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Dihomo-gamma-linolenic acid
From Wikipedia, the free encyclopedia
| dihomo-gamma linolenic acid | |
|---|---|
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| Chemical strucuture of DGLA showing physiological numbering (red) and chemical numbering (blue) conventions. |
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| Chemical name | (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid |
| Other names | cis,cis,cis-8,11,14-Eicosatrienoic acid |
| Chemical formula | C20H34O2 |
| Molecular mass | 306.483 g/mol |
| CAS number | ? |
| PubChem | 5280581 |
| Melting point | ? °C |
| SMILES | CCCCCC=CCC=CCC=CCCCCCCC(=O)O (canonical) CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O (isomeric) |
| Disclaimer and references | |
Dihomo-gamma-linolenic acid (DGLA) is 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)].
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 eiconsanoids.
- ^ Belch, Jill JF and Alexander Hill (January 2000). Evening primrose oil and borage oil in rheumatologic conditions. Retrieved on February 12, 2006. PubMed cite
- ^ 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 on 2007-01-05.
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