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{{redirect|DGLA|the algebra|Differential graded Lie algebra}}
{{chembox
{{chembox
| Watchedfields = changed
| verifiedrevid = 291015519
| Name = Dihomo-γ-linolenic acid
| Name = Dihomo-γ-linolenic acid
| ImageFile = DGLAnumbering.png
| ImageFile = DGLAnumbering.png
| ImageSize = 250px
| ImageSize = 250px
| ImageName = Dihomo-gamma linolenic acid
| ImageName = Dihomo-gamma linolenic acid
| OtherNames = ''cis'',''cis'',''cis''-8,11,14-Eicosatrienoic acid<br>DGLA
| = '''','''',''''-8,11,14- acid
| OtherNames = ''cis'',''cis'',''cis''-8,11,14-Eicosatrienoic acid; DGLA; Diroleuton ({{abbrlink|INN|International Nonproprietary Name}})
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| CASNo=1783-84-2
| CASNo=1783-84-2
| PubChem=5280581
| PubChem=5280581
| SMILES = {{SMILES|S=CCCCCC=CCC=CCC=CCCCCCCC(=O)O}} (canonical)<br />{{SMILES|S=CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O}} (isomeric)
| SMILES = CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FC398RK06S| ChemSpiderID = 4444199
| 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/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
| InChIKey = HOBAELRKJCKHQD-QNEBEIHSBE
| 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/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
| StdInChIKey = HOBAELRKJCKHQD-QNEBEIHSSA-N
}}
}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| Formula = C<sub>20</sub>H<sub>34</sub>O<sub>2</sub>
| C20H34O2
⚫
| MeltingPt =
| MolarMass = 306.483 g/[[Mole (unit)|mol]]
⚫
| MeltingPt =
}}
}}
}}
}}


'''Dihomo-γ-linolenic acid''' ('''DGLA''') is a 20-carbon [[Omega-6 fatty acid|ω−6 fatty acid]]. In physiological literature, it is given the name 20:3 (ω−6). Chemically, DGLA is a [[carboxylic acid]] with a 20-carbon chain and three ''[[cis]]'' double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of [[Gamma-linolenic acid|γ-linolenic acid]] (GLA; 18:3, ω−6). GLA, in turn, is a desaturation product of [[linoleic acid]] (18:2, ω−6).
'''Dihomo-γ-linolenic acid''' ('''DGLA''') is a 20-carbon [[Omega-6 fatty acid|ω−6 fatty acid]] In physiological literature, it is given the name 20:3 (ω−6). DGLA is a [[carboxylic acid]] with a 20-carbon chain and three ''[[cis]]'' double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of [[Gamma-linolenic acid|γ-linolenic acid]] (GLA; 18:3, ω−6). GLA, in turn, is a desaturation product of [[linoleic acid]] (18:2, ω−6).
Gamma linolenic acid.
Rev. Contemp. Pharmacother. 1, 1-45</ref><ref>Huang, Y.-S. and Mills, D. E. (Eds.), 1996.
Gamma-linolenic acid metabolism and its roles in nutrition and medicine.
AOCS Press, Champaign, Illinois, 319 pp.</ref>


== Biological effects==
== Biological effects==
The [[eicosanoid]] metabolites of DGLA are:
The [[eicosanoid]] metabolites of DGLA are:
* Series-1 [[thromboxane]]s (thromboxanes with 1 double-bond), via the [[Cyclooxygenase|COX-1 and COX-2]] pathways.
* Series-1 [[thromboxane]]s (thromboxanes with 1 double-bond), via the [[Cyclooxygenase|COX-1 and COX-2]] pathways.
* Series-1 [[prostanoid]]s, via the COX-1 and COX-2 pathways.<ref>{{cite journal | author=Fan, Yang-Yi and Robert S. Chapkin | title=Importance of Dietary γ-Linolenic Acid in Human Health and Nutrition | url=http://jn.nutrition.org/cgi/content/full/128/9/1411 | date= [[9 September]] [[1998]] | accessdate= 2007-10-16 | journal =Journal of Nutrition | volume = 128 |issue = 9 |pages = 1411–1414 | pmid=9732298 | month=Sep | day=01}}</ref>
* Series-1 [[prostanoid]]s, via the COX-1 and COX-2 pathways.<ref>{{cite journal |=Fan, Yang-Yi Robert S. | title=Importance of Dietary γ-Linolenic Acid in Human Health and Nutrition | date=9 September 1998 | journal=Journal of Nutrition | volume=128 |issue=9 |pages= | pmid=9732298 | = | =}}</ref>
* A 15-hydroxyl derivative that blocks the transformation of [[arachidonic acid]] to [[leukotriene]]s.<ref>{{cite web| author= Belch, Jill JF and Alexander Hill| title=Evening primrose oil and borage oil in rheumatologic conditions|month=January | year=2000| url= http://www.ajcn.org/cgi/content/full/71/1/352S|accessdate=February 12|accessyear=2006}}</ref>
* A 15-hydroxyl derivative that blocks the transformation of [[arachidonic acid]] to [[leukotriene]]s.<ref>{{cite |=Belch, Jill | title=Evening primrose oil and borage oil in rheumatologic conditions|= =2000| = .ajcn/711352S|= |=}}</ref>


All of these effects are anti-inflammatory. This is in marked contrast with the analogous metabolites of [[arachidonic acid]] (AA) which are the series-2 thromboxanes and prostanoids and the series-4 leukotrienes. In addition to yielding anti-inflammatory eicosanoids, DGLA [[Competitive inhibitor|competes]] with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.
All of these effects are anti-inflammatory. This is in marked contrast with the analogous metabolites of [[arachidonic acid]] (AA) which are the series-2 thromboxanes and prostanoids and the series-4 leukotrienes. In addition to yielding anti-inflammatory eicosanoids, DGLA [[Competitive |competes]] with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.


Taken orally in a small study, DGLA produced antithrombotic effects.<ref name="pmid338112">{{cite journal
Taken orally in a small study, DGLA produced antithrombotic effects.<ref name="pmid338112">{{cite journal
|author=Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP
|=Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP
⚫
|journal=British
|title=Antithrombotic potential of dihomo-γ-linolenic acid in man
⚫
|journal=British medical journal
|volume=2
|volume=2
|issue=6100
|issue=6100
|pages=1441–4
|pages=
|year=1977
|year=1977
|pmid=338112
|pmid=338112
|doi=10.1136/bmj.2.6100.1441
|pmc=1632618
}}</ref> Supplementing dietary GLA increases serum DGLA, as well as serum AA levels.<ref name="pmid9237935">{{cite journal
}}</ref> Supplementing dietary GLA increases serum DGLA, as well as serum AA levels.<ref name="pmid9237935">{{cite journal
|author=Johnson MM, Swan DD, Surette ME, ''et al.''
|author=Johnson MM
|title=Dietary supplementation with γ-linolenic acid alters fatty acid content and eicosanoid production in healthy humans
|title=Dietary supplementation with γ-linolenic acid alters fatty acid content and eicosanoid production in healthy humans
|journal=J. Nutr.
|journal=J. Nutr.
Line 45: Line 59:
|year=1997
|year=1997
|pmid=9237935
|pmid=9237935
|name-list-style=vanc|author2=Swan DD
|author3=Surette ME
|display-authors=3
|last4=Stegner
|first4=J
|last5=Chilton
|first5=T
|last6=Fonteh
|first6=AN
|last7=Chilton
|first7=FH
|doi=10.1093/jn/127.8.1435
|doi-access=free
}}</ref> Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.<ref name="pmid10917903">{{cite journal
}}</ref> Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.<ref name="pmid10917903">{{cite journal
|author=Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH
|=Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH
|title=Addition of eicosapentaenoic acid to gamma-linolenic acid-supplemented diets prevents serum arachidonic acid accumulation in humans
|journal=J. Nutr.
|journal=J. Nutr.
|volume=130
|volume=130
|issue=8
|issue=8
|pages=1925–31
|pages=1925–31
|year=2000
|=2000
|doi=10.1093/jn/130.8.1925
|month=August
|pmid=10917903
|pmid=10917903
|doi-access=free
}}</ref>
}}</ref>


[[Image:Starflower 1.jpg|thumb|right|200px|[[Borage]] is a rich source of γ-linolenic acid&mdash;the dietary precursor to DGLA.]]
[[Image:Starflower 1.jpg|thumb|right|200px|[[Borage]] is a rich source of γ-linolenic acid&mdash;the dietary precursor to DGLA.]]

== See also ==
* [[Essential fatty acid]]


==References==
==References==
{{reflist}}
{{}}


{{Fatty acids}}
{{Fatty acids}}
{{Prostanoidergics}}
{{Leukotrienergics}}


{{DEFAULTSORT:Dihomo-gamma-linolenic acid}}
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[[Category:Lipids]]
[[Category:Fatty acids]]
[[Category:Fatty acids]]
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[[Category:]]


{{biochem-stub}}

[[de:Dihomogammalinolensäure]]
[[ja:ジホモ-γ-リノレン酸]]
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