Essential fatty acid

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. The term "essential fatty acid" refers to fatty acids required for biological processes, and not those that only act as fuel.

Only two EFAs are known for humans: alpha-linolenic acid (an omega-3 fatty acid) and linoleic acid (an omega-6 fatty acid). Other fatty acids that are only "conditionally essential" include gamma-linolenic acid (an omega-6 fatty acid), lauric acid (a saturated fatty acid), and palmitoleic acid (a monounsaturated fatty acid).

When the two EFAs were first discovered in 1923, they were designated Vitamin F. In 1930, work by Burr, Burr and Miller on rats showed that the two EFAs are better classified with the fats than with the vitamins.

Functions

 * The biological effects of the ω-3 and ω-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 ω-3 and ω-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 from ω-6 EFAs and resolvins from ω-3 (in the presence of aspirin, downregulating inflammation.)
 * the isofurans, neurofurans, isoprostanes, hepoxilins, epoxyeicosatrienoic acids (EETs) and Neuroprotectin D
 * They form lipid rafts (affecting cellular signaling)
 * They act on DNA (activating or inhibiting transcription factors such as NF-κB, which is linked to pro-inflammatory cytokine production)

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 α, the next carbon β, and so forth. Since biological fatty acids can be of different lengths, the last position is labelled as a "ω", 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, the position is signified by (ω minus n). For example, the term ω-3 signifies that the first double bond exists as the third carbon-carbon bond from the terminal CH3 end (ω) of the carbon chain. The number of carbons and the number of double bonds is also listed. ω-3 18:4 (stearidonic acid) or 18:4 ω-3 or 18:4 n−3 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 ω-3 and ω-6 essential fatty acids, see Polyunsaturated fatty acids.

The essential fatty acids start with the short chain polyunsaturated fatty acids (SC-PUFA): These two fatty acids cannot be synthesised by humans, as humans lack the desaturase enzymes required for their production.
 * ω-3 fatty acids:
 * α-Linolenic acid or ALA (18:3)
 * ω-6 fatty acids:
 * Linoleic acid or LA (18:2)

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):
 * ω-3 fatty acids:
 * eicosapentaenoic acid or EPA (20:5)
 * docosahexaenoic acid or DHA (22:6)
 * ω-6 fatty acids:
 * gamma-linolenic acid or GLA (18:3)
 * dihomo-gamma-linolenic acid or DGLA (20:3)
 * arachidonic acid or AA (20:4)

ω-9 fatty acids are not essential in humans, because humans generally possess all the enzymes required for their synthesis.

Essential fatty acids
Mammals lack the ability to introduce double bonds in fatty acids beyond carbon 9 and 10, hence ω-6 linoleic acid (18:2,9,12), abbreviated LA, and the ω-3 linolenic acid (18:3,9,12,15), abbreviated ALA, are essential for man in the diet. In humans, arachidonic acid (20:4,5,8,11,14) can be synthesized from LA by desaturation and chain elongation (though some carnivores like cats cannot do this, and require arachadonate in the diet). In addition, the human body can make some long-chain ω-3 PUFAs (EPA and DHA) from the ω-3 ALA.

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. Further research has shown that human metabolism requires both ω-3 and ω-6 fatty acids. To some extent, any ω-3 and any ω-6 can relieve the worst symptoms of fatty acid deficiency for its class. 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 ω-3 or -6 fatty acids. Conjugated fatty acids like calendic acid are not normally considered essential. Authoritative sources include the whole families, without qualification.

Traditionally speaking the LC-PUFA are not essential. See (Cunnane 2003) for a discussion of the current status of the term 'essential'. Because the LC-PUFA are sometimes required, they may be considered "conditionally essential", or not essential to healthy adults.

A 2005 study has shown evidence that the ω-6 fat gamma-linolenic acid, GLA has been shown to inhibit the breast cancer promoting gene of Her2/neu.

Essential fatty acids should not be confused with essential oils, which are "essential" in the sense of being a concentrated essence.

Food sources
Almost all the polyunsaturated fat in the human diet is from EFA. Some of the food sources of ω-3 and ω-6 fatty acids are fish and shellfish, flaxseed (linseed), hemp oil, soya oil, canola (rapeseed) oil, chia seeds, pumpkin seeds, sunflower seeds, leafy vegetables, and walnuts.

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.

Plant sources of ω-3 contain neither eicosapentaenoic acid (EPA) nor docosahexaenoic acid (DHA). 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 α-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 (see Fish and plants as a source of Omega-3 for more).

The provides a very large and detailed listing of fat contents of animal and vegetable fats, including ω-3 and -6 oils. The National Institutes of Health's EFA Education group publishes 'Essential Fats in Food Oils.' This lists 40 common oils, more tightly focused on EFAs and sorted by n-6:3 ratio. list notable vegetable sources of EFAs as well as commentary and an overview of the biosynthetic pathways involved. Users can interactively search at Nutrition Data for the richest food sources of particular EFAs or other nutrients. 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
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.

Essential fatty acid deficiency
Essential fatty acid deficiency results in a dermatitis similar to that seen in zinc or biotin deficiency.

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 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.

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.

Although further research is needed, there are studies providing evidence for the role of omega-3 fatty acids in the treatment of depression during the perinatal period. Correlations have been found between depression and low levels of omega-3 fatty acids, and treatment with omega-3 supplementation shows benefit for depression as well as other mood disorders. Research also suggests that supplementation is beneficial for healthy infant development.