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class="vector-toc-numb">2</span> <span>Morphology</span> </div> </a> <ul id="toc-Morphology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Foods" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Foods"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Foods</span> </div> </a> <ul id="toc-Foods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Plant_colors" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Plant_colors"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Plant colors</span> </div> </a> <ul id="toc-Plant_colors-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bird_colors_and_sexual_selection" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Bird_colors_and_sexual_selection"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Bird colors and sexual selection</span> </div> </a> <ul id="toc-Bird_colors_and_sexual_selection-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aroma_chemicals" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Aroma_chemicals"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Aroma chemicals</span> </div> </a> <ul id="toc-Aroma_chemicals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Disease" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Disease"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Disease</span> </div> </a> <ul id="toc-Disease-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Biosynthesis</span> </div> </a> <button aria-controls="toc-Biosynthesis-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 Biosynthesis subsection</span> </button> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> <li id="toc-MEP_pathway" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#MEP_pathway"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>MEP pathway</span> </div> </a> <ul id="toc-MEP_pathway-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carotenoid_biosynthetic_pathway" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carotenoid_biosynthetic_pathway"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>Carotenoid biosynthetic pathway</span> </div> </a> <ul id="toc-Carotenoid_biosynthetic_pathway-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Regulation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Regulation"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.3</span> <span>Regulation</span> </div> </a> <ul id="toc-Regulation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Naturally_occurring_carotenoids" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Naturally_occurring_carotenoids"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Naturally occurring carotenoids</span> </div> </a> <ul id="toc-Naturally_occurring_carotenoids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>See also</span> </div> </a> <ul id="toc-See_also-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">11</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">12</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" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Carotenoid</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 45 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-45" 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">45 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/%D8%A3%D8%B4%D8%A8%D8%A7%D9%87_%D9%83%D8%A7%D8%B1%D9%88%D8%AA%D9%8A%D9%86%D8%A7%D8%AA" title="أشباه كاروتينات – Arabic" lang="ar" hreflang="ar" data-title="أشباه كاروتينات" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Carotenoide" title="Carotenoide – Asturian" lang="ast" hreflang="ast" data-title="Carotenoide" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%95%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B0%E0%A7%8B%E0%A6%9F%E0%A6%BF%E0%A6%A8%E0%A6%AF%E0%A6%BC%E0%A7%87%E0%A6%A1" title="ক্যারোটিনয়েড – Bangla" lang="bn" hreflang="bn" data-title="ক্যারোটিনয়েড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%BE%D1%82%D0%B8%D0%BD%D0%BE%D0%B8%D0%B4" title="Каротиноид – Bulgarian" lang="bg" hreflang="bg" data-title="Каротиноид" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Carotenoide" title="Carotenoide – Catalan" lang="ca" hreflang="ca" data-title="Carotenoide" 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/Karotenoidy" title="Karotenoidy – Czech" lang="cs" hreflang="cs" data-title="Karotenoidy" 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/Carotinoide" title="Carotinoide – German" lang="de" hreflang="de" data-title="Carotinoide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Karotenoidid" title="Karotenoidid – Estonian" lang="et" hreflang="et" data-title="Karotenoidid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CE%B1%CF%81%CE%BF%CF%84%CE%B5%CE%BD%CE%BF%CE%B5%CE%B9%CE%B4%CE%AD%CF%82" title="Καροτενοειδές – Greek" lang="el" hreflang="el" data-title="Καροτενοειδές" 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/Carotenoide" title="Carotenoide – Spanish" lang="es" hreflang="es" data-title="Carotenoide" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Karotenoido" title="Karotenoido – Esperanto" lang="eo" hreflang="eo" data-title="Karotenoido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Karotenoide" title="Karotenoide – Basque" lang="eu" hreflang="eu" data-title="Karotenoide" 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/%DA%A9%D8%A7%D8%B1%D9%88%D8%AA%D9%86%D9%88%D8%A6%DB%8C%D8%AF" title="کاروتنوئید – Persian" lang="fa" hreflang="fa" data-title="کاروتنوئید" 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/Carot%C3%A9no%C3%AFde" title="Caroténoïde – French" lang="fr" hreflang="fr" data-title="Caroténoïde" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Carait%C3%A9an%C3%B3ideach" title="Caraitéanóideach – Irish" lang="ga" hreflang="ga" data-title="Caraitéanóideach" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Carotenoide" title="Carotenoide – Galician" lang="gl" hreflang="gl" data-title="Carotenoide" 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/%EC%B9%B4%EB%A1%9C%ED%8B%B0%EB%85%B8%EC%9D%B4%EB%93%9C" title="카로티노이드 – Korean" lang="ko" hreflang="ko" data-title="카로티노이드" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BF%D5%A1%D6%80%D5%B8%D5%BF%D5%AB%D5%B6%D5%B8%D5%AB%D5%A4%D5%B6%D5%A5%D6%80" title="Կարոտինոիդներ – Armenian" lang="hy" hreflang="hy" data-title="Կարոտինոիդներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Karotenoidi" title="Karotenoidi – Croatian" lang="hr" hreflang="hr" data-title="Karotenoidi" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Karotenoid" title="Karotenoid – Indonesian" lang="id" hreflang="id" data-title="Karotenoid" 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/Carotenoidi" title="Carotenoidi – Italian" lang="it" hreflang="it" data-title="Carotenoidi" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A7%D7%A8%D7%95%D7%98%D7%A0%D7%95%D7%90%D7%99%D7%93" title="קרוטנואיד – Hebrew" lang="he" hreflang="he" data-title="קרוטנואיד" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%99%E1%83%90%E1%83%A0%E1%83%9D%E1%83%A2%E1%83%98%E1%83%9C%E1%83%9D%E1%83%98%E1%83%93%E1%83%94%E1%83%91%E1%83%98" title="კაროტინოიდები – Georgian" lang="ka" hreflang="ka" data-title="კაროტინოიდები" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%BE%D1%82%D0%B8%D0%BD%D0%BE%D0%B8%D0%B4%D1%82%D0%B0%D1%80" title="Каротиноидтар – Kazakh" lang="kk" hreflang="kk" data-title="Каротиноидтар" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%BE%D1%82%D0%B8%D0%BD%D0%BE%D0%B8%D0%B4%D0%B4%D0%B5%D1%80" title="Каротиноиддер – Kyrgyz" lang="ky" hreflang="ky" data-title="Каротиноиддер" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Karotino%C4%ABdi" title="Karotinoīdi – Latvian" lang="lv" hreflang="lv" data-title="Karotinoīdi" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%95%E0%B4%B0%E0%B5%8B%E0%B4%9F%E0%B5%8D%E0%B4%9F%E0%B4%BF%E0%B4%A8%E0%B5%8B%E0%B4%AF%E0%B5%8D%E0%B4%A1%E0%B5%8D" title="കരോട്ടിനോയ്ഡ് – Malayalam" lang="ml" hreflang="ml" data-title="കരോട്ടിനോയ്ഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Caroteno%C3%AFde" title="Carotenoïde – Dutch" lang="nl" hreflang="nl" data-title="Carotenoïde" 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%82%AB%E3%83%AD%E3%83%86%E3%83%8E%E3%82%A4%E3%83%89" title="カロテノイド – Japanese" lang="ja" hreflang="ja" data-title="カロテノイド" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Karotinoidlar" title="Karotinoidlar – Uzbek" lang="uz" hreflang="uz" data-title="Karotinoidlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Karotenoidy" title="Karotenoidy – Polish" lang="pl" hreflang="pl" data-title="Karotenoidy" 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/Carotenoide" title="Carotenoide – Portuguese" lang="pt" hreflang="pt" data-title="Carotenoide" 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/Carotenoid%C4%83" title="Carotenoidă – Romanian" lang="ro" hreflang="ro" data-title="Carotenoidă" 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%9A%D0%B0%D1%80%D0%BE%D1%82%D0%B8%D0%BD%D0%BE%D0%B8%D0%B4%D1%8B" title="Каротиноиды – Russian" lang="ru" hreflang="ru" data-title="Каротиноиды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Carotenoid" title="Carotenoid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Carotenoid" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%BE%D1%82%D0%B5%D0%BD%D0%BE%D0%B8%D0%B4" title="Каротеноид – Serbian" lang="sr" hreflang="sr" data-title="Каротеноид" 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-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Karotenoid" title="Karotenoid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Karotenoid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Karotenoidit" title="Karotenoidit – Finnish" lang="fi" hreflang="fi" data-title="Karotenoidit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Karotenoid" title="Karotenoid – Swedish" lang="sv" hreflang="sv" data-title="Karotenoid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%81%E0%B8%84%E0%B9%82%E0%B8%A3%E0%B8%97%E0%B8%B5%E0%B8%99%E0%B8%AD%E0%B8%A2%E0%B8%94%E0%B9%8C" title="แคโรทีนอยด์ – Thai" lang="th" hreflang="th" data-title="แคโรทีนอยด์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Karotenoid" title="Karotenoid – Turkish" lang="tr" hreflang="tr" data-title="Karotenoid" data-language-autonym="Türkçe" 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accesskey="p"><span>Printable version</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Carotenoids" hreflang="en"><span>Wikimedia Commons</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q191907" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div 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data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Class of chemical compounds; yellow, orange or red plant pigments</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Beta-Carotin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Beta-Carotin.svg/420px-Beta-Carotin.svg.png" decoding="async" width="420" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Beta-Carotin.svg/630px-Beta-Carotin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/27/Beta-Carotin.svg/840px-Beta-Carotin.svg.png 2x" data-file-width="1000" data-file-height="200" /></a><figcaption>Chemical structure of β-<a href="/wiki/Carotene" title="Carotene">carotene</a>, a common natural pigment.</figcaption></figure> <p><b>Carotenoids</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="'k' in 'kind'">k</span><span title="/ə/: 'a' in 'about'">ə</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'r' in 'rye'">r</span><span title="/ɒ/: 'o' in 'body'">ɒ</span><span title="'t' in 'tie'">t</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span><span title="/ɔɪ/: 'oi' in 'choice'">ɔɪ</span><span title="'d' in 'dye'">d</span></span>/</a></span></span>) are yellow, orange, and red <a href="/wiki/Organic_compound" title="Organic compound">organic</a> <a href="/wiki/Pigment" title="Pigment">pigments</a> that are produced by <a href="/wiki/Plant" title="Plant">plants</a> and <a href="/wiki/Algae" title="Algae">algae</a>, as well as several bacteria, archaea, and <a href="/wiki/Fungus" title="Fungus">fungi</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Carotenoids give the characteristic color to <a href="/wiki/Pumpkin" title="Pumpkin">pumpkins</a>, <a href="/wiki/Carrot" title="Carrot">carrots</a>, <a href="/wiki/Parsnip" title="Parsnip">parsnips</a>, <a href="/wiki/Maize" title="Maize">corn</a>, <a href="/wiki/Tomato" title="Tomato">tomatoes</a>, <a href="/wiki/Domestic_Canary" class="mw-redirect" title="Domestic Canary">canaries</a>, <a href="/wiki/Flamingo" title="Flamingo">flamingos</a>, <a href="/wiki/Salmon" title="Salmon">salmon</a>, <a href="/wiki/Lobster" title="Lobster">lobster</a>, <a href="/wiki/Shrimp" title="Shrimp">shrimp</a>, and <a href="/wiki/Daffodil" class="mw-redirect" title="Daffodil">daffodils</a>. Over 1,100 identified carotenoids can be further categorized into two classes – <a href="/wiki/Xanthophyll" title="Xanthophyll">xanthophylls</a> (which contain oxygen) and <a href="/wiki/Carotene" title="Carotene">carotenes</a> (which are purely <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a> and contain no oxygen).<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> </p><p>All are <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a> of <a href="/wiki/Tetraterpene" title="Tetraterpene">tetraterpenes</a>, meaning that they are produced from 8 <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> units and contain 40 carbon atoms. In general, carotenoids absorb wavelengths ranging from 400 to 550 nanometers (violet to green light). This causes the compounds to be deeply colored yellow, orange, or red. Carotenoids are the dominant pigment in <a href="/wiki/Autumn_leaf_color" title="Autumn leaf color">autumn leaf coloration</a> of about 15-30% of tree species,<sup id="cite_ref-lpi_3-0" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> but many plant colors, especially reds and purples, are due to <a href="/wiki/Polyphenol" title="Polyphenol">polyphenols</a>. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Updated_graphic_24.2.16.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Updated_graphic_24.2.16.png/220px-Updated_graphic_24.2.16.png" decoding="async" width="220" height="309" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Updated_graphic_24.2.16.png/330px-Updated_graphic_24.2.16.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/Updated_graphic_24.2.16.png/440px-Updated_graphic_24.2.16.png 2x" data-file-width="3200" data-file-height="4500" /></a><figcaption>Macular pigments of the human eye</figcaption></figure> <p>Carotenoids serve two key roles in plants and algae: they absorb light energy for use in <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>, and they provide <a href="/wiki/Photoprotection" title="Photoprotection">photoprotection</a> via <a href="/wiki/Non-photochemical_quenching" title="Non-photochemical quenching">non-photochemical quenching</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> Carotenoids that contain unsubstituted beta-ionone rings (including <a href="/wiki/%CE%92-carotene" class="mw-redirect" title="Β-carotene">β-carotene</a>, <a href="/wiki/%CE%91-carotene" class="mw-redirect" title="Α-carotene">α-carotene</a>, <a href="/wiki/%CE%92-cryptoxanthin" class="mw-redirect" title="Β-cryptoxanthin">β-cryptoxanthin</a>, and <a href="/wiki/%CE%93-carotene" class="mw-redirect" title="Γ-carotene">γ-carotene</a>) have <a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a> activity (meaning that they can be converted to <a href="/wiki/Retinol" title="Retinol">retinol</a>). In the eye, <a href="/wiki/Lutein" title="Lutein">lutein</a>, <a href="/wiki/Meso-Zeaxanthin" title="Meso-Zeaxanthin"><i>meso</i>-zeaxanthin</a>, and <a href="/wiki/Zeaxanthin" title="Zeaxanthin">zeaxanthin</a> are present as <a href="/wiki/Macula" title="Macula">macular pigments</a> whose importance in visual function, as of 2016, remains under <a href="/wiki/Clinical_research" title="Clinical research">clinical research</a>.<sup id="cite_ref-lpi_3-1" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Li_5-0" class="reference"><a href="#cite_note-Li-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_and_function">Structure and function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=1" title="Edit section: Structure and function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output 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">Main articles: <a href="/wiki/Carotenes" class="mw-redirect" title="Carotenes">carotenes</a> and <a href="/wiki/Xanthophylls" class="mw-redirect" title="Xanthophylls">xanthophylls</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:72_-_gac.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/72_-_gac.jpg/220px-72_-_gac.jpg" decoding="async" width="220" height="226" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/72_-_gac.jpg/330px-72_-_gac.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/72_-_gac.jpg/440px-72_-_gac.jpg 2x" data-file-width="2130" data-file-height="2184" /></a><figcaption><a href="/wiki/Gac" title="Gac">Gac</a> fruit, rich in lycopene</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Akita_Omoriyama_Zoo_-_panoramio.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Akita_Omoriyama_Zoo_-_panoramio.jpg/220px-Akita_Omoriyama_Zoo_-_panoramio.jpg" decoding="async" width="220" height="146" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Akita_Omoriyama_Zoo_-_panoramio.jpg/330px-Akita_Omoriyama_Zoo_-_panoramio.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Akita_Omoriyama_Zoo_-_panoramio.jpg/440px-Akita_Omoriyama_Zoo_-_panoramio.jpg 2x" data-file-width="3008" data-file-height="2000" /></a><figcaption>Ingesting carotenoid-rich foods affects the <a href="/wiki/Plumage" title="Plumage">plumage</a> of <a href="/wiki/Flamingo" title="Flamingo">flamingos</a>.</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Luteine_-_Lutein.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Luteine_-_Lutein.svg/385px-Luteine_-_Lutein.svg.png" decoding="async" width="385" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Luteine_-_Lutein.svg/578px-Luteine_-_Lutein.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/20/Luteine_-_Lutein.svg/770px-Luteine_-_Lutein.svg.png 2x" data-file-width="600" data-file-height="120" /></a><figcaption><a href="/wiki/Lutein" title="Lutein">Lutein</a>, a <a href="/wiki/Xanthophyll" title="Xanthophyll">Xanthophyll</a>.</figcaption></figure> <p>Carotenoids are produced by all photosynthetic organisms and are primarily used as <a href="/wiki/Accessory_pigment" title="Accessory pigment">accessory pigments</a> to <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a> in the light-harvesting part of photosynthesis. </p><p>They are highly <a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">unsaturated</a> with <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated double bonds</a>, which enables carotenoids to absorb light of various <a href="/wiki/Wavelength" title="Wavelength">wavelengths</a>. At the same time, the terminal groups regulate the <a href="/wiki/Chemical_polarity" title="Chemical polarity">polarity</a> and properties within <a href="/wiki/Lipid_bilayer" title="Lipid bilayer">lipid membranes</a>. </p><p>Most carotenoids are <a href="/wiki/Tetraterpenoids" class="mw-redirect" title="Tetraterpenoids">tetraterpenoids</a>, regular <span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {C40}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>40</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {C40}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/9ab4b78c554936dd4db7cdb85f7f32a6de04cb41" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:3.554ex; height:2.843ex;" alt="{\displaystyle {\ce {C40}}}"></span> <a href="/wiki/Isoprenoids" class="mw-redirect" title="Isoprenoids">isoprenoids</a>. Several modifications to these structures exist: including <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclization</a>, varying degrees of <a href="/wiki/Saturated_fat" title="Saturated fat">saturation</a> or unsaturation, and other <a href="/wiki/Functional_group" title="Functional group">functional groups</a>.<sup id="cite_ref-Maresca-2008_6-0" class="reference"><a href="#cite_note-Maresca-2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Carotenes typically contain only carbon and hydrogen, i.e., they are <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a>. Prominent members include <a href="/wiki/%CE%91-carotene" class="mw-redirect" title="Α-carotene">α-carotene</a>, <a href="/wiki/%CE%92-carotene" class="mw-redirect" title="Β-carotene">β-carotene</a>, and <a href="/wiki/Lycopene" title="Lycopene">lycopene</a>, are known as <i><a href="/wiki/Carotene" title="Carotene">carotenes</a></i>. Carotenoids containing oxygen include <a href="/wiki/Lutein" title="Lutein">lutein</a> and <a href="/wiki/Zeaxanthin" title="Zeaxanthin">zeaxanthin</a>. They are known as <i><a href="/wiki/Xanthophyll" title="Xanthophyll">xanthophylls</a></i>.<sup id="cite_ref-lpi_3-2" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Their color, ranging from pale yellow through bright orange to deep red, is directly related to their structure, especially the length of the conjugation.<sup id="cite_ref-lpi_3-3" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Xanthophylls are often yellow, giving their class name. </p><p>Carotenoids also participate in different types of cell signaling.<sup id="cite_ref-Cogdell-1978_7-0" class="reference"><a href="#cite_note-Cogdell-1978-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> They are able to signal the production of <a href="/wiki/Abscisic_acid" title="Abscisic acid">abscisic acid</a>, which regulates plant growth, <a href="/wiki/Seed_dormancy" title="Seed dormancy">seed dormancy</a>, embryo maturation and <a href="/wiki/Germination" title="Germination">germination</a>, <a href="/wiki/Cell_division" title="Cell division">cell division</a> and elongation, floral growth, and stress responses.<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> <div class="mw-heading mw-heading3"><h3 id="Photophysics">Photophysics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=2" title="Edit section: Photophysics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The length of the multiple <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated double bonds</a> determines their color and photophysics.<sup id="cite_ref-:2_9-0" class="reference"><a href="#cite_note-:2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><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> After absorbing a photon, the carotenoid transfers its excited electron to <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a> for use in photosynthesis.<sup id="cite_ref-:2_9-1" class="reference"><a href="#cite_note-:2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Upon absorption of light, carotenoids transfer excitation energy to and from <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a>. The singlet-singlet energy transfer is a lower energy state transfer and is used during photosynthesis.<sup id="cite_ref-Cogdell-1978_7-1" class="reference"><a href="#cite_note-Cogdell-1978-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The triplet-triplet transfer is a higher energy state and is essential in photoprotection.<sup id="cite_ref-Cogdell-1978_7-2" class="reference"><a href="#cite_note-Cogdell-1978-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Light produces damaging species during photosynthesis, with the most damaging being <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> (ROS).<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> As these high energy ROS are produced in the chlorophyll the energy is transferred to the carotenoid’s polyene tail and undergoes a series of reactions in which electrons are moved between the carotenoid bonds in order to find the most balanced (lowest energy) state for the carotenoid.<sup id="cite_ref-:2_9-2" class="reference"><a href="#cite_note-:2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Carotenoids defend plants against <a href="/wiki/Singlet_oxygen" title="Singlet oxygen">singlet oxygen</a>, by both energy transfer and by chemical reactions. They also protect plants by quenching triplet chlorophyll.<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> By protecting lipids from free-radical damage, which generate charged <a href="/wiki/Lipid_peroxidation" title="Lipid peroxidation">lipid peroxides</a> and other oxidised derivatives, carotenoids support crystalline architecture and hydrophobicity of lipoproteins and cellular lipid structures, hence oxygen solubility and its diffusion therein.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Structure-property_relationships">Structure-property relationships</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=3" title="Edit section: Structure-property relationships"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like some <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>, carotenoids are <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> due to the presence of long <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated</a> <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> chains.<sup id="cite_ref-lpi_3-4" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> As a consequence, carotenoids are typically present in plasma <a href="/wiki/Lipoprotein" title="Lipoprotein">lipoproteins</a> and cellular lipid structures.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Morphology">Morphology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=4" title="Edit section: Morphology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carotenoids are located primarily outside the <a href="/wiki/Cell_nucleus" title="Cell nucleus">cell nucleus</a> in different cytoplasm organelles, <a href="/wiki/Lipid_droplet" title="Lipid droplet">lipid droplets</a>, <a href="/wiki/Microbody" title="Microbody">cytosomes</a> and granules. They have been visualised and quantified by <a href="/wiki/Raman_spectroscopy" title="Raman spectroscopy">raman spectroscopy</a> in an <a href="/wiki/Algal" class="mw-redirect" title="Algal">algal</a> cell.<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><p>With the development of <a href="/wiki/Monoclonal_antibody" title="Monoclonal antibody">monoclonal antibodies</a> to <i>trans-</i><a href="/wiki/Lycopene" title="Lycopene">lycopene</a> it was possible to localise this carotenoid in different animal and human cells.<sup id="cite_ref-Petyaev_etal-2018_16-0" class="reference"><a href="#cite_note-Petyaev_etal-2018-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Aerial_image_of_Grand_Prismatic_Spring_(view_from_the_south).jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Aerial_image_of_Grand_Prismatic_Spring_%28view_from_the_south%29.jpg/220px-Aerial_image_of_Grand_Prismatic_Spring_%28view_from_the_south%29.jpg" decoding="async" width="220" height="156" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Aerial_image_of_Grand_Prismatic_Spring_%28view_from_the_south%29.jpg/330px-Aerial_image_of_Grand_Prismatic_Spring_%28view_from_the_south%29.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Aerial_image_of_Grand_Prismatic_Spring_%28view_from_the_south%29.jpg/440px-Aerial_image_of_Grand_Prismatic_Spring_%28view_from_the_south%29.jpg 2x" data-file-width="4800" data-file-height="3400" /></a><figcaption>The orange ring surrounding <a href="/wiki/Grand_Prismatic_Spring" title="Grand Prismatic Spring">Grand Prismatic Spring</a> is due to carotenoids produced by <a href="/wiki/Cyanobacteria" title="Cyanobacteria">cyanobacteria</a> and other <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Foods">Foods</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=5" title="Edit section: Foods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Beta-carotene" class="mw-redirect" title="Beta-carotene">Beta-carotene</a>, found in <a href="/wiki/Pumpkin" title="Pumpkin">pumpkins</a>, <a href="/wiki/Sweet_potato" title="Sweet potato">sweet potato</a>, <a href="/wiki/Carrot" title="Carrot">carrots</a> and <a href="/wiki/Winter_squash" title="Winter squash">winter squash</a>, is responsible for their orange-yellow colors.<sup id="cite_ref-lpi_3-5" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Dried carrots have the highest amount of carotene of any food per 100-gram serving, measured in retinol activity equivalents (provitamin A equivalents).<sup id="cite_ref-lpi_3-6" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><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> Vietnamese <a href="/wiki/Gac" title="Gac">gac</a> fruit contains the highest known concentration of the carotenoid <a href="/wiki/Lycopene" title="Lycopene">lycopene</a>.<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> Although green, <a href="/wiki/Kale" title="Kale">kale</a>, <a href="/wiki/Spinach" title="Spinach">spinach</a>, <a href="/wiki/Collard_greens" class="mw-redirect" title="Collard greens">collard greens</a>, and <a href="/wiki/Turnip_greens" class="mw-redirect" title="Turnip greens">turnip greens</a> contain substantial amounts of beta-carotene.<sup id="cite_ref-lpi_3-7" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The diet of <a href="/wiki/Flamingo" title="Flamingo">flamingos</a> is rich in carotenoids, imparting the orange-colored feathers of these birds.<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> </p><p>Reviews of preliminary research in 2015 indicated that foods high in carotenoids may reduce the risk of <a href="/wiki/Head_and_neck_cancers" class="mw-redirect" title="Head and neck cancers">head and neck cancers</a><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> and <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>.<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> There is no correlation between consumption of foods high in carotenoids and vitamin A and the risk of <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Humans and other <a href="/wiki/Animal" title="Animal">animals</a> are mostly incapable of synthesizing carotenoids, and must obtain them through their diet. Carotenoids are a common and often ornamental feature in animals. For example, the pink color of <a href="/wiki/Salmon" title="Salmon">salmon</a>, and the red coloring of cooked <a href="/wiki/Lobster" title="Lobster">lobsters</a> and scales of the yellow morph of <a href="/wiki/Common_wall_lizard" class="mw-redirect" title="Common wall lizard">common wall lizards</a> are due to carotenoids.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><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. (December 2015)">citation needed</span></a></i>]</sup> It has been proposed that carotenoids are used in ornamental traits (for extreme examples see <a href="/wiki/Puffin" title="Puffin">puffin</a> birds) because, given their physiological and chemical properties, they can be used as visible indicators of individual health, and hence are used by animals when selecting potential mates.<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>Carotenoids from the diet are stored in the fatty tissues of animals,<sup id="cite_ref-lpi_3-8" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> and exclusively <a href="/wiki/Carnivore" title="Carnivore">carnivorous</a> animals obtain the compounds from animal fat. In the human diet, <a href="/wiki/Small_intestine#Absorption" title="Small intestine">absorption</a> of carotenoids is improved when consumed with fat in a meal.<sup id="cite_ref-jfst_25-0" class="reference"><a href="#cite_note-jfst-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Cooking carotenoid-containing vegetables in oil and shredding the vegetable both increase carotenoid <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a>.<sup id="cite_ref-lpi_3-9" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-jfst_25-1" class="reference"><a href="#cite_note-jfst-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> </p> <div class="mw-heading mw-heading2"><h2 id="Plant_colors">Plant colors</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=6" title="Edit section: Plant colors"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Acer_japonicum_Vitifolium_JPG1fu.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Acer_japonicum_Vitifolium_JPG1fu.jpg/220px-Acer_japonicum_Vitifolium_JPG1fu.jpg" decoding="async" width="220" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Acer_japonicum_Vitifolium_JPG1fu.jpg/330px-Acer_japonicum_Vitifolium_JPG1fu.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Acer_japonicum_Vitifolium_JPG1fu.jpg/440px-Acer_japonicum_Vitifolium_JPG1fu.jpg 2x" data-file-width="1875" data-file-height="1250" /></a><figcaption>Yellow and orange leaf colors in autumn are due to carotenoids, which are visible after chlorophyll degrades for the season.</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Prunus_armeniaca_Nubra_Valley.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Prunus_armeniaca_Nubra_Valley.jpg/220px-Prunus_armeniaca_Nubra_Valley.jpg" decoding="async" width="220" height="298" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Prunus_armeniaca_Nubra_Valley.jpg/330px-Prunus_armeniaca_Nubra_Valley.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Prunus_armeniaca_Nubra_Valley.jpg/440px-Prunus_armeniaca_Nubra_Valley.jpg 2x" data-file-width="887" data-file-height="1200" /></a><figcaption><a href="/wiki/Apricot" title="Apricot">Apricots</a>, rich in carotenoids</figcaption></figure> <p>The most common carotenoids include lycopene and the vitamin A precursor β-carotene. In plants, the xanthophyll <a href="/wiki/Lutein" title="Lutein">lutein</a> is the most abundant carotenoid and its role in preventing age-related eye disease is currently under investigation.<sup id="cite_ref-Li_5-1" class="reference"><a href="#cite_note-Li-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Lutein and the other carotenoid pigments found in mature leaves are often not obvious because of the masking presence of <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a>. When chlorophyll is not present, as in autumn foliage, the yellows and oranges of the carotenoids are predominant. For the same reason, carotenoid colors often predominate in ripe fruit after being unmasked by the disappearance of chlorophyll. </p><p>Carotenoids are responsible for the brilliant yellows and oranges that tint <a href="/wiki/Deciduous" title="Deciduous">deciduous</a> foliage (such as dying <a href="/wiki/Autumn_leaf_color" title="Autumn leaf color">autumn leaves</a>) of certain hardwood species as <a href="/wiki/Hickory" title="Hickory">hickories</a>, <a href="/wiki/Ash_(tree)" class="mw-redirect" title="Ash (tree)">ash</a>, <a href="/wiki/Maple" title="Maple">maple</a>, <a href="/wiki/Yellow_poplar" class="mw-redirect" title="Yellow poplar">yellow poplar</a>, <a href="/wiki/Aspen" title="Aspen">aspen</a>, <a href="/wiki/Birch" title="Birch">birch</a>, <a href="/wiki/Black_cherry" class="mw-redirect" title="Black cherry">black cherry</a>, <a href="/wiki/Sycamore" title="Sycamore">sycamore</a>, <a href="/wiki/Populus_sect._Aegiros" class="mw-redirect" title="Populus sect. Aegiros">cottonwood</a>, <a href="/wiki/Sassafras" title="Sassafras">sassafras</a>, and <a href="/wiki/Alder" title="Alder">alder</a>. Carotenoids are the dominant pigment in autumn leaf coloration of about 15-30% of tree species.<sup id="cite_ref-tree1044_27-0" class="reference"><a href="#cite_note-tree1044-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> However, the reds, the purples, and their blended combinations that decorate autumn foliage usually come from another group of pigments in the cells called <a href="/wiki/Anthocyanin" title="Anthocyanin">anthocyanins</a>. Unlike the carotenoids, these pigments are not present in the leaf throughout the growing season, but are actively produced towards the end of summer.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Bird_colors_and_sexual_selection">Bird colors and sexual selection</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=7" title="Edit section: Bird colors and sexual selection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dietary carotenoids and their metabolic derivatives are responsible for bright yellow to red coloration in birds.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Studies estimate that around 2956 modern bird species display carotenoid coloration and that the ability to utilize these pigments for external coloration has evolved independently many times throughout avian evolutionary history.<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> Carotenoid coloration exhibits high levels of <a href="/wiki/Sexual_dimorphism" title="Sexual dimorphism">sexual dimorphism</a>, with adult male birds generally displaying more vibrant coloration than females of the same species.<sup id="cite_ref-Cooney-2019_31-0" class="reference"><a href="#cite_note-Cooney-2019-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>These differences arise due to the selection of yellow and red coloration in males by <a href="/wiki/Mate_choice" title="Mate choice">female preference</a>.<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><sup id="cite_ref-Cooney-2019_31-1" class="reference"><a href="#cite_note-Cooney-2019-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> In many species of birds, females invest greater time and resources into raising offspring than their male partners. Therefore, it is imperative that female birds carefully select high quality mates. Current literature supports the theory that vibrant carotenoid coloration is correlated with male quality—either though direct effects on immune function and oxidative stress,<sup id="cite_ref-33" class="reference"><a href="#cite_note-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> or through a connection between carotenoid metabolizing pathways and pathways for cellular respiration.<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-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p>It is generally considered that sexually selected traits, such as carotenoid-based coloration, evolve because they are honest signals of phenotypic and genetic quality. For instance, among males of the bird species <i><a href="/wiki/Great_tit" title="Great tit">Parus major</a></i>, the more colorfully ornamented males produce sperm that is better protected against <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a> due to increased presence of carotenoid <a href="/wiki/Antioxidant" title="Antioxidant">antioxidants</a>.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> However, there is also evidence that attractive male coloration may be a faulty signal of male quality. Among <a href="/wiki/Stickleback" title="Stickleback">stickleback</a> fish, males that are more attractive to females due to carotenoid colorants appear to under-allocate carotenoids to their germline cells.<sup id="cite_ref-Kim2020_39-0" class="reference"><a href="#cite_note-Kim2020-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Since carotinoids are beneficial antioxidants, their under-allocation to <a href="/wiki/Germline" title="Germline">germline</a> cells can lead to increased oxidative <a href="/wiki/DNA_damage_(naturally_occurring)" title="DNA damage (naturally occurring)">DNA damage</a> to these cells.<sup id="cite_ref-Kim2020_39-1" class="reference"><a href="#cite_note-Kim2020-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Therefore, female sticklebacks may risk <a href="/wiki/Fertility" title="Fertility">fertility</a> and the viability of their offspring by choosing redder, but more deteriorated partners with reduced <a href="/wiki/Sperm" title="Sperm">sperm</a> quality. </p> <div class="mw-heading mw-heading2"><h2 id="Aroma_chemicals">Aroma chemicals</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=8" title="Edit section: Aroma chemicals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Products of carotenoid degradation such as <a href="/wiki/Ionone" title="Ionone">ionones</a>, <a href="/wiki/Damascone" title="Damascone">damascones</a> and <a href="/wiki/Damascenone" title="Damascenone">damascenones</a> are also important fragrance chemicals that are used extensively in the <a href="/wiki/Perfume" title="Perfume">perfumes</a> and fragrance industry. Both β-damascenone and β-ionone although low in concentration in <a href="/wiki/Rose" title="Rose">rose</a> distillates are the key odor-contributing compounds in flowers. In fact, the sweet floral smells present in <a href="/wiki/Black_tea" title="Black tea">black tea</a>, aged <a href="/wiki/Tobacco" title="Tobacco">tobacco</a>, <a href="/wiki/Grape" title="Grape">grape</a>, and many <a href="/wiki/Fruit" title="Fruit">fruits</a> are due to the aromatic compounds resulting from carotenoid breakdown. </p> <div class="mw-heading mw-heading2"><h2 id="Disease">Disease</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=9" title="Edit section: Disease"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some carotenoids are produced by bacteria to protect themselves from oxidative immune attack. The <i>aureus</i> (golden) pigment that gives some strains of <i><a href="/wiki/Staphylococcus_aureus" title="Staphylococcus aureus">Staphylococcus aureus</a></i> their name is a carotenoid called <a href="/wiki/Staphyloxanthin" title="Staphyloxanthin">staphyloxanthin</a>. This carotenoid is a virulence factor with an <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> action that helps the microbe evade death by <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> used by the host immune system.<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> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=10" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Carotenoid_synthetic_pathway.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Carotenoid_synthetic_pathway.svg/220px-Carotenoid_synthetic_pathway.svg.png" decoding="async" width="220" height="369" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Carotenoid_synthetic_pathway.svg/330px-Carotenoid_synthetic_pathway.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/Carotenoid_synthetic_pathway.svg/440px-Carotenoid_synthetic_pathway.svg.png 2x" data-file-width="1000" data-file-height="1675" /></a><figcaption>Pathway of carotenoid synthesis</figcaption></figure> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Merge_from plainlinks metadata ambox ambox-move" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Mergefrom.svg/50px-Mergefrom.svg.png" decoding="async" width="50" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Mergefrom.svg/75px-Mergefrom.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Mergefrom.svg/100px-Mergefrom.svg.png 2x" data-file-width="50" data-file-height="20" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">It has been suggested that <i><a href="/wiki/Carotenoid_biosynthesis" title="Carotenoid biosynthesis">Carotenoid biosynthesis</a></i> be <a href="/wiki/Wikipedia:Merging" title="Wikipedia:Merging">merged</a> into this section. (<a href="/wiki/Talk:Carotenoid" title="Talk:Carotenoid">Discuss</a>)<small><i> Proposed since October 2024.</i></small></div></td></tr></tbody></table> <p>The basic building blocks of carotenoids are <a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">isopentenyl diphosphate</a> (IPP) and <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">dimethylallyl diphosphate</a> (DMAPP).<sup id="cite_ref-Nisar-2015_41-0" class="reference"><a href="#cite_note-Nisar-2015-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> These two isoprene isomers are used to create various compounds depending on the biological pathway used to synthesize the isomers.<sup id="cite_ref-Kuzuyama-2012_42-0" class="reference"><a href="#cite_note-Kuzuyama-2012-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Plants are known to use two different pathways for IPP production: the cytosolic <a href="/wiki/Mevalonic_acid" title="Mevalonic acid">mevalonic acid</a> pathway (MVA) and the plastidic <a href="/wiki/Non-mevalonate_pathway" title="Non-mevalonate pathway">methylerythritol 4-phosphate</a> (MEP).<sup id="cite_ref-Nisar-2015_41-1" class="reference"><a href="#cite_note-Nisar-2015-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> In animals, the production of <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> starts by creating IPP and DMAPP using the MVA.<sup id="cite_ref-Kuzuyama-2012_42-1" class="reference"><a href="#cite_note-Kuzuyama-2012-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> For carotenoid production plants use MEP to generate IPP and DMAPP.<sup id="cite_ref-Nisar-2015_41-2" class="reference"><a href="#cite_note-Nisar-2015-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> The MEP pathway results in a 5:1 mixture of IPP:DMAPP.<sup id="cite_ref-Kuzuyama-2012_42-2" class="reference"><a href="#cite_note-Kuzuyama-2012-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> IPP and DMAPP undergo several reactions, resulting in the major carotenoid precursor, <a href="/wiki/Geranylgeranyl_diphosphate" class="mw-redirect" title="Geranylgeranyl diphosphate">geranylgeranyl diphosphate</a> (GGPP). GGPP can be converted into carotenes or xanthophylls by undergoing a number of different steps within the carotenoid biosynthetic pathway.<sup id="cite_ref-Nisar-2015_41-3" class="reference"><a href="#cite_note-Nisar-2015-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="MEP_pathway">MEP pathway</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=11" title="Edit section: MEP pathway"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">Glyceraldehyde 3-phosphate</a> and <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvate</a>, intermediates of <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>, are converted to deoxy-D-xylulose 5-phosphate (DXP) catalyzed by <a href="/wiki/DXP_synthase" class="mw-redirect" title="DXP synthase">DXP synthase</a> (DXS). <a href="/wiki/DXP_reductoisomerase" title="DXP reductoisomerase">DXP reductoisomerase</a> catalyzes the reduction by <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADPH</a> and subsequent rearrangement.<sup id="cite_ref-Nisar-2015_41-4" class="reference"><a href="#cite_note-Nisar-2015-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kuzuyama-2012_42-3" class="reference"><a href="#cite_note-Kuzuyama-2012-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> The resulting MEP is converted to 4-(cytidine 5’-diphospho)-2-C-methyl-D-erythritol (CDP-ME) in the presence of CTP using the enzyme MEP cytidylyltransferase. CDP-ME is then converted, in the presence of <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>, to 2-phospho-4-(cytidine 5’-diphospho)-2-C-methyl-D-erythritol (CDP-ME2P). The conversion to CDP-ME2P is catalyzed by <a href="/wiki/4-(cytidine_5%27-diphospho)-2-C-methyl-D-erythritol_kinase" title="4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol kinase">CDP-ME kinase</a>. Next, CDP-ME2P is converted to 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (MECDP). This reaction occurs when MECDP synthase catalyzes the reaction and CMP is eliminated from the CDP-ME2P molecule. MECDP is then converted to (e)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate (HMBDP) via <a href="/wiki/4-hydroxy-3-methylbut-2-en-1-yl_diphosphate_synthase" title="4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase">HMBDP synthase</a> in the presence of <a href="/wiki/Flavodoxin" title="Flavodoxin">flavodoxin</a> and NADPH. HMBDP is reduced to IPP in the presence of <a href="/wiki/Ferredoxin" title="Ferredoxin">ferredoxin</a> and NADPH by the enzyme <a href="/wiki/4-Hydroxy-3-methylbut-2-enyl_diphosphate_reductase" title="4-Hydroxy-3-methylbut-2-enyl diphosphate reductase">HMBDP reductase</a>. The last two steps involving HMBPD synthase and reductase can only occur in completely <a href="/wiki/Anaerobic_respiration" title="Anaerobic respiration">anaerobic</a> environments. IPP is then able to <a href="/wiki/Isomerization" title="Isomerization">isomerize</a> to DMAPP via IPP isomerase.<sup id="cite_ref-Kuzuyama-2012_42-4" class="reference"><a href="#cite_note-Kuzuyama-2012-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Carotenoid_biosynthetic_pathway">Carotenoid biosynthetic pathway</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=12" title="Edit section: Carotenoid biosynthetic pathway"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Phytoene_desaturation_PLOS_ONE.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Phytoene_desaturation_PLOS_ONE.png/220px-Phytoene_desaturation_PLOS_ONE.png" decoding="async" width="220" height="190" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Phytoene_desaturation_PLOS_ONE.png/330px-Phytoene_desaturation_PLOS_ONE.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Phytoene_desaturation_PLOS_ONE.png/440px-Phytoene_desaturation_PLOS_ONE.png 2x" data-file-width="2062" data-file-height="1781" /></a><figcaption> The conversion of phytoene to lycopene in plants and cyanobacteria (left) differs compared to bacteria and fungi (right).</figcaption></figure> <p>Two GGPP molecules condense via <a href="/wiki/Phytoene_synthase" title="Phytoene synthase">phytoene synthase</a> (PSY), forming the 15-cis <a href="/wiki/Isomer" title="Isomer">isomer</a> of <a href="/wiki/Phytoene" title="Phytoene">phytoene</a>. PSY belongs to the <a href="/wiki/Squalene/phytoene_synthase_family" title="Squalene/phytoene synthase family">squalene/phytoene synthase family</a> and is homologous to <a href="/wiki/Farnesyl-diphosphate_farnesyltransferase" title="Farnesyl-diphosphate farnesyltransferase">squalene synthase</a> that takes part in <a href="/wiki/Steroid" title="Steroid">steroid</a> biosynthesis. The subsequent conversion of phytoene into all-trans-<a href="/wiki/Lycopene" title="Lycopene">lycopene</a> depends on the organism. Bacteria and fungi employ a single enzyme, the <a href="/wiki/Phytoene_desaturase_(lycopene-forming)" title="Phytoene desaturase (lycopene-forming)">bacterial phytoene desaturase</a> (CRTI) for the catalysis. Plants and cyanobacteria however utilize four enzymes for this process.<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> The first of these enzymes is a <a href="/wiki/15-Cis-phytoene_desaturase" title="15-Cis-phytoene desaturase">plant-type phytoene desaturase</a> which introduces two additional double bonds into 15-cis-phytoene by <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenation</a> and isomerizes two of its existing double bonds from <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">trans to cis</a> producing 9,15,9’-tri-cis-ζ-carotene. The central double bond of this tri-cis-ζ-carotene is isomerized by the <a href="/wiki/Zeta-carotene_isomerase" title="Zeta-carotene isomerase">zeta-carotene isomerase</a> Z-ISO and the resulting 9,9'-di-cis-ζ-carotene is dehydrogenated again via a <a href="/wiki/9,9%27-Dicis-zeta-carotene_desaturase" title="9,9'-Dicis-zeta-carotene desaturase">ζ-carotene desaturase (ZDS)</a>. This again introduces two double bonds, resulting in 7,9,7’,9’-tetra-cis-lycopene. <a href="/wiki/CRTISO" class="mw-redirect" title="CRTISO">CRTISO</a>, a carotenoid isomerase, is needed to convert the <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">cis</a>-lycopene into an <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">all-trans</a> lycopene in the presence of reduced <a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">FAD</a>. </p><p>This all-trans lycopene is cyclized; <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclization</a> gives rise to carotenoid diversity, which can be distinguished based on the end groups. There can be either a <a href="/wiki/Beta-ring" class="mw-redirect" title="Beta-ring">beta ring</a> or an epsilon ring, each generated by a different enzyme (<a href="/wiki/Lycopene_beta-cyclase" title="Lycopene beta-cyclase">lycopene beta-cyclase</a> [beta-LCY] or <a href="/wiki/Lycopene_epsilon-cyclase" title="Lycopene epsilon-cyclase">lycopene epsilon-cyclase</a> [epsilon-LCY]). <a href="/wiki/%CE%91-Carotene" title="Α-Carotene">α-Carotene</a> is produced when the all-trans lycopene first undergoes reaction with epsilon-LCY then a second reaction with beta-LCY; whereas <a href="/wiki/%CE%92-carotene" class="mw-redirect" title="Β-carotene">β-carotene</a> is produced by two reactions with beta-LCY. α- and β-Carotene are the most common carotenoids in the plant <a href="/wiki/Photosystem" title="Photosystem">photosystems</a> but they can still be further converted into xanthophylls by using beta-hydrolase and epsilon-hydrolase, leading to a variety of xanthophylls.<sup id="cite_ref-Nisar-2015_41-5" class="reference"><a href="#cite_note-Nisar-2015-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Regulation">Regulation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=13" title="Edit section: Regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is believed that both DXS and DXR are rate-determining enzymes, allowing them to regulate carotenoid levels.<sup id="cite_ref-Nisar-2015_41-6" class="reference"><a href="#cite_note-Nisar-2015-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> This was discovered in an experiment where DXS and DXR were genetically overexpressed, leading to increased carotenoid expression in the resulting seedlings.<sup id="cite_ref-Nisar-2015_41-7" class="reference"><a href="#cite_note-Nisar-2015-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Also, J-protein (J20) and heat shock protein 70 (Hsp70) chaperones are thought to be involved in post-transcriptional regulation of DXS activity, such that mutants with defective J20 activity exhibit reduced DXS enzyme activity while accumulating inactive DXS protein.<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> Regulation may also be caused by external <a href="/wiki/Toxin" title="Toxin">toxins</a> that affect enzymes and proteins required for synthesis. Ketoclomazone is derived from <a href="/wiki/Herbicide" title="Herbicide">herbicides</a> applied to soil and binds to DXP synthase.<sup id="cite_ref-Kuzuyama-2012_42-5" class="reference"><a href="#cite_note-Kuzuyama-2012-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> This inhibits DXP synthase, preventing synthesis of DXP and halting the MEP pathway.<sup id="cite_ref-Kuzuyama-2012_42-6" class="reference"><a href="#cite_note-Kuzuyama-2012-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> The use of this toxin leads to lower levels of carotenoids in plants grown in the contaminated soil.<sup id="cite_ref-Kuzuyama-2012_42-7" class="reference"><a href="#cite_note-Kuzuyama-2012-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Fosmidomycin" title="Fosmidomycin">Fosmidomycin</a>, an <a href="/wiki/Antibiotics" class="mw-redirect" title="Antibiotics">antibiotic</a>, is a <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">competitive inhibitor</a> of DXP reductoisomerase due to its similar structure to the enzyme.<sup id="cite_ref-Kuzuyama-2012_42-8" class="reference"><a href="#cite_note-Kuzuyama-2012-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Application of said antibiotic prevents reduction of DXP, again halting the MEP pathway. <sup id="cite_ref-Kuzuyama-2012_42-9" class="reference"><a href="#cite_note-Kuzuyama-2012-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Naturally_occurring_carotenoids">Naturally occurring carotenoids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carotenoid&action=edit&section=14" title="Edit section: Naturally occurring carotenoids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Hydrocarbons <ul><li><a href="/wiki/Lycopersene" title="Lycopersene">Lycopersene</a> 7,8,11,12,15,7',8',11',12',15'-Decahydro-γ,γ-carotene</li> <li><a href="/wiki/Phytofluene" title="Phytofluene">Phytofluene</a></li> <li><a href="/wiki/Lycopene" title="Lycopene">Lycopene</a></li> <li><a href="/w/index.php?title=Hexahydrolycopene&action=edit&redlink=1" class="new" title="Hexahydrolycopene (page does not exist)">Hexahydrolycopene</a> 15-<i>cis</i>-7,8,11,12,7',8'-Hexahydro-γ,γ-carotene</li> <li><a href="/wiki/Torulene" title="Torulene">Torulene</a> 3',4'-Didehydro-β,γ-carotene</li> <li><a href="/wiki/%CE%91-Zeacarotene" title="Α-Zeacarotene">α-Zeacarotene</a> 7',8'-Dihydro-ε,γ-carotene</li> <li><a href="/wiki/%CE%91-Carotene" title="Α-Carotene">α-Carotene</a></li> <li><a href="/wiki/%CE%92-Carotene" title="Β-Carotene">β-Carotene</a></li> <li><a href="/wiki/%CE%93-Carotene" title="Γ-Carotene">γ-Carotene</a></li> <li><a href="/wiki/%CE%94-Carotene" title="Δ-Carotene">δ-Carotene</a></li> <li><a href="/wiki/%CE%95-Carotene" title="Ε-Carotene">ε-Carotene</a></li> <li><a href="/wiki/%CE%96-Carotene" title="Ζ-Carotene">ζ-Carotene</a></li></ul></li> <li>Alcohols <ul><li><a href="/w/index.php?title=Alloxanthin&action=edit&redlink=1" class="new" title="Alloxanthin (page does not exist)">Alloxanthin</a></li> <li><a href="/wiki/Bacterioruberin" class="mw-redirect" title="Bacterioruberin">Bacterioruberin</a> 2,2'-Bis(3-hydroxy-3-methylbutyl)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-γ,γ-carotene-1,1'-diol</li> <li><a href="/w/index.php?title=Cynthiaxanthin&action=edit&redlink=1" class="new" title="Cynthiaxanthin (page does not exist)">Cynthiaxanthin</a></li> <li><a href="/w/index.php?title=Pectenoxanthin&action=edit&redlink=1" class="new" title="Pectenoxanthin (page does not exist)">Pectenoxanthin</a></li> <li><a href="/w/index.php?title=Cryptomonaxanthin&action=edit&redlink=1" class="new" title="Cryptomonaxanthin (page does not exist)">Cryptomonaxanthin</a> (3R,3'R)-7,8,7',8'-Tetradehydro-β,β-carotene-3,3'-diol</li> <li><a href="/w/index.php?title=Crustaxanthin&action=edit&redlink=1" class="new" title="Crustaxanthin (page does not exist)">Crustaxanthin</a> β,-Carotene-3,4,3',4'-tetrol</li> <li><a href="/w/index.php?title=Gazaniaxanthin&action=edit&redlink=1" class="new" title="Gazaniaxanthin (page does not exist)">Gazaniaxanthin</a> (3R)-5'-cis-β,γ-Caroten-3-ol</li> <li><a href="/w/index.php?title=OH-Chlorobactene&action=edit&redlink=1" class="new" title="OH-Chlorobactene (page does not exist)">OH-Chlorobactene</a> 1',2'-Dihydro-f,γ-caroten-1'-ol</li> <li><a href="/w/index.php?title=Loroxanthin&action=edit&redlink=1" class="new" title="Loroxanthin (page does not exist)">Loroxanthin</a> β,ε-Carotene-3,19,3'-triol</li> <li><a href="/wiki/Lutein" title="Lutein">Lutein</a> (3R,3′R,6′R)-β,ε-carotene-3,3′-diol</li> <li><a href="/w/index.php?title=Lycoxanthin&action=edit&redlink=1" class="new" title="Lycoxanthin (page does not exist)">Lycoxanthin</a> γ,γ-Caroten-16-ol</li> <li><a href="/wiki/Rhodopin" title="Rhodopin">Rhodopin</a> 1,2-Dihydro-γ,γ-caroten-l-ol</li> <li><a href="/w/index.php?title=Rhodopinol&action=edit&redlink=1" class="new" title="Rhodopinol (page does not exist)">Rhodopinol</a> a.k.a. <a href="/w/index.php?title=Warmingol&action=edit&redlink=1" class="new" title="Warmingol (page does not exist)">Warmingol</a> 13-<i>cis</i>-1,2-Dihydro-γ,γ-carotene-1,20-diol</li> <li><a href="/w/index.php?title=Saproxanthin&action=edit&redlink=1" class="new" title="Saproxanthin (page does not exist)">Saproxanthin</a> 3',4'-Didehydro-1',2'-dihydro-β,γ-carotene-3,1'-diol</li> <li><a href="/wiki/Zeaxanthin" title="Zeaxanthin">Zeaxanthin</a></li></ul></li> <li>Glycosides <ul><li><a href="/w/index.php?title=Oscillaxanthin&action=edit&redlink=1" class="new" title="Oscillaxanthin (page does not exist)">Oscillaxanthin</a> 2,2'-Bis(β-L-rhamnopyranosyloxy)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-γ,γ-carotene-1,1'-diol</li> <li><a href="/w/index.php?title=Phleixanthophyll&action=edit&redlink=1" class="new" title="Phleixanthophyll (page does not exist)">Phleixanthophyll</a> 1'-(β-D-Glucopyranosyloxy)-3',4'-didehydro-1',2'-dihydro-β,γ-caroten-2'-ol</li></ul></li> <li>Ethers <ul><li><a href="/w/index.php?title=Rhodovibrin&action=edit&redlink=1" class="new" title="Rhodovibrin (page does not exist)">Rhodovibrin</a> 1'-Methoxy-3',4'-didehydro-1,2,1',2'-tetrahydro-γ,γ-caroten-1-ol</li> <li><a href="/wiki/Spheroidene" title="Spheroidene">Spheroidene</a> 1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-γ,γ-carotene</li></ul></li> <li>Epoxides <ul><li><a href="/wiki/Diadinoxanthin" title="Diadinoxanthin">Diadinoxanthin</a> 5,6-Epoxy-7',8'-didehydro-5,6-dihydro—carotene-3,3-diol</li> <li><a href="/w/index.php?title=Luteoxanthin&action=edit&redlink=1" class="new" title="Luteoxanthin (page does not exist)">Luteoxanthin</a> 5,6: 5',8'-Diepoxy-5,6,5',8'-tetrahydro-β,β-carotene-3,3'-diol</li> <li><a href="/w/index.php?title=Mutatoxanthin&action=edit&redlink=1" class="new" title="Mutatoxanthin (page does not exist)">Mutatoxanthin</a></li> <li><a href="/wiki/Citroxanthin" class="mw-redirect" title="Citroxanthin">Citroxanthin</a></li> <li><a href="/w/index.php?title=Zeaxanthin_furanoxide&action=edit&redlink=1" class="new" title="Zeaxanthin furanoxide (page does not exist)">Zeaxanthin furanoxide</a> 5,8-Epoxy-5,8-dihydro-β,β-carotene-3,3'-diol</li> <li><a href="/w/index.php?title=Neochrome_(Carotenoid)&action=edit&redlink=1" class="new" title="Neochrome (Carotenoid) (page does not exist)">Neochrome</a> 5',8'-Epoxy-6,7-didehydro-5,6,5',8'-tetrahydro-β,β-carotene-3,5,3'-triol</li> <li><a href="/w/index.php?title=Foliachrome&action=edit&redlink=1" class="new" title="Foliachrome (page does not exist)">Foliachrome</a></li> <li><a href="/w/index.php?title=Trollichrome&action=edit&redlink=1" class="new" title="Trollichrome (page does not exist)">Trollichrome</a></li> <li><a href="/w/index.php?title=Vaucheriaxanthin&action=edit&redlink=1" class="new" title="Vaucheriaxanthin (page does not exist)">Vaucheriaxanthin</a> 5',6'-Epoxy-6,7-didehydro-5,6,5',6'-tetrahydro-β,β-carotene-3,5,19,3'-tetrol</li></ul></li> <li>Aldehydes <ul><li><a href="/w/index.php?title=Rhodopinal&action=edit&redlink=1" class="new" title="Rhodopinal (page does not exist)">Rhodopinal</a></li> <li><a href="/w/index.php?title=Warmingone&action=edit&redlink=1" class="new" title="Warmingone (page does not exist)">Warmingone</a> 13-cis-1-Hydroxy-1,2-dihydro-γ,γ-caroten-20-al</li> <li><a href="/w/index.php?title=Torularhodinaldehyde&action=edit&redlink=1" class="new" title="Torularhodinaldehyde (page does not exist)">Torularhodinaldehyde</a> 3',4'-Didehydro-β,γ-caroten-16'-al</li></ul></li> <li>Acids and acid esters <ul><li><a href="/w/index.php?title=Torularhodin&action=edit&redlink=1" class="new" title="Torularhodin (page does not exist)">Torularhodin</a> 3',4'-Didehydro-β,γ-caroten-16'-oic acid</li> <li><a href="/w/index.php?title=Torularhodin_methyl_ester&action=edit&redlink=1" class="new" title="Torularhodin methyl ester (page does not exist)">Torularhodin methyl ester</a> Methyl 3',4'-didehydro-β,γ-caroten-16'-oate</li></ul></li> <li>Ketones<span class="anchor" id="Ketocarotenoids"></span> <ul><li><a href="/w/index.php?title=Astacene&action=edit&redlink=1" class="new" title="Astacene (page does not exist)">Astacene</a></li> <li><a href="/wiki/Astaxanthin" title="Astaxanthin">Astaxanthin</a></li> <li><a href="/wiki/Canthaxanthin" title="Canthaxanthin">Canthaxanthin</a><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> a.k.a. Aphanicin, Chlorellaxanthin β,β-Carotene-4,4'-dione</li> <li><a href="/wiki/Capsanthin" title="Capsanthin">Capsanthin</a> (3R,3'S,5'R)-3,3'-Dihydroxy-β,κ-caroten-6'-one</li> <li><a href="/wiki/Capsorubin" title="Capsorubin">Capsorubin</a> (3S,5R,3'S,5'R)-3,3'-Dihydroxy-κ,κ-carotene-6,6'-dione</li> <li><a href="/w/index.php?title=Cryptocapsin&action=edit&redlink=1" class="new" title="Cryptocapsin (page does not exist)">Cryptocapsin</a> (3'R,5'R)-3'-Hydroxy-β,κ-caroten-6'-one</li> <li><a href="/w/index.php?title=2,2%27-Diketospirilloxanthin&action=edit&redlink=1" class="new" title="2,2'-Diketospirilloxanthin (page does not exist)">2,2'-Diketospirilloxanthin</a> 1,1'-Dimethoxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-γ,γ-carotene-2,2'-dione</li> <li><a href="/wiki/Echinenone" title="Echinenone">Echinenone</a> β,β-Caroten-4-one</li> <li><a href="/wiki/3%27-Hydroxyechinenone" title="3'-Hydroxyechinenone">3'-Hydroxyechinenone</a></li> <li><a href="/w/index.php?title=Flexixanthin&action=edit&redlink=1" class="new" title="Flexixanthin (page does not exist)">Flexixanthin</a> 3,1'-Dihydroxy-3',4'-didehydro-1',2'-dihydro-β,γ-caroten-4-one</li> <li>3-OH-Canthaxanthin a.k.a. Adonirubin a.k.a. <a href="/w/index.php?title=Phoenicoxanthin&action=edit&redlink=1" class="new" title="Phoenicoxanthin (page does not exist)">Phoenicoxanthin</a> 3-Hydroxy-β,β-carotene-4,4'-dione</li> <li><a href="/w/index.php?title=Hydroxyspheriodenone&action=edit&redlink=1" class="new" title="Hydroxyspheriodenone (page does not exist)">Hydroxyspheriodenone</a> 1'-Hydroxy-1-methoxy-3,4-didehydro-1,2,1',2',7',8'-hexahydro-γ,γ-caroten-2-one</li> <li><a href="/w/index.php?title=Okenone&action=edit&redlink=1" class="new" title="Okenone (page does not exist)">Okenone</a> 1'-Methoxy-1',2'-dihydro-c,γ-caroten-4'-one</li> <li><a href="/w/index.php?title=Pectenolone&action=edit&redlink=1" class="new" title="Pectenolone (page does not exist)">Pectenolone</a> 3,3'-Dihydroxy-7',8'-didehydro-β,β-caroten-4-one</li> <li><a href="/w/index.php?title=Phoeniconone&action=edit&redlink=1" class="new" title="Phoeniconone (page does not exist)">Phoeniconone</a> a.k.a. <a href="/w/index.php?title=Dehydroadonirubin&action=edit&redlink=1" class="new" title="Dehydroadonirubin (page does not exist)">Dehydroadonirubin</a> 3-Hydroxy-2,3-didehydro-β,β-carotene-4,4'-dione</li> <li><a href="/w/index.php?title=Phoenicopterone&action=edit&redlink=1" class="new" title="Phoenicopterone (page does not exist)">Phoenicopterone</a> β,ε-caroten-4-one</li> <li><a href="/w/index.php?title=Rubixanthone&action=edit&redlink=1" class="new" title="Rubixanthone (page does not exist)">Rubixanthone</a> 3-Hydroxy-β,γ-caroten-4'-one</li> <li><a href="/w/index.php?title=Siphonaxanthin&action=edit&redlink=1" class="new" title="Siphonaxanthin (page does not exist)">Siphonaxanthin</a> 3,19,3'-Trihydroxy-7,8-dihydro-β,ε-caroten-8-one</li></ul></li> <li>Esters of alcohols <ul><li><a href="/w/index.php?title=Astacein&action=edit&redlink=1" class="new" title="Astacein (page does not exist)">Astacein</a> 3,3'-Bispalmitoyloxy-2,3,2',3'-tetradehydro-β,β-carotene-4,4'-dione or 3,3'-dihydroxy-2,3,2',3'-tetradehydro-β,β-carotene-4,4'-dione dipalmitate</li> <li><a href="/wiki/Fucoxanthin" title="Fucoxanthin">Fucoxanthin</a> 3'-Acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-β,β-caroten-8-one</li> <li><a href="/w/index.php?title=Isofucoxanthin&action=edit&redlink=1" class="new" title="Isofucoxanthin (page does not exist)">Isofucoxanthin</a> 3'-Acetoxy-3,5,5'-trihydroxy-6',7'-didehydro-5,8,5',6'-tetrahydro-β,β-caroten-8-one</li> <li><a href="/w/index.php?title=Physalien&action=edit&redlink=1" class="new" title="Physalien (page does not exist)">Physalien</a></li> <li><a href="/w/index.php?title=Siphonein&action=edit&redlink=1" class="new" title="Siphonein (page does not exist)">Siphonein</a> 3,3'-Dihydroxy-19-lauroyloxy-7,8-dihydro-β,ε-caroten-8-one or 3,19,3'-trihydroxy-7,8-dihydro-β,ε-caroten-8-one 19-laurate</li></ul></li> <li><a href="/wiki/Apocarotenoid" title="Apocarotenoid">Apocarotenoids</a> <ul><li><a href="/w/index.php?title=%CE%92-Apo-2%27-carotenal&action=edit&redlink=1" class="new" title="Β-Apo-2'-carotenal (page does not exist)">β-Apo-2'-carotenal</a> 3',4'-Didehydro-2'-apo-b-caroten-2'-al</li> <li><a href="/w/index.php?title=Apo-2-lycopenal&action=edit&redlink=1" class="new" title="Apo-2-lycopenal (page does not exist)">Apo-2-lycopenal</a></li> <li><a href="/w/index.php?title=Apo-6%27-lycopenal&action=edit&redlink=1" class="new" title="Apo-6'-lycopenal (page does not exist)">Apo-6'-lycopenal</a> 6'-Apo-y-caroten-6'-al</li> <li><a href="/w/index.php?title=Azafrinaldehyde&action=edit&redlink=1" class="new" title="Azafrinaldehyde (page does not exist)">Azafrinaldehyde</a> 5,6-Dihydroxy-5,6-dihydro-10'-apo-β-caroten-10'-al</li> <li><a href="/wiki/Bixin" title="Bixin">Bixin</a> 6'-Methyl hydrogen 9'-cis-6,6'-diapocarotene-6,6'-dioate</li> <li><a href="/wiki/Citranaxanthin" title="Citranaxanthin">Citranaxanthin</a> 5',6'-Dihydro-5'-apo-β-caroten-6'-one or 5',6'-dihydro-5'-apo-18'-nor-β-caroten-6'-one or 6'-methyl-6'-apo-β-caroten-6'-one</li> <li><a href="/wiki/Crocetin" title="Crocetin">Crocetin</a> 8,8'-Diapo-8,8'-carotenedioic acid</li> <li><a href="/w/index.php?title=Crocetinsemialdehyde&action=edit&redlink=1" class="new" title="Crocetinsemialdehyde (page does not exist)">Crocetinsemialdehyde</a> 8'-Oxo-8,8'-diapo-8-carotenoic acid</li> <li><a href="/wiki/Crocin" title="Crocin">Crocin</a> Digentiobiosyl 8,8'-diapo-8,8'-carotenedioate</li> <li><a href="/w/index.php?title=Hopkinsiaxanthin&action=edit&redlink=1" class="new" title="Hopkinsiaxanthin (page does not exist)">Hopkinsiaxanthin</a> 3-Hydroxy-7,8-didehydro-7',8'-dihydro-7'-apo-b-carotene-4,8'-dione or 3-hydroxy-8'-methyl-7,8-didehydro-8'-apo-b-carotene-4,8'-dione</li> <li><a href="/w/index.php?title=Methyl_apo-6%27-lycopenoate&action=edit&redlink=1" class="new" title="Methyl apo-6'-lycopenoate (page does not exist)">Methyl apo-6'-lycopenoate</a> Methyl 6'-apo-y-caroten-6'-oate</li> <li><a href="/w/index.php?title=Paracentrone&action=edit&redlink=1" class="new" title="Paracentrone (page does not exist)">Paracentrone</a> 3,5-Dihydroxy-6,7-didehydro-5,6,7',8'-tetrahydro-7'-apo-b-caroten-8'-one or 3,5-dihydroxy-8'-methyl-6,7-didehydro-5,6-dihydro-8'-apo-b-caroten-8'-one</li> <li><a href="/w/index.php?title=Sintaxanthin&action=edit&redlink=1" class="new" title="Sintaxanthin (page does not exist)">Sintaxanthin</a> 7',8'-Dihydro-7'-apo-b-caroten-8'-one or 8'-methyl-8'-apo-b-caroten-8'-one</li></ul></li> <li>Nor- and seco-carotenoids <ul><li><a href="/w/index.php?title=Actinioerythrin&action=edit&redlink=1" class="new" title="Actinioerythrin (page does not exist)">Actinioerythrin</a> 3,3'-Bisacyloxy-2,2'-dinor-b,b-carotene-4,4'-dione</li> <li><a href="/w/index.php?title=%CE%92-Carotenone&action=edit&redlink=1" class="new" title="Β-Carotenone (page does not exist)">β-Carotenone</a> 5,6:5',6'-Diseco-b,b-carotene-5,6,5',6'-tetrone</li> <li><a href="/wiki/Peridinin" title="Peridinin">Peridinin</a> 3'-Acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,5',6'-tetrahydro-12',13',20'-trinor-b,b-caroten-19,11-olide</li> <li><a href="/w/index.php?title=Pyrrhoxanthininol&action=edit&redlink=1" class="new" title="Pyrrhoxanthininol (page does not exist)">Pyrrhoxanthininol</a> 5,6-epoxy-3,3'-dihydroxy-7',8'-didehydro-5,6-dihydro-12',13',20'-trinor-b,b-caroten-19,11-olide</li> <li><a href="/w/index.php?title=Semi-%CE%B1-carotenone&action=edit&redlink=1" class="new" title="Semi-α-carotenone (page does not exist)">Semi-α-carotenone</a> 5,6-Seco-b,e-carotene-5,6-dione</li> <li><a href="/w/index.php?title=Semi-%CE%B2-carotenone&action=edit&redlink=1" class="new" title="Semi-β-carotenone (page does not exist)">Semi-β-carotenone</a> 5,6-seco-b,b-carotene-5,6-dione or 5',6'-seco-b,b-carotene-5',6'-dione</li> <li><a href="/w/index.php?title=Triphasiaxanthin&action=edit&redlink=1" class="new" title="Triphasiaxanthin (page does not exist)">Triphasiaxanthin</a> 3-Hydroxysemi-b-carotenone 3'-Hydroxy-5,6-seco-b,b-carotene-5,6-dione or 3-hydroxy-5',6'-seco-b,b-carotene-5',6'-dione</li></ul></li> <li>Retro-carotenoids and retro-apo-carotenoids <ul><li><a href="/w/index.php?title=Eschscholtzxanthin&action=edit&redlink=1" class="new" title="Eschscholtzxanthin (page does not exist)">Eschscholtzxanthin</a> 4',5'-Didehydro-4,5'-retro-b,b-carotene-3,3'-diol</li> <li><a href="/w/index.php?title=Eschscholtzxanthone&action=edit&redlink=1" class="new" title="Eschscholtzxanthone (page does not exist)">Eschscholtzxanthone</a> 3'-Hydroxy-4',5'-didehydro-4,5'-retro-b,b-caroten-3-one</li> <li><a href="/wiki/Rhodoxanthin" title="Rhodoxanthin">Rhodoxanthin</a> 4',5'-Didehydro-4,5'-retro-b,b-carotene-3,3'-dione</li> <li><a href="/w/index.php?title=Tangeraxanthin&action=edit&redlink=1" class="new" title="Tangeraxanthin (page does not exist)">Tangeraxanthin</a> 3-Hydroxy-5'-methyl-4,5'-retro-5'-apo-b-caroten-5'-one or 3-hydroxy-4,5'-retro-5'-apo-b-caroten-5'-one</li></ul></li> <li>Higher carotenoids <ul><li><a href="/w/index.php?title=Nonaprenoxanthin&action=edit&redlink=1" class="new" title="Nonaprenoxanthin (page does not exist)">Nonaprenoxanthin</a> 2-(4-Hydroxy-3-methyl-2-butenyl)-7',8',11',12'-tetrahydro-e,y-carotene</li> <li><a href="/w/index.php?title=Decaprenoxanthin&action=edit&redlink=1" class="new" title="Decaprenoxanthin (page does not exist)">Decaprenoxanthin</a> 2,2'-Bis(4-hydroxy-3-methyl-2-butenyl)-e,e-carotene</li> <li><a href="/w/index.php?title=C.p._450&action=edit&redlink=1" class="new" title="C.p. 450 (page does not exist)">C.p. 450</a> 2-[4-Hydroxy-3-(hydroxymethyl)-2-butenyl]-2'-(3-methyl-2-butenyl)-b,b-carotene</li> <li><a href="/w/index.php?title=C.p._473&action=edit&redlink=1" class="new" title="C.p. 473 (page does not exist)">C.p. 473</a> 2'-(4-Hydroxy-3-methyl-2-butenyl)-2-(3-methyl-2-butenyl)-3',4'-didehydro-l',2'-dihydro-β,γ-caroten-1'-ol</li> <li><a href="/wiki/Bacterioruberin" class="mw-redirect" title="Bacterioruberin">Bacterioruberin</a> 2,2'-Bis(3-hydroxy-3-methylbutyl)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-γ,γ-carotene-1,1'-diol</li></ul></li></ul> <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=Carotenoid&action=edit&section=15" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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/CRT_(genetics)" title="CRT (genetics)">CRT (genetics)</a>, <a href="/wiki/Gene_cluster" title="Gene cluster">gene cluster</a> responsible for the <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of carotenoids</li> <li><a href="/wiki/E_number#E100–E199_(colours)" title="E number">E number#E100–E199 (colours)</a></li> <li><a href="/wiki/Phytochemistry" title="Phytochemistry">Phytochemistry</a></li></ul> <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=Carotenoid&action=edit&section=16" 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 mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></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 id="CITEREFNelsonCox2005" class="citation book cs1">Nelson, David L.; Cox, Michael M. (2005). <i>Principles of Biochemistry</i> (4th ed.). New York: W. H. 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title="Chlorophyll d">Chlorophyll d</a></li> <li><a href="/wiki/Chlorophyll_f" title="Chlorophyll f">Chlorophyll f</a></li> <li><a href="/wiki/Chlorin" title="Chlorin">Chlorin</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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one" title="1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one">1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one</a></li> <li><a href="/wiki/Bisdemethoxycurcumin" title="Bisdemethoxycurcumin">Bisdemethoxycurcumin</a></li> <li><a href="/wiki/Desmethoxycurcumin" title="Desmethoxycurcumin">Desmethoxycurcumin</a></li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li></ul> </div></td></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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthocyanin" title="Anthocyanin">Anthocyanins</a></li> <li><a href="/wiki/Anthocyanidin" title="Anthocyanidin">Anthocyanidins</a></li> <li><a href="/wiki/Anthoxanthin" title="Anthoxanthin">Anthoxanthins</a></li> <li><a href="/wiki/Flavan" title="Flavan">Flavans</a></li> <li><a href="/wiki/Condensed_tannin" title="Condensed tannin">Condensed tannins</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Carotenoids</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/Carotene" title="Carotene">Carotenes</a></li> <li><a href="/wiki/Retinoid" title="Retinoid">Retinoids</a></li> <li><a href="/wiki/Xanthophyll" title="Xanthophyll">Xanthophylls</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/Allophycocyanin" title="Allophycocyanin">Allophycocyanin</a></li> <li><a href="/wiki/Phycocyanin" title="Phycocyanin">Phycocyanin</a></li> <li><a href="/wiki/Phycoerythrin" title="Phycoerythrin">Phycoerythrin</a></li> <li><a href="/wiki/Phycoerythrocyanin" title="Phycoerythrocyanin">Phycoerythrocyanin</a></li> <li><a href="/wiki/Quinone" title="Quinone">Quinones</a></li> <li><a href="/wiki/Xanthonoid" title="Xanthonoid">Xanthonoids</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="Carotenoids" 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:Carotenoids" title="Template:Carotenoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Carotenoids" title="Template talk:Carotenoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Carotenoids" title="Special:EditPage/Template:Carotenoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Carotenoids" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Carotenoids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotene" title="Carotene">Carotenes</a> (C<sub>40</sub>)</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/Alpha-Carotene" class="mw-redirect" title="Alpha-Carotene">α-Carotene</a></li> <li><a href="/wiki/Beta-Carotene" class="mw-redirect" title="Beta-Carotene">β-Carotene</a></li> <li><a href="/wiki/Gamma-Carotene" class="mw-redirect" title="Gamma-Carotene">γ-Carotene</a></li> <li><a href="/wiki/Delta-Carotene" class="mw-redirect" title="Delta-Carotene">δ-Carotene</a></li> <li><a href="/wiki/Epsilon-Carotene" class="mw-redirect" title="Epsilon-Carotene">ε-Carotene</a></li> <li><a href="/wiki/Zeta-Carotene" class="mw-redirect" title="Zeta-Carotene">ζ-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/Phytoene" title="Phytoene">Phytoene</a></li> <li><a href="/wiki/Phytofluene" title="Phytofluene">Phytofluene</a></li> <li><a href="/wiki/Torulene" title="Torulene">Torulene</a></li> <li><a href="/wiki/Lycopersene" title="Lycopersene">Lycopersene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Xanthophyll" title="Xanthophyll">Xanthophylls</a> (C<sub>40</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/Antheraxanthin" title="Antheraxanthin">Antheraxanthin</a></li> <li><a href="/wiki/Astaxanthin" title="Astaxanthin">Astaxanthin</a></li> <li><a href="/wiki/Canthaxanthin" title="Canthaxanthin">Canthaxanthin</a></li> <li><a href="/wiki/Citranaxanthin" title="Citranaxanthin">Citranaxanthin</a></li> <li><a href="/wiki/Cryptoxanthin" class="mw-redirect" title="Cryptoxanthin">Cryptoxanthin</a></li> <li><a href="/wiki/Diadinoxanthin" title="Diadinoxanthin">Diadinoxanthin</a></li> <li><a href="/wiki/Diatoxanthin" title="Diatoxanthin">Diatoxanthin</a></li> <li><a href="/wiki/Dinoxanthin" title="Dinoxanthin">Dinoxanthin</a></li> <li><a href="/wiki/Echinenone" title="Echinenone">Echinenone</a></li> <li><a href="/wiki/Flavoxanthin" title="Flavoxanthin">Flavoxanthin</a></li> <li><a href="/wiki/Fucoxanthin" title="Fucoxanthin">Fucoxanthin</a></li> <li><a href="/wiki/Lutein" title="Lutein">Lutein</a></li> <li><a href="/wiki/Neoxanthin" title="Neoxanthin">Neoxanthin</a></li> <li><a href="/wiki/Rhodoxanthin" title="Rhodoxanthin">Rhodoxanthin</a></li> <li><a href="/wiki/Rubixanthin" title="Rubixanthin">Rubixanthin</a></li> <li><a href="/wiki/Violaxanthin" title="Violaxanthin">Violaxanthin</a></li> <li><a href="/wiki/Zeaxanthin" title="Zeaxanthin">Zeaxanthin</a></li> <li><a href="/w/index.php?title=Zeinoxanthin&action=edit&redlink=1" class="new" title="Zeinoxanthin (page does not exist)">Zeinoxanthin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Apocarotenoid" title="Apocarotenoid">Apocarotenoids</a> (C<sub><40</sub>)</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/Abscisic_acid" title="Abscisic acid">Abscisic acid</a></li> <li><a href="/wiki/Apocarotenal" title="Apocarotenal">Apocarotenal</a></li> <li><a href="/wiki/Bixin" title="Bixin">Bixin</a></li> <li><a href="/wiki/Crocetin" title="Crocetin">Crocetin</a></li> <li><a href="/wiki/Food_orange_7" title="Food orange 7">Food orange 7</a></li> <li><a href="/wiki/Ionone" title="Ionone">Ionones</a></li> <li><a href="/wiki/Peridinin" title="Peridinin">Peridinin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Vitamin A retinoids (C<sub>20</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/Retinal" title="Retinal">Retinal</a></li> <li><a href="/wiki/Retinoic_acid" title="Retinoic acid">Retinoic acid</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Retinoid" title="Retinoid">Retinoid drugs</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/Acitretin" title="Acitretin">Acitretin</a></li> <li><a href="/wiki/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a></li> <li><a href="/wiki/Etretinate" title="Etretinate">Etretinate</a></li> <li><a href="/wiki/Fenretinide" title="Fenretinide">Fenretinide</a></li> <li><a href="/wiki/Isotretinoin" title="Isotretinoin">Isotretinoin</a></li> <li><a href="/wiki/Tazarotene" title="Tazarotene">Tazarotene</a></li> <li><a href="/w/index.php?title=Temarotene&action=edit&redlink=1" class="new" title="Temarotene (page does not exist)">Temarotene</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a></li> <li><a href="/w/index.php?title=Zuretinol_acetate&action=edit&redlink=1" class="new" title="Zuretinol acetate (page does not exist)">Zuretinol acetate</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_terpenes_and_terpenoids_(#_of_isoprene_units)" 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"><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: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)" 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 href="/wiki/Phytosterol" title="Phytosterol">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 class="mw-selflink selflink">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 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_intermediates" 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_intermediates" 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 class="mw-selflink selflink">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 href="/wiki/Phytosterol" title="Phytosterol">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 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="Aryl_hydrocarbon_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed 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:Aryl_hydrocarbon_receptor_modulators" title="Template:Aryl hydrocarbon receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Aryl_hydrocarbon_receptor_modulators" title="Template talk:Aryl hydrocarbon receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Aryl_hydrocarbon_receptor_modulators" title="Special:EditPage/Template:Aryl hydrocarbon receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Aryl_hydrocarbon_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor">Aryl hydrocarbon receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor"><abbr title="Aryl hydrocarbon receptor">AhR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Aryl hydrocarbon receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a> <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> (e.g., <a href="/wiki/Lipoxin_A4" class="mw-redirect" title="Lipoxin A4">lipoxin A4</a>, <a href="/wiki/Prostaglandin_G2" title="Prostaglandin G2">prostaglandin G2</a>)</li> <li><a class="mw-selflink selflink">Dietary carotenoids</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Halogen" title="Halogen">Halogenated</a> <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbons</a> (e.g., <a href="/wiki/Polychlorinated_dibenzodioxin" class="mw-redirect" title="Polychlorinated dibenzodioxin">polychlorinated dibenzodioxins</a> (e.g., <a href="/wiki/2,3,7,8-Tetrachlorodibenzodioxin" title="2,3,7,8-Tetrachlorodibenzodioxin">TCDD</a>), <a href="/wiki/Dibenzofuran" title="Dibenzofuran">dibenzofurans</a>, <a href="/wiki/Biphenyl" title="Biphenyl">biphenyls</a>)</li> <li><a href="/w/index.php?title=2-(1H-Indol-3-ylcarbonyl)-4-thiazolecarboxylic_acid_methyl_ester&action=edit&redlink=1" class="new" title="2-(1H-Indol-3-ylcarbonyl)-4-thiazolecarboxylic acid methyl ester (page does not exist)">ΙΤΕ</a></li> <li><a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">Modified low-density lipoproteins</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbons</a> (e.g., <a href="/wiki/3-methylcholanthrene" class="mw-redirect" title="3-methylcholanthrene">3-methylcholanthrene</a>, <a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">benzo[a]pyrene</a>, <a href="/wiki/Benzanthracene" class="mw-redirect" title="Benzanthracene">benzanthracenes</a>, <a href="/wiki/Benzoflavone" class="mw-redirect" title="Benzoflavone">benzoflavones</a> (e.g., <a href="/wiki/%CE%92-naphthoflavone" class="mw-redirect" title="Β-naphthoflavone">β-naphthoflavone</a>))</li> <li><a href="/wiki/Tapinarof" title="Tapinarof">Tapinarof (benvitimod)</a></li> <li><a href="/wiki/Tetrapyrole" class="mw-redirect" title="Tetrapyrole">Tetrapyroles</a> (e.g., <a href="/wiki/Bilirubin" title="Bilirubin">bilirubin</a>)</li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivatives</a> (e.g., <a href="/wiki/Indigo_dye" title="Indigo dye">indigo dye</a>, <a href="/wiki/Indirubin" title="Indirubin">indirubin</a>)</li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=7-Ketocholesterol&action=edit&redlink=1" class="new" title="7-Ketocholesterol (page does not exist)">7-Ketocholesterol</a></li> <li><a href="/w/index.php?title=CH-223191&action=edit&redlink=1" class="new" title="CH-223191 (page does not exist)">CH-223191</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd></dl> </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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" 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