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Lignan - Wikipedia
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vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" 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Available in 19 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-19" 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">19 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%84%D9%8A%D8%BA%D9%86%D8%A7%D9%86" title="ليغنان – Arabic" lang="ar" hreflang="ar" data-title="ليغنان" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Lignan" title="Lignan – Catalan" lang="ca" hreflang="ca" data-title="Lignan" 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/Lignany" title="Lignany – Czech" lang="cs" hreflang="cs" data-title="Lignany" 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/Lignane" title="Lignane – German" lang="de" hreflang="de" data-title="Lignane" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9B%CE%B9%CE%B3%CE%BD%CE%AC%CE%BD%CE%B5%CF%82" title="Λιγνάνες – Greek" lang="el" hreflang="el" data-title="Λιγνάνες" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Lignano" title="Lignano – Spanish" lang="es" hreflang="es" data-title="Lignano" 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/Lignano" title="Lignano – Basque" lang="eu" hreflang="eu" data-title="Lignano" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Lignane" title="Lignane – French" lang="fr" hreflang="fr" data-title="Lignane" 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/Lignano" title="Lignano – Galician" lang="gl" hreflang="gl" data-title="Lignano" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9B%D0%B8%D0%B3%D0%BD%D0%B0%D0%BD" title="Лигнан – Macedonian" lang="mk" hreflang="mk" data-title="Лигнан" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Lignaan" title="Lignaan – Dutch" lang="nl" hreflang="nl" data-title="Lignaan" 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%AA%E3%82%B0%E3%83%8A%E3%83%B3" title="リグナン – Japanese" lang="ja" hreflang="ja" data-title="リグナン" 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/Lignan" title="Lignan – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Lignan" 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-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Lignan" title="Lignan – Romanian" lang="ro" hreflang="ro" data-title="Lignan" 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%9B%D0%B8%D0%B3%D0%BD%D0%B0%D0%BD%D1%8B" title="Лигнаны – Russian" lang="ru" hreflang="ru" data-title="Лигнаны" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Lignaanit" title="Lignaanit – Finnish" lang="fi" hreflang="fi" data-title="Lignaanit" 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/Lignan" title="Lignan – Turkish" lang="tr" hreflang="tr" data-title="Lignan" 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%9B%D1%96%D0%B3%D0%BD%D0%B0%D0%BD%D0%B8" title="Лігнани – Ukrainian" lang="uk" hreflang="uk" data-title="Лігнани" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%9C%A8%E8%84%82%E7%B4%A0" title="木脂素 – Chinese" lang="zh" hreflang="zh" data-title="木脂素" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q424634#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> 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div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the phytoestrogen. For the wood polymer, see <a href="/wiki/Lignin" title="Lignin">Lignin</a>. For the wine and table grape, see <a href="/wiki/Lignan_(grape)" class="mw-redirect" title="Lignan (grape)">Lignan (grape)</a>. For the town in Italy, see <a href="/wiki/Lignano_Sabbiadoro" title="Lignano Sabbiadoro">Lignano Sabbiadoro</a>.</div> <p>The <b>lignans</b> are a large group of low molecular weight <a href="/wiki/Polyphenol" title="Polyphenol">polyphenols</a> found in <a href="/wiki/Plant" title="Plant">plants</a>, particularly <a href="/wiki/Seed" title="Seed">seeds</a>, <a href="/wiki/Whole_grain" title="Whole grain">whole grains</a>, and vegetables.<sup id="cite_ref-lpi.oregonstate_1-0" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The name derives from the <a href="/wiki/Latin" title="Latin">Latin</a> word for "wood".<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> Lignans are precursors to <a href="/wiki/Phytoestrogen" title="Phytoestrogen">phytoestrogens</a>.<sup id="cite_ref-lpi.oregonstate_1-1" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> They may play a role as <a href="/wiki/Antifeedant" title="Antifeedant">antifeedants</a> in the defense of seeds and plants against <a href="/wiki/Herbivore" title="Herbivore">herbivores</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis_and_metabolism">Biosynthesis and metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lignan&action=edit&section=1" title="Edit section: Biosynthesis and metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1248256098">@media all and (max-width:720px){.mw-parser-output .mod-gallery{width:100%!important}}.mw-parser-output .mod-gallery{display:table}.mw-parser-output .mod-gallery-default{background:transparent;margin-top:4px}.mw-parser-output .mod-gallery-center{margin-left:auto;margin-right:auto}.mw-parser-output .mod-gallery-left{float:left}.mw-parser-output .mod-gallery-right{float:right}.mw-parser-output .mod-gallery-none{float:none}.mw-parser-output .mod-gallery-collapsible{width:100%}.mw-parser-output .mod-gallery .title,.mw-parser-output .mod-gallery .main,.mw-parser-output .mod-gallery .footer{display:table-row}.mw-parser-output .mod-gallery .title>div{display:table-cell;padding:0 4px 4px;text-align:center;font-weight:bold}.mw-parser-output .mod-gallery .main>div{display:table-cell}.mw-parser-output .mod-gallery .gallery{line-height:1.35em}.mw-parser-output .mod-gallery .footer>div{display:table-cell;padding:4px;text-align:right;font-size:85%;line-height:1em}.mw-parser-output .mod-gallery .title>div *,.mw-parser-output .mod-gallery .footer>div *{overflow:visible}.mw-parser-output .mod-gallery .gallerybox img{background:none!important}.mw-parser-output .mod-gallery .bordered-images .thumb img{border:solid var(--background-color-neutral,#eaecf0)1px}.mw-parser-output .mod-gallery .whitebg .thumb{background:var(--background-color-base,#fff)!important}</style><div class="mod-gallery mod-gallery-default mod-gallery-center"><div class="title"><div>Structures of some lignans</div></div><div class="main"><div><ul class="gallery mw-gallery-traditional nochecker bordered-images whitebg"> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:Matairesinol.png" class="mw-file-description" title="Matairesinol, illustrating the dibenzylbutyrolactone motif"><img alt="Matairesinol, illustrating the dibenzylbutyrolactone motif" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Matairesinol.png/180px-Matairesinol.png" decoding="async" width="180" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Matairesinol.png/270px-Matairesinol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/23/Matairesinol.png/360px-Matairesinol.png 2x" data-file-width="1811" data-file-height="1367" /></a></span></div> <div class="gallerytext"><a href="/wiki/Matairesinol" title="Matairesinol">Matairesinol</a>, illustrating the dibenzylbutyrolactone motif</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:Secoisolariciresinol_Structural_Formula_V.1.svg" class="mw-file-description" title="Secoisolariciresinol, illustrating the 9,9'-dihydroxydibenzylbutane motif"><img alt="Secoisolariciresinol, illustrating the 9,9'-dihydroxydibenzylbutane motif" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/Secoisolariciresinol_Structural_Formula_V.1.svg/180px-Secoisolariciresinol_Structural_Formula_V.1.svg.png" decoding="async" width="180" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/Secoisolariciresinol_Structural_Formula_V.1.svg/270px-Secoisolariciresinol_Structural_Formula_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/56/Secoisolariciresinol_Structural_Formula_V.1.svg/360px-Secoisolariciresinol_Structural_Formula_V.1.svg.png 2x" data-file-width="436" data-file-height="349" /></a></span></div> <div class="gallerytext"><a href="/wiki/Secoisolariciresinol" title="Secoisolariciresinol">Secoisolariciresinol</a>, illustrating the 9,9'-dihydroxydibenzylbutane motif</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:Justicidin_A.svg" class="mw-file-description" title="Justicidin A, illustrating the arylnaphthalene motif"><img alt="Justicidin A, illustrating the arylnaphthalene motif" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Justicidin_A.svg/162px-Justicidin_A.svg.png" decoding="async" width="162" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Justicidin_A.svg/243px-Justicidin_A.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Justicidin_A.svg/324px-Justicidin_A.svg.png 2x" data-file-width="990" data-file-height="1100" /></a></span></div> <div class="gallerytext"><a href="/wiki/Justicidin_A" title="Justicidin A">Justicidin A</a>, illustrating the arylnaphthalene motif</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:Pinoresinol.svg" class="mw-file-description" title="Pinoresinol, illustrating the furanofuran motif"><img alt="Pinoresinol, illustrating the furanofuran motif" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Pinoresinol.svg/180px-Pinoresinol.svg.png" decoding="async" width="180" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Pinoresinol.svg/270px-Pinoresinol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Pinoresinol.svg/360px-Pinoresinol.svg.png 2x" data-file-width="512" data-file-height="200" /></a></span></div> <div class="gallerytext"><a href="/wiki/Pinoresinol" title="Pinoresinol">Pinoresinol</a>, illustrating the furanofuran motif</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:Steganacin.svg" class="mw-file-description" title="Steganacin, illustrating the dibenzocyclooctadienelactone motif"><img alt="Steganacin, illustrating the dibenzocyclooctadienelactone motif" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Steganacin.svg/180px-Steganacin.svg.png" decoding="async" width="180" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Steganacin.svg/270px-Steganacin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/26/Steganacin.svg/360px-Steganacin.svg.png 2x" data-file-width="565" data-file-height="515" /></a></span></div> <div class="gallerytext"><a href="/wiki/Steganacin" title="Steganacin">Steganacin</a>, illustrating the dibenzocyclooctadienelactone motif</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 210px;"><span typeof="mw:File"><a href="/wiki/File:Podophyllotoxin2DCSD.svg" class="mw-file-description" title="Podophyllotoxin, illustrating the aryltetralin motif"><img alt="Podophyllotoxin, illustrating the aryltetralin motif" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Podophyllotoxin2DCSD.svg/159px-Podophyllotoxin2DCSD.svg.png" decoding="async" width="159" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Podophyllotoxin2DCSD.svg/238px-Podophyllotoxin2DCSD.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/26/Podophyllotoxin2DCSD.svg/318px-Podophyllotoxin2DCSD.svg.png 2x" data-file-width="512" data-file-height="580" /></a></span></div> <div class="gallerytext"><a href="/wiki/Podophyllotoxin" title="Podophyllotoxin">Podophyllotoxin</a>, illustrating the aryltetralin motif</div> </li> </ul></div></div></div> <p>Lignans and <a href="/wiki/Lignin" title="Lignin">lignin</a> differ in their molecular weight, the former being small and soluble in water, the latter being high polymers that are undigestable. Both are <a href="/wiki/Polyphenol" title="Polyphenol">polyphenolic</a> substances derived by oxidative coupling of <a href="/wiki/Monolignol" title="Monolignol">monolignols</a>. Thus, most lignans feature a C<sub>18</sub> cores, resulting from the dimerization of C<sub>9</sub> precursors. The coupling of the lignols occurs at C8. Eight classes of lignans are: "furofuran, furan, dibenzylbutane, dibenzylbutyrolactone, aryltetralin, arylnaphthalene, dibenzocyclooctadiene, and dibenzylbutyrolactol."<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><p>Many lignans are metabolized by mammalian gut microflora, producing so-called <a href="/wiki/Enterolignan" title="Enterolignan">enterolignans</a>.<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><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> </p> <div class="mw-heading mw-heading2"><h2 id="Food_sources">Food sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lignan&action=edit&section=2" title="Edit section: Food sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Flax_seed" class="mw-redirect" title="Flax seed">Flax seeds</a> and <a href="/wiki/Sesame_seed" class="mw-redirect" title="Sesame seed">sesame seeds</a> contain high levels of lignans.<sup id="cite_ref-lpi.oregonstate_1-2" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Landete_8-0" class="reference"><a href="#cite_note-Landete-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The principal lignan precursor found in flaxseeds is <a href="/wiki/Secoisolariciresinol_diglucoside" title="Secoisolariciresinol diglucoside">secoisolariciresinol diglucoside</a>.<sup id="cite_ref-lpi.oregonstate_1-3" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Landete_8-1" class="reference"><a href="#cite_note-Landete-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Other foods containing lignans include cereals (<a href="/wiki/Rye" title="Rye">rye</a>, <a href="/wiki/Wheat" title="Wheat">wheat</a>, <a href="/wiki/Oat" title="Oat">oat</a> and <a href="/wiki/Barley" title="Barley">barley</a>), <a href="/wiki/Soybean" title="Soybean">soybeans</a>, <a href="/wiki/Tofu" title="Tofu">tofu</a>, <a href="/wiki/Cruciferous_vegetables" title="Cruciferous vegetables">cruciferous vegetables</a>, such as <a href="/wiki/Broccoli" title="Broccoli">broccoli</a> and <a href="/wiki/Cabbage" title="Cabbage">cabbage</a>, and some fruits, particularly <a href="/wiki/Apricot" title="Apricot">apricots</a> and <a href="/wiki/Strawberry" title="Strawberry">strawberries</a>.<sup id="cite_ref-lpi.oregonstate_1-4" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Lignans are not present in <a href="/wiki/Seed_oil" class="mw-redirect" title="Seed oil">seed oil</a>, and their contents in whole or <a href="/wiki/Mill_(grinding)" title="Mill (grinding)">ground</a> seeds may vary according to geographic location, climate, and maturity of the seed crop, and the duration of seed storage.<sup id="cite_ref-lpi.oregonstate_1-5" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Secoisolariciresinol and matairesinol were the first plant lignans identified in foods.<sup id="cite_ref-lpi.oregonstate_1-6" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Typically, lariciresinol and pinoresinol contribute about 75% to the total lignan intake, whereas secoisolariciresinol and matairesinol contribute only about 25%.<sup id="cite_ref-lpi.oregonstate_1-7" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Foods containing lignans:<sup id="cite_ref-lpi.oregonstate_1-8" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Milder_9-0" class="reference"><a href="#cite_note-Milder-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <tbody><tr> <th>Source</th> <th>Lignan amount </th></tr> <tr> <td>Flaxseeds</td> <td>85.5 mg per oz (28.35 g) </td></tr> <tr> <td>Sesame seeds</td> <td>11.2 mg per oz </td></tr> <tr> <td><i><a href="/wiki/Brassica" title="Brassica">Brassica</a></i> vegetables</td> <td>0.3-0.8  mg per half <a href="/wiki/Cup_(unit)" title="Cup (unit)">cup</a> (125 ml) </td></tr> <tr> <td>Strawberries</td> <td>0.2 mg per half cup </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Prevalence_and_health_effects">Prevalence and health effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lignan&action=edit&section=3" title="Edit section: Prevalence and health effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lignans are the principal source of dietary <a href="/wiki/Phytoestrogen" title="Phytoestrogen">phytoestrogens</a> in typical <a href="/wiki/Western_diet" class="mw-redirect" title="Western diet">Western diets</a>, even though most research on phytoestrogen-rich diets has focused on <a href="/wiki/Soy" class="mw-redirect" title="Soy">soy</a> <a href="/wiki/Isoflavones" class="mw-redirect" title="Isoflavones">isoflavones</a>. Lignan's <a href="/wiki/Enterolignan" title="Enterolignan">enterolignan</a> products <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a> and <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a> have weak <a href="/wiki/Estrogenic" class="mw-redirect" title="Estrogenic">estrogenic</a> activity, but they may also exert biological effects through non-estrogenic means.<sup id="cite_ref-lpi.oregonstate_1-9" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>A 2021 review found that lignans have a positive effect on lipid profiles of patients with <a href="/wiki/Dyslipidemia" title="Dyslipidemia">dyslipidemia</a> related diseases.<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> As of 2022 there is limited evidence that dietary intake of lignans is associated with a reduced cancer and cardiovascular disease risk.<sup id="cite_ref-lpi.oregonstate_1-10" class="reference"><a href="#cite_note-lpi.oregonstate-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lignan&action=edit&section=4" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col div-col-small" style="column-width: 30;"> <ul><li><a href="/wiki/Herbalism" class="mw-redirect" title="Herbalism">Herbalism</a></li> <li><a href="/wiki/Pharmacognosy" title="Pharmacognosy">Pharmacognosy</a></li> <li><a href="/wiki/Flavonolignan" title="Flavonolignan">Flavonolignan</a></li></ul> </div> <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=Lignan&action=edit&section=5" 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 .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-lpi.oregonstate-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-lpi.oregonstate_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-lpi.oregonstate_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-lpi.oregonstate_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-lpi.oregonstate_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-lpi.oregonstate_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-lpi.oregonstate_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-lpi.oregonstate_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-lpi.oregonstate_1-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-lpi.oregonstate_1-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-lpi.oregonstate_1-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-lpi.oregonstate_1-10"><sup><i><b>k</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://lpi.oregonstate.edu/infocenter/phytochemicals/lignans">"Lignans"</a>. Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2010<span class="reference-accessdate">. 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class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/34635132">34635132</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nutrition+%26+Metabolism&rft.atitle=Comparisons+of+the+effects+of+different+flaxseed+products+consumption+on+lipid+profiles%2C+inflammatory+cytokines+and+anthropometric+indices+in+patients+with+dyslipidemia+related+diseases%3A+systematic+review+and+a+dose%E2%80%93response+meta-analysis+of+randomized+controlled+trials&rft.volume=18&rft.issue=1&rft.pages=91&rft.date=2021&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8504108%23id-name%3DPMC&rft_id=info%3Apmid%2F34635132&rft_id=info%3Adoi%2F10.1186%2Fs12986-021-00619-3&rft.au=Yang%2C+C.%2C+Xia%2C+H.%2C+Wan%2C+M.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8504108&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALignan" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lignan&action=edit&section=6" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20120414191253/http://www.chem.qmul.ac.uk/iupac/lignan/LG0n1.html#p11">IUPAC lignan nomenclature</a></li></ul> <div class="navbox-styles"><style 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href="/wiki/Phytoestrogens" class="mw-redirect" title="Phytoestrogens">Phytoestrogens</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/Flavanones" class="mw-redirect" title="Flavanones">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/Hesperetin" title="Hesperetin">Hesperetin</a></li> <li><a href="/wiki/Liquiritigenin" title="Liquiritigenin">Liquiritigenin</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Pinocembrin" title="Pinocembrin">Pinocembrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavones" title="Flavones">Flavones</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/Acacetin" title="Acacetin">Acacetin</a></li> <li><a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-Dihydroxyflavone</a></li> <li><a href="/wiki/Mirificin" title="Mirificin">Mirificin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prenylflavonoids" class="mw-redirect" title="Prenylflavonoids">Prenylflavonoids</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/8-Prenylnaringenin" title="8-Prenylnaringenin">8-Prenylnaringenin</a></li> <li><a href="/w/index.php?title=6-Prenylnaringenin&action=edit&redlink=1" class="new" title="6-Prenylnaringenin (page does not exist)">6-Prenylnaringenin</a></li> <li><a href="/w/index.php?title=8-Geranylnaringenin&action=edit&redlink=1" class="new" title="8-Geranylnaringenin (page does not exist)">8-Geranylnaringenin</a></li> <li><a href="/w/index.php?title=6,8-Diprenylnaringenin&action=edit&redlink=1" class="new" title="6,8-Diprenylnaringenin (page does not exist)">6,8-Diprenylnaringenin</a></li> <li><a href="/w/index.php?title=Icaritin&action=edit&redlink=1" class="new" title="Icaritin (page does not exist)">Icaritin</a></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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biochanin_A" title="Biochanin A">Biochanin A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Daidzin" title="Daidzin">Daidzin</a></li> <li><a href="/wiki/Formononetin" title="Formononetin">Formononetin</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Genistin" title="Genistin">Genistin</a></li> <li><a href="/wiki/Glycitein" title="Glycitein">Glycitein</a></li> <li><a href="/wiki/Ononin" title="Ononin">Ononin</a></li> <li><a href="/wiki/Prunetin" title="Prunetin">Prunetin</a></li> <li><a href="/wiki/Puerarin" title="Puerarin">Puerarin</a></li> <li><a href="/wiki/Tectorigenin" title="Tectorigenin">Tectorigenin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoflavanes" class="mw-redirect" title="Isoflavanes">Isoflavanes</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/Equol" title="Equol">Equol</a> (<a href="/wiki/S-Equol" class="mw-redirect" title="S-Equol"><i>S</i>-Equol</a>)</li> <li><a href="/wiki/Glabridin" title="Glabridin">Glabridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydrochalcone" title="Dihydrochalcone">Dihydrochalcones</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/Phloretin" title="Phloretin">Phloretin</a></li> <li><a href="/wiki/Phlorizin" title="Phlorizin">Phlorizin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoflavenes" class="mw-redirect" title="Isoflavenes">Isoflavenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Glabrene" title="Glabrene">Glabrene</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coumestans" class="mw-redirect" title="Coumestans">Coumestans</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/Coumestan" title="Coumestan">Coumestan</a></li> <li><a href="/wiki/Coumestrol" title="Coumestrol">Coumestrol</a></li> <li><a href="/w/index.php?title=Desmethylwedelolactone&action=edit&redlink=1" class="new" title="Desmethylwedelolactone (page does not exist)">Desmethylwedelolactone</a></li> <li><a href="/wiki/Wedelolactone" title="Wedelolactone">Wedelolactone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lignans" class="mw-redirect" title="Lignans">Lignans</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/Enterodiol" title="Enterodiol">Enterodiol</a></li> <li><a href="/wiki/Enterolactone" title="Enterolactone">Enterolactone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonolignans" class="mw-redirect" title="Flavonolignans">Flavonolignans</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/Silybin" class="mw-redirect" title="Silybin">Silybin</a></li> <li><a href="/wiki/Cinchonain-Ib" title="Cinchonain-Ib">Cinchonain-Ib</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonol" class="mw-redirect" title="Flavonol">Flavonols</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/Quercetin" title="Quercetin">Quercetin</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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">Deoxymiroestrol</a></li> <li><a href="/wiki/Miroestrol" title="Miroestrol">Miroestrol</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=%CE%91-Isosparteine&action=edit&redlink=1" class="new" title="Α-Isosparteine (page does not exist)">α-Isosparteine</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/Mycoestrogen" title="Mycoestrogen">Mycoestrogens</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/Zearalanone" title="Zearalanone">Zearalanone</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">α-Zearalanol (zeranol)</a></li> <li><a href="/wiki/Alpha-zearalenol" class="mw-redirect" title="Alpha-zearalenol">α-Zearalenol</a></li> <li><a href="/wiki/%CE%92-Zearalanol" class="mw-redirect" title="Β-Zearalanol">β-Zearalanol</a></li> <li><a href="/wiki/%CE%92-Zearalenol" title="Β-Zearalenol">β-Zearalenol</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Derivatives" scope="row" class="navbox-group" style="width:1%">Derivatives</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/Penicillamine" title="Penicillamine"><small>D</small>-Penicillamine</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthetic</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/Alkylphenol" title="Alkylphenol">Alkylphenols</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Butylated_hydroxyanisole" title="Butylated hydroxyanisole">BHA</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Bisphenol_F" title="Bisphenol F">Bisphenol F</a></li> <li><a href="/wiki/Bisphenol_S" title="Bisphenol S">Bisphenol S</a></li> <li><a href="/wiki/Dichlorodiphenyldichloroethylene" title="Dichlorodiphenyldichloroethylene">DDE</a></li> <li><a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a></li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/Dioxins_and_dioxin-like_compounds" title="Dioxins and dioxin-like compounds">Dioxins</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Enzacamene" title="Enzacamene">Enzacamene</a></li> <li><a href="/wiki/Erythrosine" title="Erythrosine">Erythrosine</a></li> <li><a href="/wiki/Heptachlor" title="Heptachlor">Heptachlor</a></li> <li><a href="/wiki/Lindane" title="Lindane">Lindane</a></li> <li><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Paraben" title="Paraben">Parabens</a></li> <li><a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a></li> <li><a href="/wiki/Pentachlorophenol" title="Pentachlorophenol">Pentachlorophenol</a></li> <li><a href="/wiki/4-Hydroxybenzoic_acid" title="4-Hydroxybenzoic acid">PHBA</a></li> <li><a href="/wiki/Phthalates" title="Phthalates">Phthalates</a></li> <li><a href="/wiki/Propyl_gallate" title="Propyl gallate">Propyl gallate</a></li> <li><a href="/wiki/Perfluorinated_compound" title="Perfluorinated compound">Perfluorinated compound</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</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>Aluminium</li> <li>Antimony</li> <li>Arsenite</li> <li>Barium</li> <li>Cadmium</li> <li><a href="/wiki/Chromium" title="Chromium">Chromium</a></li> <li><a href="/wiki/Cobalt" title="Cobalt">Cobalt</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li>Lead</li> <li>Mercury</li> <li>Nickel</li> <li>Selenite</li> <li>Tin</li> <li>Vanadate</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="Types_of_phenylpropanoids" 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:Phenylpropanoid" title="Template:Phenylpropanoid"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenylpropanoid" title="Template talk:Phenylpropanoid"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenylpropanoid" title="Special:EditPage/Template:Phenylpropanoid"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_phenylpropanoids" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">phenylpropanoids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Classes of <a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">phenylpropanoids</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/Hydroxycinnamic_acid" title="Hydroxycinnamic acid">Hydroxycinnamic acids</a></li> <li><a href="/wiki/Chromone" title="Chromone">Chromones</a> (<a href="/wiki/Furanochromone" title="Furanochromone">Furanochromones</a>)</li> <li><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehydes</a></li> <li><a href="/wiki/Monolignol" title="Monolignol">Monolignols</a></li> <li><a href="/wiki/Coumarin" title="Coumarin">Coumarins</a></li> <li><a href="/wiki/Chalcone" title="Chalcone">Chalcones</a></li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a></li> <li><a href="/wiki/Allylbenzenes" class="mw-redirect" title="Allylbenzenes">Allylbenzenes</a></li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a></li> <li><a class="mw-selflink selflink">Lignans</a></li> <li><a href="/wiki/Lignin" title="Lignin">Lignins</a></li> <li><a href="/wiki/Suberin" title="Suberin">Suberins</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Examples</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/Rhododendrin" title="Rhododendrin">Rhododendrin</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="Types_of_lignans" 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:Lignan" title="Template:Lignan"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Lignan" title="Template talk:Lignan"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Lignan" title="Special:EditPage/Template:Lignan"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_lignans" style="font-size:114%;margin:0 4em">Types of <a class="mw-selflink selflink">lignans</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Lignans</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/Arboreol" title="Arboreol">Arboreol</a></li> <li><a href="/wiki/Arctigenin" title="Arctigenin">Arctigenin</a></li> <li><a href="/w/index.php?title=Chamaecypanone_A&action=edit&redlink=1" class="new" title="Chamaecypanone A (page does not exist)">Chamaecypanone A</a> and <a href="/w/index.php?title=Chamaecypanone_B&action=edit&redlink=1" class="new" title="Chamaecypanone B (page does not exist)">B</a></li> <li><a href="/w/index.php?title=Eudesmin&action=edit&redlink=1" class="new" title="Eudesmin (page does not exist)">Eudesmin</a></li> <li><a href="/wiki/Globoidnan_A" title="Globoidnan A">Globoidnan A</a></li> <li><a href="/wiki/Gmelanone" title="Gmelanone">Gmelanone</a></li> <li><a href="/wiki/Gmelinol" title="Gmelinol">Gmelinol</a></li> <li><a href="/wiki/Gummadiol" title="Gummadiol">Gummadiol</a></li> <li><a href="/w/index.php?title=Isootobanone&action=edit&redlink=1" class="new" title="Isootobanone (page does not exist)">Isootobanone</a></li> <li><a href="/w/index.php?title=Lyoniresinol&action=edit&redlink=1" class="new" title="Lyoniresinol (page does not exist)">Lyoniresinol</a></li> <li><a href="/wiki/Macelignan" title="Macelignan">Macelignan</a></li> <li><a href="/wiki/Matairesinol" title="Matairesinol">Matairesinol</a></li> <li><a href="/w/index.php?title=Obtulignolide&action=edit&redlink=1" class="new" title="Obtulignolide (page does not exist)">Obtulignolide</a></li> <li><a href="/wiki/Pinoresinol" title="Pinoresinol">Pinoresinol</a></li> <li><a href="/wiki/Pluviatilol" title="Pluviatilol">Pluviatilol</a></li> <li><a href="/wiki/Podophyllotoxin" title="Podophyllotoxin">Podophyllotoxin</a></li> <li><a href="/wiki/Secoisolariciresinol" title="Secoisolariciresinol">Secoisolariciresinol</a></li> <li><a href="/wiki/Sesamin" title="Sesamin">Sesamin</a></li> <li><a href="/wiki/Sesamolin" title="Sesamolin">Sesamolin</a></li> <li><a href="/wiki/Steganacin" title="Steganacin">Steganacin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Lignan <a href="/wiki/Glycoside" title="Glycoside">glycosides</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/Arctiin" title="Arctiin">Arctiin</a></li> <li><a href="/wiki/Aviculin" title="Aviculin">Aviculin</a> (isolariciresinol-9'-rhamnopyranoside)</li> <li><a href="/wiki/Secoisolariciresinol_diglucoside" title="Secoisolariciresinol diglucoside">Secoisolariciresinol diglucoside</a> (SDG)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Enterolignan" title="Enterolignan">Mammalian lignans (enterolignans)</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/Enterodiol" title="Enterodiol">Enterodiol</a></li> <li><a href="/wiki/Enterolactone" title="Enterolactone">Enterolactone</a></li> <li><a href="/wiki/Lariciresinol" title="Lariciresinol">Lariciresinol</a></li> <li><a href="/wiki/Hydroxymatairesinol" title="Hydroxymatairesinol">Hydroxymatairesinol</a></li> <li><a href="/wiki/Syringaresinol" title="Syringaresinol">Syringaresinol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neolignan" class="mw-redirect" title="Neolignan">Neolignans</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/Balanophonin" title="Balanophonin">Balanophonin</a></li> <li><a href="/wiki/Eusiderin" title="Eusiderin">Eusiderin</a></li> <li><a href="/wiki/Honokiol" title="Honokiol">Honokiol</a></li> <li><a href="/wiki/Interiotherin" title="Interiotherin">Interiotherin</a></li> <li><a href="/w/index.php?title=Linderin_A&action=edit&redlink=1" class="new" title="Linderin A (page does not exist)">Linderin A</a></li> <li><a href="/wiki/Magnolol" title="Magnolol">Magnolol</a></li> <li><a href="/wiki/Megaphone_(molecule)" title="Megaphone (molecule)">Megaphone</a></li> <li><a href="/wiki/4-O-Methylhonokiol" title="4-O-Methylhonokiol">4-O-Methylhonokiol</a></li> <li><a href="/w/index.php?title=Rhaphidecursinol_A&action=edit&redlink=1" class="new" title="Rhaphidecursinol A (page does not exist)">Rhaphidecursinol A</a></li> <li><a href="/w/index.php?title=Rhaphidecursinol_B&action=edit&redlink=1" class="new" title="Rhaphidecursinol B (page does not exist)">Rhaphidecursinol B</a></li></ul> </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"> <ul><li><a href="/wiki/Cinchonain-Ib" title="Cinchonain-Ib">Cinchonain-Ib</a></li> <li><a href="/w/index.php?title=Dehydrosilybin&action=edit&redlink=1" class="new" title="Dehydrosilybin (page does not exist)">Dehydrosilybin</a></li> <li><a href="/w/index.php?title=Deoxysilycistin&action=edit&redlink=1" class="new" title="Deoxysilycistin (page does not exist)">Deoxysilycistin</a></li> <li><a href="/w/index.php?title=Deoxysilydianin&action=edit&redlink=1" class="new" title="Deoxysilydianin (page does not exist)">Deoxysilydianin</a></li> <li><a href="/w/index.php?title=Hydnocarpin&action=edit&redlink=1" class="new" title="Hydnocarpin (page does not exist)">Hydnocarpin</a></li> <li><a href="/w/index.php?title=Hydnowightin&action=edit&redlink=1" class="new" title="Hydnowightin (page does not exist)">Hydnowightin</a></li> <li><a href="/w/index.php?title=Neosilyhermin&action=edit&redlink=1" class="new" title="Neosilyhermin (page does not exist)">Neosilyhermin</a></li> <li><a href="/w/index.php?title=Palstatin&action=edit&redlink=1" class="new" title="Palstatin (page does not exist)">Palstatin</a></li> <li><a href="/w/index.php?title=Rhodiolin&action=edit&redlink=1" class="new" title="Rhodiolin (page does not exist)">Rhodiolin</a></li> <li><a href="/w/index.php?title=Salcolin_A&action=edit&redlink=1" class="new" title="Salcolin A (page does not exist)">Salcolin A</a></li> <li><a href="/w/index.php?title=Salcolin_B&action=edit&redlink=1" class="new" title="Salcolin B (page does not exist)">Salcolin B</a></li> <li><a href="/w/index.php?title=Scutellaprostin_A&action=edit&redlink=1" class="new" title="Scutellaprostin A (page does not exist)">Scutellaprostin A</a>, <a href="/w/index.php?title=Scutellaprostin_B&action=edit&redlink=1" class="new" title="Scutellaprostin B (page does not exist)">B</a>, <a href="/w/index.php?title=Scutellaprostin_C&action=edit&redlink=1" class="new" title="Scutellaprostin C (page does not exist)">C</a>, <a href="/w/index.php?title=Scutellaprostin_D&action=edit&redlink=1" class="new" title="Scutellaprostin D (page does not exist)">D</a>, <a href="/w/index.php?title=Scutellaprostin_E&action=edit&redlink=1" class="new" title="Scutellaprostin E (page does not exist)">E</a> and <a href="/w/index.php?title=Scutellaprostin_F&action=edit&redlink=1" class="new" title="Scutellaprostin F (page does not exist)">F</a></li> <li><a href="/w/index.php?title=Silandrin&action=edit&redlink=1" class="new" title="Silandrin (page does not exist)">Silandrin</a></li> <li><a href="/w/index.php?title=Silyamandin&action=edit&redlink=1" class="new" title="Silyamandin (page does not exist)">Silyamandin</a></li> <li><a href="/wiki/Silibinin" title="Silibinin">Silibinin</a></li> <li><a href="/w/index.php?title=Silybinome&action=edit&redlink=1" class="new" title="Silybinome (page does not exist)">Silybinome</a></li> <li><a href="/w/index.php?title=Silicristin&action=edit&redlink=1" class="new" title="Silicristin (page does not exist)">Silicristin</a></li> <li><a href="/w/index.php?title=Silydianin&action=edit&redlink=1" class="new" title="Silydianin (page does not exist)">Silydianin</a></li> <li><a href="/w/index.php?title=Silyhermin&action=edit&redlink=1" class="new" title="Silyhermin (page does not exist)">Silyhermin</a></li> <li><a href="/w/index.php?title=Tricin_4%27-O-(erythro-beta-guaiacylglyceryl)_ether&action=edit&redlink=1" class="new" title="Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether (page does not exist)">Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether</a></li> <li><a href="/w/index.php?title=Tricin_4%27-O-(threo-beta-guaiacylglyceryl)_ether&action=edit&redlink=1" class="new" title="Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether (page does not exist)">Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether</a></li></ul> </div></td></tr></tbody></table></div> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐5857dfdcd6‐xn2b5 Cached time: 20241203065954 Cache expiry: 2592000 Reduced 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