Dihomo-gamma-linolenic acid

Jump to: navigation, search
Dihomo-gamma linolenic acid
200px
Other names cis,cis,cis-8,11,14-Eicosatrienoic acid
DGLA
Identifiers
CAS number
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
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Dihomo-gamma-linolenic acid (DGLA) is a 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)].

Biological effects

The eicosanoid metabolites of DGLA are:

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]

File:Starflower 1.jpg
Borage is a rich source of γ-linolenic acid—the dietary precursor to DGLA.

References

  1. 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 2007-10-16.
  2. Belch, Jill JF and Alexander Hill (January 2000). Evening primrose oil and borage oil in rheumatologic conditions. Retrieved on February 12, 2006. PubMed cite
  3. Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP (1977). "Antithrombotic potential of dihomo-gamma-linolenic acid in man". British medical journal 2 (6100): 1441–4. PMID 338112.
  4. Johnson MM, Swan DD, Surette ME, et al (1997). "Dietary supplementation with gamma-linolenic acid alters fatty acid content and eicosanoid production in healthy humans". J. Nutr. 127 (8): 1435–44. PMID 9237935.
de:Dihomogammalinolensäure

Navigation WikiDoc | WikiPatient | Up To Date Pages | Recently Edited Pages | Recently Added Pictures

Table of Contents In Alphabetical Order | By Individual Diseases | Signs and Symptoms | Physical Examination | Lab Tests | Drugs

Editor Tools Become an Editor | Editors Help Menu | Create a Page | Edit a Page | Upload a Picture or File | Printable version | Permanent link | Maintain Pages | What Pages Link Here
There is no pharmaceutical or device industry support for this site and we need your viewer supported Donations | Editorial Board | Governance | Licensing | Disclaimers | Avoid Plagiarism | Policies
Linked-in.jpg