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Chem. 278, 14677-14687). Our objective was to determine whether similar derivatives are enzymatically synthesized from other C-22 fatty acids and whether these molecules possess inflammation resolution properties. The reaction of DHA, DPAn-3, and DPAn-6 with 5-, 12-, and 15-lipoxygenases produced oxylipins, which were identified and characterized by liquid chromatography coupled with tandem mass-spectrometry. DPAn-6 and DPAn-3 proved to be good substrates for 15-lipoxygenase. 15-Lipoxygenase proved to be the most efficient enzyme of the three tested for conversion of long chain polyunsaturated fatty acids to corresponding oxylipins. Since DPAn-6 is a major component of Martek DHA-S TM oil, we focused our attention on reaction products obtained from the DPAn-6 and 15-lipoxygenase reaction. (17S)-hydroxy-DPAn-6 and (10,17S)-dihydroxy-DPAn-6 were the main products of this reaction. These compounds were purified by preparatory high performance liquid chromatography techniques and further characterized by NMR, UV spectrophotometry, and tandem mass spectrometry. We tested both compounds in two animal models of acute inflammation and demonstrated that both compounds are potent anti-inflammatory agents that are active on local intravenous as well as oral administration. These oxygenated DPAn-6 compounds can thus be categorized as a new class of DPAn-6-derived resolvins.

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m/e (M+) 273.0993 (caled for C15H16N04 273.1001). 6-(Aminocarbonyl)-7,8-dihydro-6H-furo[3,2-e]indole-2carboxylic Acid (7). A suspension of 35b (0.27 g, 1.0 mmol) in methanol (15 mL) was basified with 0.1 N NaOH to pH 10 and was stirred until starting material was consumed as indicated by TLC. The solution was acidified with 0.1 N HC1 to pH 1 and chilled, and the solid was filtered and dried over P205 to yield acid 7 [0.20 g (80%)] as an off-white solid: dec pt >230 °C; lH