Dihomo-γ-linolenic acid

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"DGLA" redirects here. For the algebra, see Differential graded Lie algebra.
Dihomo-γ-linolenic acid
Dihomo-gamma linolenic acid
Names
Preferred IUPAC name
(8Z,11Z,14Z)-Icosa-8,11,14-trienoic acid
Other names
cis,cis,cis-8,11,14-Eicosatrienoic acid; DGLA; Diroleuton (
INN
Tooltip International Nonproprietary Name)
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.015.667 Edit this at Wikidata
UNII
  • InChI=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-
    Key: HOBAELRKJCKHQD-QNEBEIHSSA-N
  • 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-
    Key: HOBAELRKJCKHQD-QNEBEIHSBE
  • CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O
Properties
C20H34O2
Molar mass 306.490 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dihomo-γ-linolenic acid (DGLA) is a 20-carbon

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.[1][2]

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

competes
with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.

Taken orally in a small study, DGLA produced antithrombotic effects.[5] Supplementing dietary GLA increases serum DGLA, as well as serum AA levels.[6] Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.[7]

Borage is a rich source of γ-linolenic acid—the dietary precursor to DGLA.

See also

References

  1. ^ Horrobin, D. F., 1990a. Gamma linolenic acid. Rev. Contemp. Pharmacother. 1, 1-45
  2. ^ Huang, 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.
  3. PMID 9732298
    . Retrieved 2007-10-16.
  4. PMID 10617996
    . Retrieved February 12, 2006.
  5. PMID 338112
    .
  6. PMID 9237935
    .
  7. PMID 10917903
    .
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