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class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Chemistry</span> </div> </a> <button aria-controls="toc-Chemistry-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 Chemistry subsection</span> </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Structure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Structure</span> </div> </a> <ul id="toc-Structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Analytical_chemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Analytical_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Analytical chemistry</span> </div> </a> <ul id="toc-Analytical_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactivity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Reactivity</span> </div> </a> <ul id="toc-Reactivity-sublist" class="vector-toc-list"> <li id="toc-Extraction" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Extraction"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3.1</span> <span>Extraction</span> </div> </a> <ul id="toc-Extraction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Analysis_techniques" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Analysis_techniques"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3.2</span> <span>Analysis techniques</span> </div> </a> <ul id="toc-Analysis_techniques-sublist" class="vector-toc-list"> <li id="toc-Microscopy_analysis" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Microscopy_analysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3.2.1</span> <span>Microscopy analysis</span> </div> </a> <ul id="toc-Microscopy_analysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Quantification" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Quantification"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3.3</span> <span>Quantification</span> </div> </a> <ul id="toc-Quantification-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-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 Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Aspirational_use_as_green_chemicals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aspirational_use_as_green_chemicals"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Aspirational use as green chemicals</span> </div> </a> <ul id="toc-Aspirational_use_as_green_chemicals-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Occurrence" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Occurrence</span> </div> </a> <ul id="toc-Occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Biochemistry</span> </div> </a> <button aria-controls="toc-Biochemistry-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 Biochemistry subsection</span> </button> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis_and_metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis_and_metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Biosynthesis and metabolism</span> </div> </a> <ul id="toc-Biosynthesis_and_metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Occurrence_in_food" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Occurrence_in_food"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Occurrence in food</span> </div> </a> <ul id="toc-Occurrence_in_food-sublist" class="vector-toc-list"> <li id="toc-Astringency" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Astringency"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.1</span> <span>Astringency</span> </div> </a> <ul id="toc-Astringency-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Research</span> </div> </a> <button aria-controls="toc-Research-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 Research subsection</span> </button> <ul id="toc-Research-sublist" class="vector-toc-list"> <li id="toc-Cardiovascular_diseases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiovascular_diseases"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Cardiovascular diseases</span> </div> </a> <ul id="toc-Cardiovascular_diseases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cancer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cancer"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Cancer</span> </div> </a> <ul id="toc-Cancer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cognitive_function" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cognitive_function"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Cognitive function</span> </div> </a> <ul id="toc-Cognitive_function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phytoestrogens" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phytoestrogens"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.4</span> <span>Phytoestrogens</span> </div> </a> <ul id="toc-Phytoestrogens-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phlebotonic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phlebotonic"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.5</span> <span>Phlebotonic</span> </div> </a> <ul id="toc-Phlebotonic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gut_microbiome" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Gut_microbiome"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.6</span> <span>Gut microbiome</span> </div> </a> <ul id="toc-Gut_microbiome-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity_and_adverse_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toxicity_and_adverse_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.7</span> <span>Toxicity and adverse effects</span> </div> </a> <ul id="toc-Toxicity_and_adverse_effects-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</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"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</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"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</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">Polyphenol</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 37 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-37" 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">37 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D8%AA%D8%B9%D8%AF%D8%AF_%D8%A7%D9%84%D9%81%D9%8A%D9%86%D9%88%D9%84" title="متعدد الفينول – Arabic" lang="ar" hreflang="ar" data-title="متعدد الفينول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Polifenol" title="Polifenol – Azerbaijani" lang="az" hreflang="az" data-title="Polifenol" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Polifenoli" title="Polifenoli – Bosnian" lang="bs" hreflang="bs" data-title="Polifenoli" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Polifenol" title="Polifenol – Catalan" lang="ca" hreflang="ca" data-title="Polifenol" 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/Polyfenoly" title="Polyfenoly – Czech" lang="cs" hreflang="cs" data-title="Polyfenoly" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Polyfenol" title="Polyfenol – Danish" lang="da" hreflang="da" data-title="Polyfenol" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Polyphenole" title="Polyphenole – German" lang="de" hreflang="de" data-title="Polyphenole" 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/Pol%C3%BCfenoolid" title="Polüfenoolid – Estonian" lang="et" hreflang="et" data-title="Polüfenoolid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Polifenoles" title="Polifenoles – Spanish" lang="es" hreflang="es" data-title="Polifenoles" 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/Polifenolo" title="Polifenolo – Esperanto" lang="eo" hreflang="eo" data-title="Polifenolo" 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/Polifenol" title="Polifenol – Basque" lang="eu" hreflang="eu" data-title="Polifenol" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%D9%84%DB%8C%E2%80%8C%D9%81%D9%86%D9%84" title="پلی‌فنل – Persian" lang="fa" hreflang="fa" data-title="پلی‌فنل" 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/Polyph%C3%A9nol" title="Polyphénol – French" lang="fr" hreflang="fr" data-title="Polyphénol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Polifenois" title="Polifenois – Galician" lang="gl" hreflang="gl" data-title="Polifenois" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8F%B4%EB%A6%AC%ED%8E%98%EB%86%80" title="폴리페놀 – Korean" lang="ko" hreflang="ko" data-title="폴리페놀" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Polifenol" title="Polifenol – Indonesian" lang="id" hreflang="id" data-title="Polifenol" 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/Polifenoli" title="Polifenoli – Italian" lang="it" hreflang="it" data-title="Polifenoli" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Polifenol" title="Polifenol – Javanese" lang="jv" hreflang="jv" data-title="Polifenol" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Polyphenolum" title="Polyphenolum – Latin" lang="la" hreflang="la" data-title="Polyphenolum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Polifenol" title="Polifenol – Lombard" lang="lmo" hreflang="lmo" data-title="Polifenol" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Polifenolok" title="Polifenolok – Hungarian" lang="hu" hreflang="hu" data-title="Polifenolok" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Polifenol" title="Polifenol – Malay" lang="ms" hreflang="ms" data-title="Polifenol" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Polyfenol" title="Polyfenol – Dutch" lang="nl" hreflang="nl" data-title="Polyfenol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%9D%E3%83%AA%E3%83%95%E3%82%A7%E3%83%8E%E3%83%BC%E3%83%AB" title="ポリフェノール – Japanese" lang="ja" hreflang="ja" data-title="ポリフェノール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Polyfenol" title="Polyfenol – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Polyfenol" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Polifenole" title="Polifenole – Polish" lang="pl" hreflang="pl" data-title="Polifenole" 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/Polifenol" title="Polifenol – Portuguese" lang="pt" hreflang="pt" data-title="Polifenol" 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/Polifenol" title="Polifenol – Romanian" lang="ro" hreflang="ro" data-title="Polifenol" 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%9F%D0%BE%D0%BB%D0%B8%D1%84%D0%B5%D0%BD%D0%BE%D0%BB%D1%8B" title="Полифенолы – Russian" lang="ru" hreflang="ru" data-title="Полифенолы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Polyfenol" title="Polyfenol – Slovak" lang="sk" hreflang="sk" data-title="Polyfenol" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Polifenol" title="Polifenol – Serbian" lang="sr" hreflang="sr" data-title="Polifenol" 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/Polifenol" title="Polifenol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Polifenol" 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/Polyfenolit" title="Polyfenolit – Finnish" lang="fi" hreflang="fi" data-title="Polyfenolit" 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/Polyfenol" title="Polyfenol – Swedish" lang="sv" hreflang="sv" data-title="Polyfenol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Polifenol" title="Polifenol – Turkish" lang="tr" hreflang="tr" data-title="Polifenol" data-language-autonym="Türkçe" 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searchaux" style="display:none">Class of chemical compounds</div> <p class="mw-empty-elt"> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Tannic_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Tannic_acid.svg/290px-Tannic_acid.svg.png" decoding="async" width="290" height="290" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Tannic_acid.svg/435px-Tannic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Tannic_acid.svg/580px-Tannic_acid.svg.png 2x" data-file-width="375" data-file-height="375" /></a><figcaption>Representative chemical structure of one of many plant-derived polyphenols that comprise <a href="/wiki/Tannic_acid" title="Tannic acid">tannic acid</a>. Such compound are formed by esterification of <a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">phenylpropanoid</a>-derived <a href="/wiki/Gallic_acid" title="Gallic acid">gallic acid</a> to a monosaccharide (glucose) core.</figcaption></figure> <p><b>Polyphenols</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="/ˌ/: secondary stress follows">ˌ</span><span title="'p' in 'pie'">p</span><span title="/ɒ/: 'o' in 'body'">ɒ</span><span title="'l' in 'lie'">l</span><span title="/i/: 'y' in 'happy'">i</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'f' in 'find'">f</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="'l' in 'lie'">l</span></span>,<span class="wrap"> </span>-<span style="border-bottom:1px dotted"><span title="'n' in 'nigh'">n</span><span title="/ɒ/: 'o' in 'body'">ɒ</span><span title="'l' in 'lie'">l</span></span>/</a></span></span>) are a large family of naturally occurring <a href="/wiki/Phenols" title="Phenols">phenols</a>.<sup id="cite_ref-Quideau_1-0" class="reference"><a href="#cite_note-Quideau-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They are abundant in plants and structurally diverse.<sup id="cite_ref-Quideau_1-1" class="reference"><a href="#cite_note-Quideau-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-lpi_2-0" class="reference"><a href="#cite_note-lpi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nonaka_3-0" class="reference"><a href="#cite_note-Nonaka-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Polyphenols include <a href="/wiki/Phenolic_acid" title="Phenolic acid">phenolic acids</a>, <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a>, <a href="/wiki/Tannic_acid" title="Tannic acid">tannic acid</a>, and <a href="/wiki/Ellagitannin" title="Ellagitannin">ellagitannin</a>, some of which have been used historically as <a href="/wiki/Dye" title="Dye">dyes</a> and for <a href="/wiki/Tanning_(leather)" title="Tanning (leather)">tanning garments</a>. </p> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Curcumin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/Curcumin.svg/220px-Curcumin.svg.png" decoding="async" width="220" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/Curcumin.svg/330px-Curcumin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/40/Curcumin.svg/440px-Curcumin.svg.png 2x" data-file-width="256" data-file-height="75" /></a><figcaption><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a>, a bright yellow component of <a href="/wiki/Turmeric" title="Turmeric">turmeric</a> (<i>Curcuma longa</i>), is a well-studied polyphenol.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Etymology">Etymology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=1" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The name derives from the <a href="/wiki/Ancient_Greek" title="Ancient Greek">Ancient Greek</a> word <span title="Ancient Greek (to 1453)-language text"><span lang="grc">πολύς</span></span> (<span title="Ancient Greek (to 1453)-language romanization"><i lang="grc-Latn">polus</i></span>, meaning "many, much") and the word ‘phenol’ which refers to a chemical structure formed by attachment of an aromatic <a href="/wiki/Benzenoid" title="Benzenoid">benzenoid</a> (<a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a>) ring to a <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> (-OH) group (hence the <i>-ol</i> suffix). The term "polyphenol" has been in use at least since 1894.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Definition">Definition</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=2" title="Edit section: Definition"><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:Ellagic_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Ellagic_acid.svg/220px-Ellagic_acid.svg.png" decoding="async" width="220" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Ellagic_acid.svg/330px-Ellagic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/da/Ellagic_acid.svg/440px-Ellagic_acid.svg.png 2x" data-file-width="429" data-file-height="300" /></a><figcaption><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a>, a polyphenol</figcaption></figure> <p>The term polyphenol is not well-defined, but it is generally agreed that they are natural products with "several <a href="/wiki/Hydroxyl_groups" class="mw-redirect" title="Hydroxyl groups">hydroxyl groups</a> on <a href="/wiki/Aromatic_ring" class="mw-redirect" title="Aromatic ring">aromatic rings</a>" including four principal classes: "phenolic acids, flavonoids, stilbenes, and lignans".<sup id="cite_ref-manach_5-0" class="reference"><a href="#cite_note-manach-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Flavonoids include flavones, flavonols, flavanols, flavanones, isoflavones, proanthocyanidins, and anthocyanins. Particularly abundant flavanoids in foods are <a href="/wiki/Catechin" title="Catechin">catechin</a> (tea, fruits), <a href="/wiki/Hesperetin" title="Hesperetin">hesperetin</a> (citrus fruits), <a href="/wiki/Cyanidin" title="Cyanidin">cyanidin</a> (red fruits and berries), <a href="/wiki/Daidzein" title="Daidzein">daidzein</a> (<a href="/wiki/Soybean" title="Soybean">soybean</a>), <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a> (apple, grape, cocoa), and <a href="/wiki/Quercetin" title="Quercetin">quercetin</a> (onion, tea, apples).<sup id="cite_ref-lpi_2-1" class="reference"><a href="#cite_note-lpi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li> <li>Phenolic acids include <a href="/wiki/Caffeic_acid" title="Caffeic acid">caffeic acid</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> are polyphenols derived from <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a> found in <a href="/wiki/Flax" title="Flax">flax</a> seed and other cereals.</li></ul> <div class="mw-heading mw-heading3"><h3 id="WBSSH_definition">WBSSH definition</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=3" title="Edit section: WBSSH definition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The White–Bate-Smith–Swain–Haslam (WBSSH) definition<sup id="cite_ref-Haslam_and_Cai_6-0" class="reference"><a href="#cite_note-Haslam_and_Cai-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> characterized structural characteristics common to plant phenolics used in <a href="/wiki/Tanning_(leather)" title="Tanning (leather)">tanning</a> (i.e., the tannins).<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>In terms of properties, the WBSSH describes the polyphenols as follows: </p> <ul><li>generally moderately <a href="/wiki/Water-soluble" class="mw-redirect" title="Water-soluble">water-soluble</a> compounds</li> <li>with molecular weight of 500–4000 Da</li> <li>with >12 phenolic hydroxyl groups</li> <li>with 5–7 aromatic rings per 1000 Da</li></ul> <p>In terms of structures, the WBSSH recognizes two structural family that have these properties: </p> <ul><li><a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a> and its derivatives</li> <li><a href="/wiki/Gallic_acid" title="Gallic acid">galloyl</a> and hexahydroxydiphenoyl esters and their derivatives</li></ul> <div class="mw-heading mw-heading3"><h3 id="Quideau_definition">Quideau definition</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=4" title="Edit section: Quideau definition"><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:Raspberry_ellagitannin.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Raspberry_ellagitannin.png/300px-Raspberry_ellagitannin.png" decoding="async" width="300" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Raspberry_ellagitannin.png/450px-Raspberry_ellagitannin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/17/Raspberry_ellagitannin.png/600px-Raspberry_ellagitannin.png 2x" data-file-width="772" data-file-height="395" /></a><figcaption><a href="/wiki/Raspberry_ellagitannin" title="Raspberry ellagitannin">Raspberry ellagitannin</a>, a <a href="/wiki/Tannin" title="Tannin">tannin</a> composed of 14 gallic acid units around a core of three units of glucose, with two gallic acids as simple esters, and the remaining 12 appearing in 6 ellagic acid-type units. Ester, ether, and biaryl linkages are present, see below.</figcaption></figure> <p>According to Stéphane Quideau, the term "polyphenol" refers to compounds derived from the <a href="/wiki/Shikimate" class="mw-redirect" title="Shikimate">shikimate</a>/<a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">phenylpropanoid</a> and/or the <a href="/wiki/Polyketide" title="Polyketide">polyketide</a> pathway, featuring more than one phenolic unit and deprived of nitrogen-based functions.<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. (July 2021)">citation needed</span></a></i>]</sup> </p><p><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a>, a molecule at the core of naturally occurring phenolic compounds of varying sizes, is itself not a polyphenol by the WBSSH definition, but is by the Quideau definition. The <a href="/wiki/Raspberry_ellagitannin" title="Raspberry ellagitannin">raspberry ellagitannin</a>,<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> on the other hand, with its 14 <a href="/wiki/Gallic_acid" title="Gallic acid">gallic acid</a> moieties (most in ellagic acid-type components), and more than 40 phenolic hydroxyl groups, meets the criteria of both definitions of a polyphenol. Other examples of compounds that fall under both the WBSSH and Quideau definitions include the <a href="/wiki/Black_tea" title="Black tea">black tea</a> <a href="/wiki/Theaflavin-3-gallate" title="Theaflavin-3-gallate">theaflavin-3-gallate</a> shown below, and the hydrolyzable tannin, <a href="/wiki/Tannic_acid" title="Tannic acid">tannic acid</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2021)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=5" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Theaflavin_3-gallate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Theaflavin_3-gallate.svg/170px-Theaflavin_3-gallate.svg.png" decoding="async" width="170" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Theaflavin_3-gallate.svg/255px-Theaflavin_3-gallate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/Theaflavin_3-gallate.svg/340px-Theaflavin_3-gallate.svg.png 2x" data-file-width="885" data-file-height="720" /></a><figcaption><a href="/wiki/Theaflavin-3-gallate" title="Theaflavin-3-gallate">Theaflavin-3-gallate</a>, a plant-derived polyphenol, an ester of gallic acid and a <a href="/wiki/Theaflavin" title="Theaflavin">theaflavin</a> core. There are nine phenolic hydroxyl groups and two phenolic <a href="/wiki/Ether" title="Ether">ether</a> linkages.</figcaption></figure> <p>Polyphenols are <a href="/wiki/Reactivity_(chemistry)" title="Reactivity (chemistry)">reactive</a> species toward <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a>, hence their description as <a href="/wiki/Antioxidant" title="Antioxidant">antioxidants</a> <a href="/wiki/In_vitro" title="In vitro">in vitro</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Structure">Structure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=6" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyphenols, such as lignin, are larger molecules (<a href="/wiki/Macromolecule" title="Macromolecule">macromolecules</a>). Their upper molecular weight limit is about 800 <a href="/wiki/Dalton_(unit)" title="Dalton (unit)">daltons</a>, which allows for the possibility to rapidly diffuse across cell membranes so that they can reach intracellular sites of action or remain as pigments once the cell <a href="/wiki/Senesce" class="mw-redirect" title="Senesce">senesces</a>. Hence, many larger polyphenols are biosynthesized <i>in situ</i> from smaller polyphenols to non-hydrolyzable tannins and remain undiscovered in the plant matrix. Most polyphenols contain repeating phenolic moieties of pyrocatechol, resorcinol, pyrogallol, and phloroglucinol connected by <a href="/wiki/Esters" class="mw-redirect" title="Esters">esters</a> (hydrolyzable tannins) or more stable C-C bonds (nonhydrolyzable <a href="/wiki/Condensed_tannins" class="mw-redirect" title="Condensed tannins">condensed tannins</a>). <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">Proanthocyanidins</a> are mostly polymeric units of <a href="/wiki/Catechin" title="Catechin">catechin</a> and <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Puerarin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Puerarin.svg/220px-Puerarin.svg.png" decoding="async" width="220" height="190" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Puerarin.svg/330px-Puerarin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Puerarin.svg/440px-Puerarin.svg.png 2x" data-file-width="620" data-file-height="535" /></a><figcaption>The C-glucoside substructure of polyphenols is exemplified by the phenol-saccharide conjugate puerarin, a midmolecular-weight plant natural product. The attachment of the phenol to the saccharide is by a carbon-carbon bond. The <a href="/wiki/Isoflavone" title="Isoflavone">isoflavone</a> and its 10-atom <a href="/wiki/Benzopyran" title="Benzopyran">benzopyran</a> "fused ring" system, also a structural feature here, is common in polyphenols.</figcaption></figure> <p>Polyphenols often have functional groups beyond <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl groups</a>. <a href="/wiki/Ether" title="Ether">Ether</a> <a href="/wiki/Ester" title="Ester">ester</a> linkages are common, as are <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Tellimagrandin_II.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Tellimagrandin_II.svg/220px-Tellimagrandin_II.svg.png" decoding="async" width="220" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Tellimagrandin_II.svg/330px-Tellimagrandin_II.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Tellimagrandin_II.svg/440px-Tellimagrandin_II.svg.png 2x" data-file-width="1050" data-file-height="810" /></a><figcaption>An example of a synthetically achieved small ellagitannin, <a href="/wiki/Tellimagrandin_II" title="Tellimagrandin II">tellimagrandin II</a>, derived biosynthetically and sometimes synthetically by oxidative joining of two of the galloyl moieties of <a href="/wiki/1,2,3,4,6-pentagalloyl-glucose" class="mw-redirect" title="1,2,3,4,6-pentagalloyl-glucose">1,2,3,4,6-pentagalloyl-glucose</a></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Analytical_chemistry">Analytical chemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=7" title="Edit section: Analytical chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The analysis techniques are those of <a href="/wiki/Phytochemistry" title="Phytochemistry">phytochemistry</a>: <a href="/wiki/Extraction_(chemistry)" title="Extraction (chemistry)">extraction</a>, isolation, <a href="/wiki/Structural_elucidation" class="mw-redirect" title="Structural elucidation">structural elucidation</a>,<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> then <a href="/wiki/Quantification_(science)" title="Quantification (science)">quantification</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2021)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reactivity">Reactivity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=8" title="Edit section: Reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyphenols readily react with metal ions to form <a href="/wiki/Coordination_complexes" class="mw-redirect" title="Coordination complexes">coordination complexes</a>, some of which form <a href="/wiki/Metal-phenolic_network" title="Metal-phenolic network">Metal-phenolic Networks</a>.<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> </p> <div class="mw-heading mw-heading4"><h4 id="Extraction">Extraction</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=9" title="Edit section: Extraction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Extraction_(chemistry)" title="Extraction (chemistry)">Extraction</a> of polyphenols<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> can be performed using a solvent like water, <a href="/wiki/Hot_water_extraction" title="Hot water extraction">hot water</a>, methanol, methanol/formic acid, methanol/water/acetic or formic acid. <a href="/wiki/Liquid%E2%80%93liquid_extraction" title="Liquid–liquid extraction">Liquid–liquid extraction</a> can be also performed or <a href="/wiki/Countercurrent_chromatography" title="Countercurrent chromatography">countercurrent chromatography</a>. <a href="/wiki/Solid_phase_extraction" class="mw-redirect" title="Solid phase extraction">Solid phase extraction</a> can also be made on C18 sorbent cartridges. Other techniques are ultrasonic extraction, heat reflux extraction, microwave-assisted extraction,<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> <a href="/wiki/Critical_carbon_dioxide" class="mw-redirect" title="Critical carbon dioxide">critical carbon dioxide</a>,<sup id="cite_ref-:0_14-0" class="reference"><a href="#cite_note-:0-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><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> high-pressure <a href="/wiki/Extract#Extraction_techniques" title="Extract">liquid extraction</a><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> or use of ethanol in an immersion extractor.<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> The extraction conditions (temperature, extraction time, ratio of solvent to raw material, particle size of the sample, solvent type, and solvent concentrations) for different raw materials and extraction methods have to be optimized.<sup id="cite_ref-papoutsis2018a_18-0" class="reference"><a href="#cite_note-papoutsis2018a-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> <sup id="cite_ref-papoutsis2018b_19-0" class="reference"><a href="#cite_note-papoutsis2018b-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Mainly found in the fruit skins and seeds, high levels of polyphenols may reflect only the <i>measured extractable</i> polyphenol (EPP) content of a fruit which may also contain non-extractable polyphenols. Black tea contains high amounts of polyphenol and makes up for 20% of its weight.<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> </p><p>Concentration can be made by <a href="/wiki/Ultrafiltration" title="Ultrafiltration">ultrafiltration</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> Purification can be achieved by <a href="/wiki/Preparative_chromatography" class="mw-redirect" title="Preparative chromatography">preparative chromatography</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Analysis_techniques">Analysis techniques</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=10" title="Edit section: Analysis techniques"><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:RP_HPLC.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/RP_HPLC.PNG/220px-RP_HPLC.PNG" decoding="async" width="220" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/RP_HPLC.PNG/330px-RP_HPLC.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/RP_HPLC.PNG/440px-RP_HPLC.PNG 2x" data-file-width="617" data-file-height="506" /></a><figcaption>Reversed-phase HPLC plot of separation of phenolic compounds. Smaller <a href="/wiki/Natural_phenol" class="mw-redirect" title="Natural phenol">natural phenols</a> formed individual peaks while <a href="/wiki/Tannin" title="Tannin">tannins</a> form a <i>hump</i>.</figcaption></figure> <p><a href="/wiki/Phosphomolybdic_acid" title="Phosphomolybdic acid">Phosphomolybdic acid</a> is used as a reagent for staining phenolics in <a href="/wiki/Thin_layer_chromatography" class="mw-redirect" title="Thin layer chromatography">thin layer chromatography</a>. Polyphenols can be studied by <a href="/wiki/Spectroscopy" title="Spectroscopy">spectroscopy</a>, especially in the ultraviolet domain, by <a href="/wiki/Fractionation" title="Fractionation">fractionation</a> or <a href="/wiki/Paper_chromatography" title="Paper chromatography">paper chromatography</a>. They can also be analysed by chemical characterisation. </p><p><a href="/wiki/Instrumental_chemistry" title="Instrumental chemistry">Instrumental chemistry</a> analyses include <a href="/wiki/Separation_process" title="Separation process">separation</a> by <a href="/wiki/High_performance_liquid_chromatography" class="mw-redirect" title="High performance liquid chromatography">high performance liquid chromatography</a> (HPLC), and especially by <a href="/wiki/Reversed-phase_liquid_chromatography" class="mw-redirect" title="Reversed-phase liquid chromatography">reversed-phase liquid chromatography</a> (RPLC), can be coupled to <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a>.<sup id="cite_ref-:0_14-1" class="reference"><a href="#cite_note-:0-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Purified compounds can be identified by the means of <a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">nuclear magnetic resonance</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2021)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading5"><h5 id="Microscopy_analysis">Microscopy analysis</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=11" title="Edit section: Microscopy analysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/DMACA_reagent" class="mw-redirect" title="DMACA reagent">DMACA reagent</a> is an histological dye specific to polyphenols used in microscopy analyses. The <a href="/wiki/Autofluorescence" title="Autofluorescence">autofluorescence</a> of polyphenols can also be used, especially for localisation of lignin and <a href="/wiki/Suberin" title="Suberin">suberin</a>. Where fluorescence of the molecules themselves is insufficient for visualization by light microscopy, DPBA (diphenylboric acid 2-aminoethyl ester, also referred to as Naturstoff reagent A) has traditionally been used, at least in <a href="/wiki/Botany" title="Botany">plant science</a>, to enhance the fluorescence signal.<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> <div class="mw-heading mw-heading4"><h4 id="Quantification">Quantification</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=12" title="Edit section: Quantification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyphenolic content in vitro can be quantified by <a href="/wiki/Volumetric_titration" class="mw-redirect" title="Volumetric titration">volumetric titration</a>. An oxidizing agent, <a href="/wiki/Permanganate" title="Permanganate">permanganate</a>, is used to oxidize known concentrations of a standard tannin solution, producing a <a href="/wiki/Standard_curve" class="mw-redirect" title="Standard curve">standard curve</a>. The tannin content of the unknown is then expressed as equivalents of the appropriate hydrolyzable or condensed tannin.<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> </p><p>Some methods for quantification of total polyphenol content in vitro are based on <a href="/wiki/Colorimetry" title="Colorimetry">colorimetric</a> measurements. Some tests are relatively specific to polyphenols (for instance the Porter's assay). Total phenols (or antioxidant effect) can be measured using the <a href="/wiki/Folin%E2%80%93Ciocalteu_reaction" class="mw-redirect" title="Folin–Ciocalteu reaction">Folin–Ciocalteu reaction</a>.<sup id="cite_ref-:0_14-2" class="reference"><a href="#cite_note-:0-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Results are typically expressed as gallic acid equivalents. Polyphenols are seldom evaluated by <a href="/wiki/Antibody" title="Antibody">antibody</a> technologies.<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>Other tests measure the antioxidant capacity of a fraction. Some make use of the <a href="/wiki/ABTS" title="ABTS">ABTS</a> radical <a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a> which is reactive towards most antioxidants including phenolics, <a href="/wiki/Thiol" title="Thiol">thiols</a> and <a href="/wiki/Vitamin_C" title="Vitamin C">vitamin C</a>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> During this reaction, the blue ABTS radical cation is converted back to its colorless neutral form. The reaction may be monitored spectrophotometrically. This assay is often referred to as the <a href="/wiki/Trolox_equivalent_antioxidant_capacity" title="Trolox equivalent antioxidant capacity">Trolox equivalent antioxidant capacity</a> (TEAC) assay. The reactivity of the various antioxidants tested are compared to that of <a href="/wiki/Trolox" title="Trolox">Trolox</a>, which is a <a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a> analog. </p><p>Other antioxidant capacity assays which use Trolox as a standard include the <a href="/wiki/Diphenylpicrylhydrazyl" class="mw-redirect" title="Diphenylpicrylhydrazyl">diphenylpicrylhydrazyl</a> (DPPH), <a href="/wiki/Oxygen_radical_absorbance_capacity" title="Oxygen radical absorbance capacity">oxygen radical absorbance capacity</a> (ORAC),<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> <a href="/wiki/Ferric_reducing_ability_of_plasma" title="Ferric reducing ability of plasma">ferric reducing ability of plasma</a> (FRAP)<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> assays or inhibition of copper-catalyzed <i>in vitro</i> human <a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">low-density lipoprotein</a> oxidation.<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><p>New methods including the use of <a href="/wiki/Biosensor" title="Biosensor">biosensors</a> can help monitor the content of polyphenols in food.<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> </p><p>Quantitation results produced by the mean of <a href="/wiki/Diode_array_detector" class="mw-redirect" title="Diode array detector">diode array detector</a>–coupled HPLC are generally given as relative rather than <a href="/wiki/Absolute_value" title="Absolute value">absolute values</a> as there is a lack of commercially available <a href="/wiki/Standard_(metrology)" title="Standard (metrology)">standards</a> for all polyphenolic molecules.<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. (July 2021)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=13" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some polyphenols are traditionally used as <a href="/wiki/Dye" title="Dye">dyes</a> in <a href="/wiki/Leather_tanning" class="mw-redirect" title="Leather tanning">leather tanning</a>. For instance, in the <a href="/wiki/Indian_subcontinent" title="Indian subcontinent">Indian subcontinent</a>, <a href="/wiki/Pomegranate" title="Pomegranate">pomegranate</a> <a href="/wiki/Peel_(fruit)" title="Peel (fruit)">peel</a>, high in tannins and other polyphenols, or its juice, is employed in the dyeing of non-synthetic fabrics.<sup id="cite_ref-jindal2004_30-0" class="reference"><a href="#cite_note-jindal2004-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>Of some interest in the era of silver-based photography, pyrogallol and pyrocatechin are among the oldest <a href="/wiki/Photographic_developer" title="Photographic developer">photographic developers</a>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Gernsheim_&_Gernsheim_32-0" class="reference"><a href="#cite_note-Gernsheim_&_Gernsheim-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Aspirational_use_as_green_chemicals">Aspirational use as green chemicals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=14" title="Edit section: Aspirational use as green chemicals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Natural polyphenols have long been proposed as <a href="/wiki/Green_chemistry" title="Green chemistry">renewable</a> precursors to produce plastics or resins by <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> with <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a>,<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> as well as <a href="/wiki/Adhesive" title="Adhesive">adhesives</a> for particleboards.<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> The aims are generally to make use of plant residues from grape, olive (called <a href="/wiki/Pomace" title="Pomace">pomaces</a>), or <a href="/wiki/Pecan" title="Pecan">pecan</a> shells left after processing.<sup id="cite_ref-:0_14-3" class="reference"><a href="#cite_note-:0-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=15" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The most abundant polyphenols are the <a href="/wiki/Condensed_tannin" title="Condensed tannin">condensed tannins</a>, found in virtually all families of plants. Larger polyphenols are often concentrated in leaf tissue, the epidermis, bark layers, flowers and fruits but also play important roles in the decomposition of forest litter, and <a href="/wiki/Nutrient_cycle" title="Nutrient cycle">nutrient cycles</a> in forest ecology. Absolute concentrations of total phenols in plant tissues differ widely depending on the literature source, type of polyphenols and assay; they are in the range of 1–25% total <a href="/wiki/Natural_phenol" class="mw-redirect" title="Natural phenol">natural phenols</a> and polyphenols, calculated with reference to the dry green leaf mass.<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> </p><p>Polyphenols are also found in animals. In <a href="/wiki/Arthropod" title="Arthropod">arthropods</a>, such as insects,<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> and <a href="/wiki/Crustacean" title="Crustacean">crustaceans</a><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> polyphenols play a role in <a href="/wiki/Epicuticle" class="mw-redirect" title="Epicuticle">epicuticle</a> hardening (<a href="/wiki/Sclerotization" title="Sclerotization">sclerotization</a>). The hardening of the cuticle is due to the presence of a <a href="/wiki/Polyphenol_oxidase" title="Polyphenol oxidase">polyphenol oxidase</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> In crustaceans, there is a second oxidase activity leading to cuticle <a href="/wiki/Pigmentation" class="mw-redirect" title="Pigmentation">pigmentation</a>.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> There is apparently no polyphenol tanning occurring in <a href="/wiki/Arachnid" title="Arachnid">arachnids</a> cuticle.<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="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=16" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyphenols are thought to play diverse roles in the ecology of plants. These functions include:<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Release and suppression of growth hormones such as <a href="/wiki/Auxin" title="Auxin">auxin</a>.</li> <li>UV screens to protect against ionizing radiation and to provide coloration (<a href="/wiki/Plant_pigment" class="mw-redirect" title="Plant pigment">plant pigments</a>).<sup id="cite_ref-manach_5-1" class="reference"><a href="#cite_note-manach-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li> <li>Deterrence of herbivores (sensory properties).</li> <li>Prevention of microbial infections (<a href="/wiki/Phytoalexins" class="mw-redirect" title="Phytoalexins">phytoalexins</a>).<sup id="cite_ref-manach_5-2" class="reference"><a href="#cite_note-manach-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup></li> <li>Signaling molecules in ripening and other growth processes.</li> <li>In some woods can explain their natural <a href="/wiki/Wood_preservation" title="Wood preservation">preservation</a> against rot.<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></li></ul> <p><a href="/wiki/Flax" title="Flax">Flax</a> and <i><a href="/wiki/Myriophyllum_spicatum" title="Myriophyllum spicatum">Myriophyllum spicatum</a></i> (a submerged aquatic plant) secrete polyphenols that are involved in <a href="/wiki/Allelopathy" title="Allelopathy">allelopathic</a> interactions.<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><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> </p> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis_and_metabolism">Biosynthesis and metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=17" title="Edit section: Biosynthesis and metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyphenols incorporate smaller parts and building blocks from simpler <a href="/wiki/Natural_phenol" class="mw-redirect" title="Natural phenol">natural phenols</a>, which originate from the <a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">phenylpropanoid</a> pathway for the phenolic acids or the <a href="/wiki/Shikimic_acid" title="Shikimic acid">shikimic acid</a> pathway for <a href="/wiki/Gallotannin" title="Gallotannin">gallotannins</a> and analogs. Flavonoids and caffeic acid derivatives are biosynthesized from <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a> and <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl-CoA</a>. Complex gallotannins develop through the <i>in vitro</i> oxidation of <a href="/wiki/1,2,3,4,6-Pentagalloyl_glucose" title="1,2,3,4,6-Pentagalloyl glucose">1,2,3,4,6-pentagalloylglucose</a> or dimerization processes resulting in hydrolyzable tannins. For anthocyanidins, precursors of the condensed tannin biosynthesis, <a href="/wiki/Dihydroflavonol_reductase" class="mw-redirect" title="Dihydroflavonol reductase">dihydroflavonol reductase</a> and <a href="/wiki/Leucoanthocyanidin_reductase" title="Leucoanthocyanidin reductase">leucoanthocyanidin reductase</a> (LAR) are crucial enzymes with subsequent addition of catechin and epicatechin moieties for larger, non-hydrolyzable tannins.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>The glycosylated form develops from <a href="/wiki/Glucosyltransferase" title="Glucosyltransferase">glucosyltransferase</a> activity and increases the <a href="/wiki/Solubility" title="Solubility">solubility</a> of polyphenols.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Polyphenol_oxidase" title="Polyphenol oxidase">Polyphenol oxidase</a> (PPO) is an enzyme that catalyses the oxidation of <a href="/wiki/O-diphenol" class="mw-redirect" title="O-diphenol">o-diphenols</a> to produce <a href="/wiki/O-quinone" class="mw-redirect" title="O-quinone">o-quinones</a>. It is the rapid polymerisation of o-quinones to produce black, brown or red polyphenolic pigments that causes <a href="/wiki/Fruit_browning" class="mw-redirect" title="Fruit browning">fruit browning</a>. In insects, PPO is involved in cuticle hardening.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Occurrence_in_food">Occurrence in food</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=18" title="Edit section: Occurrence in food"><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">See also: <a href="/wiki/List_of_phytochemicals_in_food" title="List of phytochemicals in food">List of phytochemicals in food</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Natural_phenols_and_polyphenols_in_wine" class="mw-redirect" title="Natural phenols and polyphenols in wine">Natural phenols and polyphenols in wine</a> and <a href="/wiki/Natural_phenols_and_polyphenols_in_tea" class="mw-redirect" title="Natural phenols and polyphenols in tea">Natural phenols and polyphenols in tea</a></div> <p>Polyphenols comprise up to 0.2–0.3% fresh weight for many fruits. Consuming common servings of wine, chocolate, <a href="/wiki/Legume" title="Legume">legumes</a> or tea may also contribute to about one gram of intake per day.<sup id="cite_ref-lpi_2-2" class="reference"><a href="#cite_note-lpi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> According to a 2005 review on polyphenols: </p> <blockquote><p>The most important food sources are commodities widely consumed in large quantities such as fruit and vegetables, green tea, black tea, red wine, coffee, chocolate, olives, and extra virgin olive oil. Herbs and spices, nuts and algae are also potentially significant for supplying certain polyphenols. Some polyphenols are specific to particular food (flavanones in citrus fruit, isoflavones in soya, phloridzin in apples); whereas others, such as quercetin, are found in all plant products such as fruit, vegetables, cereals, leguminous plants, tea, and wine.<sup id="cite_ref-BioavailRev2005_50-0" class="reference"><a href="#cite_note-BioavailRev2005-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup></p></blockquote> <p>Some polyphenols are considered <a href="/wiki/Antinutrient" title="Antinutrient">antinutrients</a> – compounds that interfere with the absorption of <a href="/wiki/Essential_nutrient" class="mw-redirect" title="Essential nutrient">essential nutrients</a> – especially iron and other metal ions, which may bind to <a href="/wiki/Digestive_enzyme" title="Digestive enzyme">digestive enzymes</a> and other proteins, particularly in <a href="/wiki/Ruminant" title="Ruminant">ruminants</a>.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p><p>In a comparison of cooking methods, phenolic and <a href="/wiki/Carotenoid" title="Carotenoid">carotenoid</a> levels in vegetables were retained better by <a href="/wiki/Steaming" title="Steaming">steaming</a> compared to <a href="/wiki/Frying" title="Frying">frying</a>.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Polyphenols in wine, beer and various nonalcoholic juice beverages can be removed using <a href="/wiki/Finings" title="Finings">finings</a>, substances that are usually added at or near the completion of the processing of brewing.<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. (October 2020)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="Astringency">Astringency</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=19" title="Edit section: Astringency"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>With respect to food and beverages, the cause of <a href="/wiki/Astringency" class="mw-redirect" title="Astringency">astringency</a> is not fully understood, but it is measured chemically as the ability of a substance to precipitate proteins.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>Astringency increases and bitterness decrease with the mean degree of <a href="/wiki/Polymerization" title="Polymerization">polymerization</a>. For water-soluble polyphenols, molecular weights between 500 and 3000 were reported to be required for protein precipitation. However, smaller molecules might still have astringent qualities likely due to the formation of unprecipitated complexes with proteins or cross-linking of proteins with simple phenols that have 1,2-dihydroxy or 1,2,3-trihydroxy groups.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> Flavonoid configurations can also cause significant differences in sensory properties, e.g. <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a> is more bitter and astringent than its <a href="/wiki/Chiral" class="mw-redirect" title="Chiral">chiral</a> <a href="/wiki/Isomer" title="Isomer">isomer</a> <a href="/wiki/Catechin" title="Catechin">catechin</a>. In contrast, hydroxycinnamic acids do not have astringent qualities, but are bitter.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=20" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyphenols are a large, diverse group of compounds, making it difficult to determine their biological effects.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> They are not considered <a href="/wiki/Nutrient" title="Nutrient">nutrients</a>, as they are not used for growth, survival or reproduction, nor do they provide <a href="/wiki/Dietary_energy_supply" title="Dietary energy supply">dietary energy</a>. Therefore, they do not have recommended <a href="/wiki/Reference_Daily_Intake" title="Reference Daily Intake">daily intake levels</a>, as exist for <a href="/wiki/Vitamin" title="Vitamin">vitamins</a>, <a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">minerals</a>, and <a href="/wiki/Dietary_fiber" title="Dietary fiber">fiber</a>.<sup id="cite_ref-efsa-nut_57-0" class="reference"><a href="#cite_note-efsa-nut-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-nhs_58-0" class="reference"><a href="#cite_note-nhs-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-usda_59-0" class="reference"><a href="#cite_note-usda-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> In the United States, the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> issued guidance to manufacturers that polyphenols cannot be mentioned on <a href="/wiki/Food_label" class="mw-redirect" title="Food label">food labels</a> as antioxidant nutrients unless <a href="/wiki/Physiology" title="Physiology">physiological</a> evidence exists to verify such a qualification and a Dietary Reference Intake value has been established – characteristics which have not been determined for polyphenols.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-nutra_61-0" class="reference"><a href="#cite_note-nutra-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>In the <a href="/wiki/European_Union" title="European Union">European Union</a>, two <a href="/wiki/Health_claim" title="Health claim">health claims</a> were authorized between 2012 and 2015: 1) flavanols in <a href="/wiki/Cocoa_solid" class="mw-redirect" title="Cocoa solid">cocoa solids</a> at doses exceeding 200 mg per day may contribute to maintenance of vascular elasticity and normal blood flow;<sup id="cite_ref-EC-cocoa_62-0" class="reference"><a href="#cite_note-EC-cocoa-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:02_63-0" class="reference"><a href="#cite_note-:02-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> 2) olive oil polyphenols (5 mg of <a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">hydroxytyrosol</a> and its derivatives (e.g. <a href="/wiki/Oleuropein" title="Oleuropein">oleuropein</a> complex and <a href="/wiki/Tyrosol" title="Tyrosol">tyrosol</a>) may "contribute to the protection of blood lipids from oxidative damage", if consumed daily.<sup id="cite_ref-EC-olive_64-0" class="reference"><a href="#cite_note-EC-olive-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_65-0" class="reference"><a href="#cite_note-:1-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p><p>As of 2022, <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trials</a> that assessed the effect of polyphenols on health <a href="/wiki/Biomarker" title="Biomarker">biomarkers</a> are limited, with results difficult to interpret due to the wide variation of intake values for both individual polyphenols and total polyphenols.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p><p><span class="anchor" id="Antioxidant_activity"></span>Polyphenols were once considered as <a href="/wiki/Antioxidant_effect_of_polyphenols_and_natural_phenols" title="Antioxidant effect of polyphenols and natural phenols">antioxidants</a>, but this concept is obsolete.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Most polyphenols are metabolized by <a href="/wiki/Catechol-O-methyltransferase" title="Catechol-O-methyltransferase">catechol-O-methyltransferase</a>, and therefore do not have the chemical structure allowing antioxidant activity in vivo; they may exert biological activity as <a href="/wiki/Cell_signaling" title="Cell signaling">signaling molecules</a>.<sup id="cite_ref-lpi_2-3" class="reference"><a href="#cite_note-lpi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-nutra_61-1" class="reference"><a href="#cite_note-nutra-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> Some polyphenols are considered to be <a href="/wiki/Bioactive_compound" title="Bioactive compound">bioactive compounds</a><sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> for which development of dietary recommendations was under consideration in 2017.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cardiovascular_diseases">Cardiovascular diseases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=21" title="Edit section: Cardiovascular diseases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Flavonoid#History" title="Flavonoid">In the 1930s</a>, polyphenols (then called <i>vitamin P</i>) were considered as a factor in <a href="/wiki/Vascular_permeability" title="Vascular permeability">capillary permeability</a>, followed by various studies through the 21st century of a possible effect on cardiovascular diseases. For most polyphenols, there is no evidence for an effect on cardiovascular regulation, although there are some reviews showing a minor effect of consuming polyphenols, such as <a href="/wiki/Chlorogenic_acid" title="Chlorogenic acid">chlorogenic acid</a> or <a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">flavan-3-ols</a>, on blood pressure.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cancer">Cancer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=22" title="Edit section: Cancer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Higher intakes of soy isoflavones may be associated with reduced risks of breast cancer in postmenopausal women and prostate cancer in men.<sup id="cite_ref-lpi_2-4" class="reference"><a href="#cite_note-lpi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>A 2019 systematic review found that intake of soy and soy isoflavones is associated with a lower risk of <a href="/wiki/Mortality_rate" title="Mortality rate">mortality</a> from gastric, colorectal, breast and lung cancers.<sup id="cite_ref-nach_74-0" class="reference"><a href="#cite_note-nach-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> The study found that an increase in isoflavone consumption by 10 mg per day was associated with a 7% decrease in risk from all cancers, and an increase in consumption of soy protein by 5 grams per day produced a 12% reduction in breast cancer risk.<sup id="cite_ref-nach_74-1" class="reference"><a href="#cite_note-nach-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cognitive_function">Cognitive function</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=23" title="Edit section: Cognitive function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyphenols are under preliminary research for possible <a href="/wiki/Cognition" title="Cognition">cognitive effects</a> in healthy adults.<sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Phytoestrogens">Phytoestrogens</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=24" title="Edit section: Phytoestrogens"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Isoflavone" title="Isoflavone">Isoflavones</a>, which are structurally related to <a href="/wiki/17%CE%B2-estradiol" class="mw-redirect" title="17β-estradiol">17β-estradiol</a>, are classified as <a href="/wiki/Phytoestrogen" title="Phytoestrogen">phytoestrogens</a>.<sup id="cite_ref-77" class="reference"><a href="#cite_note-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> A risk assessment by the European Food Safety Authority found no cause for concern when isoflavones are consumed in a normal diet.<sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Phlebotonic">Phlebotonic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=25" title="Edit section: Phlebotonic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Diosmin#Phlebotonics" title="Diosmin">Diosmin § Phlebotonics</a></div> <p>Phlebotonics of heterogeneous composition, consisting partly of <a href="/wiki/Peel_(fruit)" title="Peel (fruit)">citrus peel</a> <a href="/wiki/Extract" title="Extract">extracts</a> (<a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a>, such as <a href="/wiki/Hesperidin" title="Hesperidin">hesperidin</a>) and synthetic compounds, are used to treat <a href="/wiki/Chronic_venous_insufficiency" title="Chronic venous insufficiency">chronic venous insufficiency</a> and <a href="/wiki/Hemorrhoid" title="Hemorrhoid">hemorrhoids</a>.<sup id="cite_ref-drugs_79-0" class="reference"><a href="#cite_note-drugs-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> Some are <a href="/wiki/Prescription_drug" title="Prescription drug">non-prescription</a> <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplements</a>, such as <a href="/wiki/Diosmin" title="Diosmin">diosmin</a>,<sup id="cite_ref-drugs_79-1" class="reference"><a href="#cite_note-drugs-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> while one other – Vasculera (Diosmiplex) – is a prescription <a href="/wiki/Medical_food" title="Medical food">medical food</a> intended for treating venous disorders.<sup id="cite_ref-dailymed-diosmiplex_80-0" class="reference"><a href="#cite_note-dailymed-diosmiplex-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup> Their mechanism of action is undefined,<sup id="cite_ref-drugs_79-2" class="reference"><a href="#cite_note-drugs-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Evidence-based_medicine" title="Evidence-based medicine">clinical evidence</a> of benefit for using phlebotonics to treat venous diseases is limited.<sup id="cite_ref-drugs_79-3" class="reference"><a href="#cite_note-drugs-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Gut_microbiome">Gut microbiome</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=26" title="Edit section: Gut microbiome"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyphenols are extensively metabolized by the <a href="/wiki/Gut_microbiota" title="Gut microbiota">gut microbiota</a> and are investigated as a potential metabolic factor in function of the gut microbiota.<sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-82" class="reference"><a href="#cite_note-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Toxicity_and_adverse_effects">Toxicity and adverse effects</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=27" title="Edit section: Toxicity and adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Adverse_effect" title="Adverse effect">Adverse effects</a> of polyphenol intake range from mild (e.g., <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a> symptoms)<sup id="cite_ref-lpi_2-5" class="reference"><a href="#cite_note-lpi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> to severe (e.g., <a href="/wiki/Hemolytic_anemia" title="Hemolytic anemia">hemolytic anemia</a> or <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>).<sup id="cite_ref-davies_83-0" class="reference"><a href="#cite_note-davies-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> In 1988, hemolytic anemia following polyphenol consumption was documented, resulting in the withdrawal of a <a href="/wiki/Catechin" title="Catechin">catechin</a>-containing drug.<sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> Polyphenols, particularly in beverages that contain them in high concentrations (tea, coffee, etc), inhibit the <a href="/wiki/Small_intestine#Absorption" title="Small intestine">absorption</a> of <a href="/wiki/Heme" title="Heme">non-haem iron</a> when consumed together in a single meal.<sup id="cite_ref-lpi_2-6" class="reference"><a href="#cite_note-lpi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SACN_85-0" class="reference"><a href="#cite_note-SACN-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WHO_86-0" class="reference"><a href="#cite_note-WHO-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CDC_87-0" class="reference"><a href="#cite_note-CDC-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> Research is limited on the effect of this inhibition on <a href="/wiki/Iron_tests" title="Iron tests">iron status</a>.<sup id="cite_ref-SACN_quote_88-0" class="reference"><a href="#cite_note-SACN_quote-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> </p><p>Metabolism of polyphenols can result in flavonoid-drug interactions, such as in <a href="/wiki/Grapefruit%E2%80%93drug_interactions" title="Grapefruit–drug interactions">grapefruit–drug interactions</a>, which involves inhibition of the liver <a href="/wiki/Enzyme" title="Enzyme">enzyme</a>, <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>, likely by grapefruit <a href="/wiki/Furanocoumarin" title="Furanocoumarin">furanocoumarins</a>, a class of polyphenol.<sup id="cite_ref-lpi_2-7" class="reference"><a href="#cite_note-lpi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-davies_83-1" class="reference"><a href="#cite_note-davies-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> The European Food Safety Authority established upper limits for some polyphenol-containing supplements and additives, such as <a href="/wiki/Green_tea_extract" class="mw-redirect" title="Green tea extract">green tea extract</a> or <a href="/wiki/Curcumin" title="Curcumin">curcumin</a>.<sup id="cite_ref-89" class="reference"><a href="#cite_note-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-90" class="reference"><a href="#cite_note-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> For most polyphenols found in the diet, an adverse effect beyond nutrient-drug interactions is unlikely.<sup id="cite_ref-lpi_2-8" class="reference"><a href="#cite_note-lpi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyphenol&action=edit&section=28" 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/Dictionary_of_natural_phenols_and_polyphenols_molecular_formulas" title="Dictionary of natural phenols and polyphenols molecular formulas">Dictionary of natural phenols and polyphenols molecular formulas</a></li> <li><a href="/wiki/Phytochemistry" title="Phytochemistry">Phytochemistry</a></li> <li><a href="/wiki/Polyphenolic_protein" class="mw-redirect" title="Polyphenolic protein">Polyphenolic proteins</a></li> <li><a href="/wiki/Secondary_metabolite" title="Secondary metabolite">Secondary metabolites</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=Polyphenol&action=edit&section=29" 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-Quideau-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Quideau_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Quideau_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFQuideauDeffieuxDouat-CasassusPouységu2011" class="citation journal cs1">Quideau S, Deffieux D, Douat-Casassus C, Pouységu L (January 2011). <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201000044">"Plant polyphenols: chemical properties, biological activities, and synthesis"</a>. <i>Angewandte Chemie</i>. <b>50</b> (3): 586–621. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi 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class="Z3988"></span></span> </li> <li id="cite_note-90"><span class="mw-cite-backlink"><b><a href="#cite_ref-90">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEFSA_Panel_on_Food_Additives_and_Nutrient_Sources_Added_to_Food2010" class="citation journal cs1">EFSA Panel on Food Additives and Nutrient Sources Added to Food (1 September 2010). <a rel="nofollow" class="external text" href="https://efsa.onlinelibrary.wiley.com/doi/epdf/10.2903/j.efsa.2010.1679">"Scientific opinion on the re-evaluation of curcumin (E 100) as a food additive"</a>. <i>EFSA Journal</i>. <b>8</b> (9). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2903%2Fj.efsa.2010.1679">10.2903/j.efsa.2010.1679</a>.</cite><span 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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"><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 href="/wiki/Carotenoid" title="Carotenoid">Carotenoids</a>) (8)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotene" title="Carotene">Carotenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Carotene" class="mw-redirect" title="Alpha-Carotene">Alpha-Carotene</a></li> <li><a href="/wiki/Beta-Carotene" class="mw-redirect" title="Beta-Carotene">Beta-Carotene</a></li> <li><a href="/wiki/Gamma-Carotene" class="mw-redirect" title="Gamma-Carotene">Gamma-Carotene</a></li> <li><a href="/wiki/Delta-Carotene" class="mw-redirect" title="Delta-Carotene">Delta-Carotene</a></li> <li><a href="/wiki/Lycopene" title="Lycopene">Lycopene</a></li> <li><a href="/wiki/Neurosporene" title="Neurosporene">Neurosporene</a></li> <li><a href="/wiki/Phytofluene" title="Phytofluene">Phytofluene</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Xanthophyll" title="Xanthophyll">Xanthophylls</a>:</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Canthaxanthin" title="Canthaxanthin">Canthaxanthin</a></li> <li><a href="/wiki/Cryptoxanthin" class="mw-redirect" title="Cryptoxanthin">Cryptoxanthin</a></li> <li><a href="/wiki/Zeaxanthin" title="Zeaxanthin">Zeaxanthin</a></li> <li><a href="/wiki/Astaxanthin" title="Astaxanthin">Astaxanthin</a></li> <li><a href="/wiki/Lutein" title="Lutein">Lutein</a></li> <li><a href="/wiki/Rubixanthin" title="Rubixanthin">Rubixanthin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polyterpenoid" class="mw-redirect" title="Polyterpenoid">Polyterpenoids</a> (many)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Natural_rubber" title="Natural rubber">Natural rubber</a></li> <li><a href="/wiki/Gutta_percha" class="mw-redirect" title="Gutta percha">Gutta percha</a></li> <li>Gutta-balatá</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Norisoprenoids (modified)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>3-oxo-α-ionol</li> <li>7,8-dihydroionone</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthesis</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Terpene synthase enzymes (many), having in common a <a href="/wiki/Terpene_synthase_N_terminal_domain" title="Terpene synthase N terminal domain">terpene synthase N terminal domain</a> (<a href="/wiki/Protein_domain" title="Protein domain">protein domain</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Activated isoprene forms</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a> (IPP)</li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a> (DMAPP)</li></ul> </div></td></tr></tbody></table></div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenolic_compound" class="mw-redirect" title="Phenolic compound">Phenolic compounds</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="navbox-styles"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_phenolic_compounds" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phenolic_compounds" title="Template:Phenolic compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenolic_compounds" title="Template talk:Phenolic compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenolic_compounds" title="Special:EditPage/Template:Phenolic compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_phenolic_compounds" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Phenolic_compound" class="mw-redirect" title="Phenolic compound">phenolic compounds</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Natural_monophenol" class="mw-redirect" title="Natural monophenol">Natural monophenols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzenediol" class="mw-redirect" title="Benzenediol">Benzenediols</a></li> <li><a href="/wiki/Benzenetriol" class="mw-redirect" title="Benzenetriol">Benzenetriols</a></li> <li><a href="/wiki/Apiole" title="Apiole">Apiole</a></li> <li><a href="/wiki/Carnosol" title="Carnosol">Carnosol</a></li> <li><a href="/wiki/Carvacrol" title="Carvacrol">Carvacrol</a></li> <li><a href="/wiki/Dillapiole" title="Dillapiole">Dillapiole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Polyphenols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Polyphenols" title="Template:Polyphenols"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Polyphenols" title="Template talk:Polyphenols"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Polyphenols" title="Special:EditPage/Template:Polyphenols"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_polyphenols" style="font-size:114%;margin:0 4em">Types of <a class="mw-selflink selflink">polyphenols</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a><br />(C6-C3-C6)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Flavonoids" title="Template:Flavonoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Flavonoids" title="Template talk:Flavonoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Flavonoids" title="Special:EditPage/Template:Flavonoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_flavonoids" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anthoxanthin" title="Anthoxanthin">Anthoxanthins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavone" title="Flavone">Flavones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a>, <a href="/wiki/Chrysin" title="Chrysin">Chrysin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonols" title="Flavonols">Flavonols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a>, <a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoflavones" class="mw-redirect" title="Isoflavones">Isoflavones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a>, <a href="/wiki/Genistein" title="Genistein">Genistein</a>, <a href="/wiki/Orobol" title="Orobol">Orobol</a> et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neoflavonoid" title="Neoflavonoid">Neoflavonoids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dalbergichromene" title="Dalbergichromene">Dalbergichromene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan" title="Flavan">Flavans</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Flavan</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Luteoliflavan&action=edit&redlink=1" class="new" title="Luteoliflavan (page does not exist)">Luteoliflavan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ols</a><br />(<a href="/wiki/Flavanol" class="mw-redirect" title="Flavanol">flavanols</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Catechin" title="Catechin">Catechin</a>, <a href="/wiki/Gallocatechol" title="Gallocatechol">Gallocatechol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan-4-ol" title="Flavan-4-ol">Flavan-4-ols</a><br />(<a href="/wiki/Flavanol" class="mw-redirect" title="Flavanol">flavanols</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apiforol" title="Apiforol">Apiforol</a>, <a href="/wiki/Luteoforol" title="Luteoforol">Luteoforol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Leucoanthocyanidin" title="Leucoanthocyanidin">Flavan-3,4-diols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Leucocyanidin" title="Leucocyanidin">Leucocyanidin</a>, <a href="/wiki/Leucodelphinidin" title="Leucodelphinidin">Leucodelphinidin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavanone" title="Flavanone">Flavanones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hesperidin" title="Hesperidin">Hesperidin</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Eriodictyol" title="Eriodictyol">Eriodictyol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavanonol" title="Flavanonol">Flavanonols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Taxifolin" title="Taxifolin">Taxifolin</a></li> <li><a href="/wiki/Aromadendrin" title="Aromadendrin">Aromadendrin</a>, et.c.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anthocyanidins" class="mw-redirect" title="Anthocyanidins">Anthocyanidins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/3-deoxyanthocyanidin" class="mw-redirect" title="3-deoxyanthocyanidin">3-deoxyanthocyanidins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyanidin" title="Cyanidin">Cyanidin</a>, <a href="/wiki/Delphinidin" title="Delphinidin">Delphinidin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=3-hydroxyanthocyanidin&action=edit&redlink=1" class="new" title="3-hydroxyanthocyanidin (page does not exist)">3-hydroxyanthocyanidin</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apigeninidin" title="Apigeninidin">Apigeninidin</a>, <a href="/wiki/Guibourtinidin" title="Guibourtinidin">Guibourtinidin</a>, et.c.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aurones" class="mw-redirect" title="Aurones">Aurones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aureusidin" title="Aureusidin">Aureusidin</a></li> <li><a href="/wiki/Leptosidin" title="Leptosidin">Leptosidin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chalcones" class="mw-redirect" title="Chalcones">Chalcones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chalcone" title="Chalcone">Chalcones</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butein" title="Butein">Butein</a>, <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">Isoliquiritigenin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydrochalcone" title="Dihydrochalcone">Dihydrochalcone</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phloretin" title="Phloretin">Phloretin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Miscellaneous</i></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/List_of_phytochemicals_in_food" title="List of phytochemicals in food">List of phytochemicals in food</a></li> <li><a href="/wiki/C-methylated_flavonoid" title="C-methylated flavonoid">C-methylated flavonoids</a></li> <li><a href="/wiki/O-methylated_flavonoid" title="O-methylated flavonoid">O-methylated flavonoids</a></li> <li><a href="/wiki/Furanoflavonoid" title="Furanoflavonoid">Furanoflavonoids</a></li> <li><a href="/wiki/Pyranoflavonoid" title="Pyranoflavonoid">Pyranoflavonoids</a></li> <li><a href="/wiki/Prenylflavonoid" title="Prenylflavonoid">Prenylflavonoids</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li> <li><a href="/wiki/Castavinol" title="Castavinol">Castavinols</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><a href="/wiki/Flavonoid_biosynthesis" title="Flavonoid biosynthesis">Flavonoid biosynthesis</a></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonolignan" title="Flavonolignan">Flavonolignans</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Silymarin" class="mw-redirect" title="Silymarin">Silymarin</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lignan" title="Lignan">Lignans</a><br />((C6-C3)<sub>2</sub>)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Matairesinol" title="Matairesinol">Matairesinol</a></li> <li><a href="/wiki/Secoisolariciresinol" title="Secoisolariciresinol">Secoisolariciresinol</a></li> <li><a href="/wiki/Pinoresinol" title="Pinoresinol">Pinoresinol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a><br />(C6-C2-C6)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/wiki/Pterostilbene" title="Pterostilbene">Pterostilbene</a></li> <li><a href="/wiki/Piceatannol" title="Piceatannol">Piceatannol</a></li> <li><a href="/wiki/Pinosylvin" title="Pinosylvin">Pinosylvin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Curcuminoid" title="Curcuminoid">Curcuminoids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tannin" title="Tannin">Tannins</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Tannin" title="Template:Tannin"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tannin" title="Template talk:Tannin"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tannin" title="Special:EditPage/Template:Tannin"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_natural_tannins" style="font-size:114%;margin:0 4em">Types of natural <a href="/wiki/Tannin" title="Tannin">tannins</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrolysable_tannin" title="Hydrolysable tannin">Hydrolysable tannins</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ellagitannin" title="Ellagitannin">Ellagitannins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Punicalagin" title="Punicalagin">Punicalagins</a></li> <li><a href="/wiki/Castalagin" title="Castalagin">Castalagins</a></li> <li><a href="/wiki/Vescalagin" class="mw-redirect" title="Vescalagin">Vescalagins</a></li> <li><a href="/wiki/Castalin" title="Castalin">Castalins</a></li> <li><a href="/wiki/Casuarictin" title="Casuarictin">Casuarictins</a></li> <li><a href="/wiki/Grandinin" title="Grandinin">Grandinins</a></li> <li><a href="/wiki/Punicalin" title="Punicalin">Punicalins</a></li> <li><a href="/wiki/Roburin_A" title="Roburin A">Roburin A</a></li> <li><a href="/wiki/Tellimagrandin_II" title="Tellimagrandin II">Tellimagrandin IIs</a></li> <li><a href="/wiki/Terflavin_B" title="Terflavin B">Terflavin B</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Gallotannin" title="Gallotannin">Gallotannins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Digalloyl_glucose" title="Digalloyl glucose">Digalloyl glucose</a></li> <li><a href="/wiki/1,3,6-Trigalloyl_glucose" title="1,3,6-Trigalloyl glucose">1,3,6-Trigalloyl glucose</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Condensed_tannin" title="Condensed tannin">Condensed tannins</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">Proanthocyanidins</a></li> <li><a href="/wiki/Polyflavonoid_tannin" class="mw-redirect" title="Polyflavonoid tannin">Polyflavonoid tannins</a></li> <li><a href="/wiki/Catechol-type_tannin" class="mw-redirect" title="Catechol-type tannin">Catechol-type tannins</a></li> <li><a href="/wiki/Pyrocatecollic_type_tannin" class="mw-redirect" title="Pyrocatecollic type tannin">Pyrocatecollic type tannins</a></li> <li><a href="/wiki/Flavolan" class="mw-redirect" title="Flavolan">Flavolans</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phlorotannin" title="Phlorotannin">Phlorotannins</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Eckol" title="Eckol">Eckol</a></li> <li><a href="/wiki/8,8%E2%80%B2-Bieckol" title="8,8′-Bieckol">8,8′-Bieckol</a></li> <li><a href="/wiki/6,6%27-Bieckol" title="6,6'-Bieckol">6,6'-Bieckol</a></li> <li><a href="/wiki/Dieckol" title="Dieckol">Dieckol</a></li> <li><a href="/wiki/Eckstolonol" title="Eckstolonol">Eckstolonol</a></li> <li><a href="/wiki/Diphlorethol" title="Diphlorethol">Diphlorethol</a></li> <li><a href="/wiki/Difucol" title="Difucol">Difucol</a></li> <li><a href="/wiki/Fucophlorethol_A" title="Fucophlorethol A">Fucophlorethol A</a></li> <li><a href="/wiki/Phlorofucofuroeckol_A" title="Phlorofucofuroeckol A">Phlorofucofuroeckol A</a></li> <li><a href="/wiki/Tetrafucol_A" title="Tetrafucol A">Tetrafucol A</a></li> <li><a href="/wiki/Trifucol" title="Trifucol">Trifucol</a></li> <li><a href="/wiki/Bifuhalol" title="Bifuhalol">Bifuhalol</a></li> <li><a href="/wiki/7-Phloroeckol" title="7-Phloroeckol">7-Phloroeckol</a></li> <li>Phlorofucofuroeckol B</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavono-ellagitannin" title="Flavono-ellagitannin">Flavono-ellagitannins</a><br />(complex tannins)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Epicutissimin_A" title="Epicutissimin A">Epicutissimin A</a></li> <li><a href="/wiki/Acutissimin_A" title="Acutissimin A">Acutissimin A</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Template:Tannin_source" title="Template:Tannin source">Tannin sources</a></li> <li><a href="/wiki/Pseudo_tannins" class="mw-redirect" title="Pseudo tannins">Pseudo tannins</a></li> <li><a href="/wiki/Synthetic_tannins" class="mw-redirect" title="Synthetic tannins">Synthetic tannins</a></li> <li>Tannin uses <ul><li><a href="/wiki/Enological_tannin" class="mw-redirect" title="Enological tannin">Enological</a></li> <li><a href="/wiki/Drilling_mud" class="mw-redirect" title="Drilling mud">Drilling</a></li> <li><a href="/wiki/Iron_gall_ink" title="Iron gall ink">Ink</a></li> <li><a href="/wiki/Tanning_(leather)" title="Tanning (leather)">Tanning</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diarylheptanoid" title="Diarylheptanoid">Diarylheptanoids</a> (C6-C7-C6)</li> <li><a href="/wiki/Anthraquinones" title="Anthraquinones">Anthraquinones</a></li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (C6-C3-C6)</li> <li><a href="/wiki/Kavalactone" title="Kavalactone">Kavalactones</a></li> <li><a href="/wiki/Naphthoquinone" title="Naphthoquinone">Naphthoquinones</a> (C6-C4)</li> <li><a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">Phenylpropanoids</a> (C6-C3)</li> <li><a href="/wiki/Xanthonoid" title="Xanthonoid">Xanthonoids</a> (C6-C1-C6)</li> <li><a href="/wiki/Coumarin" title="Coumarin">Coumarins</a> and <a href="/wiki/Isocoumarin" title="Isocoumarin">isocoumarins</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Misc</i>:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a class="mw-selflink selflink">Polyphenols</a></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromatic_acid" title="Aromatic acid">Aromatic acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Aromatic_acids" title="Template:Aromatic acids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Aromatic_acids" title="Template talk:Aromatic acids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Aromatic_acids" title="Special:EditPage/Template:Aromatic acids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Aromatic_acids" style="font-size:114%;margin:0 4em"><a href="/wiki/Aromatic_acid" title="Aromatic acid">Aromatic acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenolic_acid" title="Phenolic acid">Phenolic acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Monohydroxybenzoic_acids" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monohydroxybenzoic_acid" title="Monohydroxybenzoic acid">Monohydroxybenzoic acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Aglycones</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Hydroxybenzoic_acid" title="3-Hydroxybenzoic acid">3-Hydroxybenzoic acid</a></li> <li><a href="/wiki/4-Hydroxybenzoic_acid" title="4-Hydroxybenzoic acid">4-Hydroxybenzoic acid</a></li> <li><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycosides</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/P-Hydroxybenzoic_acid_glucoside" class="mw-redirect" title="P-Hydroxybenzoic acid glucoside">p-Hydroxybenzoic acid glucoside</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydroxybenzoic_acid" title="Dihydroxybenzoic acid">Dihydroxybenzoic acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,3-Dihydroxybenzoic_acid" title="2,3-Dihydroxybenzoic acid">2,3-Dihydroxybenzoic acid</a> (Hypogallic acid)</li> <li><a href="/wiki/2,4-Dihydroxybenzoic_acid" title="2,4-Dihydroxybenzoic acid">2,4-Dihydroxybenzoic acid</a></li> <li><a href="/wiki/2,6-Dihydroxybenzoic_acid" title="2,6-Dihydroxybenzoic acid">2,6-Dihydroxybenzoic acid</a></li> <li><a href="/wiki/3,5-Dihydroxybenzoic_acid" title="3,5-Dihydroxybenzoic acid">3,5-Dihydroxybenzoic acid</a></li> <li><a href="/wiki/Ethyl_protocatechuate" title="Ethyl protocatechuate">Ethyl protocatechuate</a></li> <li><a href="/wiki/Gentisic_acid" title="Gentisic acid">Gentisic acid</a></li> <li><a href="/wiki/Homogentisic_acid" title="Homogentisic acid">Homogentisic acid</a></li> <li><a href="/wiki/Orsellinic_acid" title="Orsellinic acid">Orsellinic acid</a></li> <li><a href="/wiki/Protocatechuic_acid" title="Protocatechuic acid">Protocatechuic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trihydroxybenzoic_acid" title="Trihydroxybenzoic acid">Trihydroxybenzoic acids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bergenin" title="Bergenin">Bergenin</a></li> <li><a href="/wiki/Chebulic_acid" title="Chebulic acid">Chebulic acid</a></li> <li><a href="/wiki/Ethyl_gallate" title="Ethyl gallate">Ethyl gallate</a></li> <li><a href="/wiki/Eudesmic_acid" title="Eudesmic acid">Eudesmic acid</a></li> <li><a href="/wiki/Gallic_acid" title="Gallic acid">Gallic acid</a></li> <li><a href="/wiki/Tannic_acid" title="Tannic acid">Tannic acid</a></li> <li><a href="/wiki/Norbergenin" title="Norbergenin">Norbergenin</a></li> <li><a href="/wiki/Phloroglucinol_carboxylic_acid" title="Phloroglucinol carboxylic acid">Phloroglucinol carboxylic acid</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li> <li><a href="/wiki/Theogallin" title="Theogallin">Theogallin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other phenolic acids</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Vanillin" title="Vanillin">Vanillin</a></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydroxycinnamic_acid" title="Hydroxycinnamic acid">Hydroxycinnamic acids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Cyano-4-hydroxycinnamic_acid" class="mw-redirect" title="Alpha-Cyano-4-hydroxycinnamic acid">α-Cyano-4-hydroxycinnamic acid</a></li> <li><a href="/wiki/Caffeic_acid" title="Caffeic acid">Caffeic acid</a></li> <li><a href="/wiki/Chicoric_acid" title="Chicoric acid">Chicoric acid</a></li> <li><a href="/wiki/Cinnamic_acid" title="Cinnamic acid">Cinnamic acid</a></li> <li><a href="/wiki/Chlorogenic_acid" title="Chlorogenic acid">Chlorogenic acid</a></li> <li><a href="/wiki/Diferulic_acids" title="Diferulic acids">Diferulic acids</a></li> <li><a href="/wiki/Coumaric_acid" title="Coumaric acid">Coumaric acid</a></li> <li><a href="/wiki/Coumarin" title="Coumarin">Coumarin</a></li> <li><a href="/wiki/Ferulic_acid" title="Ferulic acid">Ferulic acid</a></li> <li><a href="/wiki/Sinapinic_acid" title="Sinapinic acid">Sinapinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">Aromatic amino acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a></li> <li><a href="/wiki/Histidine" title="Histidine">histidine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a></li> <li><a href="/wiki/Thyroxine" class="mw-redirect" title="Thyroxine">thyroxine</a></li> <li><a href="/wiki/5-hydroxytryptophan" class="mw-redirect" title="5-hydroxytryptophan">5-hydroxytryptophan</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethanoid" title="Phenylethanoid">Phenylethanoids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tyrosol" title="Tyrosol">Tyrosol</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Oleocanthal" title="Oleocanthal">Oleocanthal</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a></li> <li><a href="/wiki/Gingerol" title="Gingerol">Gingerol</a></li> <li><a href="/wiki/Alkylresorcinol" title="Alkylresorcinol">Alkylresorcinols</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Misc</i>:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phenol" title="Phenol">Phenolic compounds</a></li> <li><a href="/wiki/Phlorotannin" title="Phlorotannin">Phlorotannins</a>)</li></ul> </div></td></tr></tbody></table></div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucosinolate" title="Glucosinolate">Glucosinolates</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Precursor to <a href="/wiki/Isothiocyanate" title="Isothiocyanate">isothiocyanates</a> <ul><li><a href="/wiki/Sinigrin" title="Sinigrin">Sinigrin</a></li> <li><a href="/wiki/Gluconasturtiin" title="Gluconasturtiin">Gluconasturtiin</a></li> <li><a href="/wiki/Glucoraphanin" title="Glucoraphanin">Glucoraphanin</a></li></ul></li> <li>Aglycone derivatives <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanates</a> <ul><li><a href="/wiki/Sulforaphane" title="Sulforaphane">Sulforaphane</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a></li> <li><a href="/wiki/Phenethyl_Isothiocyanate" class="mw-redirect" title="Phenethyl Isothiocyanate">Phenethyl Isothiocyanate</a></li></ul></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitriles</a></li> <li><a href="/wiki/Thiocyanate" title="Thiocyanate">Thiocyanates</a></li></ul></li> <li><a href="/wiki/Organosulfide" class="mw-redirect" title="Organosulfide">Organosulfides</a> <ul><li><a href="/wiki/Sulfide" title="Sulfide">Sulfides</a></li> <li><a href="/wiki/Polysulfide" title="Polysulfide">Polysulfides</a> <ul><li><a href="/wiki/Diallyl_disulfide" title="Diallyl disulfide">Diallyl disulfide</a></li></ul></li></ul></li> <li><a href="/wiki/Indole" title="Indole">Indoles</a> <ul><li><a href="/wiki/Indole-3-carbinol" title="Indole-3-carbinol">Indole-3-carbinol</a></li> <li><a href="/wiki/3,3%27-Diindolylmethane" title="3,3'-Diindolylmethane">3,3'-Diindolylmethane</a></li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a></li> <li><a href="/wiki/Alliin" title="Alliin">Alliin</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a></li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a></li> <li><a href="/wiki/Syn-propanethial-S-oxide" class="mw-redirect" title="Syn-propanethial-S-oxide">Syn-propanethial-S-oxide</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Betalain" title="Betalain">Betalains</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Betacyanin" class="mw-redirect" title="Betacyanin">Betacyanins</a> <ul><li><a href="/wiki/Betanin" title="Betanin">Betanin</a></li></ul></li> <li><a href="/wiki/Betaxanthin" class="mw-redirect" title="Betaxanthin">Betaxanthins</a> <ul><li><a href="/wiki/Indicaxanthin" title="Indicaxanthin">Indicaxanthin</a></li> <li><a href="/wiki/Vulgaxanthin" title="Vulgaxanthin">Vulgaxanthin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chlorophyll" title="Chlorophyll">Chlorophylls</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chlorophyllin" title="Chlorophyllin">Chlorophyllin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_acid" title="Organic acid">Organic acids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Saturated cyclic acids <ul><li><a href="/wiki/Phytic_acid" title="Phytic acid">Phytic acid</a></li> <li><a href="/wiki/Quinic_acid" title="Quinic acid">Quinic acid</a></li></ul></li> <li><a href="/wiki/Oxalic_acid" title="Oxalic acid">Oxalic acid</a></li> <li><a href="/wiki/Tartaric_acid" title="Tartaric acid">Tartaric acid</a></li> <li><a href="/wiki/Anacardic_acid" class="mw-redirect" title="Anacardic acid">Anacardic acid</a></li> <li><a href="/wiki/Malic_acid" title="Malic acid">Malic acid</a></li> <li><a href="/wiki/Caftaric_acid" title="Caftaric acid">Caftaric acid</a></li> <li><a href="/wiki/Coutaric_acid" title="Coutaric acid">Coutaric acid</a></li> <li><a href="/wiki/Fertaric_acid" title="Fertaric acid">Fertaric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbohydrate" title="Carbohydrate">Carbohydrates</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Monosaccharide" title="Monosaccharide">Monosaccharides</a> <ul><li><a href="/wiki/Hexose" title="Hexose">Hexoses</a></li> <li><a href="/wiki/Pentose" title="Pentose">Pentoses</a></li></ul></li> <li><a href="/wiki/Polysaccharide" title="Polysaccharide">Polysaccharides</a> <ul><li><a href="/wiki/Beta-glucan" title="Beta-glucan">Beta-glucan</a> <ul><li><a href="/wiki/Chitin" title="Chitin">Chitin</a></li> <li><a href="/wiki/Lentinan" title="Lentinan">Lentinan</a></li></ul></li> <li><a href="/wiki/Fructan" title="Fructan">Fructan</a> <ul><li><a href="/wiki/Inulin" title="Inulin">Inulins</a></li></ul></li> <li><a href="/wiki/Lignin" title="Lignin">Lignin</a></li> <li><a href="/wiki/Pectin" title="Pectin">Pectin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Misc</i>:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/List_of_phytochemicals_in_food" title="List of phytochemicals in food">List of phytochemicals and foods in which they are prominent</a></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Secondary_metabolites" 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:Secondary_metabolites" title="Template:Secondary metabolites"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Secondary_metabolites" title="Template talk:Secondary metabolites"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Secondary_metabolites" title="Special:EditPage/Template:Secondary metabolites"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Secondary_metabolites" style="font-size:114%;margin:0 4em"><a href="/wiki/Secondary_metabolite" title="Secondary metabolite">Secondary metabolites</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkaloid" title="Alkaloid">Alkaloids</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/Codeine" title="Codeine">Codeine</a></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li> <li><a href="/wiki/Atropine" title="Atropine">Atropine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Naturally_occurring_phenols" title="Naturally occurring phenols">Natural phenols</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 class="mw-selflink selflink">Polyphenols</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monoterpene" title="Monoterpene">Monoterpenoids</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/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl diphosphate</a></li> <li><a href="/wiki/Limonene" title="Limonene">Limonene</a></li> <li><a href="/wiki/Pinene" title="Pinene">Pinene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Terpenoid" title="Terpenoid">Diterpenoids</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/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl diphosphate</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Taxol</a></li> <li><a href="/wiki/Aphidicolin" title="Aphidicolin">Aphidicolin</a></li> <li><a href="/w/index.php?title=Pimaradiene&action=edit&redlink=1" class="new" title="Pimaradiene (page does not exist)">Pimaradiene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antibiotic" title="Antibiotic">Antibiotics</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/Penicillin" title="Penicillin">Penicillin</a></li> <li><a href="/wiki/Streptomycin" title="Streptomycin">Streptomycin</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Template:Enzyme_cofactors" title="Template:Enzyme cofactors">←Enzyme cofactors</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></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_phenolic_compounds" 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:Phenolic_compounds" title="Template:Phenolic compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenolic_compounds" title="Template talk:Phenolic compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenolic_compounds" title="Special:EditPage/Template:Phenolic compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_phenolic_compounds" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Phenolic_compound" class="mw-redirect" title="Phenolic compound">phenolic compounds</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Natural_monophenol" class="mw-redirect" title="Natural monophenol">Natural monophenols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzenediol" class="mw-redirect" title="Benzenediol">Benzenediols</a></li> <li><a href="/wiki/Benzenetriol" class="mw-redirect" title="Benzenetriol">Benzenetriols</a></li> <li><a href="/wiki/Apiole" title="Apiole">Apiole</a></li> <li><a href="/wiki/Carnosol" title="Carnosol">Carnosol</a></li> <li><a href="/wiki/Carvacrol" title="Carvacrol">Carvacrol</a></li> <li><a href="/wiki/Dillapiole" title="Dillapiole">Dillapiole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Polyphenols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Polyphenols" title="Template:Polyphenols"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Polyphenols" title="Template talk:Polyphenols"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Polyphenols" title="Special:EditPage/Template:Polyphenols"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_polyphenols" style="font-size:114%;margin:0 4em">Types of <a class="mw-selflink selflink">polyphenols</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a><br />(C6-C3-C6)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Flavonoids" title="Template:Flavonoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Flavonoids" title="Template talk:Flavonoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Flavonoids" title="Special:EditPage/Template:Flavonoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_flavonoids" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anthoxanthin" title="Anthoxanthin">Anthoxanthins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavone" title="Flavone">Flavones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a>, <a href="/wiki/Chrysin" title="Chrysin">Chrysin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonols" title="Flavonols">Flavonols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a>, <a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoflavones" class="mw-redirect" title="Isoflavones">Isoflavones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a>, <a href="/wiki/Genistein" title="Genistein">Genistein</a>, <a href="/wiki/Orobol" title="Orobol">Orobol</a> et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neoflavonoid" title="Neoflavonoid">Neoflavonoids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dalbergichromene" title="Dalbergichromene">Dalbergichromene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan" title="Flavan">Flavans</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Flavan</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Luteoliflavan&action=edit&redlink=1" class="new" title="Luteoliflavan (page does not exist)">Luteoliflavan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ols</a><br />(<a href="/wiki/Flavanol" class="mw-redirect" title="Flavanol">flavanols</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Catechin" title="Catechin">Catechin</a>, <a href="/wiki/Gallocatechol" title="Gallocatechol">Gallocatechol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan-4-ol" title="Flavan-4-ol">Flavan-4-ols</a><br />(<a href="/wiki/Flavanol" class="mw-redirect" title="Flavanol">flavanols</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apiforol" title="Apiforol">Apiforol</a>, <a href="/wiki/Luteoforol" title="Luteoforol">Luteoforol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Leucoanthocyanidin" title="Leucoanthocyanidin">Flavan-3,4-diols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Leucocyanidin" title="Leucocyanidin">Leucocyanidin</a>, <a href="/wiki/Leucodelphinidin" title="Leucodelphinidin">Leucodelphinidin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavanone" title="Flavanone">Flavanones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hesperidin" title="Hesperidin">Hesperidin</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Eriodictyol" title="Eriodictyol">Eriodictyol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavanonol" title="Flavanonol">Flavanonols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Taxifolin" title="Taxifolin">Taxifolin</a></li> <li><a href="/wiki/Aromadendrin" title="Aromadendrin">Aromadendrin</a>, et.c.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anthocyanidins" class="mw-redirect" title="Anthocyanidins">Anthocyanidins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/3-deoxyanthocyanidin" class="mw-redirect" title="3-deoxyanthocyanidin">3-deoxyanthocyanidins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyanidin" title="Cyanidin">Cyanidin</a>, <a href="/wiki/Delphinidin" title="Delphinidin">Delphinidin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=3-hydroxyanthocyanidin&action=edit&redlink=1" class="new" title="3-hydroxyanthocyanidin (page does not exist)">3-hydroxyanthocyanidin</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apigeninidin" title="Apigeninidin">Apigeninidin</a>, <a href="/wiki/Guibourtinidin" title="Guibourtinidin">Guibourtinidin</a>, et.c.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aurones" class="mw-redirect" title="Aurones">Aurones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aureusidin" title="Aureusidin">Aureusidin</a></li> <li><a href="/wiki/Leptosidin" title="Leptosidin">Leptosidin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chalcones" class="mw-redirect" title="Chalcones">Chalcones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chalcone" title="Chalcone">Chalcones</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butein" title="Butein">Butein</a>, <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">Isoliquiritigenin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydrochalcone" title="Dihydrochalcone">Dihydrochalcone</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phloretin" title="Phloretin">Phloretin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Miscellaneous</i></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/List_of_phytochemicals_in_food" title="List of phytochemicals in food">List of phytochemicals in food</a></li> <li><a href="/wiki/C-methylated_flavonoid" title="C-methylated flavonoid">C-methylated flavonoids</a></li> <li><a href="/wiki/O-methylated_flavonoid" title="O-methylated flavonoid">O-methylated flavonoids</a></li> <li><a href="/wiki/Furanoflavonoid" title="Furanoflavonoid">Furanoflavonoids</a></li> <li><a href="/wiki/Pyranoflavonoid" title="Pyranoflavonoid">Pyranoflavonoids</a></li> <li><a href="/wiki/Prenylflavonoid" title="Prenylflavonoid">Prenylflavonoids</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li> <li><a href="/wiki/Castavinol" title="Castavinol">Castavinols</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><a href="/wiki/Flavonoid_biosynthesis" title="Flavonoid biosynthesis">Flavonoid biosynthesis</a></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonolignan" title="Flavonolignan">Flavonolignans</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Silymarin" class="mw-redirect" title="Silymarin">Silymarin</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lignan" title="Lignan">Lignans</a><br />((C6-C3)<sub>2</sub>)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Matairesinol" title="Matairesinol">Matairesinol</a></li> <li><a href="/wiki/Secoisolariciresinol" title="Secoisolariciresinol">Secoisolariciresinol</a></li> <li><a href="/wiki/Pinoresinol" title="Pinoresinol">Pinoresinol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a><br />(C6-C2-C6)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/wiki/Pterostilbene" title="Pterostilbene">Pterostilbene</a></li> <li><a href="/wiki/Piceatannol" title="Piceatannol">Piceatannol</a></li> <li><a href="/wiki/Pinosylvin" title="Pinosylvin">Pinosylvin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Curcuminoid" title="Curcuminoid">Curcuminoids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tannin" title="Tannin">Tannins</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Tannin" title="Template:Tannin"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tannin" title="Template talk:Tannin"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tannin" title="Special:EditPage/Template:Tannin"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_natural_tannins" style="font-size:114%;margin:0 4em">Types of natural <a href="/wiki/Tannin" title="Tannin">tannins</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrolysable_tannin" title="Hydrolysable tannin">Hydrolysable tannins</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ellagitannin" title="Ellagitannin">Ellagitannins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Punicalagin" title="Punicalagin">Punicalagins</a></li> <li><a href="/wiki/Castalagin" title="Castalagin">Castalagins</a></li> <li><a href="/wiki/Vescalagin" class="mw-redirect" title="Vescalagin">Vescalagins</a></li> <li><a href="/wiki/Castalin" title="Castalin">Castalins</a></li> <li><a href="/wiki/Casuarictin" title="Casuarictin">Casuarictins</a></li> <li><a href="/wiki/Grandinin" title="Grandinin">Grandinins</a></li> <li><a href="/wiki/Punicalin" title="Punicalin">Punicalins</a></li> <li><a href="/wiki/Roburin_A" title="Roburin A">Roburin A</a></li> <li><a href="/wiki/Tellimagrandin_II" title="Tellimagrandin II">Tellimagrandin IIs</a></li> <li><a href="/wiki/Terflavin_B" title="Terflavin B">Terflavin B</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Gallotannin" title="Gallotannin">Gallotannins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Digalloyl_glucose" title="Digalloyl glucose">Digalloyl glucose</a></li> <li><a href="/wiki/1,3,6-Trigalloyl_glucose" title="1,3,6-Trigalloyl glucose">1,3,6-Trigalloyl glucose</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Condensed_tannin" title="Condensed tannin">Condensed tannins</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">Proanthocyanidins</a></li> <li><a href="/wiki/Polyflavonoid_tannin" class="mw-redirect" title="Polyflavonoid tannin">Polyflavonoid tannins</a></li> <li><a href="/wiki/Catechol-type_tannin" class="mw-redirect" title="Catechol-type tannin">Catechol-type tannins</a></li> <li><a href="/wiki/Pyrocatecollic_type_tannin" class="mw-redirect" title="Pyrocatecollic type tannin">Pyrocatecollic type tannins</a></li> <li><a href="/wiki/Flavolan" class="mw-redirect" title="Flavolan">Flavolans</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phlorotannin" title="Phlorotannin">Phlorotannins</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Eckol" title="Eckol">Eckol</a></li> <li><a href="/wiki/8,8%E2%80%B2-Bieckol" title="8,8′-Bieckol">8,8′-Bieckol</a></li> <li><a href="/wiki/6,6%27-Bieckol" title="6,6'-Bieckol">6,6'-Bieckol</a></li> <li><a href="/wiki/Dieckol" title="Dieckol">Dieckol</a></li> <li><a href="/wiki/Eckstolonol" title="Eckstolonol">Eckstolonol</a></li> <li><a href="/wiki/Diphlorethol" title="Diphlorethol">Diphlorethol</a></li> <li><a href="/wiki/Difucol" title="Difucol">Difucol</a></li> <li><a href="/wiki/Fucophlorethol_A" title="Fucophlorethol A">Fucophlorethol A</a></li> <li><a href="/wiki/Phlorofucofuroeckol_A" title="Phlorofucofuroeckol A">Phlorofucofuroeckol A</a></li> <li><a href="/wiki/Tetrafucol_A" title="Tetrafucol A">Tetrafucol A</a></li> <li><a href="/wiki/Trifucol" title="Trifucol">Trifucol</a></li> <li><a href="/wiki/Bifuhalol" title="Bifuhalol">Bifuhalol</a></li> <li><a href="/wiki/7-Phloroeckol" title="7-Phloroeckol">7-Phloroeckol</a></li> <li>Phlorofucofuroeckol B</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavono-ellagitannin" title="Flavono-ellagitannin">Flavono-ellagitannins</a><br />(complex tannins)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Epicutissimin_A" title="Epicutissimin A">Epicutissimin A</a></li> <li><a href="/wiki/Acutissimin_A" title="Acutissimin A">Acutissimin A</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Template:Tannin_source" title="Template:Tannin source">Tannin sources</a></li> <li><a href="/wiki/Pseudo_tannins" class="mw-redirect" title="Pseudo tannins">Pseudo tannins</a></li> <li><a href="/wiki/Synthetic_tannins" class="mw-redirect" title="Synthetic tannins">Synthetic tannins</a></li> <li>Tannin uses <ul><li><a href="/wiki/Enological_tannin" class="mw-redirect" title="Enological tannin">Enological</a></li> <li><a href="/wiki/Drilling_mud" class="mw-redirect" title="Drilling mud">Drilling</a></li> <li><a href="/wiki/Iron_gall_ink" title="Iron gall ink">Ink</a></li> <li><a href="/wiki/Tanning_(leather)" title="Tanning (leather)">Tanning</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diarylheptanoid" title="Diarylheptanoid">Diarylheptanoids</a> (C6-C7-C6)</li> <li><a href="/wiki/Anthraquinones" title="Anthraquinones">Anthraquinones</a></li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (C6-C3-C6)</li> <li><a href="/wiki/Kavalactone" title="Kavalactone">Kavalactones</a></li> <li><a href="/wiki/Naphthoquinone" title="Naphthoquinone">Naphthoquinones</a> (C6-C4)</li> <li><a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">Phenylpropanoids</a> (C6-C3)</li> <li><a href="/wiki/Xanthonoid" title="Xanthonoid">Xanthonoids</a> (C6-C1-C6)</li> <li><a href="/wiki/Coumarin" title="Coumarin">Coumarins</a> and <a href="/wiki/Isocoumarin" title="Isocoumarin">isocoumarins</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Misc</i>:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a class="mw-selflink selflink">Polyphenols</a></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromatic_acid" title="Aromatic acid">Aromatic acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Aromatic_acids" title="Template:Aromatic acids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Aromatic_acids" title="Template talk:Aromatic acids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Aromatic_acids" title="Special:EditPage/Template:Aromatic acids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Aromatic_acids" style="font-size:114%;margin:0 4em"><a href="/wiki/Aromatic_acid" title="Aromatic acid">Aromatic acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenolic_acid" title="Phenolic acid">Phenolic acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Monohydroxybenzoic_acids" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monohydroxybenzoic_acid" title="Monohydroxybenzoic acid">Monohydroxybenzoic acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Aglycones</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Hydroxybenzoic_acid" title="3-Hydroxybenzoic acid">3-Hydroxybenzoic acid</a></li> <li><a href="/wiki/4-Hydroxybenzoic_acid" title="4-Hydroxybenzoic acid">4-Hydroxybenzoic acid</a></li> <li><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycosides</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/P-Hydroxybenzoic_acid_glucoside" class="mw-redirect" title="P-Hydroxybenzoic acid glucoside">p-Hydroxybenzoic acid glucoside</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydroxybenzoic_acid" title="Dihydroxybenzoic acid">Dihydroxybenzoic acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,3-Dihydroxybenzoic_acid" title="2,3-Dihydroxybenzoic acid">2,3-Dihydroxybenzoic acid</a> (Hypogallic acid)</li> <li><a href="/wiki/2,4-Dihydroxybenzoic_acid" title="2,4-Dihydroxybenzoic acid">2,4-Dihydroxybenzoic acid</a></li> <li><a href="/wiki/2,6-Dihydroxybenzoic_acid" title="2,6-Dihydroxybenzoic acid">2,6-Dihydroxybenzoic acid</a></li> <li><a href="/wiki/3,5-Dihydroxybenzoic_acid" title="3,5-Dihydroxybenzoic acid">3,5-Dihydroxybenzoic acid</a></li> <li><a href="/wiki/Ethyl_protocatechuate" title="Ethyl protocatechuate">Ethyl protocatechuate</a></li> <li><a href="/wiki/Gentisic_acid" title="Gentisic acid">Gentisic acid</a></li> <li><a href="/wiki/Homogentisic_acid" title="Homogentisic acid">Homogentisic acid</a></li> <li><a href="/wiki/Orsellinic_acid" title="Orsellinic acid">Orsellinic acid</a></li> <li><a href="/wiki/Protocatechuic_acid" title="Protocatechuic acid">Protocatechuic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trihydroxybenzoic_acid" title="Trihydroxybenzoic acid">Trihydroxybenzoic acids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bergenin" title="Bergenin">Bergenin</a></li> <li><a href="/wiki/Chebulic_acid" title="Chebulic acid">Chebulic acid</a></li> <li><a href="/wiki/Ethyl_gallate" title="Ethyl gallate">Ethyl gallate</a></li> <li><a href="/wiki/Eudesmic_acid" title="Eudesmic acid">Eudesmic acid</a></li> <li><a href="/wiki/Gallic_acid" title="Gallic acid">Gallic acid</a></li> <li><a href="/wiki/Tannic_acid" title="Tannic acid">Tannic acid</a></li> <li><a href="/wiki/Norbergenin" title="Norbergenin">Norbergenin</a></li> <li><a href="/wiki/Phloroglucinol_carboxylic_acid" title="Phloroglucinol carboxylic acid">Phloroglucinol carboxylic acid</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li> <li><a href="/wiki/Theogallin" title="Theogallin">Theogallin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other phenolic acids</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Vanillin" title="Vanillin">Vanillin</a></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydroxycinnamic_acid" title="Hydroxycinnamic acid">Hydroxycinnamic acids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Cyano-4-hydroxycinnamic_acid" class="mw-redirect" title="Alpha-Cyano-4-hydroxycinnamic acid">α-Cyano-4-hydroxycinnamic acid</a></li> <li><a href="/wiki/Caffeic_acid" title="Caffeic acid">Caffeic acid</a></li> <li><a href="/wiki/Chicoric_acid" title="Chicoric acid">Chicoric acid</a></li> <li><a href="/wiki/Cinnamic_acid" title="Cinnamic acid">Cinnamic acid</a></li> <li><a href="/wiki/Chlorogenic_acid" title="Chlorogenic acid">Chlorogenic acid</a></li> <li><a href="/wiki/Diferulic_acids" title="Diferulic acids">Diferulic acids</a></li> <li><a href="/wiki/Coumaric_acid" title="Coumaric acid">Coumaric acid</a></li> <li><a href="/wiki/Coumarin" title="Coumarin">Coumarin</a></li> <li><a href="/wiki/Ferulic_acid" title="Ferulic acid">Ferulic acid</a></li> <li><a href="/wiki/Sinapinic_acid" title="Sinapinic acid">Sinapinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">Aromatic amino acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a></li> <li><a href="/wiki/Histidine" title="Histidine">histidine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a></li> <li><a href="/wiki/Thyroxine" class="mw-redirect" title="Thyroxine">thyroxine</a></li> <li><a href="/wiki/5-hydroxytryptophan" class="mw-redirect" title="5-hydroxytryptophan">5-hydroxytryptophan</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethanoid" title="Phenylethanoid">Phenylethanoids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tyrosol" title="Tyrosol">Tyrosol</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Oleocanthal" title="Oleocanthal">Oleocanthal</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a></li> <li><a href="/wiki/Gingerol" title="Gingerol">Gingerol</a></li> <li><a href="/wiki/Alkylresorcinol" title="Alkylresorcinol">Alkylresorcinols</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Misc</i>:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phenol" title="Phenol">Phenolic compounds</a></li> <li><a href="/wiki/Phlorotannin" 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