Naturally occurring, omega-3 polyunsaturated fatty acid (PUFA). Detected in small amounts in several species of algae, fungi, and in most fish oils. Also found in plant seed oils, especially black currants and various Echium species. Biosynthetic precursor of eicosapentaenoic acid (EPA); formed by desaturation of α-linolenic acid. Isoln from oil of the South African pilchard, Sardina ocellata J.: M. Matic, Biochem. J. 68, 692 (1958) PubMed. Quantification in Echium seeds: J. L. Guil-Guerrero et al., Phytochemistry 53, 451 (2000) DOI PubMed. Production by genetically remodeled canola: V. M. Ursin, J. Nutr. 133, 4271 (2003) PubMed; by transgenic soybeans: S. Sato et al., Crop Sci. 44, 646 (2004); H. Eckert et al., Planta 224, 1050 (2006) DOI PubMed. Metabolism in humans: M. J. James et al., Am. J. Clin. Nutr. 77, 1140 (2003) PubMed. Clinical effect of dietary supplementation on omega-3 index: W. S. Harris et al., Lipids 43, 805 (2008) DOI PubMed. Review of natural sources, medical uses, and role in human nutrition: J. L. Guil-Guerrero, Eur. J. Lipid Sci. Technol. 109, 1226-1236 (2007) DOI.