a href="/wiki/Ascaridole" title="Ascaridole">Ascaridole</a></li> <li><a href="/wiki/Umbellulone" title="Umbellulone">Umbellulone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sesquiterpenoids" class="mw-redirect" title="Sesquiterpenoids">Sesquiterpenoids</a> (3)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Bisabolol" title="Bisabolol">Bisabolol</a></li> <li><a href="/wiki/Cadinene" class="mw-redirect" title="Cadinene">Cadinene</a></li> <li><a href="/wiki/Cadinol" title="Cadinol">Cadinol</a></li> <li><a href="/wiki/Cedrene" title="Cedrene">Cedrene</a></li> <li>Chanootin</li> <li><a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li>Juniperol</li> <li><a href="/wiki/Longifolene" title="Longifolene">Longifolene</a></li> <li>Muurolene</li> <li>Nootkatin</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Terpenoid" title="Terpenoid">Diterpenoids</a> (4)</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%">Acyclic</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="/wiki/Phytol" title="Phytol">Phytol</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li> <li>Geranyl-linalool</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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="/wiki/Retinol" title="Retinol">Retinol</a></li> <li><a href="/wiki/Retinal" title="Retinal">Retinal</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>cis</i>-Abienol</li> <li>Epimanool</li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tricyclic</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="/wiki/Cembrene" class="mw-redirect" title="Cembrene">Cembrene</a></li> <li><a href="/wiki/Forskolin" title="Forskolin">Forskolin</a></li> <li>Manoyl oxide</li> <li>Pimaral</li> <li>Pimarol</li></ul> </div></td></tr><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="/wiki/Aphidicolin" title="Aphidicolin">Aphidicolin</a></li> <li><a href="/wiki/Gibberellin" title="Gibberellin">Gibberellin</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Resin_acid" title="Resin acid">Resin acids</a></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="/wiki/Abietic_acid" title="Abietic acid">Abietic acid</a></li> <li>Communic acid</li> <li>Dehydroabietic acid</li> <li><a href="/wiki/Isopimaric_acid" title="Isopimaric acid">Isopimaric acid</a></li> <li>Lambertianic acid</li> <li><a href="/wiki/Levopimaric_acid" title="Levopimaric acid">Levopimaric acid</a></li> <li>Mercusic acid</li> <li>Neoabietic acid</li> <li><a href="/wiki/Pimaric_acid" title="Pimaric acid">Pimaric acid</a></li> <li>Sandaracopimaric acid</li> <li>Secodehydroabietic acid</li> <li>Palustric acid</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sesterterpenoid" class="mw-redirect" title="Sesterterpenoid">Sesterterpenoids</a> (5)</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>Geranylfarnesol</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triterpenoid" class="mw-redirect" title="Triterpenoid">Triterpenoids</a> (6)</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%"><a href="/wiki/Steroid" title="Steroid">Steroids</a></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 class="mw-selflink selflink">Phytosterols</a> <ul><li><a href="/wiki/Campesterol" title="Campesterol">Campesterol</a></li> <li>Citrostadienol</li> <li><a href="/wiki/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/wiki/Sitostanol" class="mw-redirect" title="Sitostanol">Sitostanol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a></li></ul></li> <li><a href="/wiki/Tocopherol" title="Tocopherol">Tocopherols</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li> <li><a href="/wiki/Ecdysone" title="Ecdysone">Ecdysones</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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="/wiki/Betulin" title="Betulin">Betulin</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/wiki/Saponin" title="Saponin">Saponins</a></li> <li>Serratenediol</li> <li><a href="/wiki/Squalane" title="Squalane">Squalane</a></li> <li>Acids <ul><li><a href="/wiki/Oleanolic_acid" title="Oleanolic acid">Oleanolic acid</a></li> <li><a href="/wiki/Ursolic_acid" title="Ursolic acid">Ursolic acid</a></li> <li><a href="/wiki/Betulinic_acid" title="Betulinic acid">Betulinic acid</a></li> <li><a href="/wiki/Moronic_acid" title="Moronic acid">Moronic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sesquarterpenes/oids (7)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Ferrugicadiol</li> <li>Tetraprenylcurcumene</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetraterpenoid" class="mw-redirect" title="Tetraterpenoid">Tetraterpenoids</a><br />(<a href="/wiki/Carotenoid" title="Carotenoid">Carotenoids</a>) (8)</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%"><a href="/wiki/Carotene" title="Carotene">Carotenes</a></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="/wiki/Alpha-Carotene" class="mw-redirect" title="Alpha-Carotene">Alpha-Carotene</a></li> <li><a href="/wiki/Beta-Carotene" class="mw-redirect" title="Beta-Carotene">Beta-Carotene</a></li> <li><a href="/wiki/Gamma-Carotene" class="mw-redirect" title="Gamma-Carotene">Gamma-Carotene</a></li> <li><a href="/wiki/Delta-Carotene" class="mw-redirect" title="Delta-Carotene">Delta-Carotene</a></li> <li><a href="/wiki/Lycopene" title="Lycopene">Lycopene</a></li> <li><a href="/wiki/Neurosporene" title="Neurosporene">Neurosporene</a></li> <li><a href="/wiki/Phytofluene" title="Phytofluene">Phytofluene</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Xanthophyll" title="Xanthophyll">Xanthophylls</a>:</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="/wiki/Canthaxanthin" title="Canthaxanthin">Canthaxanthin</a></li> <li><a href="/wiki/Cryptoxanthin" class="mw-redirect" title="Cryptoxanthin">Cryptoxanthin</a></li> <li><a href="/wiki/Zeaxanthin" title="Zeaxanthin">Zeaxanthin</a></li> <li><a href="/wiki/Astaxanthin" title="Astaxanthin">Astaxanthin</a></li> <li><a href="/wiki/Lutein" title="Lutein">Lutein</a></li> <li><a href="/wiki/Rubixanthin" title="Rubixanthin">Rubixanthin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polyterpenoid" class="mw-redirect" title="Polyterpenoid">Polyterpenoids</a> (many)</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="/wiki/Natural_rubber" title="Natural rubber">Natural rubber</a></li> <li><a href="/wiki/Gutta_percha" class="mw-redirect" title="Gutta percha">Gutta percha</a></li> <li>Gutta-balatá</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Norisoprenoids (modified)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>3-oxo-α-ionol</li> <li>7,8-dihydroionone</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthesis</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>Terpene synthase enzymes (many), having in common a <a href="/wiki/Terpene_synthase_N_terminal_domain" title="Terpene synthase N terminal domain">terpene synthase N terminal domain</a> (<a href="/wiki/Protein_domain" title="Protein domain">protein domain</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Activated isoprene forms</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a> (IPP)</li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a> (DMAPP)</li></ul> </div></td></tr></tbody></table></div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenolic_compound" class="mw-redirect" title="Phenolic compound">Phenolic compounds</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="navbox-styles"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_phenolic_compounds121" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phenolic_compounds" title="Template:Phenolic compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenolic_compounds" title="Template talk:Phenolic compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenolic_compounds" title="Special:EditPage/Template:Phenolic compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_phenolic_compounds121" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Phenolic_compound" class="mw-redirect" title="Phenolic compound">phenolic compounds</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Natural_monophenol" class="mw-redirect" title="Natural monophenol">Natural monophenols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzenediol" class="mw-redirect" title="Benzenediol">Benzenediols</a></li> <li><a href="/wiki/Benzenetriol" class="mw-redirect" title="Benzenetriol">Benzenetriols</a></li> <li><a href="/wiki/Apiole" title="Apiole">Apiole</a></li> <li><a href="/wiki/Carnosol" title="Carnosol">Carnosol</a></li> <li><a href="/wiki/Carvacrol" title="Carvacrol">Carvacrol</a></li> <li><a href="/wiki/Dillapiole" title="Dillapiole">Dillapiole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polyphenol" title="Polyphenol">Polyphenols</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 mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Polyphenols" title="Template:Polyphenols"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Polyphenols" title="Template talk:Polyphenols"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Polyphenols" title="Special:EditPage/Template:Polyphenols"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_polyphenols177" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Polyphenol" title="Polyphenol">polyphenols</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a><br />(C6-C3-C6)</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 mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Flavonoids" title="Template:Flavonoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Flavonoids" title="Template talk:Flavonoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Flavonoids" title="Special:EditPage/Template:Flavonoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_flavonoids63" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</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%"><a href="/wiki/Anthoxanthin" title="Anthoxanthin">Anthoxanthins</a></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%"><a href="/wiki/Flavone" title="Flavone">Flavones</a></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="/wiki/Apigenin" title="Apigenin">Apigenin</a>, <a href="/wiki/Chrysin" title="Chrysin">Chrysin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonols" title="Flavonols">Flavonols</a></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="/wiki/Quercetin" title="Quercetin">Quercetin</a>, <a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoflavones" class="mw-redirect" title="Isoflavones">Isoflavones</a></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="/wiki/Daidzein" title="Daidzein">Daidzein</a>, <a href="/wiki/Genistein" title="Genistein">Genistein</a>, <a href="/wiki/Orobol" title="Orobol">Orobol</a> et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neoflavonoid" title="Neoflavonoid">Neoflavonoids</a></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="/wiki/Dalbergichromene" title="Dalbergichromene">Dalbergichromene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan" title="Flavan">Flavans</a></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%">Flavan</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="/w/index.php?title=Luteoliflavan&action=edit&redlink=1" class="new" title="Luteoliflavan (page does not exist)">Luteoliflavan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ols</a><br />(<a href="/wiki/Flavanol" class="mw-redirect" title="Flavanol">flavanols</a>)</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="/wiki/Catechin" title="Catechin">Catechin</a>, <a href="/wiki/Gallocatechol" title="Gallocatechol">Gallocatechol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan-4-ol" title="Flavan-4-ol">Flavan-4-ols</a><br />(<a href="/wiki/Flavanol" class="mw-redirect" title="Flavanol">flavanols</a>)</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="/wiki/Apiforol" title="Apiforol">Apiforol</a>, <a href="/wiki/Luteoforol" title="Luteoforol">Luteoforol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Leucoanthocyanidin" title="Leucoanthocyanidin">Flavan-3,4-diols</a></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="/wiki/Leucocyanidin" title="Leucocyanidin">Leucocyanidin</a>, <a href="/wiki/Leucodelphinidin" title="Leucodelphinidin">Leucodelphinidin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavanone" title="Flavanone">Flavanones</a></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="/wiki/Hesperidin" title="Hesperidin">Hesperidin</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Eriodictyol" title="Eriodictyol">Eriodictyol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavanonol" title="Flavanonol">Flavanonols</a></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="/wiki/Taxifolin" title="Taxifolin">Taxifolin</a></li> <li><a href="/wiki/Aromadendrin" title="Aromadendrin">Aromadendrin</a>, et.c.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anthocyanidins" class="mw-redirect" title="Anthocyanidins">Anthocyanidins</a></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%"><a href="/wiki/3-deoxyanthocyanidin" class="mw-redirect" title="3-deoxyanthocyanidin">3-deoxyanthocyanidins</a></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="/wiki/Cyanidin" title="Cyanidin">Cyanidin</a>, <a href="/wiki/Delphinidin" title="Delphinidin">Delphinidin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=3-hydroxyanthocyanidin&action=edit&redlink=1" class="new" title="3-hydroxyanthocyanidin (page does not exist)">3-hydroxyanthocyanidin</a></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="/wiki/Apigeninidin" title="Apigeninidin">Apigeninidin</a>, <a href="/wiki/Guibourtinidin" title="Guibourtinidin">Guibourtinidin</a>, et.c.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aurones" class="mw-redirect" title="Aurones">Aurones</a></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="/wiki/Aureusidin" title="Aureusidin">Aureusidin</a></li> <li><a href="/wiki/Leptosidin" title="Leptosidin">Leptosidin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chalcones" class="mw-redirect" title="Chalcones">Chalcones</a></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%"><a href="/wiki/Chalcone" title="Chalcone">Chalcones</a></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="/wiki/Butein" title="Butein">Butein</a>, <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">Isoliquiritigenin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydrochalcone" title="Dihydrochalcone">Dihydrochalcone</a></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="/wiki/Phloretin" title="Phloretin">Phloretin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Miscellaneous</i></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="/wiki/List_of_phytochemicals_in_food" title="List of phytochemicals in food">List of phytochemicals in food</a></li> <li><a href="/wiki/C-methylated_flavonoid" title="C-methylated flavonoid">C-methylated flavonoids</a></li> <li><a href="/wiki/O-methylated_flavonoid" title="O-methylated flavonoid">O-methylated flavonoids</a></li> <li><a href="/wiki/Furanoflavonoid" title="Furanoflavonoid">Furanoflavonoids</a></li> <li><a href="/wiki/Pyranoflavonoid" title="Pyranoflavonoid">Pyranoflavonoids</a></li> <li><a href="/wiki/Prenylflavonoid" title="Prenylflavonoid">Prenylflavonoids</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li> <li><a href="/wiki/Castavinol" title="Castavinol">Castavinols</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><a href="/wiki/Flavonoid_biosynthesis" title="Flavonoid biosynthesis">Flavonoid biosynthesis</a></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonolignan" title="Flavonolignan">Flavonolignans</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Silymarin" class="mw-redirect" title="Silymarin">Silymarin</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lignan" title="Lignan">Lignans</a><br />((C6-C3)<sub>2</sub>)</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="/wiki/Matairesinol" title="Matairesinol">Matairesinol</a></li> <li><a href="/wiki/Secoisolariciresinol" title="Secoisolariciresinol">Secoisolariciresinol</a></li> <li><a href="/wiki/Pinoresinol" title="Pinoresinol">Pinoresinol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a><br />(C6-C2-C6)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/wiki/Pterostilbene" title="Pterostilbene">Pterostilbene</a></li> <li><a href="/wiki/Piceatannol" title="Piceatannol">Piceatannol</a></li> <li><a href="/wiki/Pinosylvin" title="Pinosylvin">Pinosylvin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Curcuminoid" title="Curcuminoid">Curcuminoids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tannin" title="Tannin">Tannins</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 mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Tannin" title="Template:Tannin"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tannin" title="Template talk:Tannin"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tannin" title="Special:EditPage/Template:Tannin"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_natural_tannins155" style="font-size:114%;margin:0 4em">Types of natural <a href="/wiki/Tannin" title="Tannin">tannins</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrolysable_tannin" title="Hydrolysable tannin">Hydrolysable tannins</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%"><a href="/wiki/Ellagitannin" title="Ellagitannin">Ellagitannins</a></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="/wiki/Punicalagin" title="Punicalagin">Punicalagins</a></li> <li><a href="/wiki/Castalagin" title="Castalagin">Castalagins</a></li> <li><a href="/wiki/Vescalagin" class="mw-redirect" title="Vescalagin">Vescalagins</a></li> <li><a href="/wiki/Castalin" title="Castalin">Castalins</a></li> <li><a href="/wiki/Casuarictin" title="Casuarictin">Casuarictins</a></li> <li><a href="/wiki/Grandinin" title="Grandinin">Grandinins</a></li> <li><a href="/wiki/Punicalin" title="Punicalin">Punicalins</a></li> <li><a href="/wiki/Roburin_A" title="Roburin A">Roburin A</a></li> <li><a href="/wiki/Tellimagrandin_II" title="Tellimagrandin II">Tellimagrandin IIs</a></li> <li><a href="/wiki/Terflavin_B" title="Terflavin B">Terflavin B</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Gallotannin" title="Gallotannin">Gallotannins</a></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="/wiki/Digalloyl_glucose" class="mw-redirect" title="Digalloyl glucose">Digalloyl glucose</a></li> <li><a href="/wiki/1,3,6-Trigalloyl_glucose" class="mw-redirect" title="1,3,6-Trigalloyl glucose">1,3,6-Trigalloyl glucose</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Condensed_tannin" title="Condensed tannin">Condensed tannins</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">Proanthocyanidins</a></li> <li><a href="/wiki/Polyflavonoid_tannin" class="mw-redirect" title="Polyflavonoid tannin">Polyflavonoid tannins</a></li> <li><a href="/wiki/Catechol-type_tannin" class="mw-redirect" title="Catechol-type tannin">Catechol-type tannins</a></li> <li><a href="/wiki/Pyrocatecollic_type_tannin" class="mw-redirect" title="Pyrocatecollic type tannin">Pyrocatecollic type tannins</a></li> <li><a href="/wiki/Flavolan" class="mw-redirect" title="Flavolan">Flavolans</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phlorotannin" title="Phlorotannin">Phlorotannins</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="/wiki/Eckol" title="Eckol">Eckol</a></li> <li><a href="/wiki/8,8%E2%80%B2-Bieckol" title="8,8′-Bieckol">8,8′-Bieckol</a></li> <li><a href="/wiki/6,6%27-Bieckol" title="6,6'-Bieckol">6,6'-Bieckol</a></li> <li><a href="/wiki/Dieckol" title="Dieckol">Dieckol</a></li> <li><a href="/wiki/Eckstolonol" title="Eckstolonol">Eckstolonol</a></li> <li><a href="/wiki/Diphlorethol" title="Diphlorethol">Diphlorethol</a></li> <li><a href="/wiki/Difucol" title="Difucol">Difucol</a></li> <li><a href="/wiki/Fucophlorethol_A" title="Fucophlorethol A">Fucophlorethol A</a></li> <li><a href="/wiki/Phlorofucofuroeckol_A" title="Phlorofucofuroeckol A">Phlorofucofuroeckol A</a></li> <li><a href="/wiki/Tetrafucol_A" title="Tetrafucol A">Tetrafucol A</a></li> <li><a href="/wiki/Trifucol" title="Trifucol">Trifucol</a></li> <li><a href="/wiki/Bifuhalol" title="Bifuhalol">Bifuhalol</a></li> <li><a href="/wiki/7-Phloroeckol" title="7-Phloroeckol">7-Phloroeckol</a></li> <li>Phlorofucofuroeckol B</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavono-ellagitannin" title="Flavono-ellagitannin">Flavono-ellagitannins</a><br />(complex tannins)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Epicutissimin_A" title="Epicutissimin A">Epicutissimin A</a></li> <li><a href="/wiki/Acutissimin_A" title="Acutissimin A">Acutissimin A</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other Miscellaneous</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="/wiki/Template:Tannin_source" title="Template:Tannin source">Tannin sources</a></li> <li><a href="/wiki/Pseudo_tannins" class="mw-redirect" title="Pseudo tannins">Pseudo tannins</a></li> <li><a href="/wiki/Synthetic_tannins" class="mw-redirect" title="Synthetic tannins">Synthetic tannins</a></li> <li>Tannin uses <ul><li><a href="/wiki/Enological_tannin" class="mw-redirect" title="Enological tannin">Enological</a></li> <li><a href="/wiki/Drilling_mud" class="mw-redirect" title="Drilling mud">Drilling</a></li> <li><a href="/wiki/Iron_gall_ink" title="Iron gall ink">Ink</a></li> <li><a href="/wiki/Tanning_(leather)" title="Tanning (leather)">Tanning</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diarylheptanoid" title="Diarylheptanoid">Diarylheptanoids</a> (C6-C7-C6)</li> <li><a href="/wiki/Anthraquinones" title="Anthraquinones">Anthraquinones</a></li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (C6-C3-C6)</li> <li><a href="/wiki/Kavalactone" title="Kavalactone">Kavalactones</a></li> <li><a href="/wiki/Naphthoquinone" title="Naphthoquinone">Naphthoquinones</a> (C6-C4)</li> <li><a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">Phenylpropanoids</a> (C6-C3)</li> <li><a href="/wiki/Xanthonoid" title="Xanthonoid">Xanthonoids</a> (C6-C1-C6)</li> <li><a href="/wiki/Coumarin" title="Coumarin">Coumarins</a> and <a href="/wiki/Isocoumarin" title="Isocoumarin">isocoumarins</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Misc</i>:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Polyphenol" title="Polyphenol">Polyphenols</a></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromatic_acid" title="Aromatic acid">Aromatic acids</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 mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Aromatic_acids" title="Template:Aromatic acids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Aromatic_acids" title="Template talk:Aromatic acids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Aromatic_acids" title="Special:EditPage/Template:Aromatic acids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Aromatic_acids99" style="font-size:114%;margin:0 4em"><a href="/wiki/Aromatic_acid" title="Aromatic acid">Aromatic acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenolic_acid" title="Phenolic acid">Phenolic acids</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 id="Monohydroxybenzoic_acids101" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monohydroxybenzoic_acid" title="Monohydroxybenzoic acid">Monohydroxybenzoic acids</a></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%">Aglycones</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="/wiki/3-Hydroxybenzoic_acid" title="3-Hydroxybenzoic acid">3-Hydroxybenzoic acid</a></li> <li><a href="/wiki/4-Hydroxybenzoic_acid" title="4-Hydroxybenzoic acid">4-Hydroxybenzoic acid</a></li> <li><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycosides</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="/wiki/P-Hydroxybenzoic_acid_glucoside" class="mw-redirect" title="P-Hydroxybenzoic acid glucoside">p-Hydroxybenzoic acid glucoside</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydroxybenzoic_acid" title="Dihydroxybenzoic acid">Dihydroxybenzoic acids</a></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="/wiki/2,3-Dihydroxybenzoic_acid" title="2,3-Dihydroxybenzoic acid">2,3-Dihydroxybenzoic acid</a> (Hypogallic acid)</li> <li><a href="/wiki/2,4-Dihydroxybenzoic_acid" title="2,4-Dihydroxybenzoic acid">2,4-Dihydroxybenzoic acid</a></li> <li><a href="/wiki/2,6-Dihydroxybenzoic_acid" title="2,6-Dihydroxybenzoic acid">2,6-Dihydroxybenzoic acid</a></li> <li><a href="/wiki/3,5-Dihydroxybenzoic_acid" title="3,5-Dihydroxybenzoic acid">3,5-Dihydroxybenzoic acid</a></li> <li><a href="/wiki/Ethyl_protocatechuate" title="Ethyl protocatechuate">Ethyl protocatechuate</a></li> <li><a href="/wiki/Gentisic_acid" title="Gentisic acid">Gentisic acid</a></li> <li><a href="/wiki/Homogentisic_acid" title="Homogentisic acid">Homogentisic acid</a></li> <li><a href="/wiki/Orsellinic_acid" title="Orsellinic acid">Orsellinic acid</a></li> <li><a href="/wiki/Protocatechuic_acid" title="Protocatechuic acid">Protocatechuic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trihydroxybenzoic_acid" title="Trihydroxybenzoic acid">Trihydroxybenzoic acids</a></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="/wiki/Bergenin" title="Bergenin">Bergenin</a></li> <li><a href="/wiki/Chebulic_acid" title="Chebulic acid">Chebulic acid</a></li> <li><a href="/wiki/Ethyl_gallate" title="Ethyl gallate">Ethyl gallate</a></li> <li><a href="/wiki/Eudesmic_acid" title="Eudesmic acid">Eudesmic acid</a></li> <li><a href="/wiki/Gallic_acid" title="Gallic acid">Gallic acid</a></li> <li><a href="/wiki/Tannic_acid" title="Tannic acid">Tannic acid</a></li> <li><a href="/wiki/Norbergenin" title="Norbergenin">Norbergenin</a></li> <li><a href="/wiki/Phloroglucinol_carboxylic_acid" title="Phloroglucinol carboxylic acid">Phloroglucinol carboxylic acid</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li> <li><a href="/wiki/Theogallin" title="Theogallin">Theogallin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other phenolic acids</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="/wiki/Vanillin" title="Vanillin">Vanillin</a></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydroxycinnamic_acid" title="Hydroxycinnamic acid">Hydroxycinnamic acids</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="/wiki/Alpha-Cyano-4-hydroxycinnamic_acid" class="mw-redirect" title="Alpha-Cyano-4-hydroxycinnamic acid">α-Cyano-4-hydroxycinnamic acid</a></li> <li><a href="/wiki/Caffeic_acid" title="Caffeic acid">Caffeic acid</a></li> <li><a href="/wiki/Chicoric_acid" title="Chicoric acid">Chicoric acid</a></li> <li><a href="/wiki/Cinnamic_acid" title="Cinnamic acid">Cinnamic acid</a></li> <li><a href="/wiki/Chlorogenic_acid" title="Chlorogenic acid">Chlorogenic acid</a></li> <li><a href="/wiki/Diferulic_acids" title="Diferulic acids">Diferulic acids</a></li> <li><a href="/wiki/Coumaric_acid" title="Coumaric acid">Coumaric acid</a></li> <li><a href="/wiki/Coumarin" title="Coumarin">Coumarin</a></li> <li><a href="/wiki/Ferulic_acid" title="Ferulic acid">Ferulic acid</a></li> <li><a href="/wiki/Sinapinic_acid" title="Sinapinic acid">Sinapinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">Aromatic amino acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a></li> <li><a href="/wiki/Histidine" title="Histidine">histidine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a></li> <li><a href="/wiki/Thyroxine" title="Thyroxine">thyroxine</a></li> <li><a href="/wiki/5-hydroxytryptophan" class="mw-redirect" title="5-hydroxytryptophan">5-hydroxytryptophan</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethanoid" title="Phenylethanoid">Phenylethanoids</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="/wiki/Tyrosol" title="Tyrosol">Tyrosol</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Oleocanthal" title="Oleocanthal">Oleocanthal</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a></li> <li><a href="/wiki/Gingerol" title="Gingerol">Gingerol</a></li> <li><a href="/wiki/Alkylresorcinol" title="Alkylresorcinol">Alkylresorcinols</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Misc</i>:</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="/wiki/Phenol" title="Phenol">Phenolic compounds</a></li> <li><a href="/wiki/Phlorotannin" title="Phlorotannin">Phlorotannins</a>)</li></ul> </div></td></tr></tbody></table></div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucosinolate" title="Glucosinolate">Glucosinolates</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Precursor to <a href="/wiki/Isothiocyanate" title="Isothiocyanate">isothiocyanates</a> <ul><li><a href="/wiki/Sinigrin" title="Sinigrin">Sinigrin</a></li> <li><a href="/wiki/Gluconasturtiin" title="Gluconasturtiin">Gluconasturtiin</a></li> <li><a href="/wiki/Glucoraphanin" title="Glucoraphanin">Glucoraphanin</a></li></ul></li> <li>Aglycone derivatives <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanates</a> <ul><li><a href="/wiki/Sulforaphane" title="Sulforaphane">Sulforaphane</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a></li> <li><a href="/wiki/Phenethyl_Isothiocyanate" class="mw-redirect" title="Phenethyl Isothiocyanate">Phenethyl Isothiocyanate</a></li></ul></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitriles</a></li> <li><a href="/wiki/Thiocyanate" title="Thiocyanate">Thiocyanates</a></li></ul></li> <li><a href="/wiki/Organosulfide" class="mw-redirect" title="Organosulfide">Organosulfides</a> <ul><li><a href="/wiki/Sulfide" title="Sulfide">Sulfides</a></li> <li><a href="/wiki/Polysulfide" title="Polysulfide">Polysulfides</a> <ul><li><a href="/wiki/Diallyl_disulfide" title="Diallyl disulfide">Diallyl disulfide</a></li></ul></li></ul></li> <li><a href="/wiki/Indole" title="Indole">Indoles</a> <ul><li><a href="/wiki/Indole-3-carbinol" title="Indole-3-carbinol">Indole-3-carbinol</a></li> <li><a href="/wiki/3,3%27-Diindolylmethane" title="3,3'-Diindolylmethane">3,3'-Diindolylmethane</a></li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a></li> <li><a href="/wiki/Alliin" title="Alliin">Alliin</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a></li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a></li> <li><a href="/wiki/Syn-propanethial-S-oxide" class="mw-redirect" title="Syn-propanethial-S-oxide">Syn-propanethial-S-oxide</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Betalain" title="Betalain">Betalains</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="/wiki/Betacyanin" class="mw-redirect" title="Betacyanin">Betacyanins</a> <ul><li><a href="/wiki/Betanin" title="Betanin">Betanin</a></li></ul></li> <li><a href="/wiki/Betaxanthin" class="mw-redirect" title="Betaxanthin">Betaxanthins</a> <ul><li><a href="/wiki/Indicaxanthin" title="Indicaxanthin">Indicaxanthin</a></li> <li><a href="/wiki/Vulgaxanthin" title="Vulgaxanthin">Vulgaxanthin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chlorophyll" title="Chlorophyll">Chlorophylls</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chlorophyllin" title="Chlorophyllin">Chlorophyllin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_acid" title="Organic acid">Organic acids</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>Saturated cyclic acids <ul><li><a href="/wiki/Phytic_acid" title="Phytic acid">Phytic acid</a></li> <li><a href="/wiki/Quinic_acid" title="Quinic acid">Quinic acid</a></li></ul></li> <li><a href="/wiki/Oxalic_acid" title="Oxalic acid">Oxalic acid</a></li> <li><a href="/wiki/Tartaric_acid" title="Tartaric acid">Tartaric acid</a></li> <li><a href="/wiki/Anacardic_acid" class="mw-redirect" title="Anacardic acid">Anacardic acid</a></li> <li><a href="/wiki/Malic_acid" title="Malic acid">Malic acid</a></li> <li><a href="/wiki/Caftaric_acid" title="Caftaric acid">Caftaric acid</a></li> <li><a href="/wiki/Coutaric_acid" title="Coutaric acid">Coutaric acid</a></li> <li><a href="/wiki/Fertaric_acid" title="Fertaric acid">Fertaric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbohydrate" title="Carbohydrate">Carbohydrates</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Monosaccharide" title="Monosaccharide">Monosaccharides</a> <ul><li><a href="/wiki/Hexose" title="Hexose">Hexoses</a></li> <li><a href="/wiki/Pentose" title="Pentose">Pentoses</a></li></ul></li> <li><a href="/wiki/Polysaccharide" title="Polysaccharide">Polysaccharides</a> <ul><li><a href="/wiki/Beta-glucan" title="Beta-glucan">Beta-glucan</a> <ul><li><a href="/wiki/Chitin" title="Chitin">Chitin</a></li> <li><a href="/wiki/Lentinan" title="Lentinan">Lentinan</a></li></ul></li> <li><a href="/wiki/Fructan" title="Fructan">Fructan</a> <ul><li><a href="/wiki/Inulin" title="Inulin">Inulins</a></li></ul></li> <li><a href="/wiki/Lignin" title="Lignin">Lignin</a></li> <li><a href="/wiki/Pectin" title="Pectin">Pectin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Misc</i>:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/List_of_phytochemicals_in_food" title="List of phytochemicals in food">List of phytochemicals and foods in which they are prominent</a></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Phytosterols22" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phytosterols" title="Template:Phytosterols"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phytosterols" title="Template talk:Phytosterols"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phytosterols" title="Special:EditPage/Template:Phytosterols"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phytosterols22" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Phytosterols</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">C28</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Brassicasterol" title="Brassicasterol">Brassicasterol</a></li> <li><a href="/wiki/Campesterol" title="Campesterol">Campesterol</a></li> <li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a> (Vitamin D2)</li> <li><a href="/w/index.php?title=Ergostenol&action=edit&redlink=1" class="new" title="Ergostenol (page does not exist)">Ergostenol</a></li> <li><a href="/wiki/Ergostatrienol" class="mw-redirect" title="Ergostatrienol">Ergostatrienol</a></li> <li><a href="/w/index.php?title=Ergostadienol&action=edit&redlink=1" class="new" title="Ergostadienol (page does not exist)">Ergostadienol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C29</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="/wiki/Avenasterol" title="Avenasterol">δ-7-avenasterol</a></li> <li><a href="/wiki/Isofucosterol" title="Isofucosterol">δ-5-avenasterol</a></li> <li><a href="/wiki/Beta-Sitosterol" class="mw-redirect" title="Beta-Sitosterol">β-Sitosterol</a></li> <li><a href="/w/index.php?title=%CE%94-7-stigmasterol&action=edit&redlink=1" class="new" title="Δ-7-stigmasterol (page does not exist)">δ-7-stigmasterol</a></li> <li><a href="/wiki/Momordenol" title="Momordenol">Momordenol</a></li> <li><a href="/wiki/Spinasterol" title="Spinasterol">Spinasterol</a></li> <li><a href="/wiki/Stigmastanol" title="Stigmastanol">Stigmastanol</a></li> <li><a href="/w/index.php?title=Stigmastenol&action=edit&redlink=1" class="new" title="Stigmastenol (page does not exist)">Stigmastenol</a></li> <li><a href="/w/index.php?title=Stigmastadienol&action=edit&redlink=1" class="new" title="Stigmastadienol (page does not exist)">Stigmastadienol</a></li> <li><a href="/w/index.php?title=Stigmastadienone&action=edit&redlink=1" class="new" title="Stigmastadienone (page does not exist)">Stigmastadienone</a></li> <li><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a></li> <li><a href="/w/index.php?title=Stigmastenone&action=edit&redlink=1" class="new" title="Stigmastenone (page does not exist)">Stigmastenone</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Cholesterol_and_steroid_metabolic_intermediates189" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cholesterol_and_steroid_intermediates" title="Template:Cholesterol and steroid intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cholesterol_and_steroid_intermediates" title="Template talk:Cholesterol and steroid intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cholesterol_and_steroid_intermediates" title="Special:EditPage/Template:Cholesterol and steroid intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cholesterol_and_steroid_metabolic_intermediates189" style="font-size:114%;margin:0 4em"><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> and <a href="/wiki/Steroid" title="Steroid">steroid</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">Mevalonate pathway</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%">to <a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</a></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="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl-CoA</a></li> <li><a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">Acetoacetyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">HMB</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">HMB-CoA</a></li> <li><a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketone_bodies" title="Ketone bodies">Ketone bodies</a></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="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">Acetoacetic acid</a></li> <li><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">to <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></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="/wiki/Mevalonic_acid" title="Mevalonic acid">Mevalonic acid</a></li> <li><a href="/wiki/Phosphomevalonic_acid" title="Phosphomevalonic acid">Phosphomevalonic acid</a></li> <li><a href="/wiki/5-Diphosphomevalonic_acid" title="5-Diphosphomevalonic acid">5-Diphosphomevalonic acid</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geranyl-</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="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoid</a></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="/wiki/Prephytoene_diphosphate" title="Prephytoene diphosphate">Prephytoene diphosphate</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-mevalonate_pathway" title="Non-mevalonate pathway">Non-mevalonate pathway</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Deoxy-D-xylulose_5-phosphate" title="1-Deoxy-D-xylulose 5-phosphate">DOXP</a></li> <li><a href="/wiki/2-C-methylerythritol_4-phosphate" class="mw-redirect" title="2-C-methylerythritol 4-phosphate">MEP</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methylerythritol" class="mw-redirect" title="4-diphosphocytidyl-2-C-methylerythritol">CDP-ME</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methyl-D-erythritol_2-phosphate" class="mw-redirect" title="4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate">CDP-MEP</a></li> <li><a href="/wiki/2-C-methyl-D-erythritol_2,4-cyclopyrophosphate" class="mw-redirect" title="2-C-methyl-D-erythritol 2,4-cyclopyrophosphate">MEcPP</a></li> <li><a href="/wiki/(E)-4-Hydroxy-3-methyl-but-2-enyl_pyrophosphate" title="(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate">HMB-PP</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">IPP</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li><a href="/wiki/Squalene" title="Squalene">Squalene</a></li> <li><a href="/wiki/2,3-Oxidosqualene" title="2,3-Oxidosqualene">2,3-Oxidosqualene</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li></ul> <ul><li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/w/index.php?title=14-demethyllanosterol&action=edit&redlink=1" class="new" title="14-demethyllanosterol (page does not exist)">14-demethyllanosterol</a></li> <li><a href="/w/index.php?title=4alpha-Methylzymosterol&action=edit&redlink=1" class="new" title="4alpha-Methylzymosterol (page does not exist)">4alpha-Methylzymosterol</a></li> <li><a href="/w/index.php?title=Zymosterone&action=edit&redlink=1" class="new" title="Zymosterone (page does not exist)">Zymosterone</a></li> <li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Zymostenol&action=edit&redlink=1" class="new" title="Zymostenol (page does not exist)">Zymostenol</a></li> <li><a href="/wiki/Lathosterol" title="Lathosterol">Lathosterol</a></li> <li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Cholesta-7,24-dien-3-ol&action=edit&redlink=1" class="new" title="Cholesta-7,24-dien-3-ol (page does not exist)">Cholesta-7,24-dien-3-ol</a></li> <li><a href="/wiki/7-Dehydrodesmosterol" title="7-Dehydrodesmosterol">7-Dehydrodesmosterol</a></li> <li><a href="/wiki/Desmosterol" title="Desmosterol">Desmosterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">From <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> <br />to <a href="/wiki/Steroid" title="Steroid">Steroid hormones</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="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nonhuman</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%">To <a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></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="/wiki/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/w/index.php?title=Cycloeucalenol&action=edit&redlink=1" class="new" title="Cycloeucalenol (page does not exist)">Cycloeucalenol</a></li> <li><a href="/wiki/Obtusifoliol" title="Obtusifoliol">Obtusifoliol</a></li> <li><a href="/wiki/4%CE%B1-methylfecosterol" class="mw-redirect" title="4α-methylfecosterol">4α-methylfecosterol</a></li> <li><a href="/wiki/Isofucosterol" title="Isofucosterol">Isofucosterol</a></li> <li><a href="/wiki/24-Methylenelophenol" title="24-Methylenelophenol">24-Methylenelophenol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li>More <a class="mw-selflink selflink">Phytosterols</a> see <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></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="/wiki/Fecosterol" title="Fecosterol">Fecosterol</a></li> <li><a href="/wiki/Episterol" title="Episterol">Episterol</a></li> <li><a href="/wiki/Ergostatrienol" class="mw-redirect" title="Ergostatrienol">Ergostatrienol</a></li> <li><a href="/w/index.php?title=Ergostatetraenol&action=edit&redlink=1" class="new" title="Ergostatetraenol (page does not exist)">Ergostatetraenol</a></li> <li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Phytosterol&oldid=1231677322">https://en.wikipedia.org/w/index.php?title=Phytosterol&oldid=1231677322</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Phytosterols" 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