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  • 标题:The discovery and early structural studies of arachidonic acid
  • 本地全文:下载
  • 作者:Sarah A. Martin ; Alan R. Brash ; Robert C. Murphy
  • 期刊名称:JLR Papers In Press
  • 印刷版ISSN:0022-2275
  • 电子版ISSN:1539-7262
  • 出版年度:2016
  • 卷号:57
  • 期号:7
  • 页码:1126-1132
  • DOI:10.1194/jlr.R068072
  • 语种:English
  • 出版社:American Society for Biochemistry and Molecular Biology
  • 摘要: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.
  • 关键词:total synthesis ; linoleic acid ; ozonolysis ; potassium permanganate ; Hazura’s rule ; chemical analysis ; fractional crystallization ; octobromoarachidic acid ; essential fatty acid
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