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20-September-2008 09:29:05 - fatty acid Types of fats in food Unsaturated fat Monounsaturated fat Polyunsaturated fat Trans fat Omega fatty acids: ω-3 ω-6 ω-9 Saturated fat Interesterified fat See also Fatty acid Essential fatty acid Food portal Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components generally all references are to humans by any known chemical pathways; and therefore must be obtained from the diet. The term refers to those involved in biological processes, and not fatty acids which may just play a role as fuel. As many of the compounds created from essential fatty acids can be taken directly in the diet, it is possible that the amounts required in the diet if any are overestimated. It is also possible they can be underestimated as organisms can still survive in unideal, malnourished conditions. There are two families of EFAs: ω-3 or omega-3 or n-3 and ω-6 omega-6, n-6. Fats from each of these families are essential, as the body can convert one omega-3 to another omega-3, for example, but cannot create an omega-3 from scratch. They were originally designated as Vitamin F when they were discovered as essential nutrients in 1923. In 1930, work by Burr, Burr and Miller showed that they are better classified with the fats than with the vitamins.1 Contents 1 Functions 2 Nomenclature and terminology 2.1 Examples 2.2 Essentiality 3 Food sources 4 Human health 5 See also 6 References 7 External links 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 signaling2 They act on DNA activating or inhibiting transcription factors such as NFκB, which is linked to pro-inflammatory cytokine production3 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 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: Chemical structure of stearidonic acid showing physiological red and chemical blue numbering conventions. Chemical structure of stearidonic acid showing physiological red and chemical blue numbering conventions. 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: ω-3 fatty acids: α-Linolenic acid or ALA 18:3 ω-6 fatty acids: Linoleic acid or LA 18:2 These two fatty acids cannot be synthesised by humans, as 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: 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. Exceptions do occur in older people or people with a liver problem that do not completely produce a sufficient amount,citation needed and hence many supplement companies market Omega 3-6-9 blends. 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. 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. 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.4 Authoritative sources include the whole families, without qualification.567 The human body can make some long-chain PUFA arachidonic acid, EPA and DHA from lineolate or lineolinate. Traditionally speaking the LC-PUFA are not essential. See Cunnane 20038 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. Mary G. Enig has pointed out numerous studies showing the need for omega-3 and omega-6 essential fatty acids in mammalians9 A 2005 study has shown evidence that gamma-linolenic acid, GLA, a product of omega-6, has been shown to inhibit the breast cancer promoting gene of Her2/neu.10 Biologist Ray Peat has pointed out flaws in the studies purportedly showing the need for n-3 and n-6 fats. He notes that so-called EFA deficiencies have sometimes been reversed by adding B vitamins or a fat-free liver extract to the diet. In his view, 'the optional dietary level of the essential fatty acids might be close to zero, if other dietary factors were also optimized.' 1 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.11 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 IUPAC Lipid HandbookPDF 370 KiB 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. Stuchlik and Zak, 'Vegetable Lipids as Components of Functional Food'PDF 139 KiB 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 Main article: Diet and heart disease 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.12131415 See also Polyunsaturated fat Omega-3 fatty acid Omega-6 fatty acid Essential fatty acid interactions Eicosanoid Prostaglandin Leukotriene Thromboxane Nonclassic eicosanoid Endogenous Cannabinoid Essential nutrient Essential amino acid Fatty acid metabolism Fatty acid synthase Oily fish References ^ Burr, G.O., Burr, M.M. and Miller, E. 1930. On the nature and role of the fatty acids essential in nutrition. J. Biol. Chem. 86 587. Retrieved on 2007-01-17. ^ 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: 559-579. doi:10.1051/rnd:2005046. PMID 16188208. ^ Calder PC 2004. n-3 fatty acids, inflammation, and immunity--relevance to postsurgical and critically ill patients. LIPIDS 39 12: 1147-1161. doi:10.1007/s11745-004-1342-z. PMID 15736910. ^ Or at least the polyunsaturated, straight-chain methylene-interrupted ones; conjugated fatty acids like calendic acid are not. ^ Heather Hutchins, MS, RD 10/19/2005. 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. ^ Nugent K, Spigelman A, Phillips R 1996. Tissue prostaglandin levels in familial adenomatous polyposis patients treated with sulindac. Dis Colon Rectum 39 6: 659-62. doi:10.1007/BF02056946. PMID 8646953. Arachidonic acid is an essential fatty acid... ^ Carlstedt-Duke J, Brönnegård M, Strandvik B 1986. Pathological regulation of arachidonic acid release in cystic fibrosis: the putative basic defect. Proc Natl Acad Sci U S A 83 23: 9202-6. doi:10.1073/pnas.83.23.9202. PMID 3097647. The turnover of essential fatty acids is increased 7. Arachidonic acid is one of the essential fatty acids affected. ^ Cunnane SC 2003. Problems with essential fatty acids: time for a new paradigm?. Progress In Lipid Research 42 6: 544-568. doi:10.1016/S0163-78270300038-9. PMID 14559071. ^ Enig, M 2001, Know Your Fats: The Complete Primer for Understanding the Nutrition of Fats, Oils and Cholesterol First ion ed., Silver Spring, MD: Bethesda Press, ISBN 0-9678126-0-7 ^ Menendez JA, Vellon R, Colomer R, Lupu R 2005. Effect of gamma-linolenic acid on the transcriptional activity or Her2/neu Erb-2 oncogene. J Natl Cancer Inst 97 2: 1611-1615. PMID 16264182. ^ Calcium metabolism, osteoporosis and essential fatty acids: a review. . PMID 9624425. Retrieved on 2008-02-26. ^ External blockade...by polyunsaturated fatty acids . PMID 43279. Retrieved on 2007-01-18. - see page 1 of this link ^ Antiarrhythmic effects of omega-3 fatty acids . PMID 16919517. Retrieved on 2007-01-18. ^ Alpha-linolenic acid, cardiovascular disease and sudden death . PMID 17086218. Retrieved on 2007-01-18. ^ Omega-3 and health . PMID 17091903. Retrieved on 2007-01-18. External links Fats You Need -- Essential Fatty Acids USDA public domain resource, and a source for this article Cunnane Stephen C June, 2005. Essential Fatty Acids: Time for a New Paradigm?. PUFA Newsletter. Retrieved on 2006-03-14. Stillwell W, Wassall SR.. Docosahexaenoic acid: membrane properties of a unique fatty acid.. Retrieved on February 8, 2006. Chem Phys Lipids. 2003 Nov;1261:1-27 v d e Food chemistry Additives · Carbohydrates · Coloring · Enzymes · Essential fatty acids · Flavors · Lipids · Minerals · Proteins · Vitamins · Water Retrieved from http://en..org/wiki/Essential_fatty_acid Categories: Fatty acids | Carboxylic acids | Essential nutrientsHidden categories: All articles with statements | Articles with statements since January 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Česky Español Français Bahasa Indonesia Nederlands 日本語 Polski Português Suomi This page was last modified on 13 July 2008, at 21:08

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