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08-SEPTEMBER-2008 09:13:22 - Docosahexaenoic acid Docosahexaenoic acid IUPAC name 4Z,7Z,10Z,13Z,16Z,19Z-docosa- 4,7,10,13,16,19-hexaenoic acid Other names cervonic acid, DHA Identifiers CAS number 6217-54-5 PubChem 445580 SMILES CCC=CCC=CCC=CCC= CCC=CCC=CCCC=OO CC/C=C\C/C=C\C/C=C\C/C= C\C/C=C\C/C=C\CCC=OO Properties Molecular formula C22H32O2. Molar mass 328.488 g/mol Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Docosahexaenoic acid commonly known as DHA; 22:6ω-3, all-cis-docosa-4,7,10,13,16,19-hexa-enoic acid; trivial name cervonic acid is an omega-3 essential fatty acid. In chemical structure, DHA is a carboxylic acid with a 22-carbon chain1 and six cis double bonds; the first double bond is located at the third carbon from the omega end.2 Fish oils are rich in DHA. Most of the DHA in fish and more complex organisms originates in photosynthetic and heterotrophic microalgae, and becomes increasingly concentrated in organisms as it moves up the food chain. DHA is also commercially manufactured from microalgae; Crypthecodinium cohnii and another of the genus Schizochytrium.3 DHA manufactured using microalgae is vegetarian .3 Most animals make very little DHA through metabolism; however small amounts are manufactured internally through the consumption of α-linolenic acid, an omega-3 fatty acid found in chia, flax, and many other seeds and nuts. DHA is metabolized to form the docosanoids-several families of potent hormones. DHA is a major fatty acid in sperm and brain phospholipids, and especially in the retina. Dietary DHA may reduce the risk of heart disease by reducing the level of blood triglycerides in humans. Low levels of DHA result in reduction of brain serotonin levels4 and have been associated with ADHD, Alzheimer's disease, and depression, among other diseases, and there is mounting evidence that DHA supplementation may be effective in combating such diseases see external links at the end of this article. Contents 1 Central nervous system constituent 2 Metabolic synthesis 3 Health 3.1 Alzheimer's Disease 3.2 Cancer 3.3 Pregnancy and lactation 4 Nutrition 4.1 Promotion as a food additive 4.2 Algae-derived DHA in infant nutrition 4.3 Studies of vegans and vegetarians 4.4 DHA and EPA in fish oils 5 See also 6 Notes and references Central nervous system constituent DHA is the most abundant essential fatty acid polyunsaturated fatty acids, PUFAs in the brain and retina. It comprises 40% of the PUFAs in the brain and 60% of the PUFAs in the retina. 50% of the weight of the neuron's plasma membrane is composed of DHA.5 Of all the fatty acids, DHA has the largest effect on brain PUFA composition.6 DHA is found in three phospholipids: phosphatidylethanolamine, ethanolamine plasmalogens, and phosphatidylserine PS. It modulates the carrier-mediated transport of choline, glycine, and taurine, the function of delayed rectifier potassium channels, and the response of rhodopsin contained in the synaptic vesicles, among many other functions.7 DHA deficiency is associated with cognitive decline.8 PS controls apoptosis, and low DHA levels lower neural cell PS and increase neural cell death.9 DHA is depleted in the cerebral cortex of severely depressed patients.1011 Metabolic synthesis In the human body, DHA is either present in the diet or it is derived from eicosapentaenoic acid EPA, 20:5, ω-3 via docosapentaenoic acid DPA, 22:5 ω-3 as an intermediate. This had been thought to occur through an elongation step followed by the action of Δ4-desaturase. It is now more likely that DHA is biosynthesized via a C24 intermediate followed by beta oxidation in peroxisomes. Thus EPA is twice elongated yielding 24:5 ω-3, then desaturated to 24:6 ω-3, then shortened to DHA 22:6 ω-3 via beta oxidation. This pathway is known as Sprecher's shunt.1213 Health Alzheimer's Disease A large NIH drug trial is currently recruiting patients for evaluating DHA in Alzheimer's disease.14 This is the first human trial of DHA. Animal studies in the TG3 transgenic mouse model of Alzheimer's disease linked decreases in amyloid plaques and tau to dietary DHA. Animal studies also show that when combined with arachidonic acid also present in fish oil, the effectiveness of DHA for preventing plaques was less than without it. Cancer Researchers at the University of Nevada conducted a study on the effects of DHA supplementation on the growth of human colon adenocarcinoma in mice. The animals received one of four specialized diets: low-fat with corn oil omega-6 linoleic acid, high-fat with corn oil omega-6 linoleic acid, high-fat with fish oil omega-3 EPA and DHA, and high-fat with algae-derived DHA omega-3 DHA. At completion, the mice receiving a diet supplemented with algae-derived DHA had tumors that were smaller than those of mice receiving diets supplemented with omega-3 from fish oil as well as those fed both the high- and low-fat corn oil omega-6 diets. These results indicate that algae-derived DHA possesses greater tumor-suppressing properties than do corn or fish oil.15 Pregnancy and lactation DHA concentrations in breast milk range from 0.07% to greater than 1.0% of total fatty acids, with a mean of about 0.34%. DHA levels in breast milk are higher if a mother's diet is high in fish. DHA has recently gained attention as a supplement for pregnant women,16 noting studies of improved attention and visual acuity. One recent study indicates that low levels of plasma and erythrocyte DHA were associated with poor retinal development, low visual acuity, and poor cognitive development. In that same study, alpha-linolenic acid was shown as a source of fetal DHA, but that performed DHA was more readily accred. A working group from the ISSFAL International Society for the Study of Fatty Acids and Lipids recommended 300 mg/day of DHA for pregnant and lactating women, whereas the average consumption was between 45 mg and 115 mg per day of the women in the study. Other requirements are available from other sources.17 DHA has been an ingredient in several brands of premium infant formula sold in North America since 2001 after Mead Johnson, the first infant formula manufacturer to add DHA and ARA arachidonic acid to its Enfamil Lipil product, received approval by the Food and Drug Administration and Health Canada. Both DHA and ARA, manufactured by Martek Biosciences Corporation, are permitted in infant formula. The addition of DHA at dose-effective levels has been shown to improve cognitive function in both term and preterm infants. DHA makes infant formulas more like human milk than conventional formula containing Alpha-linolenic acid and linoleic acid, which are precursors to DHA. Formula sold in North America uses lipids from microorganisms grown in bioreactors as sources of DHA.183 Nutrition Promotion as a food additive DHA is actively promoted by manufacturers as a food additive. Until recently, sales other than to makers of infant formula have been minimal; however, in 2007, several DHA-fortified dairy items milk, yogurt began selling in grocery stores. There is less DHA available in the average diet than formerly, due to cattle being taken off grass and fed grain before butchering; likewise, there is less in eggs due to intensive farming. DHA is widely believed to be helpful to people with a history of heart disease, for premature infants, and to support healthy brain development especially in young children. Some manufactured DHA is a vegetarian product extracted from algae. Both types are odorless and tasteless after processing.19 Algae-derived DHA in infant nutrition The neutrality of this section is disputed. Please see the discussion on the talk page. December 2007 Please do not remove this message until the dispute is resolved. A study20 found that preterm infants fed baby formulas fortified with DHA derived directly from algae gained weight faster than infants fed formula fortified with DHA from fish oil. In addition, there are no risks of harmful contaminants such as methyl mercury or dioxins, which may be present in fish and fish oils.citation needed This is especially important for pregnant and nursing women and young children. Studies of vegans and vegetarians Vegans and vegetarians have markedly lower stores of DHA. Their bodily DHA levels do not rise much even with high dietary levels of linolenic acid. This, and features of the production and distribution of DHA in pregnant and lactating women, indicates that DHA per se is an essential nutrient.21 Since DHA is made by algae, there are vegan DHA supplements available. DHA and EPA in fish oils Fish oil is widely sold in gelatin capsules containing a mixture of omega-3 fatty acids including EPA and smaller quantities of DHA. Researchers have found that fish oil high in DHA and low in EPA lowered inflammator cytokines, such as IL-6 and IL-1β, associated with neurodegenerative and autoimmune diseases. They note that the brain normally contains DHA but no EPA.22 See also Chlorella Cyanobacteria List of omega-3 fatty acids Polyunsaturated fatty acids Eicosapentaenoic acid EPA Notes and references ^ docosa- is Greek for 22 ^ The omega end is the one furthest from the carboxyl group. ^ a b c Martek Biosciences Corporation 5 April 2007. History of Martek. Retrieved on March 10, 2007. ^ Cambridge Applied Polymers Ltd. 4 April 2006. Latest Publications on the Link between DHA and Intelligence / The Brain.. Retrieved on April 4, 2006. ^ Meharban Singh March, 2005. Essential Fatty Acids, DHA and the Human Brain from the Indian Journal of Pediatrics, Volume 72 PDF. Retrieved on October 8, 2007. ^ Youdim KA, Martin A, Joseph JA 2000. Essential fatty acids and the brain: possible health implications.. Retrieved on October 8, 2007. ^ Arthur A. Spector 1999. Essentiality of Fatty Acids from Lipids, Vol. 34. Retrieved on October 8, 2007. ^ Lukiw WJ, Cui JG, Marcheselli VL, Bodker M, Botkjaer A, Gotlinger K, Serhan CN, Bazan NG. pmid=16151530 2005 Oct. A role for docosahexaenoic acid-derived neuroprotectin D1 in neural cell survival and Alzheimer disease. J Clin Invest. 11510: 2774-83. ^ Serhan CN, Gotlinger K, Hong S, Arita M 2004. Resolvins, docosatrienes, and neuroprotectins, novel omega-3-derived mediators, and their aspirin-triggered endogenous epimers: an overview of their protective roles in catabasis. Prostaglandins Other Lipid Mediat. 73 3-4: 155-72. doi:10.1016/j.prostaglandins.2004.03.005. PMID 15290791. ^ McNamara RK, Hahn CG, Jandacek R, et al 2007. Selective deficits in the omega-3 fatty acid docosahexaenoic acid in the postmortem orbitofrontal cortex of patients with major depressive disorder. Biol. Psychiatry 62 1: 17-24. doi:10.1016/j.biopsych.2006.08.026. PMID 17188654. ^ DHA Deficit Detected in Frontal Cortex of Severely Depressed Patients September 2007. Retrieved on 2007-10-31. ^ De Caterina, R and Basta, G June, 2001. n-3 Fatty acids and the inflammatory response - biological background PDF. Retrieved on February 10, 2006. ^ Voss, M Reinhart, S Sankarappa and H Sprecher September, 1991. The metabolism of 7,10,13,16,19-docosapentaenoic acid to 4,7,10,13,16,19-docosahexaenoic acid in rat liver is independent of a 4- desaturase PDF. Retrieved on September 23, 2006. ^ National Institute on Aging July 16, 2007. DHA Phase 3 trial in Alzheimer's disease. Retrieved on August 10, 2007. ^ Martek Biosciences's DHA Shown To Inhibit Human Colon Carcinoma In Mice.. ^ Beth Vincent, MHS 2005-10-31. The Importance of DHA During Pregnancy and Breastfeeding. Retrieved on 2007-10-29. ^ Jennifer Denomme, Ken D. Stark, and Bruce J. Holub August 20. Directly Quantitated Dietary n-3 Fatty Acid Intakes of Pregnant Canadian Women Are Lower than Current Dietary Recommendations. Retrieved on October 9, 2007. ^ Connell, Gary, J. et al 2001-07-26. SOLVENTLESS EXTRACTION PROCESS. Retrieved on February 8, 2006. A patent at the WIPO. ^ Rivlin, Gary 2007-01-14. Magical or Overrated? A Food Additive in a Swirl, New York Times. Retrieved on 2007-01-15. ^ Clandinin M, Van Aerde J, Merkel K, Harris C, Springer M, Hansen J, Diersen-Schade D 2005. Growth and development of preterm infants fed infant formulas containing docosahexaenoic acid and arachidonic acid. J Pediatr 146 4: 461-8. doi:10.1016/j.jpeds.2004.11.030. PMID 15812447. ^ Muskiet F, Fokkema M, Schaafsma A, Boersma E, Crawford M 2004. Is docosahexaenoic acid DHA essential? Lessons from DHA status regulation, our ancient diet, epidemiology and randomized controlled trials. J Nutr 134 1: 183-6. PMID 14704315. ^ Vedin I, et al. June 2008. Effects of docosahexaenoic acid-rich n-3 fatty acid supplementation on cytokine release. Am J Clin Nutr 87 6: 1616-1622. v d e Lipids: fatty acids Saturated Butyric Hexanoic Caprylic Decanoic Lauric Myristic Palmitic Stearic Arachidic Behenic Lignoceric n-3 Unsaturated α-Linolenic Stearidonic Eicosapentaenoic Docosahexaenoic n-6 Unsaturated Linoleic γ-Linolenic Dihomo-γ-linolenic Arachidonic n-9 Unsaturated Oleic Erucic Nervonic Retrieved from http://en..org/wiki/Docosahexaenoic_acid Categories: Fatty acidsHidden categories: NPOV disputes from December 2007 | All NPOV disputes | All articles with statements | Articles with statements since February 2007 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 БългарÑ?ки Dansk Deutsch Español Français LatvieÅ¡u Nederlands 日本語 Português Basa Sunda Svenska 䏿–‡ This page was last modified on 13 August 2008, at 23:07
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