Dihomo-gamma-linolenic acid

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Dihomo-gamma-linolenic acid (DGLA) is 20-carbon ω-6 fatty acid. In physiological literature, it is given the name 20:3(n-6). Its systematic chemical name is all-cis-8,11,14-eicosatrienoic acid. 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)].

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.^[1]

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 eiconsanoids.

The chemical strucuture of DGLA showing physiological numbering (red) and chemical numbering (blue) conventions.

[edit] References

1. ↑  Belch, Jill JF and Alexander Hill (January 2000). Evening primrose oil and borage oil in rheumatologic conditions. Retrieved on February 12, 2006. PubMed cite
2. ↑ Fan, Yang-Yi and Chapkin, Robert S.. Importance of Dietary gamma-Linolenic Acid in Human Health and Nutrition. A review article at The American Society for Nutrition. Retrieved on 2006-02-03.

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