This MedLibrary.org supplementary page on Dihomo-gamma-linolenic acid is provided directly from the open source Wikipedia as a service to our readers. Please see the note below on authorship of this content, as well as the Wikipedia usage guidelines. To search for other content from our encyclopedia supplement, please use the form below:
Related Sponsors
| Dihomo-γ-linolenic acid | |
|---|---|
 |
|
| Other names | cis,cis,cis-8,11,14-Eicosatrienoic acid DGLA |
| Identifiers | |
| CAS number | |
| PubChem | |
| SMILES |
|
| 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).
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]
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.
|
||||||||||||||
 |
This biochemistry article is a stub. You can help Wikipedia by expanding it. |
Wikipedia content modification information:
- This page was last modified on 2 September 2008, at 21:06.
Wikipedia Authorship and Review
Wikipedia content provided here is not reviewed directly by MedLibrary.org. Wikipedia content is authored by an open community of volunteers and is not produced by or in any way affiliated with MedLibrary.org.
Wikipedia Usage Guidelines
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article on "Dihomo-gamma-linolenic acid".
The URL for this specific entry is:
All Wikipedia text is available under the terms of the GNU Free Documentation License. (See Copyrights for details). Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc.