On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family

• Main Author: Igor A. Butovich
• Format: Article
• Language: English
• Published: Elsevier 2005-11-01
• Series: Journal of Lipid Research
• Subjects: 10,17(S)-docosatriene; 10,17-dihydroxydocosahexaenoic acid; lipoxygenase; double lipoxygenation; nuclear magnetic resonance; cis,trans-geometry
• Online Access: http://www.sciencedirect.com/science/article/pii/S0022227520328686
• ISSN: 0022-2275

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.