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General information about oxylipins, a paragraph about oxyliipin formation, and a section about oxylipins and disease were added.
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{{Short description|Class of lipids}}
{{Short description|Class of lipids}}
[[Image:oxylipins.jpg|thumb|right|The structural formulae of selected oxylipins]]
[[Image:oxylipins.jpg|thumb|right|The structural formulae of selected oxylipins]]
'''Oxylipins''' constitute a family of oxygenated [[natural product]]s which are formed from [[fatty acids]] by pathways involving at least one step of [[dioxygen]]-dependent [[oxidation]].<ref>{{cite journal | vauthors = Wasternack C | year = 2007 | title = Jasmonates: an update on biosynthesis, signal transduction and action in plant stress response, growth and development | journal = Annals of Botany | volume = 100 | issue = 4| pages = 681–697 | doi = 10.1093/aob/mcm079 | pmc = 2749622 | pmid=17513307}}</ref> Oxylipins are derived from [[polyunsaturated fatty acid]]s (PUFAs) by COX enzymes ([[cyclooxygenase]]s), by LOX enzymes ([[lipoxygenase]]s), or by [[Epoxygenase#CYP epoxygenases|cytochrome P450 epoxygenase]].<ref name="pmid28034718">{{cite journal | vauthors=Barquissau V, Ghandour RA, Ailhaud G, Klingenspor M, Langin D, Amri EZ, Pisani DF | title=Control of adipogenesis by oxylipins, GPCRs and PPARs | journal= [[Biochimie]] | volume=136 | pages=3–11 | year=2017 | doi= 10.1016/j.biochi.2016.12.012 | url = https://inserm.hal.science/inserm-01430844/file/Barquissau%20et%20al%20Biochimie%2029%20nov%202016%20%281%29.pdf | pmid = 28034718 }}</ref>
'''Oxylipins''' constitute a family of oxygenated [[natural product]]s which are formed from [[fatty acids]] by pathways involving at least one step of [[dioxygen]]-dependent [[oxidation]].<ref>{{cite journal | vauthors = Wasternack C | year = 2007 | title = Jasmonates: an update on biosynthesis, signal transduction and action in plant stress response, growth and development | journal = Annals of Botany | volume = 100 | issue = 4| pages = 681–697 | doi = 10.1093/aob/mcm079 | pmc = 2749622 | pmid=17513307}}</ref> These small polar lipid compounds are metabolites of [[polyunsaturated fatty acid]]s (PUFAs) including omega-3 fatty acids and omega-6 fatty acids. <ref name=":0">{{Cite journal |last=Camunas-Alberca |first=Sandra M. |last2=Moran-Garrido |first2=Maria |last3=Sáiz |first3=Jorge |last4=Villaseñor |first4=Alma |last5=Taha |first5=Ameer Y. |last6=Barbas |first6=Coral |date=2023-07 |title=The role of oxylipins and their validation as biomarkers in the clinical context |url=https://linkinghub.elsevier.com/retrieve/pii/S0165993623001528 |journal=TrAC Trends in Analytical Chemistry |language=en |volume=164 |pages=117065 |doi=10.1016/j.trac.2023.117065}}</ref><ref name=":1">{{Cite journal |last=Watrous |first=Jeramie D. |last2=Niiranen |first2=Teemu J. |last3=Lagerborg |first3=Kim A. |last4=Henglin |first4=Mir |last5=Xu |first5=Yong-Jiang |last6=Rong |first6=Jian |last7=Sharma |first7=Sonia |last8=Vasan |first8=Ramachandran S. |last9=Larson |first9=Martin G. |last10=Armando |first10=Aaron |last11=Mora |first11=Samia |last12=Quehenberger |first12=Oswald |last13=Dennis |first13=Edward A. |last14=Cheng |first14=Susan |last15=Jain |first15=Mohit |date=2019-03 |title=Directed Non-targeted Mass Spectrometry and Chemical Networking for Discovery of Eicosanoids and Related Oxylipins |url=https://linkinghub.elsevier.com/retrieve/pii/S2451945618304379 |journal=Cell Chemical Biology |language=en |volume=26 |issue=3 |pages=433–442.e4 |doi=10.1016/j.chembiol.2018.11.015 |pmc=PMC6636917 |pmid=30661990}}</ref> Oxylipins are formed by enyzmatic or non-enzymatic oxidation of PUFAs. <ref name=":0" />

In animal species, four main pathways of oxylipin production prevail: [[Lipoxygenase|lipoxygenases]] (LOXs) pathway, cyklooxygenases (COXs) route, [[cytochrome P450]] (CYPs) pathway, and [[reactive oxygen species]] (ROS) route. <ref name=":2">{{Cite journal |last=Liang |first=Nuanyi |last2=Harsch |first2=Brian A. |last3=Zhou |first3=Sitong |last4=Borkowska |first4=Alison |last5=Shearer |first5=Gregory C. |last6=Kaddurah-Daouk |first6=Rima |last7=Newman |first7=John W. |last8=Borkowski |first8=Kamil |date=2024-01 |title=Oxylipin transport by lipoprotein particles and its functional implications for cardiometabolic and neurological disorders |url=https://linkinghub.elsevier.com/retrieve/pii/S0163782723000553 |journal=Progress in Lipid Research |language=en |volume=93 |pages=101265 |doi=10.1016/j.plipres.2023.101265}}</ref> These pathways result in formation of many different oxylipin molecules which are important for number of processes in living organisms. The processes include inflamation, blood flow, energy metabolism, cellular life, cell signaling, or muscle contractions. <ref name=":0" /><ref name=":1" /><ref name=":2" /> Oxylipins have both pro- and anti-inflamatory roles. <ref>{{Cite journal |last=Wolfer |first=Arnaud M. |last2=Gaudin |first2=Mathieu |last3=Taylor-Robinson |first3=Simon D. |last4=Holmes |first4=Elaine |last5=Nicholson |first5=Jeremy K. |date=2015-12-01 |title=Development and Validation of a High-Throughput Ultrahigh-Performance Liquid Chromatography–Mass Spectrometry Approach for Screening of Oxylipins and Their Precursors |url=https://pubs.acs.org/doi/10.1021/acs.analchem.5b02794 |journal=Analytical Chemistry |language=en |volume=87 |issue=23 |pages=11721–11731 |doi=10.1021/acs.analchem.5b02794 |issn=0003-2700}}</ref>


Oxylipins are widespread in [[aerobic organisms]] including [[plant]]s, [[animal]]s and [[fungi]]. Many of oxylipins have [[physiological]] significance.<ref>{{cite journal | vauthors = Zhao J, Davis LC, Verpoorte R | year = 2005 | title = Elicitor signal transduction leading to production of plant secondary metabolites | journal = Biotechnol. Adv. | volume = 23 | issue = 4| pages = 283–333 | doi = 10.1016/j.biotechadv.2005.01.003 | pmid = 15848039 }}</ref><ref>{{cite journal | vauthors = Bolwell GP, Bindschedler LV, Blee KA, Butt VS, Davies DR, Gardner SL, Gerrish C, Minibayeva F | year = 2002 | title = The apoplastic oxidative burst in response to biotic stress in plants: a three-component system | journal = J. Exp. Bot. | volume = 53 | issue = 372| pages = 1367–1376 | doi = 10.1093/jexbot/53.372.1367 | pmid = 11997382 | doi-access = }}</ref> Typically, oxylipins are not stored in tissues but are formed on demand by liberation of precursor [[fatty acids]] from [[esterified]] forms.
Oxylipins are widespread in [[aerobic organisms]] including [[plant]]s, [[animal]]s and [[fungi]]. Many of oxylipins have [[physiological]] significance.<ref>{{cite journal | vauthors = Zhao J, Davis LC, Verpoorte R | year = 2005 | title = Elicitor signal transduction leading to production of plant secondary metabolites | journal = Biotechnol. Adv. | volume = 23 | issue = 4| pages = 283–333 | doi = 10.1016/j.biotechadv.2005.01.003 | pmid = 15848039 }}</ref><ref>{{cite journal | vauthors = Bolwell GP, Bindschedler LV, Blee KA, Butt VS, Davies DR, Gardner SL, Gerrish C, Minibayeva F | year = 2002 | title = The apoplastic oxidative burst in response to biotic stress in plants: a three-component system | journal = J. Exp. Bot. | volume = 53 | issue = 372| pages = 1367–1376 | doi = 10.1093/jexbot/53.372.1367 | pmid = 11997382 | doi-access = }}</ref> Typically, oxylipins are not stored in tissues but are formed on demand by liberation of precursor [[fatty acids]] from [[esterified]] forms.
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Oxylipins in [[animal]]s, referred to as [[eicosanoids]] (Greek [[icosa]]; twenty) because of their formation from twenty-carbon [[essential fatty acids]], have potent and often opposing effects on e.g. [[smooth muscle]] ([[vasculature]], [[myometrium]]) and [[blood platelet]]s. Certain [[eicosanoids]] ([[leukotrienes]] [[Leukotriene B4|B4]] and [[Leukotriene C4|C4]]) are [[proinflammatory]] whereas others ([[resolvins]], protectins) are [[antiinflammatory]] and are involved in the resolution process which follows tissue injury. Plant oxylipins are mainly involved in control of [[ontogenesis]], [[reproductive]] processes and in the resistance to various microbial [[pathogen]]s and other [[Pest (organism)|pests]].
Oxylipins in [[animal]]s, referred to as [[eicosanoids]] (Greek [[icosa]]; twenty) because of their formation from twenty-carbon [[essential fatty acids]], have potent and often opposing effects on e.g. [[smooth muscle]] ([[vasculature]], [[myometrium]]) and [[blood platelet]]s. Certain [[eicosanoids]] ([[leukotrienes]] [[Leukotriene B4|B4]] and [[Leukotriene C4|C4]]) are [[proinflammatory]] whereas others ([[resolvins]], protectins) are [[antiinflammatory]] and are involved in the resolution process which follows tissue injury. Plant oxylipins are mainly involved in control of [[ontogenesis]], [[reproductive]] processes and in the resistance to various microbial [[pathogen]]s and other [[Pest (organism)|pests]].


Oxylipins most often act in an [[Autocrine signalling|autocrine]] or [[Paracrine signalling|paracrine]] manner, notably in targeting [[peroxisome proliferator-activated receptor]]s (PPARs) to modify [[adipocyte]] formation and function.<ref name="pmid28034718" />
Oxylipins most often act in an [[Autocrine signalling|autocrine]] or [[Paracrine signalling|paracrine]] manner, notably in targeting [[peroxisome proliferator-activated receptor]]s (PPARs) to modify [[adipocyte]] formation and function.<ref name="pmid28034718">{{cite journal |vauthors=Barquissau V, Ghandour RA, Ailhaud G, Klingenspor M, Langin D, Amri EZ, Pisani DF |year=2017 |title=Control of adipogenesis by oxylipins, GPCRs and PPARs |url=https://inserm.hal.science/inserm-01430844/file/Barquissau%20et%20al%20Biochimie%2029%20nov%202016%20%281%29.pdf |journal=[[Biochimie]] |volume=136 |pages=3–11 |doi=10.1016/j.biochi.2016.12.012 |pmid=28034718}}</ref>


Most oxylipins in the body are derived from [[linoleic acid]] or [[alpha-linolenic acid]]. Linoleic acid oxylipins are usually present in blood and tissue in higher concentrations than any other [[polyunsaturated fatty acid|PUFA]] oxylipin, despite the fact that alpha-linolenic acid is more readily metabolized to oxylipin.<ref name="pmid26374175">{{cite journal | vauthors=Gabbs M, Leng S, Devassy JG, Monirujjaman M, Aukema HM | title=Advances in Our Understanding of Oxylipins Derived from Dietary PUFAs| journal= [[Advances in Nutrition]] | volume=6 | issue=5 | pages=513–540 | year=2015 | doi= 10.3945/an.114.007732 |pmid = 26374175 | pmc=4561827 }}</ref>
Most oxylipins in the body are derived from [[linoleic acid]] or [[alpha-linolenic acid]]. Linoleic acid oxylipins are usually present in blood and tissue in higher concentrations than any other [[polyunsaturated fatty acid|PUFA]] oxylipin, despite the fact that alpha-linolenic acid is more readily metabolized to oxylipin.<ref name="pmid26374175">{{cite journal | vauthors=Gabbs M, Leng S, Devassy JG, Monirujjaman M, Aukema HM | title=Advances in Our Understanding of Oxylipins Derived from Dietary PUFAs| journal= [[Advances in Nutrition]] | volume=6 | issue=5 | pages=513–540 | year=2015 | doi= 10.3945/an.114.007732 |pmid = 26374175 | pmc=4561827 }}</ref>
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In general, oxylipins derived from [[omega-6 fatty acid]]s are more pro-inflammatory, vasoconstrictive, and proliferative than those derived from [[omega-3 fatty acid]]s.<ref name="pmid26374175" /> The omega-3 [[eicosapentaenoic acid]] (EPA)-derived and [[docosahexaenoic acid]] (DHA)-derived oxylipins are anti-inflammatory and vasodilatory.<ref name="pmid26374175" /> In a clinical trial of men with high [[triglyceride]]s, 3 grams daily of DHA compared with placebo (olive oil) given for 91 days nearly tripled the DHA in red blood cells while reducing oxylipins in those cells.<ref name="pmid25411526">{{cite journal | vauthors=Shichiri M, Adkins Y, Ishida N, Umeno A, Shigeri Y, Yoshida Y, Fedor DM, Mackey BE, Kelley DS | title=DHA concentration of red blood cells is inversely associated with markers of lipid peroxidation in men taking DHA supplement | journal=Journal of Clinical Biochemistry and Nutrition | volume=55 |issue=3 | pages=196–202 | year=2014 | url=https://www.jstage.jst.go.jp/article/jcbn/55/3/55_14-22/_article | doi= 10.3164/jcbn.14-22| pmid =25411526 | pmc=4227822 }}</ref> Both groups were given Vitamin C ([[ascorbyl palmitate]]) and Vitamin E (mixed [[tocopherol]]) supplements.<ref name="pmid25411526" />
In general, oxylipins derived from [[omega-6 fatty acid]]s are more pro-inflammatory, vasoconstrictive, and proliferative than those derived from [[omega-3 fatty acid]]s.<ref name="pmid26374175" /> The omega-3 [[eicosapentaenoic acid]] (EPA)-derived and [[docosahexaenoic acid]] (DHA)-derived oxylipins are anti-inflammatory and vasodilatory.<ref name="pmid26374175" /> In a clinical trial of men with high [[triglyceride]]s, 3 grams daily of DHA compared with placebo (olive oil) given for 91 days nearly tripled the DHA in red blood cells while reducing oxylipins in those cells.<ref name="pmid25411526">{{cite journal | vauthors=Shichiri M, Adkins Y, Ishida N, Umeno A, Shigeri Y, Yoshida Y, Fedor DM, Mackey BE, Kelley DS | title=DHA concentration of red blood cells is inversely associated with markers of lipid peroxidation in men taking DHA supplement | journal=Journal of Clinical Biochemistry and Nutrition | volume=55 |issue=3 | pages=196–202 | year=2014 | url=https://www.jstage.jst.go.jp/article/jcbn/55/3/55_14-22/_article | doi= 10.3164/jcbn.14-22| pmid =25411526 | pmc=4227822 }}</ref> Both groups were given Vitamin C ([[ascorbyl palmitate]]) and Vitamin E (mixed [[tocopherol]]) supplements.<ref name="pmid25411526" />

== Oxylipins and disease ==
Oxylipins play important role in many diseases, for example, [[diabetes]], [[obesity]], [[Cardiovascular disease|cardiovascular diseases]], [[cancer]], [[COVID-19]], or [[Neurodegenerative disease|neurodegenerative disorders]]. Changes in oxylipin metabolism have been reported in these diseases. <ref name=":1" /> <ref name=":2" /> <ref>{{Cite journal |last=Biagini |first=Denise |last2=Oliveri |first2=Paolo |last3=Baj |first3=Andreina |last4=Gasperina |first4=Daniela Dalla |last5=Ferrante |first5=Francesca Drago |last6=Lomonaco |first6=Tommaso |last7=Ghimenti |first7=Silvia |last8=Lenzi |first8=Alessio |last9=Bonini |first9=Andrea |last10=Vivaldi |first10=Federico |last11=Oger |first11=Camille |last12=Galano |first12=Jean-Marie |last13=Balas |first13=Laurence |last14=Durand |first14=Thierry |last15=Maggi |first15=Fabrizio |date=2023-12 |title=The effect of SARS-CoV-2 variants on the plasma oxylipins and PUFAs of COVID-19 patients |url=https://doi.org/10.1016/j.prostaglandins.2023.106770 |journal=Prostaglandins &amp; Other Lipid Mediators |volume=169 |pages=106770 |doi=10.1016/j.prostaglandins.2023.106770 |issn=1098-8823}}</ref> <ref name=":3">{{Cite journal |last=Chistyakov |first=Dmitry V. |last2=Azbukina |first2=Nadezhda V. |last3=Lopachev |first3=Alexander V. |last4=Goriainov |first4=Sergei V. |last5=Astakhova |first5=Alina A. |last6=Ptitsyna |first6=Elena V. |last7=Klimenko |first7=Anna S. |last8=Poleshuk |first8=Vsevolod V. |last9=Kazanskaya |first9=Rogneda B. |last10=Fedorova |first10=Tatiana N. |last11=Sergeeva |first11=Marina G. |date=2024-04 |title=Plasma oxylipin profiles reflect Parkinson's disease stage |url=https://doi.org/10.1016/j.prostaglandins.2023.106788 |journal=Prostaglandins &amp; Other Lipid Mediators |volume=171 |pages=106788 |doi=10.1016/j.prostaglandins.2023.106788 |issn=1098-8823}}</ref> <ref>{{Cite journal |last=Chaves-Filho |first=Adriano B. |last2=Diniz |first2=Larissa S. |last3=Santos |first3=Rosangela S. |last4=Lima |first4=Rodrigo S. |last5=Oreliana |first5=Hector |last6=Pinto |first6=Isabella F.D. |last7=Dantas |first7=Lucas S. |last8=Inague |first8=Alex |last9=Faria |first9=Rodrigo L. |last10=Medeiros |first10=Marisa H.G. |last11=Glezer |first11=Isaías |last12=Festuccia |first12=William T. |last13=Yoshinaga |first13=Marcos Y. |last14=Miyamoto |first14=Sayuri |date=2023-11 |title=Plasma oxylipin profiling by high resolution mass spectrometry reveal signatures of inflammation and hypermetabolism in amyotrophic lateral sclerosis |url=https://linkinghub.elsevier.com/retrieve/pii/S0891584923005993 |journal=Free Radical Biology and Medicine |language=en |volume=208 |pages=285–298 |doi=10.1016/j.freeradbiomed.2023.08.019}}</ref> <ref>{{Cite journal |last=Tans |first=Roel |last2=Bande |first2=Rieke |last3=van Rooij |first3=Arno |last4=Molloy |first4=Billy J. |last5=Stienstra |first5=Rinke |last6=Tack |first6=Cees J. |last7=Wevers |first7=Ron A. |last8=Wessels |first8=Hans J.C.T. |last9=Gloerich |first9=Jolein |last10=van Gool |first10=Alain J. |date=2020-09 |title=Evaluation of cyclooxygenase oxylipins as potential biomarker for obesity-associated adipose tissue inflammation and type 2 diabetes using targeted multiple reaction monitoring mass spectrometry |url=https://linkinghub.elsevier.com/retrieve/pii/S0952327820301150 |journal=Prostaglandins, Leukotrienes and Essential Fatty Acids |language=en |volume=160 |pages=102157 |doi=10.1016/j.plefa.2020.102157}}</ref> In 2021, [[Alzheimer's disease]] was associated with changes in oxylipin levels in plasma and cerebrospinal fluid (CSF) for the first time. <ref>{{Cite journal |last=Borkowski |first=Kamil |last2=Pedersen |first2=Theresa L. |last3=Seyfried |first3=Nicholas T. |last4=Lah |first4=James J. |last5=Levey |first5=Allan I. |last6=Hales |first6=Chadwick M. |last7=Dammer |first7=Eric B. |last8=Blach |first8=Colette |last9=Louie |first9=Gregory |last10=Kaddurah-Daouk |first10=Rima |last11=Newman |first11=John W. |last12=Alzheimer’s Disease Metabolomics Consortium |date=2021-12 |title=Association of plasma and CSF cytochrome P450, soluble epoxide hydrolase, and ethanolamide metabolism with Alzheimer’s disease |url=https://alzres.biomedcentral.com/articles/10.1186/s13195-021-00893-6 |journal=Alzheimer's Research & Therapy |language=en |volume=13 |issue=1 |doi=10.1186/s13195-021-00893-6 |issn=1758-9193 |pmc=PMC8422756 |pmid=34488866}}</ref> Interestingly, improvement in neurodegenerative diseases and also cardiovascular diseases may be achieved by using inhibitors of an enzyme (soluble epoxide hydrolase) involved in formation of oxylipins. <ref>{{Cite journal |last=Imig |first=John D. |last2=Hammock |first2=Bruce D. |date=2009-10 |title=Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases |url=https://www.nature.com/articles/nrd2875 |journal=Nature Reviews Drug Discovery |language=en |volume=8 |issue=10 |pages=794–805 |doi=10.1038/nrd2875 |issn=1474-1776 |pmc=PMC3021468 |pmid=19794443}}</ref> <ref>{{Cite journal |last=Wagner |first=Karen M. |last2=McReynolds |first2=Cindy B. |last3=Schmidt |first3=William K. |last4=Hammock |first4=Bruce D. |date=2017-12 |title=Soluble epoxide hydrolase as a therapeutic target for pain, inflammatory and neurodegenerative diseases |url=https://linkinghub.elsevier.com/retrieve/pii/S0163725817301547 |journal=Pharmacology & Therapeutics |language=en |volume=180 |pages=62–76 |doi=10.1016/j.pharmthera.2017.06.006 |pmc=PMC5677555 |pmid=28642117}}</ref> In [[Parkinson's disease]], oxylipin profiles reflect the stage of the disease. This should be taken into consideration when choosing the suitable medication for Parkinson's disease. <ref name=":3" />


==References==
==References==

Revision as of 20:11, 19 March 2024

The structural formulae of selected oxylipins

Oxylipins constitute a family of oxygenated natural products which are formed from fatty acids by pathways involving at least one step of dioxygen-dependent oxidation.[1] These small polar lipid compounds are metabolites of polyunsaturated fatty acids (PUFAs) including omega-3 fatty acids and omega-6 fatty acids. [2][3] Oxylipins are formed by enyzmatic or non-enzymatic oxidation of PUFAs. [2]

In animal species, four main pathways of oxylipin production prevail: lipoxygenases (LOXs) pathway, cyklooxygenases (COXs) route, cytochrome P450 (CYPs) pathway, and reactive oxygen species (ROS) route. [4] These pathways result in formation of many different oxylipin molecules which are important for number of processes in living organisms. The processes include inflamation, blood flow, energy metabolism, cellular life, cell signaling, or muscle contractions. [2][3][4] Oxylipins have both pro- and anti-inflamatory roles. [5]

Oxylipins are widespread in aerobic organisms including plants, animals and fungi. Many of oxylipins have physiological significance.[6][7] Typically, oxylipins are not stored in tissues but are formed on demand by liberation of precursor fatty acids from esterified forms.

Biosynthesis

Biosynthesis of oxylipins is initiated by dioxygenases or monooxygenases; however also non-enzymatic autoxidative processes contribute to oxylipin formation (phytoprostanes, isoprostanes). Dioxygenases include lipoxygenases (plants, animals, fungi), heme-dependent fatty acid oxygenases (plants, fungi), and cyclooxygenases (animals). Fatty acid hydroperoxides or endoperoxides are formed by action of these enzymes. Monooxygenases involved in oxylipin biosynthesis are members of the cytochrome P450 superfamily and can oxidize double bonds with epoxide formation or saturated carbons forming alcohols. Nature has evolved numerous enzymes which metabolize oxylipins into secondary products, many of which possess strong biological activity. Of special importance are the cytochrome P450 enzymes in animals, including CYP5A1 (thromboxane synthase), CYP8A1 (prostacyclin synthase), and the CYP74 family of hydroperoxide-metabolizing enzymes in plants, lower animals and bacteria. In the plant and animal kingdoms the C18 and C20 polyenoic fatty acids, respectively, are the major precursors of oxylipins.

Structure and function

Oxylipins in animals, referred to as eicosanoids (Greek icosa; twenty) because of their formation from twenty-carbon essential fatty acids, have potent and often opposing effects on e.g. smooth muscle (vasculature, myometrium) and blood platelets. Certain eicosanoids (leukotrienes B4 and C4) are proinflammatory whereas others (resolvins, protectins) are antiinflammatory and are involved in the resolution process which follows tissue injury. Plant oxylipins are mainly involved in control of ontogenesis, reproductive processes and in the resistance to various microbial pathogens and other pests.

Oxylipins most often act in an autocrine or paracrine manner, notably in targeting peroxisome proliferator-activated receptors (PPARs) to modify adipocyte formation and function.[8]

Most oxylipins in the body are derived from linoleic acid or alpha-linolenic acid. Linoleic acid oxylipins are usually present in blood and tissue in higher concentrations than any other PUFA oxylipin, despite the fact that alpha-linolenic acid is more readily metabolized to oxylipin.[9]

Linoleic acid oxylipins can be anti-inflammatory, but are more often pro-inflammatory, associated with atherosclerosis, non-alcoholic fatty liver disease, and Alzheimer's disease.[9] Centenarians have shown reduced levels of linoleic acid oxylipins in their blood circulation.[10] Lowering dietary linoleic acid results in fewer linoleic acid oxylipins in humans.[11] From 1955 to 2005 the linoleic acid content of human adipose tissue has risen an estimated 136% in the United States.[12]

In general, oxylipins derived from omega-6 fatty acids are more pro-inflammatory, vasoconstrictive, and proliferative than those derived from omega-3 fatty acids.[9] The omega-3 eicosapentaenoic acid (EPA)-derived and docosahexaenoic acid (DHA)-derived oxylipins are anti-inflammatory and vasodilatory.[9] In a clinical trial of men with high triglycerides, 3 grams daily of DHA compared with placebo (olive oil) given for 91 days nearly tripled the DHA in red blood cells while reducing oxylipins in those cells.[13] Both groups were given Vitamin C (ascorbyl palmitate) and Vitamin E (mixed tocopherol) supplements.[13]

Oxylipins and disease

Oxylipins play important role in many diseases, for example, diabetes, obesity, cardiovascular diseases, cancer, COVID-19, or neurodegenerative disorders. Changes in oxylipin metabolism have been reported in these diseases. [3] [4] [14] [15] [16] [17] In 2021, Alzheimer's disease was associated with changes in oxylipin levels in plasma and cerebrospinal fluid (CSF) for the first time. [18] Interestingly, improvement in neurodegenerative diseases and also cardiovascular diseases may be achieved by using inhibitors of an enzyme (soluble epoxide hydrolase) involved in formation of oxylipins. [19] [20] In Parkinson's disease, oxylipin profiles reflect the stage of the disease. This should be taken into consideration when choosing the suitable medication for Parkinson's disease. [15]

References

  1. ^ Wasternack C (2007). "Jasmonates: an update on biosynthesis, signal transduction and action in plant stress response, growth and development". Annals of Botany. 100 (4): 681–697. doi:10.1093/aob/mcm079. PMC 2749622. PMID 17513307.
  2. ^ a b c Camunas-Alberca, Sandra M.; Moran-Garrido, Maria; Sáiz, Jorge; Villaseñor, Alma; Taha, Ameer Y.; Barbas, Coral (2023-07). "The role of oxylipins and their validation as biomarkers in the clinical context". TrAC Trends in Analytical Chemistry. 164: 117065. doi:10.1016/j.trac.2023.117065. {{cite journal}}: Check date values in: |date= (help)
  3. ^ a b c Watrous, Jeramie D.; Niiranen, Teemu J.; Lagerborg, Kim A.; Henglin, Mir; Xu, Yong-Jiang; Rong, Jian; Sharma, Sonia; Vasan, Ramachandran S.; Larson, Martin G.; Armando, Aaron; Mora, Samia; Quehenberger, Oswald; Dennis, Edward A.; Cheng, Susan; Jain, Mohit (2019-03). "Directed Non-targeted Mass Spectrometry and Chemical Networking for Discovery of Eicosanoids and Related Oxylipins". Cell Chemical Biology. 26 (3): 433–442.e4. doi:10.1016/j.chembiol.2018.11.015. PMC 6636917. PMID 30661990. {{cite journal}}: Check date values in: |date= (help)CS1 maint: PMC format (link)
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