Dihomo-gamma-linolenic acid

Jump to: navigation, search
Template:Chembox E number
Dihomo-gamma linolenic acid
Other names cis,cis,cis-8,11,14-Eicosatrienoic acid
DGLA
Identifiers
3D model (JSmol)
ECHA InfoCard Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
Properties
C20H34O2
Molar mass 306.483 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Dihomo-gamma-linolenic acid (DGLA) is a 20-carbon ω-6 fatty acid. In physiological literature, it is given the name 20:3(n-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 [18:3(n-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.[3] Supplementing dietary GLA increases serum DGLA without increasing serum AA.[4]

File:Starflower 1.jpg
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 gamma -Linolenic Acid in Human Health and Nutrition". Journal of Nutrition. 128 (9): 1411–1414. Retrieved 2007-10-16. Check date values in: |year= (help)
  2. Belch, Jill JF and Alexander Hill (January 2000). "Evening primrose oil and borage oil in rheumatologic conditions". Retrieved February 12. Unknown parameter |accessyear= ignored (|access-date= suggested) (help); Check date values in: |accessdate= (help) PubMed cite
  3. Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP (1977). "Antithrombotic potential of dihomo-gamma-linolenic acid in man". British medical journal. 2 (6100): 1441–4. PMID 338112.
  4. Johnson MM, Swan DD, Surette ME; et al. (1997). "Dietary supplementation with gamma-linolenic acid alters fatty acid content and eicosanoid production in healthy humans". J. Nutr. 127 (8): 1435–44. PMID 9237935.

de:Dihomogammalinolensäure


Linked-in.jpg