Dihomo-gamma-linolenic acid

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Dihomo-γ-linolenic acid

Other names	cis,cis,cis-8,11,14-Eicosatrienoic acid DGLA
Identifiers
CAS number
PubChem	5280581
SMILES	`CCCCCC=CCC=CCC=CCCCCCCC(=O)O (canonical) CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O (isomeric)`
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-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).

[edit] Biological effects

The eicosanoid metabolites of DGLA are:

Series-1 thromboxanes (thromboxanes with 1 double-bond), via the COX-1 and COX-2 pathways.
Series-1 prostanoids, via the COX-1 and COX-2 pathways.^[1]
A 15-hydroxyl derivative that blocks the transformation of arachidonic acid to leukotrienes.^[2]

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 γ-linolenic acid—the dietary precursor to DGLA.

[edit] References

^ 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 on 2007-10-16.
^ Belch, Jill JF and Alexander Hill (January 2000). "Evening primrose oil and borage oil in rheumatologic conditions". Retrieved on February 12, 2006.
^ 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.
^ 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.

v • d • e Lipids: fatty acids

Saturated	Butyric • Hexanoic • Caprylic • Decanoic • Lauric • Myristic • Palmitic • Stearic • Arachidic • Behenic • Lignoceric

n−3 Unsaturated	α-Linolenic • Stearidonic • Eicosapentaenoic • Docosahexaenoic

n−6 Unsaturated	Linoleic • γ-Linolenic • Dihomo-γ-linolenic • Arachidonic

n−9 Unsaturated	Oleic • Erucic • Nervonic

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