Essential fatty acid - Wikipedia https://en.wikipedia.

org/wiki/Essential_fatty_acid

Essential fatty acid

From Wikipedia, the free encyclopedia

Essential fatty acids, or EFAs, are fatty acids that humans and other animals must ingest because the body
requires them for good health but cannot synthesize them.[1]

The term "essential fatty acid" refers to fatty acids required for biological processes but does not include the fats
that only act as fuel. Essential fatty acids should not be confused with essential oils, which are "essential" in the
sense of being a concentrated essence.

Only two fatty acids are known to be essential for humans: alpha-linolenic acid (an omega-3 fatty acid) and
linoleic acid (an omega-6 fatty acid).[2] Some other fatty acids are sometimes classified as "conditionally
essential," meaning that they can become essential under some developmental or disease conditions; examples
include docosahexaenoic acid (an omega-3 fatty acid) and gamma-linolenic acid (an omega-6 fatty acid).

When the two EFAs were discovered in 1923, they were designated "vitamin F", but in 1929, research on rats
showed that the two EFAs are better classified as fats rather than vitamins.[3]

Contents
1 Functions
2 Nomenclature and terminology
2.1 Examples
2.2 Essential fatty acids
3 Food sources
4 Human health
4.1 Essential fatty acid deficiency
4.2 Treatment for depression
5 See also
6 References

Functions
The biological effects of the -3 and -6 fatty acids are mediated by their mutual interactions, see
Essential fatty acid interactions for detail.

In the body, essential fatty acids serve multiple functions. In each of these, the balance between dietary -3 and
-6 strongly affects function.

They are modified to make

the classic eicosanoids (affecting inflammation and many other cellular functions)
the endocannabinoids (affecting mood, behavior and inflammation)
the lipoxins which are a group of eicosanoid derivatives formed via the lipoxygenase pathway from
-6 EFAs and resolvins from -3 (in the presence of acetylsalicylic acid, downregulating
inflammation)

1 of 7 12/19/2016 09:37 PM
Essential fatty acid - Wikipedia https://en.wikipedia.org/wiki/Essential_fatty_acid

the isofurans, neurofurans, isoprostanes, hepoxilins, epoxyeicosatrienoic acids (EETs) and

Neuroprotectin D
They form lipid rafts (affecting cellular signaling)[4]
They act on DNA (activating or inhibiting transcription factors such as NF-B, which is linked to
pro-inflammatory cytokine production)[5]

Nomenclature and terminology

Fatty acids are straight chain hydrocarbons possessing a carboxyl (COOH) group at one end. The carbon next to
the carboxylate is known as , the next carbon , and so forth. Since biological fatty acids can be of different
lengths, the last position is labelled as a "", the last letter in the Greek alphabet. Since the physiological
properties of unsaturated fatty acids largely depend on the position of the first unsaturation relative to the end
position and not the carboxylate. For example, the term -3 signifies that the first double bond exists as the
third carbon-carbon bond from the terminal CH3 end () of the carbon chain. The number of carbons and the
number of double bonds is also listed.

-3 18:4 (stearidonic acid) or 18:4 -3 or 18:4 n3 indicates an 18-carbon chain with 4 double bonds, and with
the first double bond in the third position from the CH3 end. Double bonds are cis and separated by a single
methylene (CH2) group unless otherwise noted. So in free fatty acid form, the chemical structure of stearidonic
acid is:

Examples

For complete tables of -3 and -6 essential fatty acids, see Polyunsaturated fatty acids.

The essential fatty acids start with the short chain polyunsaturated fatty acids (SC-PUFA):

-3 fatty acids:
-Linolenic acid or ALA (18:3n-3)
-6 fatty acids:
Linoleic acid or LA (18:2n-6)

These two fatty acids cannot be synthesized by humans because humans lack the desaturase enzymes required
for their production.

They form the starting point for the creation of longer and more desaturated fatty acids, which are also referred
to as long-chain polyunsaturated fatty acids (LC-PUFA):

-3 fatty acids:
eicosapentaenoic acid or EPA (20:5n-3)
docosahexaenoic acid or DHA (22:6n-3)
-6 fatty acids:
gamma-linolenic acid or GLA (18:3n-6)
dihomo-gamma-linolenic acid or DGLA (20:3n-6)

2 of 7 12/19/2016 09:37 PM
Essential fatty acid - Wikipedia https://en.wikipedia.org/wiki/Essential_fatty_acid

arachidonic acid or AA (20:4n-6)

-9 fatty acids are not essential in humans because they can be synthesized from carbohydrates or other fatty
acids.

Essential fatty acids

Mammals lack the ability to introduce double bonds in fatty acids beyond carbon 9 and 10, hence -6 linoleic
acid (18:2,9,12), abbreviated LA (18:2n-6), and the -3 linolenic acid (18:3,9,12,15), abbreviated ALA
(18:3n-3), are essential for humans in the diet. In humans, arachidonic acid (20:4,5,8,11,14, abbreviated
20:4n-6) can be synthesized from LA by alternative desaturation and chain elongation.

Humans can convert both LA and ALA to docosapentaenoic acid (22:5n-6) and docosahexaenoic acid (22:6n-3;
DHA) respectively, although the conversion to DHA is limited, resulting in lower blood levels of DHA than
through direct ingestion. This is illustrated by studies in vegans and vegetarians.[6] If there is relatively more
LA than ALA in the diet it favors the formation of docosapentaenoic acid (22:5n-6) from LA rather than
docosahexaenoic acid (22:6n-3) from ALA. This effect can be altered by changing the relative ratio of
LA:ALA, but is more effective when total intake of polyunsaturated fatty acids is low. However, the capacity to
convert LA to AA and ALA to DHA in the preterm infant is limited, and preformed AA and DHA may be
required to meet the needs of the developing brain. Both AA and DHA are present in breastmilk and contribute
along with the parent fatty acids LA and ALA to meeting the requirements of the newborn infant. Many infant
formulas have AA and DHA added to them with an aim to make them more equivalent to human milk.

Essential nutrients are defined as those that cannot be synthesized de novo in sufficient quantities for normal
physiological function. This definition is met for LA and ALA but not the longer chain derivatives in adults.[7]
The longer chain derivatives particularly, however, have pharmacological properties that can modulate disease
processes, but this should not be confused with dietary essentiality.

Between 1930 and 1950, arachidonic acid and linolenic acid were termed 'essential' because each was more or
less able to meet the growth requirements of rats given fat-free diets. However, they were yet to be recognized
as essential nutrients for humans. In the 1950s Arild Hansen showed that infants fed skimmed milk developed
essential fatty acid deficiency. It was characterized by an increased food intake, poor growth, and a scaly
dermatitis, and was cured by the administration of corn oil.

Later work by Hansen randomized 426 children, mainly black, to four treatments: modified cow's milk formula,
skimmed milk formula, skimmed milk formula with coconut oil, or cow's milk formula with corn oil. The
infants who received the skimmed milk formula or the formula with coconut oil developed essential fatty acid
deficiency signs and symptoms. This could be cured by administration of ethyl linoleate (the ethyl ester of
linoleic acid) with about 1% of the energy intake.[8]

Collins et al. 1970[9] were the first to demonstrate linoleic acid deficiency in adults. They found that patients
undergoing intravenous nutrition with glucose became isolated from their fat supplies and rapidly developed
biochemical signs of essential fatty acid deficiency (an increase in 20:3n-9/20:4n-6 ratio in plasma) and skin
symptoms. This could be treated by infusing lipids, and later studies showed that topical application of
sunflower oil would also resolve the dermal symptoms.[10] Linoleic acid has a specific role in maintaining the
skin water-permeability barrier, probably as constituents of acylglycosylceramides. This role cannot be met by
any -3 fatty acids or by arachidonic acid.

The main physiological requirement for -6 fatty acids is attributed to arachidonic acid. Arachidonic acid is the
major precursor of prostaglandins, leukotrienes, and anandamides that play a vital role in cell signaling.

3 of 7 12/19/2016 09:37 PM
Essential fatty acid - Wikipedia https://en.wikipedia.org/wiki/Essential_fatty_acid

Metabolites from the -3 pathway, mainly from eicosapentaenoic acid, are mostly inactive, and this explains
why -3 fatty acids do not correct the reproductive failure in rats where arachidonic is needed to make active
prostaglandins that cause uterine contraction.[11] To some extent, any -3 or -6 can contribute to the growth-
promoting effects of EFA deficiency, but only -6 fatty acids can restore reproductive performance and correct
the dermatitis in rats. Particular fatty acids are still needed at critical life stages (e.g. lactation) and in some
disease states.

In nonscientific writing, common usage is that the term essential fatty acid comprises all the -3 or -6 fatty
acids. Conjugated fatty acids like calendic acid are not considered essential. Authoritative sources include the
whole families, but generally only make dietary recommendations for LA and ALA with the exception of DHA
for infants under the age of 6 months. Recent reviews by WHO/FAO in 2009 and the European Food Safety
Authority[12] have reviewed the evidence and made recommendations for minimal intakes of LA and ALA and
have also recommended intakes of longer chain -3 fatty acids based on the association of oily fish
consumption with a lower risk of cardiovascular disease. Some earlier review lumped all polyunsaturated fatty
acids together without qualification whether they were short or long-chain PUFA or whether they were -3 and
-6 PUFA.[13][14][15]

Traditionally speaking, the LC-PUFAs are not essential. Because the LC-PUFA are sometimes required, they
may be considered "conditionally essential", or not essential to healthy adults.[16]

Food sources
Some of the food sources of -3 and -6 fatty acids are fish and shellfish, flaxseed (linseed) and flaxseed oil,
hemp seed, olive oil, soya oil, canola (rapeseed) oil, chia seeds, pumpkin seeds, sunflower seeds, leafy
vegetables, and walnuts; but most of these food sources are poor sources of EFA's. Flaxseed are the best source
of -3 EFA, next is chiaseed, lastly hempseed; sunflower and starflower seeds are the best sources of -6 EFA.

Essential fatty acids play a part in many metabolic processes, and there is evidence to suggest that low levels of
essential fatty acids, or the wrong balance of types among the essential fatty acids, may be a factor in a number
of illnesses, including osteoporosis.[17]

Fish is the main source of the heart disease-fighting omega-3 fats eicosapentaenoic acid (EPA) and
docosahexaenoic acid (DHA), but some plant-based foods also contain omega-3 in the form of alpha-linolenic
acid (ALA), which also helps heart health.[18] The human body can (and in case of a purely vegetarian diet
often must unless certain algae or supplements derived from them are consumed) convert -linolenic acid
(ALA) to EPA and subsequently DHA. This however requires more metabolic work, which is thought to be the
reason that the absorption of essential fatty acids is much greater from animal rather than plant sources.

The IUPAC Lipid Handbook provides a very large and detailed listing of fat contents of animal and vegetable
fats, including -3 and -6 oils.[19] The National Institutes of Health's EFA Education group publishes Essential
Fats in Food Oils.[20] This lists 40 common oils, more tightly focused on EFAs and sorted by n-6:3 ratio.
Vegetable Lipids as Components of Functional Food lists notable vegetable sources of EFAs as well as
commentary and an overview of the biosynthetic pathways involved.[21] Careful readers will note that these
sources are not in excellent agreement. EFA content of vegetable sources varies with cultivation conditions.
Animal sources vary widely, both with the animal's feed and that the EFA makeup varies markedly with fats
from different body parts.

Human health

4 of 7 12/19/2016 09:37 PM
Essential fatty acid - Wikipedia https://en.wikipedia.org/wiki/Essential_fatty_acid

Almost all the polyunsaturated fats in the human diet are EFAs. Essential fatty acids play an important role in
the life and death of cardiac cells.[22][23][24][25]

Essential fatty acid deficiency

Essential fatty acid deficiency results in a dermatitis similar to that seen in zinc or biotin deficiency.[26]:485

Biologist Ray Peat has claimed there are flaws in the studies showing the need for -3 and -6 (also called n-3
and n-6) fats. He further claims that EFA deficiencies have sometimes been reversed by adding B vitamins or a
fat-free liver extract to the diet. In his view, 'the optimal dietary level of the "essential fatty acids" might be
close to zero, if other dietary factors were also optimized.'[27] However, these views are contrary to the
scientific consensus.

Treatment for depression

Research suggests that high intakes of fish and omega-3 fatty acids are linked to decreased rates of major
depression. Omega-3 fatty acids, such as docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) are
important for enzymatic pathways required to metabolize long-chain (i.e. 14 to 22 carbons) polyunsaturated
fatty acids (PUFAs). Low plasma concentrations of DHA predict low concentrations of cerebrospinal fluid
5-hydroxyindoleacetic acid (5-HIAA). It is found that low concentrations of 5-HIAA in the brain is associated
with depression and suicide.[28]

There are high concentrations of DHA in synaptic membranes of the brain. This is critical for synaptic
transmission and membrane fluidity. The omega-6 fatty acid to omega-3 fatty acid ratio is important to avoid
imbalance of membrane fluidity. Membrane fluidity affects function of enzymes such as adenylate cyclase and
ion channels such as calcium, potassium, and sodium, which in turn affects receptor numbers and functioning,
as well as serotonin neurotransmitter levels. It is evident that western diets are deficient in omega-3 and
excessive in omega-6, and balancing of this ratio would confer numerous health benefits.[29]

Clinical research suggests a benefit of omega-3 fatty acids in the treatment of depression during the perinatal
period.[28] A meta-analysis of trials of EPA supplements for depression in non-pregnant adults concluded that
supplements with more than 60% EPA are effective, but those containing primarily DHA, or less than 60%
EPA, were not effective.[30]

See also
Eicosanoid
Hydroxyeicosatetraenoic acid
Leukotriene
Prostaglandin
Thromboxane
Specialized proresolving mediators
Endogenous cannabinoid
Essential amino acid
Essential fatty acid interactions
Fatty acid metabolism
Fatty acid synthase
Nonclassic eicosanoid

5 of 7 12/19/2016 09:37 PM
Essential fatty acid - Wikipedia
Oily fish
Omega-3 fatty acid
Omega-6 fatty acid
Polyunsaturated fat
References
1. Robert S. Goodhart; Maurice E. Shils (1980). Modern
Nutrition in Health and Disease (6th ed.).
Philadelphia: Lea and Febinger. pp. 134138.
ISBN 0-8121-0645-8.
2. Whitney Ellie; Rolfes SR (2008). Understanding
Nutrition (11th ed.). California: Thomson Wadsworth.
p. 154.
3. Burr, G.O., Burr, M.M. and Miller, E. (1930). "On the
nature and role of the fatty acids essential in
nutrition" (PDF). J. Biol. Chem. 86 (587). Retrieved
2007-01-17.
4. Stillwell W, Shaikh SR, Zerouga M, Siddiqui R,
Wassall SR (2005). "Docosahexaenoic acid affects
cell signaling by altering lipid rafts". Reproduction,
Nutrition, Development. 45 (5): 55979.
doi:10.1051/rnd:2005046. PMID 16188208.
5. Calder PC (December 2004). "n-3 fatty acids,
inflammation, and immunity--relevance to
postsurgical and critically ill patients". Lipids. 39
(12): 114761. doi:10.1007/s11745-004-1342-z.
PMID 15736910.
6. Sanders TA. DHA Status of vegetarians.
Prostaglandins Leukotrienes Essential Fatty Acids
2009; 81(2-3):137-41.
doi:10.1016/j.plefa.2009.05.013 PMID 19500961
7. FAO/WHO Fats and fatty acids in human nutrition.
Report of an expert consultation. FAO Food and
Nutrition Paper 91, Rome 2011. ISSN 0254-4725
8. Wiese, H; Hansen, A; Adams, DJ (1958). "Text".
Journal of Nutrition. 66 (3): 345360.
PMID 13611579.
9. "Plasma lipids in human linoleic acid deficiency.".
Nutr Metab. 13 (3): 15067. 1971.
doi:10.1159/000175332. PMID 5001758.
10. Prottey, C; Hartop, PJ; Press, M (1975). "Correction
of the cutaneous manifestations of essential fatty acid
deficiency in man by application of sunflower-seed
oil to the skin.". J Invest Dermatol. 64 (4): 22834.
doi:10.1111/1523-1747.ep12510667. PMID 1117180.
11. Sanders T and Emery P. The Molecular Basis of
Human Nutrition, Taylor Frances, London, 2003
ISBN 0-748-40753-7
6 of 7
https://en.wikipedia.org/wiki/Essential_fatty_acid
12. Jones, A (2010). "EFSA Scientific Opinion on
Dietary Reference Values for fats, including saturated
fatty acids, polyunsaturated fatty acids,
monounsaturated fatty acids, trans fatty acids and
cholesterol". EFSA Journal. 8 (3): 1461.
doi:10.2903/j.efsa.2010.1461.
13. Heather Hutchins, MS, RD (2005-10-19).
"Symposium Highlights -- Omega-3 Fatty Acids:
Recommendations for Therapeutics and Prevention".
"Omega-3 fatty acids and their counterparts, n-6 fatty
acids, are essential polyunsaturated fatty acids
(PUFA) because they cannot be synthesized de novo
in the body."
14. Nugent KP, Spigelman AD, Phillips RK (June 1996).
"Tissue prostaglandin levels in familial adenomatous
polyposis patients treated with sulindac". Diseases of
the Colon and Rectum. 39 (6): 65962.
doi:10.1007/BF02056946. PMID 8646953.
"Arachidonic acid is an essential fatty acid"
15. Carlstedt-Duke J, Brnnegrd M, Strandvik B
(December 1986). "Pathological regulation of
arachidonic acid release in cystic fibrosis: the putative
basic defect". Proceedings of the National Academy
of Sciences of the United States of America. 83 (23):
92026. doi:10.1073/pnas.83.23.9202. PMC 387103
. PMID 3097647. "[T]he turnover of essential fatty
acids is increased (7). Arachidonic acid is one of the
essential fatty acids affected."
16. Cunnane SC (November 2003). "Problems with
essential fatty acids: time for a new paradigm?".
Progress in Lipid Research. 42 (6): 54468.
doi:10.1016/S0163-7827(03)00038-9.
PMID 14559071.
17. Kruger MC, Horrobin DF (September 1997).
"Calcium metabolism, osteoporosis and essential fatty
acids: a review". Progress in Lipid Research. 36
(23): 13151. doi:10.1016/S0163-7827(97)00007-6.
PMID 9624425.
18. Cleveland Clinic - Plant Sources of omega 3s
(http://my.clevelandclinic.org/services/heart
/prevention/nutrition/food-choices/plant-sources-
of-omega-3s)
19. IUPAC Lipid Handbook (http://www.iupac.org
/publications/pac/2001/pdf/7304x0685.pdf)
20. Essential Fats in Food Oils (http://efaeducation.org
/Bal_pdfs/FatsOils.pdf)
12/19/2016 09:37 PM
Essential fatty acid - Wikipedia https://en.wikipedia.org/wiki/Essential_fatty_acid

21. Vegetable Lipids as Components of Functional Food
(http://publib.upol.cz/~obd/fulltext/Biomedic146-2
/LF11_2002-1.pdf), Stuchlik and Zak
22. Honor E, Barhanin J, Attali B, Lesage F, Lazdunski
M (March 1994). "External blockade of the major
cardiac delayed-rectifier K+ channel (Kv1.5) by
polyunsaturated fatty acids". Proceedings of the
National Academy of Sciences of the United States of
America. 91 (5): 193741.
doi:10.1073/pnas.91.5.1937. PMC 43279 .
PMID 8127910.
23. Reiffel JA, McDonald A (August 2006).
"Antiarrhythmic effects of omega-3 fatty acids". The
American Journal of Cardiology. 98 (4A): 50i60i.
doi:10.1016/j.amjcard.2005.12.027. PMID 16919517.
24. Landmark K, Alm CS (November 2006). "[Alpha-
linolenic acid, cardiovascular disease and sudden
death]". Tidsskrift for Den Norske Lgeforening (in
Norwegian). 126 (21): 27924. PMID 17086218.
25. Herbaut C (September 2006). "[Omega-3 and
health]". Revue mdicale de Bruxelles (in French). 27
(4): S35560. PMID 17091903.
26. James, William; Berger, Timothy; Elston, Dirk
(2005). Andrews' Diseases of the Skin: Clinical
Dermatology. (10th ed.). Saunders. ISBN
0-7216-2921-0.
27. http://raypeat.com/articles/nutrition/oils-
in-context.shtml
28. Rees AM, Austin MP, Parker G (April 2005). "Role
of omega-3 fatty acids as a treatment for depression
in the perinatal period". The Australian and New
Zealand Journal of Psychiatry. 39 (4): 27480.
doi:10.1111/j.1440-1614.2005.01565.x.
PMID 15777365.
29. Logan AC (November 2004). "Omega-3 fatty acids
and major depression: a primer for the mental health
professional". Lipids in Health and Disease. 3 (1): 25.
doi:10.1186/1476-511X-3-25. PMC 533861 .
PMID 15535884.
30. Sublette, ME; Ellis, SP; Geant, AL; Mann, JJ (2011).
"Meta-analysis of the effects of eicosapentaenoic acid
(EPA) in clinical trials in depression". The Journal of
Clinical Psychiatry. 72 (12): 157784.
doi:10.4088/JCP.10m06634. PMC 3534764 .
PMID 21939614.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Essential_fatty_acid&oldid=747463011"

Categories: Essential fatty acids

This page was last modified on 2 November 2016, at 14:39.

Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may
apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia is a registered
trademark of the Wikimedia Foundation, Inc., a non-profit organization.

7 of 7 12/19/2016 09:37 PM