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|ImageFile=Mead acid.png |
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| verifiedrevid = 439734690 |
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| ImageFile=Mead acid.png |
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|IUPACName=(5Z,8Z,11Z)-Eicosa-5,8,11-trienoic acid |
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| PIN=(5''Z'',8''Z'',11''Z'')-Icosa-5,8,11-trienoic acid |
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| CASNo= 20590-32-3 |
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|Section1={{Chembox Identifiers |
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| PubChem=5312531 |
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| SMILES=CCCCCCCCC=CCC=CCC=CCCCC(=O)O |
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| CASNo= 20590-32-3 |
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| UNII = JQS194YH3X |
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| PubChem=5312531 |
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| SMILES=CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O |
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| ChemSpiderID = 4471956 |
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| InChI = 1/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15- |
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| InChIKey = UNSRRHDPHVZAHH-YOILPLPUBD |
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| StdInChI = 1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15- |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = UNSRRHDPHVZAHH-YOILPLPUSA-N |
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|Section2= {{Chembox Properties |
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| Formula=C<sub>20</sub>H<sub>34</sub>O<sub>2</sub> |
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| Formula=C<sub>20</sub>H<sub>34</sub>O<sub>2</sub> |
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| MolarMass=306.48276 |
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| MolarMass=306.48276 |
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'''Mead acid''' is an ], first characterized by James F. Mead.<ref>{{cite book | last1=Siegel | first1=George J. |last2=Albers | first2=R. Wayne | title=Basic neurochemistry: molecular, cellular, and medical aspects, Volume 1 | page=40 |edition=7th | year=2006 | publisher=Elsevier | url=https://books.google.com/books?id=Af0IyHtGCMUC&q=James+Mead+mead+acid&pg=PA40 | quote=One of these is 20:3ω9, termed 'Mead acid' after its discovery by James Mead....| isbn=9780080472072 }}</ref> As with some other omega-9 ]s, animals can make Mead acid ''de novo''. Its elevated presence in the blood is an indication of ] ].<ref name= Ichi >{{cite journal |url=https://www.sciencedirect.com/science/article/pii/S1388198113002369 |date=January 2014 |volume=1841 |issue=1 |pages=204–213 |title=Identification of genes and pathways involved in the synthesis of Mead acid (20:3n−9), an indicator of essential fatty acid deficiency |author1=Ichi I |author2=Kono N |author3=Arita Y |author4=Haga S |journal=Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids |doi=10.1016/j.bbalip.2013.10.013|pmid=24184513}}</ref> Mead acid is found in large quantities in ]. |
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'''Mead acid''' is an ], first characterized by James F. Mead..<ref name=Enig>{{cite journal |
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| journal = Wise Traditions in Food, Farming and the Healing Arts |
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| year = Spring, 2005 |
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| title=A Reply to Ray Peat on Essential Fatty Acid Deficiency |
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| url = http://www.westonaprice.org/knowyourfats/essentialfattyaciddef.html |
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| author = Mary Enig | accessdate = 2007-10-22 |archiveurl = http://web.archive.org/web/20071007203449/http://www.westonaprice.org/knowyourfats/essentialfattyaciddef.html |archivedate = 2007-10-07}}</ref> Like some other omega-9 ]s animals can make Mead acid ''de novo''. Its elevated presence in the blood is an indication of ] ]. Mead acid is found in large quantities in ]. |
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== Chemistry == |
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== Chemistry == |
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Chemically, Mead acid is a ] with a 20-] chain and three ]-interrupted '']'' double bonds. The first double bond is located at the ninth carbon from the omega end. In physiological literature, it is given the name 20:3(n-9). See ] for an explanation of the naming system. In the presence of ], ] or ] Mead acid can form various hydroxy (]) and hydoperoxy (HpETE) products .<ref name=cyberlipid>{{cite web |
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Mead acid, also referred to as eicosatrienoic acid, is chemically a ] with a 20-carbon chain and three ]-interrupted '']'' double bonds, as is typical for polyunsaturated fatty acids. The first double bond is located at the ninth carbon from the omega end. In physiological literature, it is given the name 20:3 (n-9). (See {{slink|Fatty acid|Nomenclature}} for an explanation of the naming system.) In the presence of ], ], or ], mead acid can form various ] (HETE) and hydroperoxy (HpETE) products.<ref name="Hamberg1993">{{Cite journal |last1=Oliw |first1=E.H. |last2=Hornsten |first2=L. |last3=Sprecher |first3=H. |last4=Hamberg |first4=M. |date=1993 |title=Oxygenation of 5,8,11-Eicosatrienoic Acid by Prostaglandin Endoperoxide Synthase and by Cytochrome P450 Monooxygenase: Structure and Mechanism of Formation of Major Metabolites |journal=Archives of Biochemistry and Biophysics |language=en |volume=305 |issue=2 |pages=288–297 |doi=10.1006/abbi.1993.1425 |pmid=8373167}}</ref><ref name=cyberlipid>{{cite web |
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| title=PROSTAGLANDINS AND RELATED COMPOUNDS |
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| title=PROSTAGLANDINS AND RELATED COMPOUNDS |
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| url= http://www.cyberlipid.org/prost1/pros0002.htm |
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| url= http://www.cyberlipid.org/prost1/pros0002.htm |
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| archive-url=https://web.archive.org/web/20180413060119/http://www.cyberlipid.org/prost1/pros0002.htm |
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| archive-date=April 13, 2018 |
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| url-status=dead |
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|author= Cyberlipid Center |
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|author= Cyberlipid Center |
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|accessdate=2007-10-24}}</ref> |
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|access-date=2007-10-24}}</ref> |
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== Physiology == |
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== Physiology == |
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Two fatty acids, ] and ], are considered ]s (EFAs) in humans and other mammals. Both are 18 carbon fatty acids unlike mead acid, which has 20 carbons. Linoleic is an ω-6 fatty acid whereas linolenic is ω-3 and mead is ω-9. One study examined patients with ] and suspected EFA deficiency; they were found to have blood-levels of mead acid about 13-fold higher than reference subjects.<ref name=Siguel>{{cite journal |url=http://www.clinchem.org/cgi/reprint/33/10/1869 |journal=Clinical Chemistry |volume=33 |pages=1869–1873 |date=October 1, 1987 |title=Criteria for essential fatty acid deficiency in plasma as assessed by capillary column gas–liquid chromatography |author1=EN Siguel |author2=KM Chee |author3=JX Gong |author4=EJ Schaefer |access-date=2007-10-24 |issue=10 |doi=10.1093/clinchem/33.10.1869 |pmid=3665042 |archive-url=https://web.archive.org/web/20110927014210/http://www.clinchem.org/cgi/reprint/33/10/1869 |archive-date=September 27, 2011 |url-status=dead |doi-access=free }}</ref> Under severe conditions of essential fatty acid deprivation, mammals will elongate and desaturate ] to make mead acid, (20:3, ''n''−9).<ref name"Geissler2017">{{cite book|vauthors = Geissler C, Powers H|title = Human Nutrition|year=2017|publisher = Oxford University Press|isbn =9 78-0-19-876802-9|page=174}}</ref> This has been documented to a lesser extent in vegetarians and semi-vegetarians following an unbalanced diet.<ref name="phinney1990">{{cite journal |vauthors = Phinney SD, Odin RS, Johnson SB, Holman RT |title = Reduced arachidonate in serum phospholipids and cholesteryl esters associated with vegetarian diets in humans |journal = Am. J. Clin. Nutr. |volume = 51 |issue = 3 |pages = 385–92 |year = 1990 |pmid = 2106775|doi = 10.1093/ajcn/51.3.385 }}</ref><ref name=Hornstra> |
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Two fatty acids, ] and ], are considered essential in humans and other mammals. Both are 18 carbon fatty acids unlike mead acid, which has 20 carbons. Linoleic is an ω-6 fatty acid whereas linolenic is ω-3 and mead is ω-9. |
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{{cite journal |
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| date=September 2007 |
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| journal=Fats of Life Newsletter |
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| title= Essential Polyunsaturated Fatty Acids and Early Human Development |
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| first=Gerard |
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| last=Hornstra |
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| access-date=2007-10-23 |
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| url=http://www.fatsoflife.com/pufa/article.asp?nid=1&edition=this&id=484 |
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| archive-url=https://web.archive.org/web/20080607194856/http://www.fatsoflife.com/pufa/article.asp?nid=1&edition=this&id=484 |
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| archive-date=June 7, 2008 |
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}}</ref> |
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Mead acid has been found to decrease ]ic activity. This may be important in treating conditions where inhibition of bone formation is desired.<ref name="HamazakiSuzuki2008">{{cite journal|last1=Hamazaki|first1=Tomohito|last2=Suzuki|first2=Nobuo|last3=Widyowati|first3=Retno|last4=Miyahara|first4=Tatsuro|last5=Kadota|first5=Shigetoshi|last6=Ochiai|first6=Hiroshi|last7=Hamazaki|first7=Kei|title=The Depressive Effects of 5,8,11-Eicosatrienoic Acid (20:3n-9) on Osteoblasts|journal=Lipids|volume=44|issue=2|year=2008|pages=97–102|issn=0024-4201|doi=10.1007/s11745-008-3252-8|pmid=18941818|s2cid=4011759}}</ref> |
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Under severe conditions of essential fatty acid deprivation, mammals will elongate and desaturate ] to make mead acid, (20:3, ''n''−9).<ref name="lipomics">{{cite web|url=http://www.lipomics.com/resources/fatty_acids/20_3n9.htm |author=Lipomics|title = Mead acid| accessdate= February 14, 2006}}</ref> This also occurs to a lesser extent in ] and semi-vegetarians.<ref name="phinney1990">{{cite web| author=Phinney, SD, RS Odin, SB Johnson and RT Holman |title=Reduced arachidonate in serum phospholipids and cholesteryl esters associated with vegetarian diets in humans|url=http://intl.ajcn.org/cgi/content/abstract/51/3/385|accessdate=February 11, 2006|year=1990}}</ref><ref name=Hornstra>{{cite journal| month=September | year=2007 | |
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journal=Fats of Life Newsletter | |
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title= Essential Polyunsaturated Fatty Acids and Early Human Development | |
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author= Gerard Hornstra | accessdate = 2007-10-23 | |
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url=http://www.fatsoflife.com/pufa/article.asp?nid=1&edition=this&id=484| format={{dead link|date=April 2009}} – <sup></sup> |archiveurl = http://web.archive.org/web/20080607194856/http://www.fatsoflife.com/pufa/article.asp?nid=1&edition=this&id=484 |archivedate = 2008-06-07}}</ref> |
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== Role in inflammation == |
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One study examined patients with ] and suspected EFA deficiency. They were found to have blood-levels of Mead acid 1263% higher than reference subjects.<ref name=Siguel>{{cite journal |
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| url= http://www.clinchem.org/cgi/reprint/33/10/1869 |
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| journal=Clinical Chemistry| volume= 33|pages=1869–1873| date= October 1, 1987 | title=Criteria for essential fatty acid deficiency in plasma as assessed by capillary column gas-liquid chromatography |
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|author= EN Siguel, KM Chee, JX Gong and EJ Schaefer |
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| accessdate = 2007-10-24 |
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| issue= 10 |
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| pmid= 3665042 |
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}}</ref> |
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]s are enzymes known to play a large role in inflammatory processes through oxidation of unsaturated fatty acids, most notably, the formation of ] from ] (AA). AA has the same chain length as Mead acid but an additional ω-6 double bond. When physiological levels of arachidonic acid are low, other unsaturated fatty acids including mead and linoleic acid are oxidized by COX. Cyclooxygenase breaks the ] C-H bond of AA to synthesize prostaglandin H2, but breaks a stronger ] C-H bond when it encounters Mead acid instead.<ref name="Hamberg1993" /> |
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==Role in inflammation== |
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Mead acid is also converted to ]s ] and ].<ref name="Hammarstrom 1981 JBC">{{cite journal |vauthors = Hammarström S|title=Conversion of 5,8,11-Eicosatrienoic Acid to Leukotrienes C3 and D3|journal = Journal of Biological Chemistry|volume=256 |issue = 3 |year = 1981 |pages=2275–2279 |doi=10.1016/S0021-9258(19)69773-5|pmid=6780563 |url = http://www.jbc.org/content/256/5/2275.full.pdf|doi-access = free}}</ref> |
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Prostaglandin H synthases (also known as ]) are enzymes known to play a large role in inflammatory processes through oxidation of unsaturated fatty acids. Most notably, the formation of ] from ] which is very similar in structure to mead acid. When physiological levels of arachidonic acid are low, other unsaturated fatty acids including mead and linoleic acid are oxidized by COX. |
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Mead acid is metabolized by ] to 5-hydroxyeicosatrienoic acid (5-HETrE)<ref name="pmid2988021">{{cite journal |vauthors = Wei YF, Evans RW, Morrison AR, Sprechert H, Jakschik BA |title = Double bond requirement for the 5-lipoxygenase pathway |journal = Prostaglandins |volume = 29 |issue = 4 |pages = 537–45 |year = 1985 |pmid = 2988021 |doi=10.1016/0090-6980(85)90078-4}}</ref> and then by ] to 5-oxoeicosatrienoic acid (5-oxo-ETrE).<ref name="PowellRokach2013">{{cite journal|last1=Powell|first1=William S.|last2=Rokach|first2=Joshua|title=The eosinophil chemoattractant 5-oxo-ETE and the OXE receptor|journal=Progress in Lipid Research|volume=52|issue=4|year=2013|pages=651–665|issn=0163-7827|doi=10.1016/j.plipres.2013.09.001|pmid=24056189|pmc=5710732}}</ref> |
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Mead acid is also converted to ] ] and ].<ref name="Hammarstrom 1981 JBC">, Conversion of 5,8,11-Eicosatrienoic Acidt o Leukotrienes C3 and D3 Journal of Biological Chemistry (1981) vol. 256, p. 2275</ref> |
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5-Oxo-ETrE is as potent as its arachidonic acid-derived analog, ] (5-oxo-ETE), in stimulating human blood ]s and ]s;<ref name="PatelCossette2008">{{cite journal|last1=Patel|first1=P.|last2=Cossette|first2=C.|last3=Anumolu|first3=J. R.|last4=Gravel|first4=S.|last5=Lesimple|first5=A.|last6=Mamer|first6=O. A.|last7=Rokach|first7=J.|last8=Powell|first8=W. S.|title=Structural Requirements for Activation of the 5-Oxo-6E,8Z, 11Z,14Z-eicosatetraenoic Acid (5-Oxo-ETE) Receptor: Identification of a Mead Acid Metabolite with Potent Agonist Activity|journal=Journal of Pharmacology and Experimental Therapeutics|volume=325|issue=2|year=2008|pages=698–707|issn=0022-3565|doi=10.1124/jpet.107.134908|pmid=18292294|s2cid=19936422}}</ref> |
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it presumably does so by binding to the 5-oxo-ETE receptor (]) and therefore may be, like 5-oxo-ETE, a mediator of human allergic and inflammatory reactions.<ref name="PowellRokach2013"/> |
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== See also == |
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== See also == |
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*] – lists of ω-3, -6 and -9 fatty acids; some others. |
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*] – lists of ω-3 and ω-6 fatty acids; some others. |
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