Gamma-linolenic acid or GLA (-Linolenic acid), (INN and USAN gamolenic acid) is a fatty acid

found primarily in vegetable oils. When acting on GLA, 5-lipoxygenase produces no leukotrienes and
the conversion by the enzyme of arachidonic acid to leukotrienes is inhibited.

Contents
[hide]

1Chemistry

2History

3Dietary sources

4Source of eicosanoids

5Health and medicine

6Notes and references

Chemistry[edit]
GLA is categorized as an n6 (also called 6 or omega-6) fatty acid, meaning that the first double
bond on the methyl end (designated with n or ) is the sixth bond. In physiological literature, GLA is
designated as 18:3 (n6). GLA is a carboxylic acid with an 18-carbon chain and three cis double
bonds. It is an isomer of -linolenic acid, which is a polyunsaturated n3 (omega-3) fatty acid, found
in rapeseed canola oil, soy beans, walnuts, flax seed (linseed oil), perilla, chia, and hemp seed.

History[edit]
GLA was first isolated from the seed oil of evening primrose. This herbal plant was grown by Native
Americans to treat swelling in the body. In the 17th century, it was introduced to Europe and became
a popular folk remedy, earning the name king's cure-all. In 1919, Heiduschka and Lft extracted the
oil from evening primrose seeds and described an unusual linolenic acid, which they name -. Later,
the exact chemical structure was characterized by Riley.[1]
Although there are - and - forms of linolenic acid, there is no - form. One was once identified, but
it turned out to be an artifact of the original analytical process.[2]

Dietary sources[edit]
GLA is obtained from vegetable oils such as evening primrose (Oenothera biennis) oil
(EPO), blackcurrant seed oil, borage seed oil, and hemp seed oil. GLA is also found in varying
amounts in edible hemp seeds, oats, barley,[3] and spirulina. Normal safflower (Carthamus tinctorius)
oil does not contain GLA, but a genetically modified GLA safflower oil available in commercial
quantities since 2011 contains 40% GLA.[4] Borage oil contains 20% GLA, evening primrose oil
ranges from 8% to 10% GLA, and black-currant oil contains 15-20%. [5]
The human body produces GLA from linoleic acid (LA). This reaction is catalyzed by 6-
desaturase (D6D), an enzyme that allows the creation of a double bond on the sixth carbon counting
from the carboxyl terminus. LA is consumed sufficiently in most diets, from such abundant sources
as cooking oils and meats. However, a lack of GLA can occur when there is a reduction of the
efficiency of the D6D conversion (for instance, as people grow older or when there are specific
dietary deficiencies) or in disease states wherein there is excessive consumption of GLA
metabolites.[6]

Source of eicosanoids[edit]

The seed oil of Oenothera biennis (evening primrose) is a source of GLA

From GLA, the body forms dihomo--linolenic acid (DGLA). This is one of the body's three sources
of eicosanoids (along with AA and EPA.) DGLA is the precursor of the prostaglandin PGH1, which in
turn forms PGE1 and the thromboxane TXA1. Both PGE11 and TXA1 are anti-
inflammatory; thromboxane TXA1, unlike its series-2 variant, induces vasodilation, and inhibits
platelet[7] consequently, TXA1 modulates (reduces) the pro-inflammatory properties of the
thromboxane TXA2. PGE1has a role in regulation of immune system function and is used as the
medicine alprostadil.
Unlike AA and EPA, DGLA cannot yield leukotrienes. However, it can inhibit the formation of pro-
inflammatory leukotrienes from AA.[8]
Although GLA is an n6 fatty acid, a type of acid that is, in general, pro-inflammatory, it has anti-
inflammatory properties. (See discussion at Essential fatty acid interactions: The paradox of dietary
GLA.)

Health and medicine[edit]

GLA has been promoted as medication for a variety of ailments including breast pain and eczema, in
particular by David Horrobin (1939 2003), whose marketing of evening primrose oil was described
by the British Medical Journal (BMJ) as ethically dubious the substance was likely to be
remembered as "a remedy for which there is no disease".[9] In 2002 the UK's Medicines and
Healthcare products Regulatory Agency withdrew marketing authorisations for evening primrose oil
as an eczema remedy.[10] Another single source suggests that Evening Primrose Oil with adjuvant
vitamin E, may reduce breast pain.[11]

Notes and references[edit]

1. Jump up^ Yung-Sheng Huang, Vincent A. Ziboh (2001). Gamma-Linolenic Acid: Recent
Advances in Biotechnology and Clinical Applications. AOCS Press. p. 259. ISBN 1-893997-17-0.
Retrieved 2007-12-07.

2. Jump up^ Eckey, EW (1954). Vegetable Fats and Oils (volume 123 of American Chemical
Society monograph series). Reinhold. p. 542.
3. Jump up^ Qureshi A.A., Schnoes H. K., Din Z. Z., Peterson D.M., et al. (1984).
"Determination of the structure of cholesterol inhibitor II isolated from high-protein barley flour
(HPBF)". Fed. Proc. 43 (7): 2626.

4. Jump up^ Nykiforuk, C.; Shewmaker, C. (19 August 2011). "High level accumulation of
gamma linolenic acid in transgenic safflower (Carthamus tinctorius) seeds". Transgenic
Research. 21 (2): 36781. doi:10.1007/s11248-011-9543-5. PMID 21853296.

5. Jump up^ Flider, Frank J (May 2005). "GLA: Uses and New Sources" (PDF). INFORM. 16 (5):
279282. Archived from the original (PDF) on 2014-01-12.

6. Jump up^ Horrobin DF (From the Efamol Research Institute. Kentville. Nova Scotia. Canada)
(1993). "Fatty acid metabolism in health and disease: the role of delta-6-desaturase" (pdf). Am. J. Clin.
Nutr. 57 (5 Suppl): 732S736S; discussion 736S737S. PMID 8386433.

7. Jump up^ King, Michael W. "Introduction to the Eicosanoids". The Medical Biochemistry
Page. 19962013 themedicalbiochemistrypage.org, LLC. Retrieved 23 July 2013.

8. Jump up^ Belch JJ, Hill A (2000). "Evening primrose oil and borage oil in rheumatologic
conditions". Am. J. Clin. Nutr. 71 (1 Suppl): 352S6S. PMID 10617996. Retrieved 2007-12-07. DGLA
itself cannot be converted to LTs but can form a 15-hydroxyl derivative that blocks the transformation
of arachidonic acid to LTs. Increasing DGLA intake may allow DGLA to act as a competitive inhibitor of
2-series PGs and 4-series LTs and, thus, suppress inflammation.

9. Jump up^ Richmond, C. (2003). "David Horrobin". BMJ. 326 (7394):

885. doi:10.1136/bmj.326.7394.885.

10. Jump up^ Williams, H. C (2003). "Evening primrose oil for atopic dermatitis: Time To Say
Goodnight". BMJ. 327 (7428): 1358
9. doi:10.1136/bmj.327.7428.1358. JSTOR 25457999. PMC 292973 . PMID 14670851.