title: The discovery and early structural studies of arachidonic acid.
abstract: Arachidonic acid and esterified arachidonate are ubiquitous components of every mammalian cell. This polyunsaturated fatty acid serves very important biochemical roles, including being the direct precursor of bioactive lipid mediators such as prostaglandin and leukotrienes. This 20 carbon fatty acid with four double bonds was first isolated and identified from mammalian tissues in 1909 by Percival Hartley. This was accomplished prior to the advent of chromatography or any spectroscopic methodology (MS, infrared, UV, or NMR). The name, arachidonic, was suggested in 1913 based on its relationship to the well-known arachidic acid (C20:0). It took until 1940 before the positions of the four double bonds were defined at 5,8,11,14 of the 20-carbon chain. Total synthesis was reported in 1961 and, finally, the configuration of the double bonds was confirmed as all-cis-5,8,11,14. By the 1930s, the relationship of arachidonic acid within the family of essential fatty acids helped cue an understanding of its structure and the biosynthetic pathway. Herein, we review the findings leading up to the discovery of arachidonic acid and the progress toward its complete structural elucidation.
authors.affiliation: Department of Pharmacology, University of Colorado Denver, Aurora, CO 80045.
authors.forename: Sarah A
authors.initials: SA
authors.lastname: Martin
authors.affiliation: Department of Pharmacology, Vanderbilt University School of Medicine, Nashville, TN 37232.
authors.forename: Alan R
authors.initials: AR
authors.lastname: Brash
authors.affiliation: Department of Pharmacology, University of Colorado Denver, Aurora, CO 80045 Robert.Murphy@ucdenver.edu.
authors.forename: Robert C
authors.initials: RC
authors.lastname: Murphy
mesh_terms: D016718:Arachidonic Acid / Q000737:chemistry* / Q000378:metabolism; D001671:Biochemistry / Q000266:history*; D005231:Fatty Acids, Unsaturated / Q000737:chemistry* / Q000378:metabolism; D049673:History, 20th Century; D049674:History, 21st Century; D006801:Humans
chemical_list: D005231:Fatty Acids, Unsaturated; D016718:Arachidonic Acid
keywords: Hazura’s rule; chemical analysis; essential fatty acid; fractional crystallization; linoleic acid; octobromoarachidic acid; ozonolysis; potassium permanganate; total synthesis