Enzymatically oxygenated derivatives of the ω-3 fatty acids cis-4,7,10,13,16,19-docosahexaenoic acid (DHA) and cis-5,8,11,14,17-eicosapentaenoic acid, known as resolvins, have potent inflammation resolution activity (Serhan, C. N., Clish, C. B., Brannon, J., Colgan, S. P., Chiang, N., and Gronert, K. (2000) J. Exp. Med. 192, 1197–1204; Hong, S., Gronert, K., Devchand, P. R., Moussignac, R., and Serhan, C. N. (2003) J. Biol. 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™ 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. Enzymatically oxygenated derivatives of the ω-3 fatty acids cis-4,7,10,13,16,19-docosahexaenoic acid (DHA) and cis-5,8,11,14,17-eicosapentaenoic acid, known as resolvins, have potent inflammation resolution activity (Serhan, C. N., Clish, C. B., Brannon, J., Colgan, S. P., Chiang, N., and Gronert, K. (2000) J. Exp. Med. 192, 1197–1204; Hong, S., Gronert, K., Devchand, P. R., Moussignac, R., and Serhan, C. N. (2003) J. Biol. 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™ 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. Enzymatically formed oxygenation products of C-20 and C-22 long chain polyunsaturated fatty acids (LC-PUFAs), 4The abbreviations used are: LC-PUFA, long chain polyunsaturated fatty acid; ARA, Na-MES, 2-(N-morpholino)ethanesulfonic acid sodium salt; ARA, cis-5,8,11,14-eicosatetraenoic acid/arachidonic acid; EPA, cis-5,8,11,14,17-eicosapentaenoic acid; DHA, cis-4,7,10,13,16,19-docosahexaenoic acid; 10,17-HDHA, 10,17-dihydroxy-4,7,11,13,15,19-docosahexaenoic acid; (17S)-HDHA, (17S)-hydroxy-4,7,10,13,15,19-docosahexaenoic acid; TNF, tumor necrosis factor; HPLC, high performance liquid chromatography; 17-HDPAn-6, 17-hydroxy-4,7,10,13,15-docosapentaenoic acid; 10,17-HDPAn-6, 10,17-dihydroxy-4,7,11,13,15-docosapentaenoic acid; LC, liquid chromatography; MS, mass spectrometry; MS/MS, tandem mass spectrometry; VCD, vibrational circular dichroism; PBS, phosphate-buffered saline; ANOVA, analysis of variance. have important biological roles in inflammation, allergies, and blood clotting and are thus believed to have therapeutic potential in several chronic immune diseases (1Serhan C.N. Gotlinger K.H. Hong S. Lu Y. Siegelman J. Baer T. Yang R. Colgan S.P. Petasis N.A. J. Immunology. 2006; 176: 1848-1859Crossref PubMed Scopus (372) Google Scholar, 2Serhan C.N. Clish C.B. Brannon J. Colgan S.P. Chiang N. Gronert K. J. Exp. Med. 2000; 192: 1197-1204Crossref PubMed Scopus (946) Google Scholar, 3Hong S. Gronert K. Devchand P.R. Moussignac R. Serhan C.N. J. Biol. Chem. 2003; 278: 14677-14687Abstract Full Text Full Text PDF PubMed Scopus (840) Google Scholar, 4Serhan C.N. Hong S. Groner K. Colgan S.P. Devchand P.R. Mirick G. Moussignac R.L. J. Exp. Med. 2002; 196: 1025-1037Crossref PubMed Scopus (1349) Google Scholar, 5Marcheselli V.L. Hong S. Lukiw W.J. Tian X.H. Gronert K. Musto A. Hardy M. Gimenez J.M. Chiang N. Serhan C.N. Bazan N.G. J. Biol. Chem. 2003; 278: 43807-43817Abstract Full Text Full Text PDF PubMed Scopus (678) Google Scholar, 6Farooqui A.A. Horrocks L.A. Farooqui T. J. Neurochem. 2007; 101: 577-599Crossref PubMed Scopus (336) Google Scholar, 7Maderna P. 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M. R. E. G. and in to this been the of the of in of been that a of and DPAn-6 be a in in a of DPAn-6 was to of which in with a in a J. 2007; PubMed Scopus Google Scholar). the of of DPAn-6 in these is a for products of DPAn-6 in resolution of LC-PUFA, DPAn-3 with and in is known to be a potent of S. T. K. T. Biol. 2000; PubMed Scopus Google Scholar, J. A. PubMed Scopus Google Scholar, M. PubMed Google Scholar). this a potent on the of is known to to tumor inflammation, and to the that anti-inflammatory activity of DPAn-3 be products as in the of and M. 2003; Full Text Full Text PDF PubMed Scopus Google Scholar). The of this was to determine whether are formed from the C-22 DPAn-6 and DPAn-3, by to to products formed from to to products from the and to whether these compounds have anti-inflammatory also the for and of a of other C-22 that be as potential anti-inflammatory from from and (17S)-hydroxy-4,7,10,13,15,19-docosahexaenoic acid were from necrosis was from fatty acids were from were from were from high performance liquid chromatography were from was from was from and were from other and were from were from of DHA, DPAn-3, and DPAn-6 with 15-Lipoxygenase for of of 15-lipoxygenase a of was of DHA, DPAn-3 fatty acids in sodium and the reaction were The of the derivatives of the fatty acids was products were by UV an of T. Y. T. Samuelsson B. PubMed Scopus Google Scholar). of 15-Lipoxygenase with DHA, DPAn-3, and was used to substrates DPAn-3, and in sodium with a The was by and the with the enzyme the was UV described for The was were in were with a of the with a of an by a in this is the have that the for of the PubMed Scopus Google Scholar, PubMed Scopus Google Scholar). was used to the with the was used to the of the of DHA, DPAn-3, and DPAn-6 with 5-, 12-, and 15-Lipoxygenase for of the of was to a reaction fatty acid in and the of was to a fatty acid in and the 15-lipoxygenase of 15-lipoxygenase was to a reaction fatty acids in sodium were for three reaction were for products were with sodium and with on were and reaction products by chromatography coupled with tandem mass The reaction of 15-lipoxygenase with DPAn-6 described was for the of 17-hydroxy-4,7,10,13,15-docosapentaenoic acid and 10,17-dihydroxy-4,7,11,13,15-docosapentaenoic acid from of of and were a of on a C.N. Clish C.B. Brannon J. Colgan S.P. Chiang N. Gronert K. J. Exp. Med. 2000; 192: 1197-1204Crossref PubMed Scopus (946) Google on an preparatory with a The with a of and B. of and and of The used for of compounds was and were and and corresponding to of were and from several of was by UV as well as by were a and compounds were with were and with sodium to of was with was by and UV was on an a a of and were in and reaction and analysis was on a liquid chromatography with an mass analysis of the products of the of fatty acids and was on an with an mass with an on an with an were in was used as and with and of The was The was on a the same described for of the compounds similar a of were by of was in and used for were on a a and were for and were for were and were and was the same as that was used as a was to by of in and the compounds with of The were sodium to the corresponding The were on a as the a of The were as by as a The same was for 17-HDPAn-6, and the of of the two was to be the same as for The was tested with circular were by for and and were by of were was on the J. and Scholar) was by the of the in a with the of the corresponding in a compounds used for were and was by the and PBS, J. and Scholar). The of was as the of the in a The of in the was as the and of the corresponding in the of three of was used to the of from with well The of the in the was by was as of the of in the by the of in the and were a of in both and for and for and for and were by the were and were and for the and and for the animal were in with the for the and of as and by the of the of the the were and of was in the J. PubMed Scopus Google Scholar). were with of of the DPAn-6 compounds were to in of PBS, by of of in of was the to an was to the as a the were and in the were of from animal was and the were and to and were on as the Proc. Exp. Biol. Med. PubMed Scopus Google Scholar). were to the in The DPAn-6-derived in the in of to oral in to of to to and synthesized to as and in this were with of in in of the in the of the were by and The oral of the two DPAn-6 resolvins. the were by oral to the The two DPAn-6 were in PBS, and and and and the synthesized was a of was was as in the was and the was by to from the of the same for animal were in with to with are as with conversion of DHA, DPAn-3, and DPAn-6 with can be these of DPAn-6 was to of DPAn-3 and of were to derivatives by 15-lipoxygenase. These were also by which that these a with a was and this to the in three we also enzyme of the three substrates with 15-lipoxygenase the enzyme with and the the the was DPAn-3 the for the with which the enzyme DPAn-6 to products was that for and and for DPAn-3, and The reaction was with of the in sodium and products were by are and as a of for DPAn-3 DPAn-6 and are of with of substrates with in a new of with 5-, 12-, and a of products formed DHA, DPAn-3, and DPAn-6 are with the the produced which were by sodium to the corresponding The derivatives were in by products were identified on and of compounds and which were and for and derivatives and were and for of compounds and which were and for and DPAn-6 derivatives and were and for that in of oxygenation are in formed of DHA, DPAn-3, and DPAn-6 with 15-lipoxygenase in a new formed of DHA, DPAn-3, and DPAn-6 with in a new formed of DHA, DPAn-3, and DPAn-6 with in a new of the 15-lipoxygenase was the most efficient in fatty acids to oxylipins, and of the fatty acids to of the products characterized DPAn-6 DPAn-3 as substrates were similar to obtained from DHA, as (1Serhan C.N. Gotlinger K.H. Hong S. Lu Y. Siegelman J. Baer T. Yang R. Colgan S.P. Petasis N.A. J. Immunology. 2006; 176: 1848-1859Crossref PubMed Scopus (372) Google Scholar, 3Hong S. Gronert K. Devchand P.R. Moussignac R. Serhan C.N. J. Biol. Chem. 2003; 278: 14677-14687Abstract Full Text Full Text PDF PubMed Scopus (840) Google Scholar, 5Marcheselli V.L. Hong S. Lukiw W.J. Tian X.H. Gronert K. Musto A. Hardy M. Gimenez J.M. Chiang N. Serhan C.N. Bazan N.G. J. Biol. Chem. 2003; 278: 43807-43817Abstract Full Text Full Text PDF PubMed Scopus (678) Google Scholar). the 15-lipoxygenase products were oxygenated the 17-HDPAn-6, and from the fatty These compounds a with an and and derivatives were produced from three fatty The derivatives an with and which are of a The derivatives an of two by a The main formed with fatty acids was the the in three several other as well as derivatives were was the main formed was to oxygenation the in the products were also The was formed from and DPAn-3 and from DPAn-6 a of the for of the of oxylipins, that was of the and of 15-Lipoxygenase DPAn-6 the of products obtained of DPAn-6 was with 15-lipoxygenase. The main products that were formed were and similar to is described for the reaction. several other compounds derivatives and and compounds were These were on as well as UV the a UV with a of and a with other the of DPAn-6 UV and and the and with and which are of an the The for by these other compounds was of the main products of and in compounds that were further characterized and used for other of purified and The reaction by was purified by preparatory techniques described of were from several and further and for of with as described The the UV of the main mass of the main in with main by The with the of with an the UV of the main mass of the main in with main by The with the of and described a UV with an The in was to be were with the as in the and of The of and in both the and the were with the and were with by and The that was the The to produced to and with to a and a and and The were on several of as C. J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar, J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar) have described obtained from of several compounds that are of a a have produced a with a of to and this is in of the produced in this also that the is acid. is on the that the of is of the this is that the these is a of of with produced by C. J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar) are similar produced and purified to a UV with a and and of a in the The was to be The mass with of with and of DPAn-6 and is with the for this are in The the of with two of the a of and of these two as in the of 17-HDPAn-6, with were that have the of The and and were similar to of as well acid for and C. J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar, J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar). of for and for were the that the was acid. as described with known be for which are used for were in of in the of chromatography was used for of of and on is the same for similar compounds the same are used M. A. J. B. 2005; PubMed Scopus Google Scholar, C. 2000; PubMed Scopus Google Scholar). this the and was used to the of The was in and were the in is that the of the similar for that this enzymatically and 15-lipoxygenase is in the of as well as DPAn-6 the and of both compounds were by to be and were with and were for and for The corresponding were and of both compounds in PBS, was to be of as in the same were for for for for for for for and for that a of and that the a that is in PBS, The of compounds was tested in and as described was both compounds were for and for of DPAn-6 in the acute inflammation of the was used to anti-inflammatory activity of DPAn-6 resolvins. were by and was the to the were and were the of in the an in the was to the of the by both and 10,17-HDPAn-6, the to the was The major of the DPAn-6-derived compounds was to the of and the of in the a from active immune to resolution of the The two DPAn-6 compounds a of a animal were as as a of in this of and in from by by by by by by by by in a new two DPAn-6 were tested in a to anti-inflammatory activity in a animal and in a in of acute also to local administration. The intravenous in this were in the to for the and to for local administration. were an intravenous to for in that both and DPAn-6 intravenous and in in the and activity of these compounds for intravenous administration. was similar to the known and the potent the was of the The was active in similar in as with the intravenous of this The activity this oral in this was to the of DPAn-6 resolvins. from this are in The in this the from the in that the of produced a in the same of the The to the that of with in the by was of the the and high the The high of was most and the other the of was most The and high of this the DPAn-6 compounds in the of Scholar). The of in acid is used in these 15-lipoxygenase the of acid from M. 2002; PubMed Scopus Google Scholar). the and on DHA, and DPAn-3 with for oxygenated the substrates the ω-6 as be from with these S. Gronert K. Devchand P.R. Moussignac R. Serhan C.N. J. Biol. 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DHA, other such as DPAn-6 and DPAn-3, and are in in blood and several that these other be produced and as E. Am. J. Clin. Nutr. 2006; PubMed Google Scholar, J. Nutr. 2002; PubMed Google Scholar, N. 2007; PubMed Scopus Google Scholar, T. N. 2003; PubMed Scopus Google Scholar, T. R. W. J. J. N. J. 2004; Full Text Full Text PDF PubMed Scopus Google Scholar, T. J. M. N. J. Full Text Full Text PDF PubMed Google Scholar). biological of these DPAn-6-derived to be of with 15-lipoxygenase that DPAn-6 was to and DPAn-3 were thus that such DPAn-6 with 15-lipoxygenase in a enzyme was in the of a DPAn-3 the DPAn-6 proved to be the that was most to The reaction is a several such as from of the to and enzyme the substrates on which 15-lipoxygenase PubMed Scopus Google Scholar). The for acid and is PubMed Scopus Google and the for and is T. T. K. P. 2007; PubMed Scopus Google Scholar). some of the were was to of as is for the reaction. the are for the with which 15-lipoxygenase DHA, DPAn-3, and DPAn-6 to with other to the of in the and DPAn-3 are ω-3 fatty and the for DPAn-6 be to the that is an ω-6 fatty acid. the of the to the enzyme the as well as the for the of of the and the is to the of the in the of the main for our attention on DPAn-6-derived from the that is a of our J. 2007; PubMed Scopus Google Scholar). have that in a this the The major the two is that in to DHA, the DHA-S™ We thus that DPAn-6 to the anti-inflammatory activity of this and this Since most are produced by of on we DPAn-6 was a for and characterized the products of these The major products of the most efficient and 10,17-HDPAn-6, were characterized and for and further for anti-inflammatory of these of and these are important that in the the major produced by characterized as acid, was to be potent acid, in in a (1Serhan C.N. Gotlinger K.H. Hong S. Lu Y. Siegelman J. Baer T. Yang R. Colgan S.P. Petasis N.A. J. Immunology. 2006; 176: 1848-1859Crossref PubMed Scopus (372) Google Scholar). be that have that the is an the is produced a reaction. acid, activity in the same was to be biologically our of in and as by high resolution were the same as products described by C. J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar, J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar). that is from the main in and is in with a the major in and a in as described by Serhan (1Serhan C.N. Gotlinger K.H. Hong S. Lu Y. Siegelman J. Baer T. Yang R. Colgan S.P. Petasis N.A. J. Immunology. 2006; 176: 1848-1859Crossref PubMed Scopus (372) Google Scholar, J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar). is known to with an the ω-6 been with several such as acid, acid, and acid, was used C. J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar, R. A. T. PubMed Scopus Google Scholar). Serhan have demonstrated that is the main of the reaction of with and that in to compounds of DHA, to S. Gronert K. Devchand P.R. Moussignac R. Serhan C.N. J. Biol. Chem. 2003; 278: 14677-14687Abstract Full Text Full Text PDF PubMed Scopus (840) Google Scholar, 4Serhan C.N. Hong S. Groner K. Colgan S.P. Devchand P.R. Mirick G. Moussignac R.L. J. Exp. Med. 2002; 196: 1025-1037Crossref PubMed Scopus (1349) Google Scholar). Our chromatography that DPAn-6 is by to used such as VCD, that are used to determine for is this class of molecules is in thus the of to a of as described to a and we thus that this the and a to is for described by C. J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar, J. 2006; Full Text Full Text PDF PubMed Scopus Google Scholar). of these two DPAn-6 derived can be the used of C. C. Y. Curr. Opin. 2002; Google Scholar, J. 2000; PubMed Scopus Google Scholar, C. B. P. Adv. Scopus Google Scholar). on this a good have the and a C. B. P. Adv. Scopus Google Scholar). The two and 10,17-HDPAn-6, of the that are and this high the of these compounds was that of a of other used such as and the of both DPAn-6-derived be with and used in were produced and was purified that the in the animal were to these DPAn-6 resolvins. the of acute inflammation, both and were The DPAn-6 to used by Serhan and S. Gronert K. Devchand P.R. Moussignac R. Serhan C.N. J. Biol. Chem. 2003; 278: 14677-14687Abstract Full Text Full Text PDF PubMed Scopus (840) Google Scholar, 4Serhan C.N. Hong S. Groner K. Colgan S.P. Devchand P.R. Mirick G. Moussignac R.L. J. Exp. Med. 2002; 196: 1025-1037Crossref PubMed Scopus (1349) Google Scholar) with in the same by and similar to that for resolvins, which our the were the same of of the have (1Serhan C.N. Gotlinger K.H. Hong S. Lu Y. Siegelman J. Baer T. Yang R. Colgan S.P. Petasis N.A. J. Immunology. 2006; 176: 1848-1859Crossref PubMed Scopus (372) Google Scholar). both DPAn-6 to the in and both compounds were as as the a a animal Interestingly, both compounds and is with a described by T. M. 2004; is and in to the is to the by which the DPAn-6 in the of acute inflammation, to the resolvins. The is a used of acute inflammation and been used to the of M. Serhan C.N. J. Exp. Med. 2007; PubMed Scopus Google Scholar). our inflammation was by this both and by a intravenous was similar to the to synthesized (17S)-HDHA, also compounds also the both compounds with the oral The 17-HDPAn-6, for was active the to activity the and high The most in in were for and for These that is potent 17-HDPAn-6, that of to that to in for we the for the in with activity R.L. J. 2002; PubMed Scopus Google Scholar, Sci. 2004; PubMed Scopus Google Scholar). on to the resolvins, in both by to compounds and activity similar in acute inflammation these DPAn-6-derived to resolvins, which in a to inflammation and can thus be categorized as DPAn-6-derived resolvins. be to determine whether inflammation, such as that in can be by DPAn-6 fatty acid by of these DPAn-6-derived a of to be to the and therapeutic of both and 10,17-HDPAn-6, these a new class of therapeutic resolvins. We for and and for
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