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alpha-linolenate; alpha-linolenic acid [C18:3w3] (ALA)

[C18:3w3]. Function: - precursor to eicosapentaenoic (EPA) & docosahexaenoic acids (DHA) - in humans, conversion may be limited [1]. - while conversion of linoleic acid (LA) to arachidonic acid (AA) is generally very efficient, conversion of alpha linolenic acid (ALA) to EPA & DHA is not - in healthy individuals, 5-10% of ALA is converted to EPA, & 2-5% to DHA [2] - conversion is more efficient for women than for men - a possible explanation for the low conversion of ALA to EPA, a 3-enzyme process, is that the initial enzyme, 6-desaturase (EC 1.14.99.25), is rate limiting in humans, as it is in rodents [4] - ALA itself may reduce risk of cardiovascular disease [3] a) ventricular fibrillation b) platelet aggregation - ALA stimulates secretion of glucagon-like peptide 1 (GLP-1) from the gastrointestinal tract via FFAR1 & FFAR4 [4,5] Laboratory: - alpha-linolenate in erythrocytes - alpha-linolenate in serum/plasma

General

fatty acid, omega-3 (Epanova) linolenate; linolenic acid [C18:3]

Properties

COMPARTMENT: membrane SIZE: MW = 278.4 G/MOL

Database Correlations

PUBCHEM correlations

References

  1. Burdge G. Alpha-linolenic acid metabolism in men and women: nutritional and biological implications. Curr Opin Clin Nutr Metab Care. 2004 Mar;7(2):137-44. PMID: 15075703
  2. 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
  3. Lanzmann-Petithory D. Alpha-linolenic acid and cardiovascular diseases. J Nutr Health Aging. 2001;5(3):179-83. Review. PMID: 11458289
  4. Hirasawa A, Tsumaya K, Awaji T et al Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. Nat Med. 2005 Jan;11(1):90-4 PMID: 15619630
  5. Edfalk S, Steneberg P, Edlund H. Gpr40 is expressed in enteroendocrine cells and mediates free fatty acid stimulation of incretin secretion. Diabetes. 2008 Sep;57(9):2280-7 PMID: 18519800