TY - JOUR
T1 - Identification of 14,2
AU - Yokokura, Yoshiyuki
AU - Isobe, Yosuke
AU - Matsueda, Shinnosuke
AU - Iwamoto, Ryo
AU - Goto, Tomomi
AU - Yoshioka, Takeshi
AU - Urabe, Daisuke
AU - Inoue, Masayuki
AU - Arai, Hiroyuki
AU - Arita, Makoto
N1 - Publisher Copyright:
© 2014 The Authors 2014. Published by Oxford University Press on behalf of the Japanese Biochemical Society. All rights reserved.
PY - 2014/12/1
Y1 - 2014/12/1
N2 - Docosahexaenoic acid (DHA) exhibits anti-inflammatory activity related to some of its oxygenated metabolites, such as D-series resolvins, protectin and maresin. Here, we analysed the lipids in inflammatory exudates using liquid chromatography-tandem mass spectrometry and identified a novel DHA metabolite, 14,20-dihydroxy-DHA (14,20-diHDHA) and showed that it is biosynthesized by eosinophils through the 12/15-lipoxygenase pathway. The chemical structure of the dominant 14,20-diHDHA isomer, which is endogenously biosynthesized by eosinophils, was identified as 14S,20R-diHDHA using chemically synthesized stereoisomers. Nanogram doses of 14,20-diHDHA displayed a potent anti-inflammatory action by limiting neutrophil infiltration in zymosan-induced peritonitis. The in vivo formation and potent anti-inflammatory action of 14,20-diHDHA may contribute to the protective effects of DHA.
AB - Docosahexaenoic acid (DHA) exhibits anti-inflammatory activity related to some of its oxygenated metabolites, such as D-series resolvins, protectin and maresin. Here, we analysed the lipids in inflammatory exudates using liquid chromatography-tandem mass spectrometry and identified a novel DHA metabolite, 14,20-dihydroxy-DHA (14,20-diHDHA) and showed that it is biosynthesized by eosinophils through the 12/15-lipoxygenase pathway. The chemical structure of the dominant 14,20-diHDHA isomer, which is endogenously biosynthesized by eosinophils, was identified as 14S,20R-diHDHA using chemically synthesized stereoisomers. Nanogram doses of 14,20-diHDHA displayed a potent anti-inflammatory action by limiting neutrophil infiltration in zymosan-induced peritonitis. The in vivo formation and potent anti-inflammatory action of 14,20-diHDHA may contribute to the protective effects of DHA.
KW - 15-lipoxygenase
KW - anti-inflammation
KW - lipidomics 12
KW - omega-3 polyunsaturated fatty acid
UR - https://www.scopus.com/pages/publications/84922464551
UR - https://www.scopus.com/pages/publications/84922464551#tab=citedBy
U2 - 10.1093/jb/mvu044
DO - 10.1093/jb/mvu044
M3 - Article
C2 - 25012818
AN - SCOPUS:84922464551
SN - 0021-924X
VL - 156
SP - 315
EP - 321
JO - Journal of biochemistry
JF - Journal of biochemistry
IS - 6
ER -