Iodination of docosahexaenoic acid by lactoperoxidase and thyroid gland in vitro: formation of an lodolactone.
In the presence of iodide, hydrogen peroxide and lactoperoxidase, docosahexaenoic acid (22:6 omega 3) was converted into iodinated compounds. The major product was identified as 5-iodo-4-hydroxy-7, 10, 13, 16, 19-docosapentaenoic acid, gamma-lactone, on the basis of 125 I incorporation, mass spectrometry, chemical modifications and proton nuclear magnetic resonance spectroscopy. Iodolactonization of docosahexaenoic acid occurred in the rat thyroid in vitro and was inhibited by the peroxidase inhibit or methimazole. These data indicate that formation of an idolactone constitutes one pathway of docosahexaenoic acid metabolism which could be expressed in tissues containing an iodide peroxidase.
D000818:Animals; D001095:Arachidonic Acids; D004281:Docosahexaenoic Acids; D004537:Eicosanoic Acids / Q000378:metabolism*; D005231:Fatty Acids, Unsaturated / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D006861:Hydrogen Peroxide; D066298:In Vitro Techniques; D007454:Iodides / Q000378:metabolism*; D007783:Lactones / Q000378:metabolism*; D007784:Lactoperoxidase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D010544:Peroxidases / Q000378:metabolism*; D051381:Rats; D013961:Thyroid Gland / Q000378:metabolism*
C026915:6-iodo-5-hydroxy-eicosatrienoic acid, delta-lactone; D001095:Arachidonic Acids; D004537:Eicosanoic Acids; D005231:Fatty Acids, Unsaturated; D007454:Iodides; D007783:Lactones; D004281:Docosahexaenoic Acids; C031204:5-iodo-4-hydroxy-7,10,13,16,19-docosapentaenoic acid gamma-lactone; D006861:Hydrogen Peroxide; D007784:Lactoperoxidase; D010544:Peroxidases