4,7,10,13,16,19-docosahexaenoic acid [C22:6w3]; cervonic acid (DHA, Doconexent)
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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]
- 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
Notes
- present in fish oils in varying amounts
- not found in plant sources excepting certain seaweeds
- Pharmaceutical/Neutraceutical: Lipil (Expecta) 200 mg[9]
More general terms
Additional terms
Component of
- docosahexaenoate/eicosapentaenoate/ubiquinone/vitamin e
- docosahexaenoate/eicosapentaenoate/phytosterol
- docosahexaenoate/eicosapentaenoate/phosphatidylserine
- docosahexaenoate/eicosapentaenoate/folic acid/hypericum perforatum
- docosahexaenoate/eicosapentaenoate
- cobalamin/docosahexaenoate/eicosapentaenoate/pyridoxine
- cobalamin/docosahexaenoate/eicosapentaenoate/folic acid/phytosterol/policosanol/pyridoxine
- cholecalciferol/docosahexaenoate/eicosapentaenoate/vitamin e
- ascorbate/copper gluconate/docosahexaenoate/eicosapentaenoate/lutein/zeaxanthin/zinc oxide
- ascorbate/calcium carbonate/cholecalciferol/choline bitartrate/cobalamin/docosahexaenoate/eicosapentaenoate/ferrous fumarate/folic acid/nicotinic acid/potassium iodide/pyridoxine/riboflavin/thiamine/vitamin e/zinc oxide
- alpha tocopherol/ascorbate/cholecalciferol/docosahexaenoate/ferrous fumarate/folic acid/pyridoxine/sodium docusate
- alpha tocopherol/ascorbate/calcium phosphate/cholecalciferol/docosahexaenoate/ferrous fumarate/folic acid/pyridoxine/sodium docusate
- alpha tocopherol/ascorbate/calcium citrate/carbonyl iron/cholecalciferol/docosahexaenoate/folic acid/nicotinamide/potassium iodide/pyridoxine/riboflavin/sodium docusate/thiamine/zinc oxide
- alpha tocopherol/ascorbate/beta carotene/calcium carbonate/cholecalciferol/cobalamin/docosahexaenoate/folic acid/magnesium oxide/nicotinamide/pyridoxine/riboflavin/thiamine/zinc oxide
- alpha tocopherol/ascorbate/calcium phosphate/docosahexaenoate/eicosapentaenoate/ferrous fumarate/folic acid/pyridoxine
- cobalamin/docosahexaenoate/eicosapentaenoate/folic acid/phytosterol/pyridoxine
- docosahexaenoate/eicosapentaenoate/vitamin e
- alpha tocopherol/ascorbate/calcium phosphate/docosahexaenoate/eicosapentaenoate/folic acid/pyridoxine
References
- ↑ 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: https://www.ncbi.nlm.nih.gov/pubmed/11118147
- ↑ Salem, M et al, Docosahexenoic acid: membrane function and metabolism. in: Health Effects of Polyunsaturated Fatty Acids in Seafoods, Academic Press, 1986
- ↑ 3.0 3.1 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: https://www.ncbi.nlm.nih.gov/pubmed/14556634
- ↑ 4.0 4.1 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: https://www.ncbi.nlm.nih.gov/pubmed/12936959
- ↑ 5.0 5.1 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: https://www.ncbi.nlm.nih.gov/pubmed/12716664
- ↑ 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: https://www.ncbi.nlm.nih.gov/pubmed/12654166
- ↑ 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: https://www.ncbi.nlm.nih.gov/pubmed/12065621
- ↑ 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: https://www.ncbi.nlm.nih.gov/pubmed/10419166
- ↑ 9.0 9.1 Mead Johnson, Evansville IL 47721 http:://ww.ExpectLIPIL.com
- ↑ 10.0 10.1 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 <PubMed> PMID: https://www.ncbi.nlm.nih.gov/pubmed/20959577 <Internet> http://jama.ama-assn.org/cgi/content/full/304/15/1675
- ↑ 11.0 11.1 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 <PubMed> PMID: https://www.ncbi.nlm.nih.gov/pubmed/21518693 <Internet> http://aje.oxfordjournals.org/content/early/2011/04/19/aje.kwr027.abstract
- ↑ 12.0 12.1 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
- ↑ 13.0 13.1 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 <PubMed> PMID: https://www.ncbi.nlm.nih.gov/pubmed/28324081 <Internet> http://jamanetwork.com/journals/jama/article-abstract/2612605
- ↑ 14.0 14.1 Collins CT et al. Docosahexaenoic acid and bronchopulmonary dysplasia in preterm infants. N Engl J Med 2017 Mar 30; 376:1245 <PubMed> PMID: https://www.ncbi.nlm.nih.gov/pubmed/28355511 <Internet> http://www.nejm.org/doi/10.1056/NEJMoa1611942