dihomo-γ-linolenic acid
{{redirect|DGLA|the algebra|Differential graded Lie algebra}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 291015519
| Name = Dihomo-γ-linolenic acid
| ImageFile = DGLAnumbering.png
| ImageSize = 250px
| ImageName = Dihomo-gamma linolenic acid
| PIN = (8Z,11Z,14Z)-Icosa-8,11,14-trienoic acid
| OtherNames = cis,cis,cis-8,11,14-Eicosatrienoic acid; DGLA; Diroleuton ({{abbrlink|INN|International Nonproprietary Name}})
| Section1 = {{Chembox Identifiers
| CASNo=1783-84-2
| PubChem=5280581
| SMILES = CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FC398RK06S| ChemSpiderID = 4444199
| InChI = 1/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
| InChIKey = HOBAELRKJCKHQD-QNEBEIHSBE
| StdInChI = 1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
| StdInChIKey = HOBAELRKJCKHQD-QNEBEIHSSA-N
}}
| Section2 = {{Chembox Properties
| C=20|H=34|O=2
| MeltingPt =
}}
}}
Dihomo-γ-linolenic acid (DGLA) is a 20-carbon ω−6 fatty acid (also called, cis,cis,cis-8,11,14-eicosatrienoic acid). In physiological literature, it is given the name 20:3 (ω−6). 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 (Delta 6 desaturase) of linoleic acid (18:2, ω−6). DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. DGLA is an extremely uncommon fatty acid, found only in trace amounts in animal products.Horrobin, D. F., 1990a.
Gamma linolenic acid.
Rev. Contemp. Pharmacother. 1, 1-45Huang, Y.-S. and Mills, D. E. (Eds.), 1996.
Gamma-linolenic acid metabolism and its roles in nutrition and medicine.
AOCS Press, Champaign, Illinois, 319 pp.
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.{{cite journal |author1=Fan, Yang-Yi |author2=Chapkin, Robert S. | title=Importance of Dietary γ-Linolenic Acid in Human Health and Nutrition | date=9 September 1998 | journal=Journal of Nutrition | volume=128 | issue=9 | pages=1411–4 | pmid=9732298 | doi=10.1093/jn/128.9.1411 | doi-access=free}}
- A 15-hydroxyl derivative that blocks the transformation of arachidonic acid to leukotrienes.{{cite journal |author1=Belch, Jill J.F. |author-link=Jill Belch |author2=Hill, Alexander |title=Evening primrose oil and borage oil in rheumatologic conditions |journal=The American Journal of Clinical Nutrition |date=January 2000 |volume=71 |issue=1 Suppl |pages=352S–6S |doi=10.1093/ajcn/71.1.352S |pmid=10617996 |doi-access=free }}
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.{{cite journal
|vauthors=Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP |title=Antithrombotic potential of dihomo-γ-linolenic acid in man
|journal=British Medical Journal
|volume=2
|issue=6100
|pages=1441–1444
|year=1977
|pmid=338112
|doi=10.1136/bmj.2.6100.1441
|pmc=1632618
}} Supplementing dietary GLA increases serum DGLA, as well as serum AA levels.{{cite journal
|author=Johnson MM
|title=Dietary supplementation with γ-linolenic acid alters fatty acid content and eicosanoid production in healthy humans
|journal=J. Nutr.
|volume=127
|issue=8
|pages=1435–44
|year=1997
|pmid=9237935
|name-list-style=vanc|author2=Swan DD
|author3=Surette ME
|display-authors=3
|last4=Stegner
|first4=J
|last5=Chilton
|first5=T
|last6=Fonteh
|first6=AN
|last7=Chilton
|first7=FH
|doi=10.1093/jn/127.8.1435
|doi-access=free
}} Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.{{cite journal
|vauthors=Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH |title=Addition of eicosapentaenoic acid to gamma-linolenic acid-supplemented diets prevents serum arachidonic acid accumulation in humans
|journal=J. Nutr.
|volume=130
|issue=8
|pages=1925–31
|date=August 2000
|doi=10.1093/jn/130.8.1925
|pmid=10917903
|doi-access=free
}}
Image:Starflower 1.jpg is a rich source of γ-linolenic acid—the dietary precursor to DGLA.]]
See also
References
{{Reflist}}
{{Fatty acids}}
{{Prostanoidergics}}
{{Leukotrienergics}}
{{DEFAULTSORT:Dihomo-gamma-linolenic acid}}