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Dihomo-γ-linolenic acid

Names
Other names cis,cis,cis-8,11,14-Eicosatrienoic acid DGLA
Identifiers
CAS Number	1783-84-2
3D model (JSmol)	Interactive image
ECHA InfoCard	100.015.667
PubChem CID	5280581
CompTox Dashboard (EPA)	DTXSID00912351
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

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:

• 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.
• A 15-hydroxyl derivative that blocks the transformation of arachidonic acid to leukotrienes.

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.

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. {{cite web}}: Check date values in: |accessdate= (help); Unknown parameter |accessyear= ignored (|access-date= suggested) (help); 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)

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