Arachidonic acid description

HETE, 5-Hvifroxy-b.h,11,14-ricosateiraenoie acid (S)-5 -hydroxy-6-irans-8,11,14-cis-eicosatetraenoic acid. C HjjOj mol wt 320.48. C 74.96%, H 10.06%, O 14.98%, Important intermediate in a series of biosynthetic processes leading from arachidonic add. q.v., to a number of biologically active compounds. First discovered during the transformation of arachidonic acid by rabbit peritoneal polymorphonuclear leukocytes P. Borgeat et al, J. Biol. Chem. 251, 7816 (1976). Revised description eidem, ibid. 

The initial description of biological activities of arachidonic acid metabolites arising from cytochrome P450 mono-oxygenases reveals similarities to prostanoids, i.e. they can act as secretagogues and local modulators of circulating hormones and their principal activity is circumscribed to the... 

Early attempts at description of the changes in lipid composition included a diminished degree of unsaturation in deficient animals, indicated by a decrease of the iodine value of tissue lipids. When alkaline isomerization technique became available for measurement of polyenoic acids, the deficient animal was found to have a diminished content of dienoic acid and tetraenoic acid but an enhanced content of trienoic acid (Rieckehoff et al., 1949). Through supplementation with single fatty acids, it was discovered that 1in-oleic acid induced increases in tetraenoic acid (arachidonic acid) but that linolenic acid induced increases in pentaene and hexaene acids (Widmer Holman, 1950). These experiments prompted more elegant ones in the laboratories of Mead and Klenk in which the metabolism of linoleic acid to arachidonic acid, linolenic acid to penta-enoic and hexaenoic acids, and oleic to eicosatrienoic acid were described in detail (Mead, 1971). 

FIGURE 5.10 Chemical structure of anandamide. Three models of anandamide (arachidonoyl ethanolamide, AEA) are shown. In the first one (on the top) the region inherited from arachidonic acid (C20 4(o6) is framed. Note the four-double bonds in the cis (Z) configuration (see Chapter 1 for a description of unsaturated fatty acids). The ethanolamine part is shaded in rose. The two other models show an energy-minimized structure of anandamide in tube and sphere rendition. The arrows indicate the correspondence of chemical groups between the models. 

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