| Dihomo-γ-linolenic acid | |
|---|---|
 |
|
| Other names | cis,cis,cis-8,11,14-Eicosatrienoic acid DGLA |
| Identifiers | |
| CAS number | 1783-84-2  |
| 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 |
| (what is this?) (verify) 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). 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.[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, as well as serum AA levels.[4] Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.[5]
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. http://jn.nutrition.org/cgi/content/full/128/9/1411. Retrieved 2007-10-16.
- ^ Belch, Jill JF and Alexander Hill (January 2000). "Evening primrose oil and borage oil in rheumatologic conditions". http://www.ajcn.org/cgi/content/full/71/1/352S. Retrieved 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.
- ^ Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH (August 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.
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