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08-SEPTEMBER-2008 09:13:22 - Dihomo-gamma-linolenic acid Dihomo-γ-linolenic acid Dihomo-gamma linolenic acid Other names cis,cis,cis-8,11,14-Eicosatrienoic acid DGLA Identifiers CAS number PubChem 5280581 SMILES CCCCCC=CCC=CCC=CCCCCCCC=OO canonical CCCCC\C=C/C\C=C/C\C=C/CCCCCCC=OO 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 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 Borage is a rich source of γ-linolenic acid-the dietary precursor to DGLA. Borage is a rich source of γ-linolenic acid-the dietary precursor to DGLA. 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. v d e Lipids: fatty acids Saturated Butyric Hexanoic Caprylic Decanoic Lauric Myristic Palmitic Stearic Arachidic Behenic Lignoceric n-3 Unsaturated α-Linolenic Stearidonic Eicosapentaenoic Docosahexaenoic n-6 Unsaturated Linoleic γ-Linolenic Dihomo-γ-linolenic Arachidonic n-9 Unsaturated Oleic Erucic Nervonic This biochemistry article is a stub. Retrieved from http://en..org/wiki/Dihomo-gamma-linolenic_acid Categories: Lipids | Fatty acids | Biochemistry stubs Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch 日本語 This page was last modified on 14 July 2008, at 19:2
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