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Essential fatty acid

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Not to be confused withessential oil.

Essential fatty acids,orEFAs,arefatty acidsthat are required by humans and other animals for normalphysiological functionthat cannot besynthesized in the body.[1][2]⁠ As they are not synthesized in the body, the essential fatty acids –Alpha -linolenic acid(ALA) andlinoleic acid– must be obtained from food or from adietary supplement.[1][3][4]Essential fatty acids are needed for various cellularmetabolic processesand for the maintenance and function of tissues and organs.[1][5]These fatty acids also are precursors to vitamins,cofactors,and derivatives, includingprostaglandins,leukotrienes,thromboxanes,lipoxins,and others.[6]

Only two fatty acids are known to be essential for humans: Alpha -linolenic acid (anOmega −3 fatty acid) and linoleic acid (anOmega −6 fatty acid). These are supplied to the body either as the free fatty acid, or more commonly as some glyceride derivative.[7]ALA can be converted intoeicosapentaenoic acidanddocosahexaenoic acid,but the conversion amount is small, requiring intake from food or supplements.[1]Deficiency in Omega −3 fatty acids are very common. The average American has a dietry ratio between Omega −6 fatty acids and Omega −3 fatty acids of 20:1.

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 asfatsrather thanvitamins.[8]

Functions

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For the biological effects of the ω−3 and ω−6 fatty acids which are mediated by their mutual interactions, seeEssential fatty acid interactions.

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.

Nomenclature and terminology

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Main article:Fatty acid § Nomenclature

Fatty acids comprise analiphatichydrocarbonchain plus acarboxyl group(–COOH) at one end, and terminated by amethyl group(–CH3) at the other end. They are almost always straight-chained. The carbon next to the carboxylate is known as α, the next carbon β, and so forth. Since biological fatty acids can be of diverse lengths, the last position is often labelled as "ω",the last letter in theGreek Alpha bet.In the expressionω−x,the minus symbol represents subtraction, indicating how many carbons away from the terminal end (ω) of the chain that the first unsaturated carbon-carbon bond appears. Typically, the number of carbons and the number of double bonds are also listed in short descriptions of unsaturated fatty acids. For instance, ω−3 18:4, or 18:4 ω−3, or 18:4 n−3 indicatestearidonic acid,an 18-carbon chain with 4 double bonds, and with a double bond between the third and fourth carbon atoms from the CH3end. Double bonds arecisand separated by a single methylene (CH2) group unless otherwise noted. In free fatty acid form, the chemical structure of stearidonic acid is:

Examples

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Polyunsaturated fatty acidswith 16- and 18-carbon chains are sometimes classified asshort chain polyunsaturated fatty acids(SC-PUFA), as opposed tolong-chain polyunsaturated fatty acids(LC-PUFA), which have more than 18 carbon atoms.[11]

Both the essential fatty acids are SC-PUFA with an 18-carbon chain:

These two fatty acids cannot besynthesizedby humans because humans lack thedesaturaseenzymesrequired for their production.

They form the starting point for the creation of more desaturated fatty acids, most of which also have a longer carbon chain:

Except for GLA, which has a short 18-carbon chain, these fatty acids have more than 18 carbon atoms and are typically classified as LC-PUFA.[11]

ω−9 fatty acidsare not essential in humans because they can be synthesized from carbohydrates or other fatty acids.

Essentiality in human diet

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Mammals lack the ability to introduce double bonds in fatty acids beyond carbon 9 and 10, hence the Omega −6 linoleic acid (18:2n−6; LA) and the Omega −3Alpha -linolenic acid(18:3n−3; ALA) are essential for humans in the diet. However, humans can convert both LA and ALA to fatty acids with longer carbon chains and a larger number of double bonds, by alternative desaturation and chain elongation.[12][6]

In humans, arachidonic acid (20:4n−6; AA) can be synthesized from LA. In turn, AA can be converted to an even longer fatty acid, the docosapentaenoic acid (22:5n−6; DPA). Similarly, ALA can be converted to docosahexaenoic acid (22:6n−3; DHA), although the latter conversion is limited, resulting in lower blood levels of DHA than through direct ingestion. This is illustrated by studies in vegans and vegetarians.[13]If there is relatively more LA than ALA in the diet it favors the formation of DPA from LA rather than DHA 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.

In preterm infants, the capacity to convert LA to AA and ALA to DHA 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 nutrientsare defined as those that cannot be synthesizedde novoin sufficient quantities for normal physiological function. This definition is met for LA and ALA but not the longer chain derivatives in adults.[14]The longer chain derivatives particularly, however, have pharmacological properties that can modulate disease processes, but this should not be confused with dietary essentiality.

One study demonstrated 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.[15]This could be treated by infusing lipids, and later studies showed that topical application of sunflower oil would also resolve the dermal symptoms.[16]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 ω−3 fatty acids or by arachidonic acid.

The main physiological requirement for ω−6 fatty acids is attributed toarachidonic acid,which is the major precursor ofprostaglandins,leukotrienesthat play a vital role in cell signaling, and an endogenous cannabinoidanandamide.[17]Metabolites from the ω−3 pathway, mainly from eicosapentaenoic acid, are mostly inactive.[18]

Reviews by the European Food Safety Authority[19]made recommendations for minimal intakes of LA and ALA and have also recommended intakes of longer chain ω−3 fatty acids based on the association of oily fish consumption with a lower risk of cardiovascular disease.[20][21]

Food sources

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Some of the food sources of ω−3 and ω−6 fatty acids arefishandshellfish,seaweed oil,flaxseed(linseed) andflaxseed oil,hemp seed,olive oil,soya oil,canola (rapeseed) oil,chia seeds,pumpkin seeds,sunflower seeds,leafy vegetables,andwalnuts.

Essential fatty acids play a part in manymetabolic 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, includingosteoporosis.[22]

Fish is the main source of the longer Omega −3 fats; eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), though they initially acquire these fats through the consumption of algae and seaweed. Some plant-based foods contain Omega −3 in the form of Alpha -linolenic acid (ALA), which appears to have a modest benefit for cardiovascular health.[23]The human body can (and in case of a purely vegetarian diet often must unless certainalgaeor supplements derived from them are consumed) convert ALA to EPA and subsequently DHA. This elongation of ALA is inefficient. Conversion to DHA is higher in women than in men; this is thought to reflect the need to provide DHA to the fetus and infant during pregnancy and breast feeding.[24]

TheIUPAC Lipid Handbookprovides a very large and detailed listing of fat contents of animal and vegetable fats, including ω−3 and −6 oils.[25]TheNational Institutes of Health's EFA Education group publishesEssential Fats in Food Oils.[26]This lists 40 common oils, more tightly focused on EFAs and sorted by n−6:3 ratio.Vegetable Lipids as Components of Functional Foodlists notable vegetable sources of EFAs as well as commentary and an overview of the biosynthetic pathways involved.[27]However, these sources are not in perfect 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

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Main article:Diet and heart disease

Essential fatty acids play an important role in the life and death of cardiac cells.[28][29][30][31]Additionally, essential fatty acids are crucial for the development of several endocannabinoids with a multitude of functions in the body, such as docosahexaenoyl ethanolamide (DHA-EA/synaptamide).

Reference intake values

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Reference intake values for as published by the Panel on Dietetic Products, Nutrition and Allergies of theEuropean Food Safety Authority(EFSA).[32]

Common name Type Reference intake values
Alpha-Linolenic acid(ALA) Omega−3 2 g
Linoleic acid(LA) Omega−6 10 g

In the United States, theAdequate Intake(AI) for Omega −3 fatty acids is for ALA. It is based on the median intake, and for adults the values are 1.6 g/day for men and 1.1 g/day for women. EPA and DHA contribute about 10 percent of total Omega −3 intake. The AI for Omega −6 fatty acids is for linoleic acid and is also based on the median intake: 17 g/day for younger men, dropping to 14 g/day for men over 50 years old; for younger women 12 g/d, and 11 g/day for women over 50. Studies have shown that smaller intakes reverse the symptoms of deficiency, but there is inadequate information to set anEstimated Average Requirement(EAR) for either.[33]

Essential fatty acid deficiency

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Essential fatty acid deficiencyresults in adermatitissimilar to that seen inzincorbiotin deficiency.[34]

See also

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References

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  1. ^abcd"Omega-3 Fatty Acids".Office of Dietary Supplements, US National Institutes of Health. 15 February 2023.Retrieved22 July2024.
  2. ^Robert S. Goodhart; Maurice E. Shils (1980).Modern Nutrition in Health and Disease(6th ed.). Philadelphia: Lea and Febinger. pp.134–138.ISBN978-0-8121-0645-9.
  3. ^Vaughan JG, Geissler C, Nicholson B, Dowle E, Rice E (2009).The new Oxford book of food plants.Oxford University Press US. pp. 212–235.ISBN978-0-19-954946-7.Retrieved13 October2010.
  4. ^Kaur N, Chugh V, Gupta AK (October 2014)."Essential fatty acids as functional components of foods- a review".Journal of Food Science and Technology.51(10): 2289–303.doi:10.1007/s13197-012-0677-0.PMC4190204.PMID25328170.
  5. ^Chipponi JX, Bleier JC, Santi MT, Rudman D (May 1982)."Deficiencies of essential and conditionally essential nutrients".The American Journal of Clinical Nutrition.35(5 Suppl): 1112–6.doi:10.1093/ajcn/35.5.1112.PMID6805293.
  6. ^abDas, Undurti N. (2006). "Essential Fatty Acids: Biochemistry, Physiology and Pathology".Biotechnology Journal.1(4): 420–439.doi:10.1002/biot.200600012.PMID16892270.S2CID25945627.
  7. ^Whitney Ellie; Rolfes SR (2008).Understanding Nutrition(11th ed.). California: Thomson Wadsworth. p. 154.
  8. ^Burr GO, Burr MM (April 1930)."On the nature and role of the fatty acids essential in nutrition".J. Biol. Chem.86(2): 587–621.doi:10.1016/S0021-9258(20)78929-5.
  9. ^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): 559–79.doi:10.1051/rnd:2005046.PMID16188208.
  10. ^Calder PC (December 2004)."n-3 fatty acids, inflammation, and immunity--relevance to postsurgical and critically ill patients".Lipids.39(12): 1147–61.doi:10.1007/s11745-004-1342-z.PMC7101959.PMID15736910.
  11. ^abBuckley MT, et al. (2017)."Selection in Europeans on Fatty Acid Desaturases Associated with Dietary Changes".Mol Biol Evol.34(6): 1307–1318.doi:10.1093/molbev/msx103.PMC5435082.PMID28333262.
  12. ^Simopoulos, Artemis P. (1999)."Essential fatty acids in health and chronic disease".The American Journal of Clinical Nutrition.70(3): 560s–569s.doi:10.1093/ajcn/70.3.560s.PMID10479232.
  13. ^Sanders TA (2009). "DHA Status of vegetarians".Prostaglandins Leukotrienes Essential Fatty Acids.81(2–3): 137–41.doi:10.1016/j.plefa.2009.05.013.PMID19500961.
  14. ^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
  15. ^Collins FD, Sinclair AJ, Royle JP, Coats DA, Maynard AT, Leonard RF (1971). "Plasma lipids in human linoleic acid deficiency".Nutr Metab.13(3): 150–67.doi:10.1159/000175332.PMID5001758.
  16. ^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): 228–34.doi:10.1111/1523-1747.ep12510667.PMID1117180.
  17. ^Maccarrone, M; Finazzi-Agró, A (22 August 2003)."The endocannabinoid system, anandamide and the regulation of mammalian cell apoptosis".Cell Death & Differentiation.10(9): 946–955.doi:10.1038/sj.cdd.4401284.PMID12934069.
  18. ^Sanders, Tom; Emery, Peter (2003).Molecular Basis of Human Nutrition.London: Taylor Frances.ISBN9780367806323.
  19. ^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.
  20. ^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): 659–62.doi:10.1007/BF02056946.PMID8646953.S2CID25642190.Arachidonic acid is an essential fatty acid…
  21. ^Carlstedt-Duke J, Brönnegård 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): 9202–6.Bibcode:1986PNAS...83.9202C.doi:10.1073/pnas.83.23.9202.PMC387103.PMID3097647.[T]he turnover of essential fatty acids is increased (7). Arachidonic acid is one of the essential fatty acids affected.
  22. ^Kruger MC, Horrobin DF (September 1997). "Calcium metabolism, osteoporosis and essential fatty acids: a review".Progress in Lipid Research.36(2–3): 131–51.doi:10.1016/S0163-7827(97)00007-6.PMID9624425.
  23. ^Pan A, Chen M, Chowdhury R, et al. (December 2012)."α-Linolenic acid and risk of cardiovascular disease: a systematic review and meta-analysis".Am. J. Clin. Nutr.(Systematic review).96(6): 1262–73.doi:10.3945/ajcn.112.044040.PMC3497923.PMID23076616.
  24. ^Burdge GC, Calder PC (September 2005)."Conversion of Alpha -linolenic acid to longer-chain polyunsaturated fatty acids in human adults"(PDF).Reprod. Nutr. Dev.45(5): 581–97.doi:10.1051/rnd:2005047.PMID16188209.Archived(PDF)from the original on 2017-08-15.
  25. ^"IUPAC Lipid Handbook"(PDF).iupac.org.Archived(PDF)from the original on 2006-02-12.
  26. ^"Essential Fats in Food Oils"(PDF).efaeducation.org.Archived(PDF)from the original on 2014-12-10.
  27. ^Vegetable Lipids as Components of Functional FoodArchived2006-03-20 at theWayback Machine,Stuchlik and Zak
  28. ^Honoré 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): 1937–41.Bibcode:1994PNAS...91.1937H.doi:10.1073/pnas.91.5.1937.PMC43279.PMID8127910.
  29. ^Reiffel JA, McDonald A (August 2006). "Antiarrhythmic effects of Omega -3 fatty acids".The American Journal of Cardiology.98(4A): 50i–60i.doi:10.1016/j.amjcard.2005.12.027.PMID16919517.
  30. ^Landmark K, Alm CS (November 2006)."[Alpha-linolenic acid, cardiovascular disease and sudden death]".Tidsskrift for den Norske Lægeforening(in Norwegian).126(21): 2792–4.PMID17086218.
  31. ^Herbaut C (September 2006). "[Omega-3 and health]".Revue Médicale de Bruxelles(in French).27(4): S355–60.PMID17091903.
  32. ^European Food Safety Authority (EFSA) (2009-07-01)."Labelling reference intake values for n-3 and n-6 polyunsaturated fatty acids".EFSA Journal.7(7): 1176.doi:10.2903/j.efsa.2009.1176.ISSN1831-4732.
  33. ^Food and Nutrition Board (2004)."DIETARY REFERENCE INTAKES for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids"(PDF).pp. 422–514. Archived fromthe original(PDF)on 2022-06-27.
  34. ^James, William D.; Elston, Dirk; Treat, James R.; Rosenbach, Misha A.; Neuhaus, Isaac (2019-01-18).Andrews' Diseases of the Skin: Clinical Dermatology.Elsevier Health Sciences. p. 482.ISBN9780323551885.
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