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The ] metabolites of DGLA are: The ] metabolites of DGLA are:
* Series-1 ]s (thromboxanes with 1 double-bond), via the ] pathways. * Series-1 ]s (thromboxanes with 1 double-bond), via the ] pathways.
* Series-1 ]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= ] ] | accessdate= 2007-10-16 | journal =Journal of Nutrition | volume = 128 |issue = 9 |pages = 1411–1414 | pmid=9732298 | month=Sep | day=01}}</ref> * Series-1 ]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>
* A 15-hydroxyl derivative that blocks the transformation of ] to ]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 ] to ]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, 2006}}</ref>


All of these effects are anti-inflammatory. This is in marked contrast with the analogous metabolites of ] (AA) which are the series-2 thromboxanes and prostanoids and the series-4 leukotrienes. In addition to yielding anti-inflammatory eicosanoids, DGLA ] 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 ] (AA) which are the series-2 thromboxanes and prostanoids and the series-4 leukotrienes. In addition to yielding anti-inflammatory eicosanoids, DGLA ] with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.
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==References== ==References==
{{reflist}} {{Reflist}}


{{Fatty acids}} {{Fatty acids}}


{{DEFAULTSORT:Dihomo-Gamma-Linolenic Acid}}
] ]
] ]

Revision as of 10:29, 19 November 2009

Dihomo-γ-linolenic acid
Dihomo-gamma linolenic acid
Names
Other names cis,cis,cis-8,11,14-Eicosatrienoic acid
DGLA
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.015.667 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • CCCCCC=CCC=CCC=CCCCCCCC(=O)O (canonical)
    CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O (isomeric)
Properties
Chemical formula C20H34O2
Molar mass 306.483 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Dihomo-γ-linolenic acid (DGLA) is a 20-carbon 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 γ-linolenic acid (GLA; 18:3, ω−6). GLA, in turn, is a desaturation product of linoleic acid (18:2, ω−6).

Biological effects

The eicosanoid metabolites of DGLA are:

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 competes with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.

Taken orally in a small study, DGLA produced antithrombotic effects. Supplementing dietary GLA increases serum DGLA, as well as serum AA levels. Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.

Borage is a rich source of γ-linolenic acid—the dietary precursor to DGLA.

References

  1. Fan, Yang-Yi and Robert S. Chapkin (9 September, 1998). "Importance of Dietary γ-Linolenic Acid in Human Health and Nutrition". Journal of Nutrition. 128 (9): 1411–1414. PMID 9732298. Retrieved 2007-10-16. {{cite journal}}: Check date values in: |date= (help); Unknown parameter |day= ignored (help); Unknown parameter |month= ignored (help)
  2. Belch, Jill JF and Alexander Hill (2000). "Evening primrose oil and borage oil in rheumatologic conditions". Retrieved February 12, 2006. {{cite web}}: Unknown parameter |month= ignored (help)
  3. Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP (1977). "Antithrombotic potential of dihomo-γ-linolenic acid in man". British medical journal. 2 (6100): 1441–4. PMID 338112.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Johnson MM, Swan DD, Surette ME; et al. (1997). "Dietary supplementation with γ-linolenic acid alters fatty acid content and eicosanoid production in healthy humans". J. Nutr. 127 (8): 1435–44. PMID 9237935. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  5. Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH (2000). "Addition of eicosapentaenoic acid to gamma-linolenic acid-supplemented diets prevents serum arachidonic acid accumulation in humans". J. Nutr. 130 (8): 1925–31. PMID 10917903. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Lipids: fatty acids
Saturated
ω−3 Unsaturated
ω−5 Unsaturated
ω−6 Unsaturated
ω−7 Unsaturated
ω−9 Unsaturated
ω−10 Unsaturated
ω−11 Unsaturated
ω−12 Unsaturated


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