Role of Human 15-Lipoxygenase-2 in the Biosynthesis of the Lipoxin Intermediate, 5S,15S-diHpETE, Implicated with the Altered Positional Specificity of Human 15-Lipoxygenase-1.


Journal

Biochemistry
ISSN: 1520-4995
Titre abrégé: Biochemistry
Pays: United States
ID NLM: 0370623

Informations de publication

Date de publication:
27 10 2020
Historique:
pubmed: 14 10 2020
medline: 10 4 2021
entrez: 13 10 2020
Statut: ppublish

Résumé

The oxylipins, 5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid (5S,12S-diHETE) and 5S,15S-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid (5S,15S-diHETE), have been identified in cell exudates and have chemotactic activity toward eosinophils and neutrophils. Their biosynthesis has been proposed to occur by sequential oxidations of arachidonic acid (AA) by lipoxygenase enzymes, specifically through oxidation of AA by h5-LOX followed by h12-LOX, h15-LOX-1, or h15-LOX-2. In this work, h15-LOX-1 demonstrates altered positional specificity when reacting with 5S-HETE, producing 90% 5S,12S-diHETE, instead of 5S,15S-diHETE, with kinetics 5-fold greater than that of h12-LOX. This is consistent with previous work in which h15-LOX-1 reacts with 7S-HDHA, producing the noncanonical, DHA-derived, specialized pro-resolving mediator, 7S,14S-diHDHA. It is also determined that oxygenation of 5S-HETE by h15-LOX-2 produces 5S,15S-diHETE and its biosynthetic

Identifiants

pubmed: 33048542
doi: 10.1021/acs.biochem.0c00622
pmc: PMC7721368
mid: NIHMS1650494
doi:

Substances chimiques

Arachidonic Acids 0
Hydroxyeicosatetraenoic Acids 0
Lipoxins 0
Arachidonic Acid 27YG812J1I
ALOX15 protein, human EC 1.13.11.33
ALOX15B protein, human EC 1.13.11.33
Arachidonate 15-Lipoxygenase EC 1.13.11.33

Types de publication

Journal Article Research Support, N.I.H., Extramural

Langues

eng

Sous-ensembles de citation

IM

Pagination

4118-4130

Subventions

Organisme : NHGRI NIH HHS
ID : R01 HG011405
Pays : United States
Organisme : NHLBI NIH HHS
ID : R00 HL136784
Pays : United States
Organisme : NIGMS NIH HHS
ID : R35 GM131835
Pays : United States
Organisme : NHLBI NIH HHS
ID : K99 HL136784
Pays : United States
Organisme : NIGMS NIH HHS
ID : R01 GM105671
Pays : United States
Organisme : NHLBI NIH HHS
ID : R01 HL114405
Pays : United States

Références

Acta Physiol Scand. 1989 Dec;137(4):571-2
pubmed: 2557732
Biochem J. 1996 Mar 15;314 ( Pt 3):911-6
pubmed: 8615788
J Biol Chem. 1993 Mar 25;268(9):6288-92
pubmed: 8454601
J Lipid Res. 2012 Dec;53(12):2546-59
pubmed: 22984144
Prostaglandins. 1982 Sep;24(3):405-18
pubmed: 6296925
Eur J Clin Invest. 2010 Jan;40(1):11-7
pubmed: 19912316
Science. 2013 Jan 11;339(6116):166-72
pubmed: 23307734
Proc Natl Acad Sci U S A. 1989 May;86(9):3438-42
pubmed: 2541448
J Nat Prod. 2003 Feb;66(2):230-5
pubmed: 12608855
Proc Natl Acad Sci U S A. 1974 Sep;71(9):3400-4
pubmed: 4215079
Biochemistry. 2018 Dec 4;57(48):6726-6734
pubmed: 30407793
Nature. 1991 Nov 14;354(6349):149-52
pubmed: 1944593
Prostaglandins Other Lipid Mediat. 2006 Mar;79(1-2):84-92
pubmed: 16516812
J Biol Chem. 2010 Feb 19;285(8):5369-76
pubmed: 20026599
Atherosclerosis. 2012 Nov;225(1):121-7
pubmed: 22980500
J Biol Chem. 1997 Sep 26;272(39):24410-6
pubmed: 9305900
Science. 2011 Jan 14;331(6014):217-9
pubmed: 21233389
Adv Lipid Res. 1985;21:47-77
pubmed: 2992241
Prostaglandins Leukot Essent Fatty Acids. 2003 Aug-Sep;69(2-3):99-109
pubmed: 12895592
J Biol Chem. 1996 Oct 11;271(41):25412-8
pubmed: 8810309
Biochim Biophys Acta. 1982 Dec 13;713(3):638-46
pubmed: 6817812
Eicosanoids. 1991;4(2):65-74
pubmed: 1910864
Proc Natl Acad Sci U S A. 1997 Jun 10;94(12):6148-52
pubmed: 9177185
Prostaglandins Med. 1981 Jun;6(6):557-70
pubmed: 6267638
J Clin Lipidol. 2018 Jul - Aug;12(4):1047-1060
pubmed: 29730187
Biochemistry. 2009 Sep 15;48(36):8721-30
pubmed: 19645454
Biochem Biophys Res Commun. 1984 Feb 14;118(3):943-9
pubmed: 6422933
Prostaglandins. 1982 May;23(5):713-24
pubmed: 6289381
J Clin Invest. 1993 Sep;92(3):1357-65
pubmed: 7690778
Blood. 1999 Feb 15;93(4):1399-405
pubmed: 9949184
Biochem Biophys Res Commun. 1987 Dec 31;149(3):1063-9
pubmed: 3122743
Proc Natl Acad Sci U S A. 2001 Apr 24;98(9):5152-7
pubmed: 11320251
J Nat Prod. 2014 Oct 24;77(10):2241-7
pubmed: 25247845
J Lipid Res. 2020 Jul;61(7):1087-1103
pubmed: 32404334
Bioorg Med Chem. 2016 Nov 1;24(21):5380-5387
pubmed: 27647374
Eur Respir J. 2014 Aug;44(2):394-404
pubmed: 24696116
FASEB J. 2019 May;33(5):6140-6153
pubmed: 30735438
Prostaglandins Leukot Med. 1985 Feb;17(2):199-212
pubmed: 3920680
Am J Pathol. 2010 Oct;177(4):1576-91
pubmed: 20813960
Br J Pharmacol. 1992 Sep;107(1):226-32
pubmed: 1330161
J Biol Chem. 1982 Nov 25;257(22):13515-9
pubmed: 6292193
Circulation. 1985 Oct;72(4):698-701
pubmed: 3896560
J Biol Chem. 1982 Jun 25;257(12):7056-67
pubmed: 6806263
Arch Biochem Biophys. 2010 Nov 15;503(2):161-74
pubmed: 20801095
Biochimie. 2014 Apr;99:1-7
pubmed: 24262603
J Nat Prod. 2009 Oct;72(10):1857-63
pubmed: 19848434
Cell Prolif. 2018 Oct;51(5):e12472
pubmed: 30062726
Biochemistry. 2014 Jul 15;53(27):4407-19
pubmed: 24893149
Mol Cell Endocrinol. 2012 Jul 6;358(1):88-95
pubmed: 22502743
Cell. 2010 Mar 19;140(6):871-82
pubmed: 20303877
Eur J Biochem. 1989 Apr 1;180(3):527-33
pubmed: 2496978
Biochim Biophys Acta. 1989 Aug 8;1004(2):158-68
pubmed: 2546590
Arterioscler Thromb Vasc Biol. 2017 Oct;37(10):1828-1839
pubmed: 28775075
Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:263-90
pubmed: 12432923
Eur J Biochem. 1987 Dec 15;169(3):593-601
pubmed: 3121318
J Pharmacol Exp Ther. 2002 Mar;300(3):868-75
pubmed: 11861792
Blood. 2012 Oct 11;120(15):e60-72
pubmed: 22904297
FEBS Lett. 2009 Nov 3;583(21):3478-84
pubmed: 19818771
Biochim Biophys Acta. 1992 Jan 13;1133(2):223-34
pubmed: 1310055
Biochem Biophys Res Commun. 1995 Feb 6;207(1):273-9
pubmed: 7857276
Nat Rev Immunol. 2008 May;8(5):349-61
pubmed: 18437155
J Immunol. 1990 Mar 1;144(5):1893-900
pubmed: 2155268
J Biol Chem. 1976 Dec 25;251(24):7816-20
pubmed: 826538
Biochim Biophys Acta. 1994 Jan 20;1210(3):308-16
pubmed: 8305485
Lipids. 1990 Oct;25(10):618-23
pubmed: 2127820
Inflamm Res. 1995 Mar;44(3):121-4
pubmed: 7552576
PLoS One. 2014 Aug 11;9(8):e104094
pubmed: 25111178
Biochemistry. 2016 May 24;55(20):2832-40
pubmed: 27145229
J Nat Prod. 2014 Apr 25;77(4):910-6
pubmed: 24576195
Br J Pharmacol. 2015 Sep;172(17):4319-30
pubmed: 26040494
Biochem Biophys Res Commun. 1982 Aug;107(3):951-8
pubmed: 6814433
J Exp Med. 1996 Apr 1;183(4):1633-43
pubmed: 8666921
Biochemistry. 2008 Jul 15;47(28):7364-75
pubmed: 18570379
Biochim Biophys Acta. 2015 Apr;1851(4):308-30
pubmed: 25316652
Prostaglandins Other Lipid Mediat. 2013 Jul-Aug;104-105:84-92
pubmed: 22951339
Protein Eng. 1995 Mar;8(3):275-82
pubmed: 7479689
J Mol Biol. 1996 Dec 20;264(5):1145-53
pubmed: 9000636

Auteurs

Steven C Perry (SC)

Department of Chemistry and Biochemistry, University of California, Santa Cruz, Santa Cruz, California 95064, United States.

Thomas Horn (T)

Department of Chemistry and Biochemistry, University of California, Santa Cruz, Santa Cruz, California 95064, United States.

Benjamin E Tourdot (BE)

Department of Pharmacology, University of Michigan Medical School, Ann Arbor, Michigan 48109, United States.

Adriana Yamaguchi (A)

Department of Pharmacology, University of Michigan Medical School, Ann Arbor, Michigan 48109, United States.

Chakrapani Kalyanaraman (C)

Department of Pharmaceutical Chemistry, School of Pharmacy, University of California, San Francisco, San Francisco, California 94158, United States.

William S Conrad (WS)

Department of Chemistry and Biochemistry, University of California, Santa Cruz, Santa Cruz, California 95064, United States.

Oluwayomi Akinkugbe (O)

Department of Chemistry and Biochemistry, University of California, Santa Cruz, Santa Cruz, California 95064, United States.

Michael Holinstat (M)

Department of Pharmacology, University of Michigan Medical School, Ann Arbor, Michigan 48109, United States.

Matthew P Jacobson (MP)

Department of Pharmaceutical Chemistry, School of Pharmacy, University of California, San Francisco, San Francisco, California 94158, United States.

Theodore R Holman (TR)

Department of Chemistry and Biochemistry, University of California, Santa Cruz, Santa Cruz, California 95064, United States.

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