| Revision as of 12:12, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 476769547 of page Gamma-Linolenic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 18:51, 15 September 2024 edit SilverLocust (talk | contribs)Autopatrolled, Administrators25,265 edits cleanup from move |
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{{More citations needed|date=December 2021|find=Gamma-Linolenic Acid}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{About|γ-Linole'''n'''ic acid|alpha-linolenic acid|α-Linolenic acid|linoleic acid (no "n")|Linoleic acid}} |
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{{lowercase title}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443832369 |
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| verifiedrevid = 476992532 |
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| Name = '''γ-Linolenic acid''' |
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| OtherNames= Gamma-linolenic acid, GLA |
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| Name = '''γ-Linolenic acid''' |
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| ImageFile = GLAnumbering.png |
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| ImageFile = GLAnumbering.png |
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| ImageSize = 250px |
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| ImageSize = 250px |
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| ImageFileL2 = Gamma linolenic acid spacefill.png |
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| ImageFileL2 = Gamma linolenic acid spacefill.png |
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| ImageFileR2 = Gamma linolenic acid.png |
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| ImageFileR2 = Gamma linolenic acid.png |
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| IUPACName = all-''cis''-6,9,12-octadecatrienoic acid |
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| PIN = (6''Z'',9''Z'',12''Z'')-Octadeca-6,9,12-trienoic acid |
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| OtherNames= Gamma-linolenic acid, gamolenic acid, GLA |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| IUPHAR_ligand = 4710 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4444436 |
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| ChemSpiderID = 4444436 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 506-26-3 |
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| CASNo = 506-26-3 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 28661 |
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| ChEBI = 28661 |
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| SMILES = O=C(O)CCCC\C=C/C\C=C/C\C=C/CCCCC |
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| SMILES = O=C(O)CCCC\C=C/C\C=C/C\C=C/CCCCC |
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| PubChem = 5280933 |
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| PubChem = 5280933 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=18 | H=30 | O=2 |
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| Formula = C<sub>18</sub>H<sub>30</sub>O<sub>2</sub> |
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| Appearance = Colorless oil |
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| MolarMass = ] g/] |
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|Section6={{Chembox Pharmacology |
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| ATCCode_prefix = D11 |
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| ATCCode_suffix = AX02 |
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'''γ-Linolenic acid''' or '''GLA''' (]: '''gamolenic acid''') is an ], or omega-6, fatty acid found primarily in seed oils. When acting on GLA, ] produces no ]s and the conversion by the enzyme of ] to leukotrienes is inhibited. |
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==Chemistry== |
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GLA is categorized as an ] (also called ω−6 or omega-6) fatty acid, meaning that the first double bond on the methyl end (designated with ''n'' or ω) is the sixth bond. In physiological literature, GLA is designated as 18:3 (''n''−6). GLA is a ] with an 18-carbon chain and three '']'' ]s. It is a ] of ], which is a polyunsaturated ''n''−3 (omega-3) fatty acid, found in ] ] oil, ]s, ]s, ] seed (]), ], ], and ] seed. |
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==History== |
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GLA was first isolated from the seed oil of ]. This herbal plant was grown by ]s to treat swelling in the body. |
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In the 17th century, it was introduced to Europe and became a popular folk remedy, earning the name ''king's cure-all.'' |
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In 1919, Heiduschka and Lüft extracted the oil from evening primrose seeds and described an unusual linolenic acid, which they name γ-. |
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Later, the exact chemical structure was characterized by Riley.<ref name=Huang>{{cite book |
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| title=Gamma-Linolenic Acid: Recent Advances in Biotechnology and Clinical Applications |
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| author= Yung-Sheng Huang, Vincent A. Ziboh |
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| url=https://books.google.com/books?id=vU5KdI_FXZwC&q=++%22gamma+linolenic+acid%22&pg=PR7 |
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| year= 2001 |publisher=AOCS Press|pages=259 |isbn= 1-893997-17-0 |
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| access-date=2007-12-07}}</ref> |
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Although there are α- and γ- forms of linolenic acid, there is no β- form. One was once identified, but it turned out to be an artifact of the original analytical process.<ref name='Eckey1954'>{{cite book | last = Eckey | first = EW | title = Vegetable Fats and Oils (volume 123 of American Chemical Society monograph series) | publisher = Reinhold | year = 1954 | pages = 542 }}</ref> |
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==Dietary sources== |
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GLA is obtained from vegetable oils such as evening primrose ('']'') oil (EPO), ] seed oil, ], and ]. GLA is also found in varying amounts in edible ] seeds, oats, barley,<ref>{{cite journal | author = Qureshi A.A. | author2 = Schnoes H.K. | author3 = Din Z.Z. | author4 = Peterson D.M. | journal = Fed. Proc. | volume = 43 | issue=7 | title=Determination of the structure of cholesterol inhibitor II isolated from high-protein barley flour (HPBF) | pages = 2626 | year = 1984 | display-authors = etal}}</ref> and ].<ref>{{cite journal | author = Golmakani M.T. | author2 = Mendiola J.A. | author3 = Rezaei K. | author4 = Ibáñez E. | journal = J. Supercritical Fluids | volume = 62 | title=Expanded ethanol with {{chem|CO|2}} and pressurized ethyl lactate to obtain fractions enriched in γ-Linolenic Acid from ''Arthrospira platensis'' (Spirulina) | pages = 109–115 | year = 2012 | doi = 10.1016/j.supflu.2011.11.026 | hdl = 10261/43494 | url=http://doi.org/10.1016/j.supflu.2011.11.026| hdl-access = free }}</ref> Normal ] (''Carthamus tinctorius'') oil does not contain GLA, but a genetically modified GLA safflower oil available in commercial quantities since 2011 contains 40% GLA.<ref>{{cite journal|last1=Nykiforuk|first1=Cory L.|display-authors=etal|title=High level accumulation of gamma linolenic acid (C18:3Δ6,9,12 cis) in transgenic safflower (''Carthamus tinctorius'') seeds|journal=Transgenic Research|date=19 August 2011|doi=10.1007/s11248-011-9543-5|volume=21|issue=2|pages=367–381|pmid=21853296|s2cid=17870059}}</ref> Borage oil contains 20% GLA, evening primrose oil ranges from 8% to 10% GLA, and black-currant oil contains 15–20%.<ref>{{cite journal|last=Flider |first=Frank J. |title=GLA: Uses and new sources |journal=INFORM |date=May 2005 |volume=16 |issue=5 |pages=279–282 |url=http://www.adoniskish.com/PDF/Super%20Mix/gla.pdf |url-status=dead |archive-url=https://web.archive.org/web/20140112160125/http://www.adoniskish.com/PDF/Super%20Mix/gla.pdf |archive-date=2014-01-12 }}</ref> |
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The human body produces GLA from ] (LA). This reaction is catalyzed by Δ<sup>6</sup>-] (D6D), an enzyme that allows the creation of a double bond on the sixth carbon counting from the carboxyl terminus. LA is consumed sufficiently in most diets, from such abundant sources as ]s and ]s. However, a lack of GLA can occur when there is a reduction of the efficiency of the D6D conversion (for instance, as people grow older or when there are specific dietary deficiencies) or in disease states wherein there is excessive consumption of GLA metabolites.<ref name="pmid8386433">{{cite journal |author=Horrobin D.F. (From the Efamol Research Institute. Kentville. Nova Scotia. Canada) |title=Fatty acid metabolism in health and disease: the role of delta-6-desaturase |journal=] |volume=57 |issue=5 Suppl |pages=732S–736S; discussion 736S–737S |year=1993 |pmid=8386433 |doi=10.1093/ajcn/57.5.732S|doi-access=free }}</ref> |
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==Source of eicosanoids== |
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] |
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From GLA, the body forms ] (DGLA). This is one of the body's three sources of ]s (along with ] and ].) DGLA is the precursor of the ] PGH<sub>1</sub>, which in turn forms PGE<sub>1</sub> and the ] TXA<sub>1</sub>. Both PGE1<sub>1</sub> and TXA<sub>1</sub> are anti-inflammatory; ] TXA<sub>1</sub>, unlike its series-2 variant, induces vasodilation, and inhibits platelet<ref>{{cite web|last=King|first=Michael W|title=Introduction to the Eicosanoids|url=http://themedicalbiochemistrypage.org/eicosanoids.php|work=The Medical Biochemistry Page|publisher=1996–2013 themedicalbiochemistrypage.org, LLC|access-date=23 July 2013}}</ref> consequently, TXA<sub>1</sub> modulates (reduces) the pro-inflammatory properties of the thromboxane TXA<sub>2</sub>. PGE<sub>1</sub> has a role in regulation of ] function and is used as the medicine ]. |
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Unlike AA and EPA, DGLA cannot yield ]s. However, it can inhibit the formation of pro-inflammatory leukotrienes from AA.<ref name="Belch">{{cite journal |vauthors=Belch JJ, Hill A |title=Evening primrose oil and borage oil in rheumatologic conditions |journal=American Journal of Clinical Nutrition |volume=71 |issue=1 Suppl |pages=352S–356S |year=2000 |pmid=10617996 |doi= 10.1093/ajcn/71.1.352s| quote=DGLA itself cannot be converted to LTs but can form a 15-hydroxyl derivative that blocks the transformation of arachidonic acid to LTs. Increasing DGLA intake may allow DGLA to act as a competitive inhibitor of 2-series PGs and 4-series LTs and, thus, suppress inflammation. |doi-access=free }}</ref> |
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Although GLA is an ''n''−6 fatty acid, a type of acid that is, in general, pro-inflammatory{{Citation needed|reason=This seems to be earlier since refuted thinking|date=October 2021}}, it has anti-inflammatory properties. ''(See discussion at ].)'' |
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==Topical use== |
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In 2002, the UK ] withdrew marketing authorisations for evening primrose oil as an ] remedy.<ref name=goodnight>{{cite journal|jstor=25457999|doi=10.1136/bmj.327.7428.1358|title=Evening primrose oil for atopic dermatitis: Time To Say Goodnight|year=2003|last1=Williams|first1=H.C.|journal=BMJ|volume=327|issue=7428|pages=1358–9|pmid=14670851|pmc=292973}}</ref> <!--The BMJ commented in 2003 that it had taken 20 years to demonstrate that the substance was of no use in atopic dermatitis, and called for more transparency in the research on which drug licensing decisions were taken.<ref name=Smith2003>{{cite journal|doi = 10.1136/bmj.327.7428.0-h|title = The drugs don't work|year = 2003|last1 = Smith|first1 = R.|journal = BMJ|volume = 327|issue = 7428|pages = 0–h}}</ref> an article from 2003 is outdated--> |
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==Notes and references== |
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{{Reflist|30em}} |
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{{Fatty acids}} |
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{{Prostanoidergics}} |
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{{Leukotrienergics}} |
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{{DEFAULTSORT:Linolenic Acid, γ-}} |
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