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4,7,10,13,16,19-docosahexaenoic acid [C22:6w3]; cervonic acid (DHA, Doconexent)

Function: - ligand for retinoid X receptor in mouse brain - may be preferentially associated with phosphatidylserine & phosphatidylethanolamine - cholesterol has a low affinity for DHA-containing phospholipids; this reduced affinity may serve as a mechanism for triggering the formation of lipid microdomains such as lipid rafts [3] - neuroprotectin D1 may mediate some of the protective actions of DHA. Structure: - [C22:6w3] Expression: - synthesis of docosahexaenoic acid from eicosapentaenoic acid & from alpha-linolenic acid is limited in humans [4,5] - DHA in tissues % phospholipid tissue species 37 phosphatidylserine gray matter human 24 phosphatidylethanolamine gray matter human 6 phosphatidylserine white matter human 3 phosphatidylethanolamine white matter human 34 phosphatidylserine synaptic membrane rat 32 phosphatidylethanolamine synaptic membrane rat 43 phosphatidylethanolamine synaptic membrane mouse 37 phosphatidylserine synaptic vesicle rat 31 phosphatidylethanolamine synaptic vesicle rat Pathology: - high serum levels associated with high-grade prostate cancer [11] Pharmacology: - DHA may play a protective role in Alzheimer's disease [6-8] - DHA penetrates blood brain barrier [15] - higher brain DHA may correlate with better cognitive measures in apoE4 carriers [15] - EPA & DHA intake up to 0.20 grams daily is associated with decreased cardiovascular risk (odds ratio 0.64) [12] - does not lower risk for postpartum depression or improve offspring's cognitive or language development [10] - prenatal docosahexaenoic acid (DHA) supplementation does not lead to improved IQ in school-aged children [13] - enteral supplementation with docosahexaenoic acid does not improve respiratory outcomes (bronchopulmonary dysplasia) for extremely premature infants [14] - see omega-3 fatty acid Laboratory: - docosahexaenoate in erythrocytes - docosahexaenoate in serum/plasma Notes: 1) present in fish oils in varying amounts 2) not found in plant sources excepting certain seaweeds 3) Pharmaceutical/Neutraceutical: Lipil (Expecta) 200 mg [9]

Related

fatty acid composition of brain neuroprotectin D1 (NPD1)

General

fatty acid, omega-3 (Epanova)

Properties

COMPARTMENT: membrane SIZE: MW = 328.5 G/MOL

Database Correlations

PUBCHEM correlations

References

  1. de Urquiza AM et al Docosahexaenoic acid, a ligand for the retinoid X receptor in mouse brain. Science. 2000 Dec 15;290(5499):2140-4. PMID: 11118147
  2. Salem, M et al, Docosahexenoic acid: membrane function and metabolism. in: Health Effects of Polyunsaturated Fatty Acids in Seafoods, Academic Press, 1986
  3. Shaikh SR, Cherezov V, Caffrey M, Stillwell W, Wassall SR. Interaction of cholesterol with a docosahexaenoic acid- containing phosphatidylethanolamine: trigger for microdomain/ raft formation? Biochemistry. 2003 Oct 21;42(41):12028-37 PMID: 14556634
  4. Davis BC, Kris-Etherton PM. Achieving optimal essential fatty acid status in vegetarians: current knowledge and practical implications. Am J Clin Nutr. 2003 Sep;78(3 Suppl):640S-646S. Review. PMID: 12936959
  5. James MJ, Ursin VM, Cleland LG. Metabolism of stearidonic acid in human subjects: comparison with the metabolism of other n-3 fatty acids. Am J Clin Nutr. 2003 May;77(5):1140-5. PMID: 12716664
  6. Tully AM, Roche HM, Doyle R, Fallon C, Bruce I, Lawlor B, Coakley D, Gibney MJ. Low serum cholesteryl ester-docosahexaenoic acid levels in Alzheimer's disease: a case-control study. Br J Nutr. 2003 Apr;89(4):483-9. PMID: 12654166
  7. Hashimoto M, Hossain S, Shimada T, Sugioka K, Yamasaki H, Fujii Y, Ishibashi Y, Oka J, Shido O. Docosahexaenoic acid provides protection from impairment of learning ability in Alzheimer's disease model rats. J Neurochem. 2002 Jun;81(5):1084-91. PMID: 12065621
  8. Kyle DJ, Schaefer E, Patton G, Beiser A. Low serum docosahexaenoic acid is a significant risk factor for Alzheimer's dementia. Lipids. 1999;34 Suppl:S245. PMID: 10419166
  9. Mead Johnson, Evansville IL 47721 http:://ww.ExpectLIPIL.com
  10. Makrides M et al Effect of DHA Supplementation During Pregnancy on Maternal Depression and Neurodevelopment of Young Children JAMA. 2010;304(15):1675-1683. doi:10.1001/jama.2010.1507 PMID: 20959577 http://jama.ama-assn.org/cgi/content/full/304/15/1675
  11. Brasky TM et al Serum Phospholipid Fatty Acids and Prostate Cancer Risk: Results From the Prostate Cancer Prevention Trial Am. J. Epidemiol April 24, 2011 PMID: 21518693 http://aje.oxfordjournals.org/content/early/2011/04/19/aje.kwr027.abstract
  12. Office of Dietary Supplements, National Institutes of Health Nutritional Research Series: Advancing the Role of Evidence- based Reviews in Nutrition Research and Applications Volume 4: Effects of Eicosapentanoic Acid and Docosahexanoic Acid on Mortality Across Diverse Settings: Systematic Review and Meta-Analysis of Randomized Trials and Prospective Cohorts http://www.ahrq.gov/clinic/tp/nutritn4tp.htm
  13. Gould JF, Treyvaud K, Yelland LN et al. Seven-year follow-up of children born to women in a randomized trial of prenatal DHA supplementation. JAMA 2017 Mar 21; 317:1173 PMID: 28324081 http://jamanetwork.com/journals/jama/article-abstract/2612605
  14. Collins CT et al. Docosahexaenoic acid and bronchopulmonary dysplasia in preterm infants. N Engl J Med 2017 Mar 30; 376:1245 PMID: 28355511 http://www.nejm.org/doi/10.1056/NEJMoa1611942
  15. George J Omega-3 Supplements Show Benefit in APOE4 Carriers. Trial finds DHA can penetrate the brain before dementia onset. MedPage Today November 1, 2024 https://www.medpagetoday.com/meetingcoverage/ctad/112713

Component-of

alpha tocopherol/ascorbate/beta carotene/calcium carbonate/cholecalciferol/cobalamin/docosahexaenoate/folic acid/magnesium oxide/nicotinamide/pyridoxine/riboflavin/thiamine/zinc oxide alpha tocopherol/ascorbate/calcium citrate/carbonyl iron/cholecalciferol/docosahexaenoate/folic acid/nicotinamide/potassium iodide/pyridoxine/riboflavin/sodium docusate/thiamine/zinc oxide alpha tocopherol/ascorbate/calcium phosphate/cholecalciferol/docosahexaenoate/ferrous fumarate/folic acid/pyridoxine/sodium docusate alpha tocopherol/ascorbate/calcium phosphate/docosahexaenoate/eicosapentaenoate/ferrous fumarate/folic acid/pyridoxine alpha tocopherol/ascorbate/calcium phosphate/docosahexaenoate/eicosapentaenoate/folic acid/pyridoxine alpha tocopherol/ascorbate/calcium phosphate/docosahexaenoate/ferrous fumarate/folic acid/pyridoxine/sodium docusate alpha tocopherol/ascorbate/cholecalciferol/docosahexaenoate/ferrous fumarate/folic acid/pyridoxine/sodium docusate ascorbate/calcium carbonate/cholecalciferol/choline bitartrate/cobalamin/docosahexaenoate/eicosapentaenoate/ferrous fumarate/folic acid/nicotinic acid/potassium iodide/pyridoxine/riboflavin/thiamine/vitamin e/zinc oxide ascorbate/copper gluconate/docosahexaenoate/eicosapentaenoate/lutein/zeaxanthin/zinc oxide cholecalciferol/docosahexaenoate/eicosapentaenoate/vitamin e cobalamin/docosahexaenoate/eicosapentaenoate/folic acid/phytosterol/policosanol/pyridoxine cobalamin/docosahexaenoate/eicosapentaenoate/folic acid/phytosterol/pyridoxine cobalamin/docosahexaenoate/eicosapentaenoate/pyridoxine docosahexaenoate/eicosapentaenoate docosahexaenoate/eicosapentaenoate/folic acid/hypericum perforatum docosahexaenoate/eicosapentaenoate/phosphatidylserine docosahexaenoate/eicosapentaenoate/phytosterol docosahexaenoate/eicosapentaenoate/ubiquinone/vitamin e docosahexaenoate/eicosapentaenoate/vitamin e docosahexaenoate/omega 3 fatty acid ethyl esters