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Biosynthesis, Biological Functions, and Receptors of Leukotriene B4 and 12(S)-Hydroxyheptadecatrienoic Acid

  • Toshiaki OkunoEmail author
  • Takehiko Yokomizo
Chapter

Abstract

Leukotriene B4 (LTB4, 5(S),12(R)-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid) is an inflammatory lipid mediator derived from arachidonic acid by the sequential actions of cytosolic phospholipase A2 (cPLA2), 5-lipoxygenase (5-LOX), and leukotriene A4 hydrolase (LTA4H). LTB4 was initially recognized as a chemotactic factor of leukocytes functioning via LTB4 receptor 1 (BLT1). The LTB4-BLT1 axis is now known to play important roles in acute and chronic inflammation and immune diseases. Leukotriene B4 receptor 2 (BLT2) was originally identified as a low-affinity receptor of LTB4, but BLT2 is now known to be a high-affinity receptor of 12(S)-hydroxyheptadeca-5Z,8E,10E-trienoic acid (12-HHT). The 12-HHT metabolite of prostaglandin (PG) H2 is biosynthesized by cyclooxygenase (COX) enzymes from arachidonic acid. Although 12-HHT has long been considered a by-product of thromboxane A2 (TxA2) production, the 12-HHT-BLT2 axis plays important roles in epithelial cells. Herein, we summarize the biosynthesis, biological functions, and receptors of LTB4 and 12-HHT.

Keywords

BLT1 BLT2 Eicosanoid GPCR LTB4 12-HHT 

References

  1. 1.
    T. Shimizu, Annu. Rev. Pharmacol. Toxicol. 49, 123 (2009)CrossRefGoogle Scholar
  2. 2.
    J.Z. Haeggström, C.D. Funk, Chem. Rev. 111, 5866 (2011)PubMedCrossRefPubMedCentralGoogle Scholar
  3. 3.
    M. Wan, X. Tang, A. Stsiapanava, J.Z. Haeggström, Semin. Immunol. 33, 3 (2017)PubMedCrossRefPubMedCentralGoogle Scholar
  4. 4.
    T. Yokomizo, T. Izumi, K. Chang, Y. Takuwa, T. Shimizu, Nature 387, 620 (1997)PubMedPubMedCentralCrossRefGoogle Scholar
  5. 5.
    T. Yokomizo, K. Kato, K. Terawaki, T. Izumi, T. Shimizu, J. Exp. Med. 192, 421 (2000)PubMedPubMedCentralCrossRefGoogle Scholar
  6. 6.
    T. Okuno, Y. Iizuka, H. Okazaki, T. Yokomizo, R. Taguchi, T. Shimizu, J. Exp. Med. 205, 759 (2008)PubMedPubMedCentralCrossRefGoogle Scholar
  7. 7.
    K. Saeki, T. Yokomizo, Semin. Immunol. 33, 30 (2017)PubMedPubMedCentralCrossRefGoogle Scholar
  8. 8.
    R.C. Murphy, M.A. Gijón, Biochem. J. 405, 379 (2007)PubMedCrossRefPubMedCentralGoogle Scholar
  9. 9.
    D.J. Welsch, D.P. Creely, S.D. Hauser, K.J. Mathis, G.G. Krivi, P.C. Isakson, Proc. Natl. Acad. Sci. U. S. A. 91, 9745 (1994)PubMedPubMedCentralCrossRefGoogle Scholar
  10. 10.
    B.K. Lam, J.F. Penrose, G.J. Freeman, K.F. Austen, Proc. Natl. Acad. Sci. U. S. A. 91, 7663 (1994)PubMedPubMedCentralCrossRefGoogle Scholar
  11. 11.
    D.W. Nicholson, A. Ali, J.P. Vaillancourt, J.R. Calaycay, R.A. Mumford, R.J. Zamboni, A.W. Ford-Hutchinson, Proc. Natl. Acad. Sci. U. S. A. 90, 2015 (1993)PubMedPubMedCentralCrossRefGoogle Scholar
  12. 12.
    S.P. Cole, J. Biol. Chem. 289, 30880 (2014)PubMedPubMedCentralCrossRefGoogle Scholar
  13. 13.
    M.E. Anderson, R.D. Allison, A. Meister, Proc. Natl. Acad. Sci. U. S. A. 79, 1088 (1982)PubMedPubMedCentralCrossRefGoogle Scholar
  14. 14.
    C.W. Lee, R.A. Lewis, E.J. Corey, K.F. Austen, Immunology 48, 27 (1983)PubMedPubMedCentralGoogle Scholar
  15. 15.
    J. Gillard, A.W. Ford-Hutchinson, C. Chan, S. Charleson, D. Denis, A. Foster, R. Fortin, S. Leger, C.S. McFarlane, H. Morton, H. Piechuta, D. Riendeau, C.A. Rouzer, J. Rokach, R. Young, D.E. MacIntyre, L. Peterson, T. Bach, G. Eiermann, Can. J. Physiol. Pharmacol. 67, 456 (1989)PubMedCrossRefPubMedCentralGoogle Scholar
  16. 16.
    D.K. Miller, J.W. Gillard, P.J. Vickers, S. Sadowski, C. Léveillé, J.A. Mancini, P. Charleson, R.A. Dixon, A.W. Ford-Hutchinson, R. Fortin, J.Y. Gauthier, J. Rodkey, R. Rosen, C. Rouzer, I.S. Sigal, C.D. Strader, J.F. Evans, Nature 343, 278 (1990)PubMedCrossRefPubMedCentralGoogle Scholar
  17. 17.
    O. Werz, J. Gerstmeier, S. Libreros, X. De la Rosa, M. Werner, P.C. Norris, N. Chiang, C.N. Serhan, Nat. Commun. 9, 59 (2018)PubMedPubMedCentralCrossRefGoogle Scholar
  18. 18.
    C. Lehmann, J. Homann, A.K. Ball, R. Blöcher, T.K. Kleinschmidt, D. Basavarajappa, C. Angioni, N. Ferreiros, A.K. Häfner, O. Rådmark, E. Proschak, J.Z. Haeggström, G. Geisslinger, M.J. Parnham, D. Steinhilber, A.S. Kahnt, FASEB J. 29, 5029 (2015)PubMedCrossRefPubMedCentralGoogle Scholar
  19. 19.
    B. Samuelsson, Science 220, 568 (1983)PubMedCrossRefPubMedCentralGoogle Scholar
  20. 20.
    J.Z. Haeggström, A. Wetterholm, Cell. Mol. Life Sci. 59, 742 (2002)PubMedCrossRefPubMedCentralGoogle Scholar
  21. 21.
    M.M. Thunnissen, P. Nordlund, J.Z. Haeggström, Nat. Struct. Biol. 8, 131 (2001)PubMedCrossRefPubMedCentralGoogle Scholar
  22. 22.
    R.J. Snelgrove, P.L. Jackson, M.T. Hardison, B.D. Noerager, A. Kinloch, A. Gaggar, S. Shastry, S.M. Rowe, Y.M. Shim, T. Hussell, J.E. Blalock, Science 330, 90 (2010)PubMedPubMedCentralCrossRefGoogle Scholar
  23. 23.
    A. Fradin, J.A. Zirrolli, J. Maclouf, L. Vausbinder, P.M. Henson, R.C. Murphy, J. Immunol. 143, 3680 (1989)PubMedPubMedCentralGoogle Scholar
  24. 24.
    J.E. McGee, F.A. Fitzpatrick, Proc. Natl. Acad. Sci. U. S. A. 83, 1349 (1986)PubMedPubMedCentralCrossRefGoogle Scholar
  25. 25.
    F. Grimminger, U. Sibelius, W. Seeger, Am. J. Physiol. 261, L195 (1991)PubMedCrossRefPubMedCentralGoogle Scholar
  26. 26.
    S. Zarini, M.A. Gijón, A.E. Ransome, R.C. Murphy, A. Sala, Proc. Natl. Acad. Sci. U. S. A. 106, 8296 (2009)PubMedPubMedCentralCrossRefGoogle Scholar
  27. 27.
    J.E. Fabre, J.L. Goulet, E. Riche, M. Nguyen, K. Coggins, S. Offenbacher, B.H. Koller, J. Clin. Invest. 109, 1373 (2002)PubMedPubMedCentralCrossRefGoogle Scholar
  28. 28.
    H. Sumimoto, S. Minakami, J. Biol. Chem. 265, 4348 (1990)PubMedPubMedCentralGoogle Scholar
  29. 29.
    Y. Kikuta, E. Kusunose, H. Sumimoto, Y. Mizukami, K. Takeshige, T. Sakaki, Y. Yabusaki, M. Kusunose, Arch. Biochem. Biophys. 355, 201 (1998)PubMedCrossRefPubMedCentralGoogle Scholar
  30. 30.
    Y. Kikuta, E. Kusunose, M. Kusunose, J. Biochem. 127, 1047 (2000)PubMedCrossRefPubMedCentralGoogle Scholar
  31. 31.
    T. Yokomizo, Y. Ogawa, N. Uozumi, K. Kume, T. Izumi, T. Shimizu, J. Biol. Chem. 271, 2844 (1996)PubMedCrossRefPubMedCentralGoogle Scholar
  32. 32.
    T. Yokomizo, T. Izumi, T. Takahashi, T. Kasama, Y. Kobayashi, F. Sato, Y. Taketani, T. Shimizu, J. Biol. Chem. 268, 18128 (1993)PubMedPubMedCentralGoogle Scholar
  33. 33.
    C.M. Ensor, H. Zhang, H.H. Tai, Biochem. J. 330 (Pt 1), 103 (1998)PubMedPubMedCentralCrossRefGoogle Scholar
  34. 34.
    C.B. Clish, B.D. Levy, N. Chiang, H.H. Tai, C.N. Serhan, J. Biol. Chem. 275, 25372 (2000)PubMedCrossRefPubMedCentralGoogle Scholar
  35. 35.
    P. Borgeat, B. Samuelsson, J. Biol. Chem. 254, 7865 (1979)PubMedPubMedCentralGoogle Scholar
  36. 36.
    A.W. Ford-Hutchinson, M.A. Bray, M.V. Doig, M.E. Shipley, M.J. Smith, Nature 286, 264 (1980)PubMedCrossRefPubMedCentralGoogle Scholar
  37. 37.
    B. Colom, J.V. Bodkin, M. Beyrau, A. Woodfin, C. Ody, C. Rourke, T. Chavakis, K. Brohi, B.A. Imhof, S. Nourshargh, Immunity 42, 1075 (2015)PubMedPubMedCentralCrossRefGoogle Scholar
  38. 38.
    T. Lämmermann, P.V. Afonso, B.R. Angermann, J.M. Wang, W. Kastenmüller, C.A. Parent, R.N. Germain, Nature 498, 371 (2013)PubMedCrossRefGoogle Scholar
  39. 39.
    M.F. Costa, R. de Souza-Martins, M.C. de Souza, C.F. Benjamim, B. Piva, B.L. Diaz, M. Peters-Golden, M. Henriques, C. Canetti, C. Penido, J. Leukoc. Biol. 87, 323 (2010)PubMedCrossRefPubMedCentralGoogle Scholar
  40. 40.
    K. Goodarzi, M. Goodarzi, A.M. Tager, A.D. Luster, U.H. von Andrian, Nat. Immunol. 4, 965 (2003)PubMedPubMedCentralCrossRefGoogle Scholar
  41. 41.
    F. Okamoto, K. Saeki, H. Sumimoto, S. Yamasaki, T. Yokomizo, J. Biol. Chem. 285, 41113 (2010)PubMedPubMedCentralCrossRefGoogle Scholar
  42. 42.
    S.P. Lee, C.H. Serezani, A.I. Medeiros, M.N. Ballinger, M. Peters-Golden, J. Immunol. 182, 530 (2009)PubMedCrossRefPubMedCentralGoogle Scholar
  43. 43.
    H. Widegren, M. Andersson, P. Borgeat, L. Flamand, S. Johnston, L. Greiff, Respir. Med. 105, 997 (2011)PubMedCrossRefPubMedCentralGoogle Scholar
  44. 44.
    E. Gaudreault, J. Gosselin, J. Immunol. 180, 6211 (2008)PubMedCrossRefPubMedCentralGoogle Scholar
  45. 45.
    M. Wan, A. Sabirsh, A. Wetterholm, B. Agerberth, J.Z. Haeggström, FASEB J. 21, 2897 (2007)PubMedCrossRefPubMedCentralGoogle Scholar
  46. 46.
    L. Flamand, M.J. Tremblay, P. Borgeat, J. Immunol. 178, 8036 (2007)PubMedCrossRefPubMedCentralGoogle Scholar
  47. 47.
    R.J. Griffiths, E.R. Pettipher, K. Koch, C.A. Farrell, R. Breslow, M.J. Conklyn, M.A. Smith, B.C. Hackman, D.J. Wimberly, A.J. Milici, D.N. Scampoli, J.B. Cheng, J.S. Pippar, C.J. Pazoles, N.S. Doherty, L.S. Melvin, L.A. Reiter, M.S. Biggars, F.C. Falkner, D.Y. Mitchell, T.E. Liston, H.J. Showell, Proc. Natl. Acad. Sci. U. S. A. 92, 517 (1995)PubMedPubMedCentralCrossRefGoogle Scholar
  48. 48.
    N. Ahmadzadeh, M. Shingu, M. Nobunaga, T. Tawara, Inflammation 15, 497 (1991)PubMedCrossRefPubMedCentralGoogle Scholar
  49. 49.
    L.B. Klickstein, C. Shapleigh, E.J. Goetzl, J. Clin. Invest. 66, 1166 (1980)PubMedPubMedCentralCrossRefGoogle Scholar
  50. 50.
    P.J. Barnes, Nat. Rev. Drug. Discov. 12, 543 (2013)PubMedCrossRefPubMedCentralGoogle Scholar
  51. 51.
    J.L. Corhay, M. Henket, D. Nguyen, B. Duysinx, J. Sele, R. Louis, Chest 136, 1047 (2009)PubMedCrossRefPubMedCentralGoogle Scholar
  52. 52.
    H. Qiu, A. Gabrielsen, H.E. Agardh, M. Wan, A. Wetterholm, C.H. Wong, U. Hedin, J. Swedenborg, G.K. Hansson, B. Samuelsson, G. Paulsson-Berne, J.Z. Haeggström, Proc. Natl. Acad. Sci. U. S. A. 103, 8161 (2006)PubMedPubMedCentralCrossRefGoogle Scholar
  53. 53.
    R. Spanbroek, R. Grabner, K. Lotzer, M. Hildner, A. Urbach, K. Ruhling, M.P. Moos, B. Kaiser, T.U. Cohnert, T. Wahlers, A. Zieske, G. Plenz, H. Robenek, P. Salbach, H. Kuhn, O. Radmark, B. Samuelsson, A.J. Habenicht, Proc. Natl. Acad. Sci. U. S. A. 100, 1238 (2003)PubMedPubMedCentralCrossRefGoogle Scholar
  54. 54.
    D. Wang, R.N. Dubois, Nat. Rev. Cancer 10, 181 (2010)PubMedPubMedCentralCrossRefGoogle Scholar
  55. 55.
    W.G. Tong, X.Z. Ding, R. Hennig, R.C. Witt, J. Standop, P.M. Pour, T.E. Adrian, Clin. Cancer Res. 8, 3232 (2002)PubMedGoogle Scholar
  56. 56.
    A. Stsiapanava, U. Olsson, M. Wan, T. Kleinschmidt, D. Rutishauser, R.A. Zubarev, B. Samuelsson, A. Rinaldo-Matthis, J.Z. Haeggström, Proc. Natl. Acad. Sci. U. S. A. 111, 4227 (2014)PubMedPubMedCentralCrossRefGoogle Scholar
  57. 57.
    C.N. Serhan, Nature 510, 92 (2014)PubMedPubMedCentralCrossRefGoogle Scholar
  58. 58.
    N.L. Rao, P.J. Dunford, X. Xue, X. Jiang, K.A. Lundeen, F. Coles, J.P. Riley, K.N. Williams, C.A. Grice, J.P. Edwards, L. Karlsson, A.M. Fourie, J. Pharmacol. Exp. Ther. 321, 1154 (2007)PubMedCrossRefGoogle Scholar
  59. 59.
    D.W. Goldman, E.J. Goetzl, J. Immunol. 129, 1600 (1982)PubMedGoogle Scholar
  60. 60.
    D.W. Goldman, E.J. Goetzl, J. Exp. Med. 159, 1027 (1984)PubMedCrossRefPubMedCentralGoogle Scholar
  61. 61.
    R.R. Gorman, P.L. Ruppel, A.H. Lin, Adv. Prostaglandin. Thromboxane. Leukot. Res. 15, 661 (1985)PubMedPubMedCentralGoogle Scholar
  62. 62.
    A.H. Lin, P.L. Ruppel, R.R. Gorman, Prostaglandins 28, 837 (1984)PubMedCrossRefPubMedCentralGoogle Scholar
  63. 63.
    J.S. Bomalaski, S. Mong, Prostaglandins 33, 855 (1987)PubMedCrossRefPubMedCentralGoogle Scholar
  64. 64.
    T. Yokomizo, K. Kato, H. Hagiya, T. Izumi, T. Shimizu, J. Biol. Chem. 276, 12454 (2001)PubMedCrossRefPubMedCentralGoogle Scholar
  65. 65.
    W.W. Huang, E.A. Garcia-Zepeda, A. Sauty, H.C. Oettgen, M.E. Rothenberg, A.D. Luster, J. Exp. Med. 188, 1063 (1998)PubMedPubMedCentralCrossRefGoogle Scholar
  66. 66.
    K. Kuniyeda, T. Okuno, K. Terawaki, M. Miyano, T. Yokomizo, T. Shimizu, J. Biol. Chem. 282, 3998 (2007)PubMedCrossRefPubMedCentralGoogle Scholar
  67. 67.
    T. Okuno, T. Yokomizo, T. Hori, M. Miyano, T. Shimizu, J. Biol. Chem. 280, 32049 (2005)PubMedCrossRefPubMedCentralGoogle Scholar
  68. 68.
    T. Okuno, H. Ago, K. Terawaki, M. Miyano, T. Shimizu, T. Yokomizo, J. Biol. Chem. 278, 41500 (2003)PubMedCrossRefPubMedCentralGoogle Scholar
  69. 69.
    Y. Nakanishi, M. Tan, T. Ichiki, A. Inoue, J.I. Yoshihara, N. Maekawa, I. Takenoshita, K. Yanagida, S. Yamahira, S. Yamaguchi, J. Aoki, T. Nagamune, T. Yokomizo, T. Shimizu, M. Nakamura, Sci. Signal. 11, (2018)PubMedCrossRefPubMedCentralGoogle Scholar
  70. 70.
    Y. Aratake, T. Okuno, T. Matsunobu, K. Saeki, R. Takayanagi, S. Furuya, T. Yokomizo, FASEB J. 26, 4068 (2012)PubMedCrossRefPubMedCentralGoogle Scholar
  71. 71.
    R. Gaudreau, M.E. Beaulieu, Z. Chen, C. Le Gouill, P. Lavigne, J. Stanková, M. Rola-Pleszczynski, J. Biol. Chem. 279, 10338 (2004)PubMedCrossRefPubMedCentralGoogle Scholar
  72. 72.
    Z. Chen, R. Gaudreau, C. Le Gouill, M. Rola-Pleszczynski, J. Stanková, Mol. Pharmacol. 66, 377 (2004)PubMedCrossRefPubMedCentralGoogle Scholar
  73. 73.
    R. Gaudreau, C. Le Gouill, M.H. Venne, J. Stanková, M. Rola-Pleszczynski, J. Biol. Chem. 277, 31567 (2002)PubMedCrossRefPubMedCentralGoogle Scholar
  74. 74.
    S. Basu, V.R. Jala, S. Mathis, S.T. Rajagopal, A. Del Prete, P. Maturu, J.O. Trent, B. Haribabu, J. Biol. Chem. 282, 10005 (2007)PubMedCrossRefPubMedCentralGoogle Scholar
  75. 75.
    A. Sabirsh, R.P. Bywater, J. Bristulf, C. Owman, J.Z. Haeggström, Biochemistry 45, 5733 (2006)PubMedCrossRefPubMedCentralGoogle Scholar
  76. 76.
    T. Hori, T. Okuno, K. Hirata, K. Yamashita, Y. Kawano, M. Yamamoto, M. Hato, M. Nakamura, T. Shimizu, T. Yokomizo, M. Miyano, S. Yokoyama, Nat. Chem. Biol. 14, 262 (2018)PubMedCrossRefPubMedCentralGoogle Scholar
  77. 77.
    B. Haribabu, M.W. Verghese, D.A. Steeber, D.D. Sellars, C.B. Bock, R. Snyderman, J. Exp. Med. 192, 433 (2000)PubMedPubMedCentralCrossRefGoogle Scholar
  78. 78.
    A.M. Tager, J.H. Dufour, K. Goodarzi, S.D. Bercury, U.H. von Andrian, A.D. Luster, J. Exp. Med. 192, 439 (2000)PubMedPubMedCentralCrossRefGoogle Scholar
  79. 79.
    M.L. Patnode, J.K. Bando, M.F. Krummel, R.M. Locksley, S.D. Rosen, J. Exp. Med. 211, 1281 (2014)PubMedPubMedCentralCrossRefGoogle Scholar
  80. 80.
    V.L. Ott, J.C. Cambier, J. Kappler, P. Marrack, B.J. Swanson, Nat. Immunol. 4, 974 (2003)PubMedPubMedCentralCrossRefGoogle Scholar
  81. 81.
    A.M. Tager, S.K. Bromley, B.D. Medoff, S.A. Islam, S.D. Bercury, E.B. Friedrich, A.D. Carafone, R.E. Gerszten, A.D. Luster, Nat. Immunol. 4, 982 (2003)PubMedPubMedCentralCrossRefGoogle Scholar
  82. 82.
    C.H. Serezani, D.M. Aronoff, R.G. Sitrin, M. Peters-Golden, Blood 114, 3316 (2009)PubMedPubMedCentralCrossRefGoogle Scholar
  83. 83.
    A. Toda, K. Terawaki, S. Yamazaki, K. Saeki, T. Shimizu, T. Yokomizo, Biochimie 92, 682 (2010)PubMedPubMedCentralCrossRefGoogle Scholar
  84. 84.
    F. Sasaki, T. Koga, M. Ohba, K. Saeki, T. Okuno, K. Ishikawa, T. Nakama, S. Nakao, S. Yoshida, T. Ishibashi, H. Ahmadieh, M.R. Kanavi, A. Hafezi-Moghadam, J.M. Penninger, K.H. Sonoda, T. Yokomizo, JCI Insight 3 (2018)Google Scholar
  85. 85.
    K. Kato, T. Yokomizo, T. Izumi, T. Shimizu, J. Exp. Med. 192, 413 (2000)PubMedPubMedCentralCrossRefGoogle Scholar
  86. 86.
    S. Wang, E. Gustafson, L. Pang, X. Qiao, J. Behan, M. Maguire, M. Bayne, T. Laz, J. Biol. Chem. 275, 40686 (2000)PubMedCrossRefPubMedCentralGoogle Scholar
  87. 87.
    Y. Tryselius, N.E. Nilsson, K. Kotarsky, B. Olde, C. Owman, Biochem. Biophys. Res. Commun. 274, 377 (2000)PubMedCrossRefPubMedCentralGoogle Scholar
  88. 88.
    M. Kamohara, J. Takasaki, M. Matsumoto, T. Saito, T. Ohishi, H. Ishii, K. Furuichi, J. Biol. Chem. 275, 27000 (2000)PubMedPubMedCentralGoogle Scholar
  89. 89.
    Y. Iizuka, T. Yokomizo, K. Terawaki, M. Komine, K. Tamaki, T. Shimizu, J. Biol. Chem. 280, 24816 (2005)PubMedCrossRefPubMedCentralGoogle Scholar
  90. 90.
    M. Liu, K. Saeki, T. Matsunobu, T. Okuno, T. Koga, Y. Sugimoto, C. Yokoyama, S. Nakamizo, K. Kabashima, S. Narumiya, T. Shimizu, T. Yokomizo, J. Exp. Med. 211, 1063 (2014)PubMedPubMedCentralCrossRefGoogle Scholar
  91. 91.
    Y. Iizuka, T. Okuno, K. Saeki, H. Uozaki, S. Okada, T. Misaka, T. Sato, H. Toh, M. Fukayama, N. Takeda, Y. Kita, T. Shimizu, M. Nakamura, T. Yokomizo, FASEB J. 24, 4678 (2010)PubMedCrossRefPubMedCentralGoogle Scholar
  92. 92.
    T. Okuno, T. Ishitani, T. Yokomizo, PLoS One 10, e0117888 (2015)PubMedPubMedCentralCrossRefGoogle Scholar
  93. 93.
    M. Hamberg, J. Svensson, B. Samuelsson, Proc. Natl. Acad. Sci. U. S. A. 71, 3824 (1974)PubMedPubMedCentralCrossRefGoogle Scholar
  94. 94.
    M. Hamberg, B. Samuelsson, J. Biol. Chem. 242, 5344 (1967)PubMedPubMedCentralGoogle Scholar
  95. 95.
    E. Ricciotti, G.A. FitzGerald, Arterioscler. Thromb. Vasc. Biol. 31, 986 (2011)PubMedPubMedCentralCrossRefGoogle Scholar
  96. 96.
    W.L. Smith, D.L. DeWitt, R.M. Garavito, Annu. Rev. Biochem. 69, 145 (2000)PubMedCrossRefPubMedCentralGoogle Scholar
  97. 97.
    C. Brink, S.E. Dahlén, J. Drazen, J.F. Evans, D.W. Hay, S. Nicosia, C.N. Serhan, T. Shimizu, T. Yokomizo, Pharmacol. Rev. 55, 195 (2003)PubMedCrossRefPubMedCentralGoogle Scholar
  98. 98.
    S. Narumiya, Y. Sugimoto, F. Ushikubi, Physiol. Rev. 79, 1193 (1999)PubMedCrossRefPubMedCentralGoogle Scholar
  99. 99.
    M. Bäck, S.E. Dahlén, J.M. Drazen, J.F. Evans, C.N. Serhan, T. Shimizu, T. Yokomizo, G.E. Rovati, Pharmacol. Rev. 63, 539 (2011)PubMedCrossRefPubMedCentralGoogle Scholar
  100. 100.
    H. John, K. Cammann, W. Schlegel, Prostaglandins Other Lipid Mediat. 56, 53 (1998)PubMedCrossRefPubMedCentralGoogle Scholar
  101. 101.
    M. Hecker, V. Ullrich, J. Biol. Chem. 264, 141 (1989)PubMedPubMedCentralGoogle Scholar
  102. 102.
    M. Hecker, M. Haurand, V. Ullrich, U. Diczfalusy, S. Hammarström, Arch. Biochem. Biophys. 254, 124 (1987)PubMedCrossRefPubMedCentralGoogle Scholar
  103. 103.
    J.E. Vincent, F.J. Zijlstra, H. van Vliet, Prostaglandins Med. 5, 79 (1980)PubMedCrossRefPubMedCentralGoogle Scholar
  104. 104.
    J.E. Vincent, F.J. Zijlstra, H. van Vliet, Adv. Prostaglandin Thromboxane Res. 6, 463 (1980)PubMedPubMedCentralGoogle Scholar
  105. 105.
    T. Matsunobu, T. Okuno, C. Yokoyama, T. Yokomizo, J. Lipid Res. 54, 2979 (2013)PubMedPubMedCentralCrossRefGoogle Scholar
  106. 106.
    T. Frömel, K. Kohlstedt, R. Popp, X. Yin, K. Awwad, E. Barbosa-Sicard, A.C. Thomas, R. Lieberz, M. Mayr, I. Fleming, Basic Res. Cardiol. 108, 319 (2013)PubMedCrossRefPubMedCentralGoogle Scholar
  107. 107.
    P. Bui, S. Imaizumi, S.R. Beedanagari, S.T. Reddy, O. Hankinson, Drug Metab. Dispos. 39, 180 (2011)PubMedPubMedCentralCrossRefGoogle Scholar
  108. 108.
    M. Hecker, V. Ullrich, Eicosanoids 1, 19 (1988)PubMedPubMedCentralGoogle Scholar
  109. 109.
    M. Ohba, K. Saeki, T. Koga, T. Okuno, Y. Kobayashi, T. Yokomizo, Biochem. Biophys. Res. Commun. 504, 562 (2018)PubMedCrossRefPubMedCentralGoogle Scholar
  110. 110.
    T. Tojo, Q. Wang, T. Okuno, T. Yokomizo, Y. Kobayashi, Synlett 24, 1545 (2013)CrossRefGoogle Scholar
  111. 111.
    Y. Ishii, K. Saeki, M. Liu, F. Sasaki, T. Koga, K. Kitajima, C. Meno, T. Okuno, T. Yokomizo, FASEB J. 30, 933 (2016)PubMedCrossRefPubMedCentralGoogle Scholar
  112. 112.
    S. Iwamoto, T. Koga, M. Ohba, T. Okuno, M. Koike, A. Murakami, A. Matsuda, T. Yokomizo, Sci. Rep. 7, 13267 (2017)PubMedPubMedCentralCrossRefGoogle Scholar
  113. 113.
    J.M. Houthuijzen, L.G. Daenen, J.M. Roodhart, I. Oosterom, M.T. van Jaarsveld, K.M. Govaert, M.E. Smith, S.J. Sadatmand, H. Rosing, F. Kruse, B.J. Helms, N. van Rooijen, J.H. Beijnen, B. Haribabu, C.H. van de Lest, E.E. Voest, Nat. Commun. 5, 5275 (2014)PubMedCrossRefPubMedCentralGoogle Scholar
  114. 114.
    D.L. van der Velden, G.A. Cirkel, J.M. Houthuijzen, E. van Werkhoven, J.M.L. Roodhart, L.G.M. Daenen, S. Kaing, J. Gerrits, N.M. Verhoeven-Duif, C. Grootscholten, H. Boot, C. Sessa, H.J. Bloemendal, F.Y. De Vos, E.E. Voest, Cancer Chemother. Pharmacol. 81, 911 (2018)PubMedCrossRefPubMedCentralGoogle Scholar

Copyright information

© Springer Nature Singapore Pte Ltd. 2019

Authors and Affiliations

  1. 1.Department of BiochemistryJuntendo University School of MedicineTokyoJapan

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