On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family.
Potato tuber lipoxygenase was shown to convert 17(S)-hydro(pero)xydocasahexaenoic acid in 10,17(S)-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid [10,17(S)-diHDHA] which was formed apparently through a double lipoxygenation mechanism. No traces of 10,17(S)-dihydro(pero)xydocosahexa-4Z,7Z,11E,13E,15Z,19Z-enoic acid were found among the reaction products. It is very likely that a described earlier "neuroprotectin D1" [or "10,17(S)docosatriene"], a novel and potent anti-inflammatory compound derived from docosahexaenoic acid, was, in fact, 10,17(S)-dihydroxydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid formed through a double lipoxygenation mechanism instead of a previously thought epoxidation/isomerization mechanism.
Butovich
Igor A
IA
Department of Ophthalmology, University of Texas Southwestern Medical Center, Dallas, TX 75390-9057, USA. igor.butovich@utsouthwestern.edu
D000893:Anti-Inflammatory Agents / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D004281:Docosahexaenoic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008084:Lipoxygenase / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011198:Solanum tuberosum / Q000201:enzymology; D013025:Glycine max / Q000201:enzymology
D000893:Anti-Inflammatory Agents; C487679:protectin D1; D004281:Docosahexaenoic Acids; D008084:Lipoxygenase