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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" > Toggle the table of contents </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">Oxidative stress</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 32 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-32" aria-hidden="true" > 32 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Oksidatiewe_stres" title="Oksidatiewe stres – Afrikaans" lang="af" hreflang="af" data-title="Oksidatiewe stres" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target">Afrikaans</a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D8%AC%D9%87%D8%A7%D8%AF_%D8%AA%D8%A3%D9%83%D8%B3%D8%AF%D9%8A" title="إجهاد تأكسدي – Arabic" lang="ar" hreflang="ar" data-title="إجهاد تأكسدي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Oksidativni_stres" title="Oksidativni stres – Bosnian" lang="bs" hreflang="bs" data-title="Oksidativni stres" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Estr%C3%A8s_oxidatiu" title="Estrès oxidatiu – Catalan" lang="ca" hreflang="ca" data-title="Estrès oxidatiu" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Oxida%C4%8Dn%C3%AD_stres" title="Oxidační stres – Czech" lang="cs" hreflang="cs" data-title="Oxidační stres" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Oxidativer_Stress" title="Oxidativer Stress – German" lang="de" hreflang="de" data-title="Oxidativer Stress" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Oks%C3%BCdatiivne_stress" title="Oksüdatiivne stress – Estonian" lang="et" hreflang="et" data-title="Oksüdatiivne stress" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9F%CE%BE%CE%B5%CE%B9%CE%B4%CF%89%CF%84%CE%B9%CE%BA%CF%8C_%CF%83%CF%84%CF%81%CE%B5%CF%82" title="Οξειδωτικό στρες – Greek" lang="el" hreflang="el" data-title="Οξειδωτικό στρες" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Estr%C3%A9s_oxidativo" title="Estrés oxidativo – Spanish" lang="es" hreflang="es" data-title="Estrés oxidativo" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-ext mw-list-item"><a href="https://ext.wikipedia.org/wiki/Estr%C3%A9s_oxidativu" title="Estrés oxidativu – Extremaduran" lang="ext" hreflang="ext" data-title="Estrés oxidativu" data-language-autonym="Estremeñu" data-language-local-name="Extremaduran" class="interlanguage-link-target">Estremeñu</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D8%B1%D8%B3_%D8%A7%DA%A9%D8%B3%DB%8C%D8%AF%D8%A7%D8%AA%DB%8C%D9%88" title="استرس اکسیداتیو – Persian" lang="fa" hreflang="fa" data-title="استرس اکسیداتیو" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Stress_oxydant" title="Stress oxydant – French" lang="fr" hreflang="fr" data-title="Stress oxydant" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Estr%C3%A9s_oxidativo" title="Estrés oxidativo – Galician" lang="gl" hreflang="gl" data-title="Estrés oxidativo" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%82%B0%ED%99%94_%EC%8A%A4%ED%8A%B8%EB%A0%88%EC%8A%A4" title="산화 스트레스 – Korean" lang="ko" hreflang="ko" data-title="산화 스트레스" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Stres_oksidatif" title="Stres oksidatif – Indonesian" lang="id" hreflang="id" data-title="Stres oksidatif" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Stress_ossidativo" title="Stress ossidativo – Italian" lang="it" hreflang="it" data-title="Stress ossidativo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Tekanan_oksidatif" title="Tekanan oksidatif – Malay" lang="ms" hreflang="ms" data-title="Tekanan oksidatif" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Oxidatieve_stress" title="Oxidatieve stress – Dutch" lang="nl" hreflang="nl" data-title="Oxidatieve stress" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E9%85%B8%E5%8C%96%E3%82%B9%E3%83%88%E3%83%AC%E3%82%B9" title="酸化ストレス – Japanese" lang="ja" hreflang="ja" data-title="酸化ストレス" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Stres_oksydacyjny" title="Stres oksydacyjny – Polish" lang="pl" hreflang="pl" data-title="Stres oksydacyjny" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Stress_oxidativo" title="Stress oxidativo – Portuguese" lang="pt" hreflang="pt" data-title="Stress oxidativo" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Stres_oxidativ" title="Stres oxidativ – Romanian" lang="ro" hreflang="ro" data-title="Stres oxidativ" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9E%D0%BA%D0%B8%D1%81%D0%BB%D0%B8%D1%82%D0%B5%D0%BB%D1%8C%D0%BD%D1%8B%D0%B9_%D1%81%D1%82%D1%80%D0%B5%D1%81%D1%81" title="Окислительный стресс – Russian" lang="ru" hreflang="ru" data-title="Окислительный стресс" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sd mw-list-item"><a href="https://sd.wikipedia.org/wiki/%D8%A2%DA%AA%D8%B3%D9%8A%DA%8A%D9%8A%D9%86%D9%BD_%D8%A7%D9%90%D8%B3%D9%BD%D8%B1%D9%8A%D8%B3" title="آڪسيڊينٽ اِسٽريس – Sindhi" lang="sd" hreflang="sd" data-title="آڪسيڊينٽ اِسٽريس" data-language-autonym="سنڌي" data-language-local-name="Sindhi" class="interlanguage-link-target">سنڌي</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Oksidativni_stres" title="Oksidativni stres – Slovenian" lang="sl" hreflang="sl" data-title="Oksidativni stres" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9E%D0%BA%D1%81%D0%B8%D0%B4%D0%B0%D1%82%D0%B8%D0%B2%D0%BD%D0%B8_%D1%81%D1%82%D1%80%D0%B5%D1%81" title="Оксидативни стрес – Serbian" lang="sr" hreflang="sr" data-title="Оксидативни стрес" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Oksidatiivinen_stressi" title="Oksidatiivinen stressi – Finnish" lang="fi" hreflang="fi" data-title="Oksidatiivinen stressi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Oxidativ_stress" title="Oxidativ stress – Swedish" lang="sv" hreflang="sv" data-title="Oxidativ stress" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Oksidatif_stres" title="Oksidatif stres – Turkish" lang="tr" hreflang="tr" data-title="Oksidatif stres" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9E%D0%BA%D0%B8%D1%81%D0%BB%D1%8E%D0%B2%D0%B0%D0%BB%D1%8C%D0%BD%D0%B8%D0%B9_%D1%81%D1%82%D1%80%D0%B5%D1%81" title="Окислювальний стрес – Ukrainian" lang="uk" hreflang="uk" data-title="Окислювальний стрес" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Free radical toxicity</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Free_Radical_Toxicity.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Free_Radical_Toxicity.svg/400px-Free_Radical_Toxicity.svg.png" decoding="async" width="400" height="433" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Free_Radical_Toxicity.svg/600px-Free_Radical_Toxicity.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Free_Radical_Toxicity.svg/800px-Free_Radical_Toxicity.svg.png 2x" data-file-width="603" data-file-height="652" /></a><figcaption> Oxidative stress mechanisms in tissue injury. Free radical toxicity induced by <a href="/wiki/Xenobiotics" class="mw-redirect" title="Xenobiotics">xenobiotics</a> and the subsequent detoxification by cellular enzymes (termination).</figcaption></figure> Oxidative stress reflects an imbalance between the systemic manifestation of <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> and a biological system's ability to readily <a href="/wiki/Detoxification" title="Detoxification">detoxify</a> the reactive intermediates or to repair the resulting damage.<a href="#cite_note-Springer_New_York_2010_pp._4278–4278-1">[1]</a> Disturbances in the normal <a href="/wiki/Redox" title="Redox">redox</a> state of cells can cause toxic effects through the production of <a href="/wiki/Peroxide" title="Peroxide">peroxides</a> and <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radicals</a> that damage all components of the cell, including <a href="/wiki/Protein" title="Protein">proteins</a>, <a href="/wiki/Lipid" title="Lipid">lipids</a>, and <a href="/wiki/DNA" title="DNA">DNA</a>. Oxidative stress from <a href="/wiki/Cellular_respiration" title="Cellular respiration">oxidative metabolism</a> causes base damage, as well as <a href="/wiki/DNA_damage_(naturally_occurring)" title="DNA damage (naturally occurring)">strand breaks in DNA</a>. Base damage is mostly indirect and caused by the reactive oxygen species generated, e.g., O− 2 (<a href="/wiki/Superoxide" title="Superoxide">superoxide</a> radical), OH (<a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> radical) and <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style>H2O2 (<a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a>).<a href="#cite_note-2">[2]</a> Further, some reactive oxidative species act as cellular messengers in redox signaling. Thus, oxidative stress can cause disruptions in normal mechanisms of <a href="/wiki/Cellular_signaling" class="mw-redirect" title="Cellular signaling">cellular signaling</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] In humans, oxidative stress is thought to be involved in the development of <a href="/wiki/Attention_deficit_hyperactivity_disorder" title="Attention deficit hyperactivity disorder">attention deficit hyperactivity disorder</a>,<a href="#cite_note-pmid24232168-3">[3]</a> <a href="/wiki/Cancer" title="Cancer">cancer</a>,<a href="#cite_note-cancer-4">[4]</a> <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>,<a href="#cite_note-pmid23585717-5">[5]</a> <a href="/wiki/Lafora_disease" title="Lafora disease">Lafora disease</a>,<a href="#cite_note-pmid24838580-6">[6]</a> <a href="/wiki/Alzheimer%27s_syndrome" class="mw-redirect" title="Alzheimer's syndrome">Alzheimer's disease</a>,<a href="#cite_note-pmid16978905-7">[7]</a> <a href="/wiki/Atherosclerosis" title="Atherosclerosis">atherosclerosis</a>,<a href="#cite_note-pmid18072094-8">[8]</a> <a href="/wiki/Heart_failure" title="Heart failure">heart failure</a>,<a href="#cite_note-pmid7494558-9">[9]</a> <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a>,<a href="#cite_note-pmid22145601-10">[10]</a><a href="#cite_note-bipolar-11">[11]</a> <a href="/wiki/Fragile_X_syndrome" title="Fragile X syndrome">fragile X syndrome</a>,<a href="#cite_note-pmid18843266-12">[12]</a> <a href="/wiki/Sickle-cell_disease" class="mw-redirect" title="Sickle-cell disease">sickle-cell disease</a>,<a href="#cite_note-pmid16371026-13">[13]</a> <a href="/wiki/Lichen_planus" title="Lichen planus">lichen planus</a>,<a href="#cite_note-pmid20372767-14">[14]</a> <a href="/wiki/Vitiligo" title="Vitiligo">vitiligo</a>,<a href="#cite_note-pmid18454264-15">[15]</a> <a href="/wiki/Autism" title="Autism">autism</a>,<a href="#cite_note-James-2004-16">[16]</a> <a href="/wiki/Infection" title="Infection">infection</a>, <a href="/wiki/Chronic_fatigue_syndrome" class="mw-redirect" title="Chronic fatigue syndrome">chronic fatigue syndrome</a>,<a href="#cite_note-pmid16085177-17">[17]</a> and <a href="/wiki/Major_depressive_disorder" title="Major depressive disorder">depression</a>;<a href="#cite_note-pmid26579881-18">[18]</a> however, reactive oxygen species can be beneficial, as they are used by the <a href="/wiki/Immune_system" title="Immune system">immune system</a> as a way to attack and kill <a href="/wiki/Pathogen" title="Pathogen">pathogens</a>.<a href="#cite_note-SegalRev-19">[19]</a> Short-term oxidative stress may also be important in prevention of <a href="/wiki/Aging" class="mw-redirect" title="Aging">aging</a> by induction of a process named <a href="/wiki/Hormesis" title="Hormesis">mitohormesis</a>,<a href="#cite_note-pmid18316025-20">[20]</a> and is required to initiate stress response processes in plants.<a href="#cite_note-21">[21]</a> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chemical_and_biological_effects">Chemical and biological effects</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=1" title="Edit section: Chemical and biological effects">edit</a>]</div> Chemically, oxidative stress is associated with increased production of oxidizing species or a significant decrease in the effectiveness of <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> defenses, such as <a href="/wiki/Glutathione" title="Glutathione">glutathione</a>.<a href="#cite_note-pmid11368918-22">[22]</a> The effects of oxidative stress depend upon the size of these changes, with a cell being able to overcome small perturbations and regain its original state. However, more severe oxidative stress can cause cell death, and even moderate oxidation can trigger <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>, while more intense stresses may cause <a href="/wiki/Necrosis" title="Necrosis">necrosis</a>.<a href="#cite_note-pmid2009322-23">[23]</a> Production of reactive oxygen species is a particularly destructive aspect of oxidative stress. Such species include <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radicals</a> and <a href="/wiki/Peroxide" title="Peroxide">peroxides</a>. Some of the less reactive of these species (such as <a href="/wiki/Superoxide" title="Superoxide">superoxide</a>) can be converted by <a href="/wiki/Redox" title="Redox">oxidoreduction reactions</a> with <a href="/wiki/Transition_metal" title="Transition metal">transition metals</a> or other redox cycling compounds (including <a href="/wiki/Quinone" title="Quinone">quinones</a>) into more aggressive radical species that can cause extensive cellular damage.<a href="#cite_note-pmid15892631-24">[24]</a> Most long-term effects are caused by damage to DNA.<a href="#cite_note-pmid15112233-25">[25]</a> DNA damage induced by <a href="/wiki/Ionizing_radiation" title="Ionizing radiation">ionizing radiation</a> is similar to oxidative stress, and these lesions have been implicated in <a href="/wiki/Aging" class="mw-redirect" title="Aging">aging</a> and cancer. Biological effects of single-base damage by radiation or oxidation, such as <a href="/wiki/8-Oxoguanine" title="8-Oxoguanine">8-oxoguanine</a> and <a href="/wiki/Thymine_glycol" title="Thymine glycol">thymine glycol</a>, have been extensively studied. Recently the focus has shifted to some of the more complex lesions. Tandem DNA lesions are formed at substantial frequency by ionizing radiation and metal-<a href="/wiki/Catalyzed" class="mw-redirect" title="Catalyzed">catalyzed</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">H2O2 reactions. Under <a href="/wiki/Hypoxia_(medical)" class="mw-redirect" title="Hypoxia (medical)">anoxic conditions</a>, the predominant double-base lesion is a species in which C8 of guanine is linked to the 5-methyl group of an adjacent 3'-thymine (G[8,5- Me]T).<a href="#cite_note-pmid18616294-26">[26]</a> Most of these <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>-derived species are produced by normal <a href="/wiki/Cellular_respiration" title="Cellular respiration">aerobic metabolism</a>. Normal cellular defense mechanisms destroy most of these. Repair of oxidative damages to DNA is frequent and ongoing, largely keeping up with newly induced damages. In rat urine, about 74,000 oxidative DNA adducts per cell are excreted daily.<a href="#cite_note-Helbock-27">[27]</a> There is also a steady state level of oxidative damages in the DNA of a cell. There are about 24,000 oxidative DNA adducts per cell in young rats and 66,000 adducts per cell in old rats.<a href="#cite_note-Helbock-27">[27]</a> Likewise, any damage to cells is constantly repaired. However, under the severe levels of oxidative stress that cause necrosis, the damage causes <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> depletion, preventing controlled apoptotic death and causing the cell to simply fall apart.<a href="#cite_note-pmid9801070-28">[28]</a><a href="#cite_note-pmid10391922-29">[29]</a> <a href="/wiki/Polyunsaturated_fatty_acids" class="mw-redirect" title="Polyunsaturated fatty acids">Polyunsaturated fatty acids</a>, particularly <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a> and <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a>, are primary targets for free radical and singlet oxygen oxidations. For example, in tissues and cells, the free radical oxidation of linoleic acid produces <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> mixtures of 13-hydroxy-9Z,11E-octadecadienoic acid, 13-hydroxy-9E,11E-octadecadienoic acid, 9-hydroxy-10E,12-E-octadecadienoic acid (9-EE-HODE), and 11-hydroxy-9Z,12-Z-octadecadienoic acid as well as <a href="/wiki/4-Hydroxynonenal" title="4-Hydroxynonenal">4-Hydroxynonenal</a> while singlet oxygen attacks linoleic acid to produce (presumed but not yet proven to be racemic mixtures of) 13-hydroxy-9Z,11E-octadecadienoic acid, 9-hydroxy-10E,12-Z-octadecadienoic acid, 10-hydroxy-8E,12Z-octadecadienoic acid, and 12-hydroxy-9Z-13-E-octadecadienoic (see <a href="/wiki/13-Hydroxyoctadecadienoic_acid" title="13-Hydroxyoctadecadienoic acid">13-Hydroxyoctadecadienoic acid</a> and <a href="/wiki/9-Hydroxyoctadecadienoic_acid" title="9-Hydroxyoctadecadienoic acid">9-Hydroxyoctadecadienoic acid</a>).<a href="#cite_note-pmid25499849-30">[30]</a><a href="#cite_note-riahi-31">[31]</a><a href="#cite_note-ReferenceA-32">[32]</a> Similar attacks on arachidonic acid produce a far larger set of products including various <a href="/wiki/Isoprostanes" class="mw-redirect" title="Isoprostanes">isoprostanes</a>, hydroperoxy- and hydroxy- eicosatetraenoates, and 4-hydroxyalkenals.<a href="#cite_note-riahi-31">[31]</a><a href="#cite_note-pmid24856297-33">[33]</a> While many of these products are used as markers of oxidative stress, the products derived from linoleic acid appear far more predominant than arachidonic acid products and therefore easier to identify and quantify in, for example, atheromatous plaques.<a href="#cite_note-pmid12618275-34">[34]</a> Certain linoleic acid products have also been proposed to be markers for specific types of oxidative stress. For example, the presence of racemic 9-HODE and 9-EE-HODE mixtures reflects free radical oxidation of linoleic acid whereas the presence of racemic 10-hydroxy-8E,12Z-octadecadienoic acid and 12-hydroxy-9Z-13-E-octadecadienoic acid reflects singlet oxygen attack on linoleic acid.<a href="#cite_note-ReferenceA-32">[32]</a><a href="#cite_note-pmid25499849-30">[30]</a> In addition to serving as markers, the linoleic and arachidonic acid products can contribute to tissue and/or DNA damage but also act as signals to stimulate pathways which function to combat oxidative stress.<a href="#cite_note-riahi-31">[31]</a><a href="#cite_note-pmid21424583-35">[35]</a><a href="#cite_note-36">[36]</a><a href="#cite_note-37">[37]</a><a href="#cite_note-pmid22009064-38">[38]</a> <table class="wikitable"> <tbody><tr> <th>Oxidant</th> <th>Description </th></tr> <tr> <td>•O− 2, <a href="/wiki/Superoxide" title="Superoxide">superoxide</a> anion </td> <td>One-electron reduction state of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">O2, formed in many autoxidation reactions and by the <a href="/wiki/Electron_transport_chain" title="Electron transport chain">electron transport chain</a>. Rather unreactive but can release Fe2+ from iron-sulfur proteins and <a href="/wiki/Ferritin" title="Ferritin">ferritin</a>. Undergoes dismutation to form <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">H2O2 spontaneously or by enzymatic catalysis and is a precursor for metal-catalyzed •OH formation. </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">H2O2, <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> </td> <td>Two-electron reduction state, formed by dismutation of •O− 2 or by direct reduction of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">O2. Lipid-soluble and thus able to diffuse across membranes. </td></tr> <tr> <td>•OH, <a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">hydroxyl radical</a> </td> <td>Three-electron reduction state, formed by <a href="/wiki/Fenton%27s_reagent" title="Fenton's reagent">Fenton reaction</a> and decomposition of <a href="/wiki/Peroxynitrite" title="Peroxynitrite">peroxynitrite</a>. Extremely reactive, will attack most cellular components </td></tr> <tr> <td>ROOH, <a href="/wiki/Hydroperoxide" title="Hydroperoxide">organic hydroperoxide</a> </td> <td>Formed by radical reactions with cellular components such as <a href="/wiki/Lipid" title="Lipid">lipids</a> and <a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">nucleobases</a>. </td></tr> <tr> <td>RO•, alkoxy and ROO•, peroxy radicals </td> <td>Oxygen centred organic radicals. Lipid forms participate in <a href="/wiki/Lipid_peroxidation" title="Lipid peroxidation">lipid peroxidation</a> reactions. Produced in the presence of oxygen by radical addition to double bonds or hydrogen abstraction. </td></tr> <tr> <td>HOCl, <a href="/wiki/Hypochlorous_acid" title="Hypochlorous acid">hypochlorous acid</a> </td> <td>Formed from <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">H2O2 by <a href="/wiki/Myeloperoxidase" title="Myeloperoxidase">myeloperoxidase</a>. Lipid-soluble and highly reactive. Will readily oxidize protein constituents, including <a href="/wiki/Thiol_group" class="mw-redirect" title="Thiol group">thiol groups</a>, <a href="/wiki/Amino_group" class="mw-redirect" title="Amino group">amino groups</a> and <a href="/wiki/Methionine" title="Methionine">methionine</a>. </td></tr> <tr> <td>ONOO-, <a href="/wiki/Peroxynitrite" title="Peroxynitrite">peroxynitrite</a> </td> <td>Formed in a rapid reaction between •O− 2 and NO•. Lipid-soluble and similar in reactivity to hypochlorous acid. Protonation forms peroxynitrous acid, which can undergo homolytic cleavage to form hydroxyl radical and <a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">nitrogen dioxide</a>. </td></tr></tbody></table> Table adapted from.<a href="#cite_note-39">[39]</a><a href="#cite_note-40">[40]</a><a href="#cite_note-pmid9189713-41">[41]</a> <div class="mw-heading mw-heading2"><h2 id="Production_and_consumption_of_oxidants">Production and consumption of oxidants</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=2" title="Edit section: Production and consumption of oxidants">edit</a>]</div> One source of reactive oxygen under normal conditions in humans is the leakage of activated oxygen from <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> during <a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">oxidative phosphorylation</a>. <a href="/wiki/E._coli" class="mw-redirect" title="E. coli">E. coli</a> mutants that lack an active electron transport chain produce as much <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> as wild-type cells, indicating that other enzymes contribute the bulk of oxidants in these organisms.<a href="#cite_note-42">[42]</a> One possibility is that multiple redox-active <a href="/wiki/Flavoprotein" title="Flavoprotein">flavoproteins</a> all contribute a small portion to the overall production of oxidants under normal conditions.<a href="#cite_note-43">[43]</a><a href="#cite_note-44">[44]</a> Other enzymes capable of producing superoxide are <a href="/wiki/Xanthine_oxidase" title="Xanthine oxidase">xanthine oxidase</a>, NADPH oxidases and <a href="/wiki/Cytochrome_P450_oxidase" class="mw-redirect" title="Cytochrome P450 oxidase">cytochromes P450</a>. Hydrogen peroxide is produced by a wide variety of enzymes including several oxidases. Reactive oxygen species play important roles in cell signalling, a process termed <a href="/wiki/Redox_signaling" class="mw-redirect" title="Redox signaling">redox signaling</a>. Thus, to maintain proper cellular <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a>, a balance must be struck between reactive oxygen production and consumption.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] The best studied cellular antioxidants are the enzymes <a href="/wiki/Superoxide_dismutase" title="Superoxide dismutase">superoxide dismutase</a> (SOD), <a href="/wiki/Catalase" title="Catalase">catalase</a>, and <a href="/wiki/Glutathione_peroxidase" title="Glutathione peroxidase">glutathione peroxidase</a>. Less well studied (but probably just as important) enzymatic antioxidants are the peroxiredoxins and the recently discovered <a href="/wiki/Sulfiredoxin" title="Sulfiredoxin">sulfiredoxin</a>. Other enzymes that have antioxidant properties (though this is not their primary role) include paraoxonase, glutathione-S transferases, and aldehyde dehydrogenases.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] The amino acid methionine is prone to oxidation, but oxidized methionine can be reversible. Oxidation of methionine is shown to inhibit the phosphorylation of adjacent Ser/Thr/Tyr sites in proteins.<a href="#cite_note-pmid19527223-45">[45]</a> This gives a plausible mechanism for cells to couple oxidative stress signals with cellular mainstream signaling such as phosphorylation. <div class="mw-heading mw-heading2"><h2 id="Diseases">Diseases</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=3" title="Edit section: Diseases">edit</a>]</div> Oxidative stress is suspected to be important in <a href="/wiki/Neurodegenerative_disease" title="Neurodegenerative disease">neurodegenerative diseases</a> including <a href="/wiki/Motor_neuron_disease" class="mw-redirect" title="Motor neuron disease">Lou Gehrig's disease</a> (aka MND or ALS), <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>, <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a>, <a href="/wiki/Huntington%27s_disease" title="Huntington's disease">Huntington's disease</a>, <a href="/wiki/Major_depressive_disorder" title="Major depressive disorder">depression</a>, <a href="/wiki/Multiple_sclerosis" title="Multiple sclerosis">multiple sclerosis</a> and <a href="/wiki/Multiple_system_atrophy" title="Multiple system atrophy">multiple system atrophy</a>.<a href="#cite_note-pmid21653539-46">[46]</a><a href="#cite_note-pmid21487518-47">[47]</a> It is also indicated in Neurodevelopmental conditions such as <a href="/wiki/Autism" title="Autism">Autism Spectrum Disorder</a>.<a href="#cite_note-Hollis2017-48">[48]</a> Indirect evidence via monitoring biomarkers such as reactive oxygen species, and <a href="/wiki/Reactive_nitrogen_species" title="Reactive nitrogen species">reactive nitrogen species</a> production indicates oxidative damage may be involved in the pathogenesis of these diseases,<a href="#cite_note-pmid16825950-49">[49]</a><a href="#cite_note-pmid22131939-50">[50]</a> while cumulative oxidative stress with disrupted mitochondrial respiration and mitochondrial damage are related to Alzheimer's disease, Parkinson's disease, and other neurodegenerative diseases.<a href="#cite_note-pmid22212484-51">[51]</a> Oxidative stress is thought to be linked to certain <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a>, since oxidation of <a href="/wiki/LDL" class="mw-redirect" title="LDL">LDL</a> in the vascular <a href="/wiki/Endothelium" title="Endothelium">endothelium</a> is a precursor to <a href="/wiki/Atheromatous_plaque" class="mw-redirect" title="Atheromatous plaque">plaque</a> formation. Oxidative stress also plays a role in the <a href="/wiki/Ischemic_cascade" title="Ischemic cascade">ischemic cascade</a> due to oxygen <a href="/wiki/Reperfusion_injury" title="Reperfusion injury">reperfusion injury</a> following <a href="/wiki/Hypoxia_(medical)" class="mw-redirect" title="Hypoxia (medical)">hypoxia</a>. This cascade includes both <a href="/wiki/Strokes" class="mw-redirect" title="Strokes">strokes</a> and <a href="/wiki/Heart_attacks" class="mw-redirect" title="Heart attacks">heart attacks</a>. Oxidative stress has also been implicated in <a href="/wiki/Chronic_fatigue_syndrome" class="mw-redirect" title="Chronic fatigue syndrome">chronic fatigue syndrome</a> (ME/CFS).<a href="#cite_note-52">[52]</a> Oxidative stress also contributes to tissue injury following irradiation and <a href="/wiki/Hyperoxia" title="Hyperoxia">hyperoxia</a>, as well as in diabetes. In hematological cancers, such as leukemia, the impact of oxidative stress can be bilateral. Reactive oxygen species can disrupt the function of immune cells, promoting <a href="/wiki/Immune_evasion" class="mw-redirect" title="Immune evasion">immune evasion</a> of leukemic cells. On the other hand, high levels of oxidative stress can also be selectively toxic to cancer cells.<a href="#cite_note-53">[53]</a><a href="#cite_note-54">[54]</a> Oxidative stress is likely to be involved in age-related development of cancer. The reactive species produced in oxidative stress can cause direct damage to the DNA and are therefore <a href="/wiki/Mutagenic" class="mw-redirect" title="Mutagenic">mutagenic</a>, and it may also suppress <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a> and promote proliferation, invasiveness and <a href="/wiki/Metastasis" title="Metastasis">metastasis</a>.<a href="#cite_note-cancer-4">[4]</a> Infection by <a href="/wiki/Helicobacter_pylori" title="Helicobacter pylori">Helicobacter pylori</a> which increases the production of reactive oxygen and nitrogen species in human stomach is also thought to be important in the development of <a href="/wiki/Gastric_cancer" class="mw-redirect" title="Gastric cancer">gastric cancer</a>.<a href="#cite_note-55">[55]</a> Oxidative stress can cause DNA damage in neurons.<a href="#cite_note-Welty2022-56">[56]</a> In neuronal <a href="/wiki/Progenitor_cell" title="Progenitor cell">progenitor cells</a>, <a href="/wiki/DNA_damage_(naturally_occurring)" title="DNA damage (naturally occurring)">DNA damage</a> is associated with increased secretion of amyloid beta proteins Aβ40 and Aβ42.<a href="#cite_note-Welty2022-56">[56]</a> This association supports the existence of a causal relationship between oxidative DNA damage and Aβ accumulation and suggests that oxidative DNA damage may contribute to <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a> (AD) pathology.<a href="#cite_note-Welty2022-56">[56]</a> AD is associated with an accumulation of DNA damage (double-strand breaks) in vulnerable neuronal and glial cell populations from early stages onward,<a href="#cite_note-57">[57]</a> and DNA double-strand breaks are increased in the <a href="/wiki/Hippocampus" title="Hippocampus">hippocampus</a> of AD brains compared to non-AD control brains.<a href="#cite_note-58">[58]</a> <div class="mw-heading mw-heading2"><h2 id="Antioxidants_as_supplements">Antioxidants as supplements</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=4" title="Edit section: Antioxidants as supplements">edit</a>]</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">Further information: <a href="/wiki/Antioxidant" title="Antioxidant">Antioxidant</a></div> The use of antioxidants to prevent some diseases is controversial.<a href="#cite_note-pmid8624173-59">[59]</a> In a high-risk group like smokers, high doses of <a href="/wiki/Carotene" title="Carotene">beta carotene</a> increased the rate of lung cancer since high doses of beta-carotene in conjunction of high <a href="/wiki/Oxygen_tension" class="mw-redirect" title="Oxygen tension">oxygen tension</a> due to smoking results in a <a href="/wiki/Pro-oxidant" title="Pro-oxidant">pro-oxidant</a> effect and an antioxidant effect when oxygen tension is not high.<a href="#cite_note-pmid16472151-60">[60]</a><a href="#cite_note-pmid11259865-61">[61]</a> In less high-risk groups, the use of <a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a> appears to reduce the risk of <a href="/wiki/Heart_disease" class="mw-redirect" title="Heart disease">heart disease</a>.<a href="#cite_note-pmid10656300-62">[62]</a> However, while consumption of food rich in vitamin E may reduce the risk of coronary heart disease in middle-aged to older men and women, using vitamin E supplements also appear to result in an increase in total mortality, heart failure, and <a href="/wiki/Hemorrhagic_stroke" class="mw-redirect" title="Hemorrhagic stroke">hemorrhagic stroke</a>. The American Heart Association therefore recommends the consumption of food rich in antioxidant vitamins and other nutrients, but does not recommend the use of vitamin E supplements to prevent cardiovascular disease.<a href="#cite_note-pmid19451807-63">[63]</a> In other diseases, such as <a href="/wiki/Alzheimer%27s" class="mw-redirect" title="Alzheimer's">Alzheimer's</a>, the evidence on vitamin E supplementation is also mixed.<a href="#cite_note-pmid16227450-64">[64]</a><a href="#cite_note-pmid15753151-65">[65]</a> Since dietary sources contain a wider range of carotenoids and vitamin E <a href="/wiki/Tocopherol" title="Tocopherol">tocopherols</a> and <a href="/wiki/Tocotrienol" title="Tocotrienol">tocotrienols</a> from whole foods, ex post facto epidemiological studies can have differing conclusions than artificial experiments using isolated compounds. <a href="/wiki/AstraZeneca" title="AstraZeneca">AstraZeneca</a>'s radical scavenging <a href="/wiki/Nitrone" title="Nitrone">nitrone</a> drug <a href="/wiki/NXY-059" class="mw-redirect" title="NXY-059">NXY-059</a> shows some efficacy in the treatment of stroke.<a href="#cite_note-pmid16507608-66">[66]</a> Oxidative stress (as formulated in <a href="/wiki/Denham_Harman" title="Denham Harman">Denham Harman</a>'s <a href="/wiki/Free-radical_theory_of_aging" title="Free-radical theory of aging">free-radical theory of aging</a>) is also thought to contribute to the aging process. While there is good evidence to support this idea in model organisms such as <a href="/wiki/Drosophila_melanogaster" title="Drosophila melanogaster">Drosophila melanogaster</a> and <a href="/wiki/Caenorhabditis_elegans" title="Caenorhabditis elegans">Caenorhabditis elegans</a>,<a href="#cite_note-pmid8415630-67">[67]</a><a href="#cite_note-pmid14616064-68">[68]</a> recent evidence from <a href="/wiki/Michael_Ristow" title="Michael Ristow">Michael Ristow</a>'s laboratory suggests that oxidative stress may also promote life expectancy of Caenorhabditis elegans by inducing a secondary response to initially increased levels of reactive oxygen species.<a href="#cite_note-pmid17908557-69">[69]</a> The situation in mammals is even less clear.<a href="#cite_note-pmid12208343-70">[70]</a><a href="#cite_note-pmid12086680-71">[71]</a><a href="#cite_note-pmid17090411-72">[72]</a> Recent <a href="/wiki/Epidemiological" class="mw-redirect" title="Epidemiological">epidemiological</a> findings support the process of <a href="/wiki/Mitohormesis" class="mw-redirect" title="Mitohormesis">mitohormesis</a>, but a 2007 meta-analysis finds that in studies with a low risk of bias (randomization, blinding, follow-up), some popular antioxidant supplements (vitamin A, beta carotene, and vitamin E) may increase mortality risk (although studies more prone to bias reported the reverse).<a href="#cite_note-pmid17327526-73">[73]</a> The USDA removed the table showing the <a href="/wiki/Oxygen_Radical_Absorbance_Capacity" class="mw-redirect" title="Oxygen Radical Absorbance Capacity">Oxygen Radical Absorbance Capacity</a> (ORAC) of Selected Foods Release 2 (2010) table due to the lack of evidence that the antioxidant level present in a food translated into a related antioxidant effect in the body.<a href="#cite_note-USDA-74">[74]</a> <div class="mw-heading mw-heading2"><h2 id="Metal_catalysts">Metal catalysts</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=5" title="Edit section: Metal catalysts">edit</a>]</div> Metals such as <a href="/wiki/Iron" title="Iron">iron</a>, <a href="/wiki/Copper" title="Copper">copper</a>, <a href="/wiki/Chromium" title="Chromium">chromium</a>, <a href="/wiki/Vanadium" title="Vanadium">vanadium</a>, and <a href="/wiki/Cobalt" title="Cobalt">cobalt</a> are capable of redox cycling in which a single <a href="/wiki/Electron" title="Electron">electron</a> may be accepted or donated by the metal. This action catalyzes production of reactive <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radicals</a> and reactive oxygen species.<a href="#cite_note-75">[75]</a> The presence of such metals in biological systems in an uncomplexed form (not in a protein or other protective metal complex) can significantly increase the level of oxidative stress. These metals are thought to induce <a href="/wiki/H.J.H._Fenton" class="mw-redirect" title="H.J.H. Fenton">Fenton</a> reactions and the Haber-Weiss reaction, in which <a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">hydroxyl radical</a> is generated from hydrogen peroxide.<a href="#cite_note-76">[76]</a> The hydroxyl radical then can modify amino acids. For example, meta-<a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a> and ortho-<a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a> form by hydroxylation of <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>. Other reactions include lipid peroxidation and oxidation of nucleobases. Metal-catalyzed oxidations also lead to irreversible modification of arginine, lysine, proline, and threonine. Excessive oxidative-damage leads to protein degradation or aggregation.<a href="#cite_note-pmid16796807-77">[77]</a><a href="#cite_note-pmid18445586-78">[78]</a> The reaction of transition metals with proteins oxidated by reactive oxygen or nitrogen species can yield reactive products that accumulate and contribute to aging and disease. For example, in <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's</a> patients, peroxidized lipids and proteins accumulate in lysosomes of the brain cells.<a href="#cite_note-pmid15909857-79">[79]</a> <div class="mw-heading mw-heading2"><h2 id="Non-metal_redox_catalysts">Non-metal redox catalysts</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=6" title="Edit section: Non-metal redox catalysts">edit</a>]</div> Certain organic compounds in addition to metal redox catalysts can also produce reactive oxygen species. One of the most important classes of these is the <a href="/wiki/Quinone" title="Quinone">quinones</a>. Quinones can redox cycle with their conjugate <a href="/wiki/Semiquinone" title="Semiquinone">semiquinones</a> and <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinones</a>, in some cases catalyzing the production of superoxide from dioxygen or hydrogen peroxide from superoxide.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <div class="mw-heading mw-heading2"><h2 id="Immune_defense">Immune defense</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=7" title="Edit section: Immune defense">edit</a>]</div> The immune system uses the lethal effects of oxidants by making the production of oxidizing species a central part of its mechanism of killing pathogens; with activated <a href="/wiki/Phagocyte" title="Phagocyte">phagocytes</a> producing both reactive oxygen and nitrogen species. These include superoxide (•O− 2), nitric oxide (•NO) and their particularly reactive product, peroxynitrite (ONOO-).<a href="#cite_note-pmid10922044-80">[80]</a> Although the use of these highly reactive compounds in the cytotoxic response of phagocytes causes damage to host tissues, the non-specificity of these oxidants is an advantage since they will damage almost every part of their target cell.<a href="#cite_note-pmid9189713-41">[41]</a> This prevents a pathogen from escaping this part of immune response by mutation of a single molecular target. <div class="mw-heading mw-heading2"><h2 id="Male_infertility">Male infertility</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=8" title="Edit section: Male infertility">edit</a>]</div> <a href="/wiki/Sperm" title="Sperm">Sperm</a> <a href="/wiki/DNA_fragmentation" title="DNA fragmentation">DNA fragmentation</a> appears to be an important factor in the <a href="/wiki/Cause_(medicine)" title="Cause (medicine)">cause</a> of <a href="/wiki/Male_infertility" title="Male infertility">male infertility</a>, since men with high DNA fragmentation levels have significantly lower odds of conceiving.<a href="#cite_note-pmid24745838-81">[81]</a> Oxidative stress is the major cause of DNA fragmentation in <a href="/wiki/Spermatozoon" title="Spermatozoon">spermatozoa</a>.<a href="#cite_note-pmid24745838-81">[81]</a> A high level of the oxidative DNA damage <a href="/wiki/8-oxo-2%27-deoxyguanosine" class="mw-redirect" title="8-oxo-2'-deoxyguanosine">8-oxo-2'-deoxyguanosine</a> is associated with abnormal spermatozoa and male infertility.<a href="#cite_note-pmid23874641-82">[82]</a> <div class="mw-heading mw-heading2"><h2 id="Aging">Aging</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=9" title="Edit section: Aging">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Ageing" title="Ageing">Ageing</a></div> In a rat model of premature aging, oxidative stress induced <a href="/wiki/DNA_damage_(naturally_occurring)" title="DNA damage (naturally occurring)">DNA damage</a> in the <a href="/wiki/Neocortex" title="Neocortex">neocortex</a> and <a href="/wiki/Hippocampus" title="Hippocampus">hippocampus</a> was substantially higher than in normally aging control rats.<a href="#cite_note-pmid24709042-83">[83]</a> Numerous studies have shown that the level of 8-oxo-2'-deoxyguanosine, a product of oxidative stress, increases with age in the brain and muscle DNA of the <a href="/wiki/Mouse" title="Mouse">mouse</a>, <a href="/wiki/Rat" title="Rat">rat</a>, <a href="/wiki/Gerbil" class="mw-redirect" title="Gerbil">gerbil</a> and <a href="/wiki/Human" title="Human">human</a>.<a href="#cite_note-84">[84]</a> Further information on the association of oxidative DNA damage with aging is presented in the article <a href="/wiki/DNA_damage_theory_of_aging" title="DNA damage theory of aging">DNA damage theory of aging</a>. However, it was recently shown that the fluoroquinolone antibiotic <a href="/wiki/Enoxacin" title="Enoxacin">Enoxacin</a> can diminish aging signals and promote lifespan extension in nematodes C. elegans by inducing oxidative stress.<a href="#cite_note-pmid29986212-85">[85]</a> <div class="mw-heading mw-heading2"><h2 id="Origin_of_eukaryotes">Origin of eukaryotes</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=10" title="Edit section: Origin of eukaryotes">edit</a>]</div> The <a href="/wiki/Great_oxygenation_event" class="mw-redirect" title="Great oxygenation event">great oxygenation event</a> began with the biologically induced appearance of oxygen in the <a href="/wiki/Earth%27s_atmosphere" class="mw-redirect" title="Earth's atmosphere">Earth's atmosphere</a> about 2.45 billion years ago. The rise of oxygen levels due to <a href="/wiki/Cyanobacteria" title="Cyanobacteria">cyanobacterial</a> <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a> in ancient microenvironments was probably highly toxic to the surrounding biota. Under these conditions, the selective pressure of oxidative stress is thought to have driven the evolutionary transformation of an <a href="/wiki/Archaea" title="Archaea">archaeal</a> lineage into the first <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a>.<a href="#cite_note-pmid20731852-86">[86]</a> Oxidative stress might have acted in synergy with other environmental stresses (such as <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> radiation and/or <a href="/wiki/Desiccation" title="Desiccation">desiccation</a>) to drive this selection. Selective pressure for efficient repair of oxidative DNA damages may have promoted the evolution of eukaryotic sex involving such features as cell-<a href="/wiki/Cell_fusion" title="Cell fusion">cell fusions</a>, <a href="/wiki/Cytoskeleton" title="Cytoskeleton">cytoskeleton</a>-mediated <a href="/wiki/Chromosome" title="Chromosome">chromosome</a> movements and emergence of the <a href="/wiki/Nuclear_membrane" class="mw-redirect" title="Nuclear membrane">nuclear membrane</a>.<a href="#cite_note-pmid20731852-86">[86]</a> Thus, the evolution of <a href="/wiki/Meiosis" title="Meiosis">meiotic</a> sex and eukaryogenesis may have been inseparable processes that evolved in large part to facilitate repair of oxidative DNA damages.<a href="#cite_note-pmid20731852-86">[86]</a><a href="#cite_note-87">[87]</a><a href="#cite_note-pmid29436502-88">[88]</a> <div class="mw-heading mw-heading2"><h2 id="COVID-19_and_cardiovascular_injury">COVID-19 and cardiovascular injury</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=11" title="Edit section: COVID-19 and cardiovascular injury">edit</a>]</div> It has been proposed that oxidative stress may play a major role in determining cardiac complications in <a href="/wiki/COVID-19#Cardiovascular_system" title="COVID-19">COVID-19</a>.<a href="#cite_note-89">[89]</a><a href="#cite_note-90">[90]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=12" title="Edit section: See also">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 30em;"> <ul><li><a href="/wiki/Antioxidative_stress" title="Antioxidative stress">Antioxidative stress</a></li> <li><a href="/wiki/Acatalasia" title="Acatalasia">Acatalasia</a></li> <li><a href="/wiki/Bruce_Ames" title="Bruce Ames">Bruce Ames</a></li> <li><a href="/wiki/Malondialdehyde" title="Malondialdehyde">Malondialdehyde</a>, an oxidative stress marker</li> <li><a href="/wiki/Free-radical_theory_of_aging#Mitochondria" title="Free-radical theory of aging">Mitochondrial free radical theory of aging</a></li> <li><a href="/wiki/Hormesis" title="Hormesis">Mitohormesis</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Pro-oxidant" title="Pro-oxidant">Pro-oxidant</a></li> <li><a href="/wiki/Reductive_stress" title="Reductive stress">Reductive stress</a></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Oxidative_stress&action=edit&section=13" title="Edit section: References">edit</a>]</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 reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-Springer_New_York_2010_pp._4278–4278-1"><a href="#cite_ref-Springer_New_York_2010_pp._4278–4278_1-0">^</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1">"Oxidative Stress". Handbook of Disease Burdens and Quality of Life Measures. 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