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Dihomo-gamma-linolenic acid
   
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Dihomo-?-linolenic acid
Dihomo-gamma linolenic acid
Other names cis,cis,cis-8,11,14-Eicosatrienoic acid
DGLA
Identifiers
CAS number
PubChem 5280581
SMILES
Properties
Molecular formula 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 references

Dihomo-?-linolenic acid (DGLA) is a 20-carbon ?-6 fatty acid. In physiological literature, it is given the name 20:3 (?-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 ?-linolenic acid (GLA; 18:3, ?-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]

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

References

  1. ^ Fan, Yang-Yi and Robert S. Chapkin (9 September 1998). "Importance of Dietary ?-Linolenic Acid in Human Health and Nutrition". Journal of Nutrition 128 (9): 1411–1414. PMID 9732298. Retrieved on 2007-10-16. 
  2. ^ Belch, Jill JF and Alexander Hill (January 2000). "Evening primrose oil and borage oil in rheumatologic conditions". Retrieved on February 12, 2006.
  3. ^ Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP (1977). "Antithrombotic potential of dihomo-?-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 ?-linolenic acid alters fatty acid content and eicosanoid production in healthy humans". J. Nutr. 127 (8): 1435–44. PMID 9237935. 


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Dihomo-gamma-linolenic acid
Dihovo
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Dihyah Kalbi
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Dihydrexidine
Dihydroactinidiolide
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