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)xydocasahaenoic acid in 10,17 (S)-dihydro (pero)sydocasahexa-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)-dihdro(pero)xydocasahexa-4Z,7Z,11E,13E,15Z,19Z-enoic acid were found among the reaction products. (sic) It is very likely that a described earlier neuroprotectin D1 [or 10,17(S)docosatriene], a novel and potent amti-inflammatory compound derived from docosahexaeonic acid, was, in fact, 10,17 (S)-dihydroxydocasahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid fromed through a double lipoxygenation mechanism instead of a previously thought epoxidation/ isomerization mechanism.-Butovich, I.A. On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family.