ω-Hydroxylation of lipoxin B4 by human neutrophil microsomes: Identification of ω-hydroxy metabolite of lipoxin B4 and catalysis by leukotriene B4 ω-hydroxylase (cytochrome P-450LTBω)

Mizukami Yoichi, Hideki Sumimoto, Isobe Ryuichi, Minakami Shigeki

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Abstract

Lipoxin B4 (LXB4) is metabolized either by human neutrophils or by the neutrophil microsomes to a polar compound on a reverse-phase high-performance liquid chromatography. The metabolite is identified as 20-hydroxy-lipoxin B4 (20-OH-LXB4), a novel member in the arachidonic acid cascade, on the basis of ultraviolet spectrometry and gas chromatography-mass spectrometry. The neutrophil microsomes convert LXB4 to its 20-hydroxy derivative under aerobic condition in the presence of NADPH. The reaction is inhibited by carbon monoxide, an inhibitor of cytochrome P-450 (P-450), and by antibodies raised against NADPH-P-450 reductase. A P-450 is thus involved in the ω-hydroxylation of LXB4. The P-450 appears to be the one responsible for leukotriene B4 (LTB4) ω-hydroxylation, P-450LTBω, based on the following observations. The formation of 20-OH-LXB4 is inhibited solely by substrates of P-450LTBω such as LTB4 and leukotriene B5 among various fatty acids including prostaglandins. The order of the inhibitory potencies of these substances on the LXB4 ω-hydroxylation is the same as that of their affinities for LTB4 ω-hydroxylase. LTB4 inhibits the reaction in a competitive manner with the Ki value of 0.2 μM, which agrees with the Km value for the LTB4 ω-hydroxylation (0.3 μM).

Original languageEnglish
Pages (from-to)87-93
Number of pages7
JournalBiochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism
Volume1168
Issue number1
DOIs
Publication statusPublished - May 20 1993

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Hydroxylation
Leukotriene B4
Cytochromes
Metabolites
Microsomes
Mixed Function Oxygenases
Catalysis
Neutrophils
NADP
High performance liquid chromatography
Reverse-Phase Chromatography
Carbon Monoxide
Arachidonic Acid
Gas chromatography
Gas Chromatography-Mass Spectrometry
Spectrometry
Prostaglandins
Mass spectrometry
lipoxin B4
Spectrum Analysis

All Science Journal Classification (ASJC) codes

  • Biophysics
  • Biochemistry
  • Endocrinology

Cite this

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title = "ω-Hydroxylation of lipoxin B4 by human neutrophil microsomes: Identification of ω-hydroxy metabolite of lipoxin B4 and catalysis by leukotriene B4 ω-hydroxylase (cytochrome P-450LTBω)",
abstract = "Lipoxin B4 (LXB4) is metabolized either by human neutrophils or by the neutrophil microsomes to a polar compound on a reverse-phase high-performance liquid chromatography. The metabolite is identified as 20-hydroxy-lipoxin B4 (20-OH-LXB4), a novel member in the arachidonic acid cascade, on the basis of ultraviolet spectrometry and gas chromatography-mass spectrometry. The neutrophil microsomes convert LXB4 to its 20-hydroxy derivative under aerobic condition in the presence of NADPH. The reaction is inhibited by carbon monoxide, an inhibitor of cytochrome P-450 (P-450), and by antibodies raised against NADPH-P-450 reductase. A P-450 is thus involved in the ω-hydroxylation of LXB4. The P-450 appears to be the one responsible for leukotriene B4 (LTB4) ω-hydroxylation, P-450LTBω, based on the following observations. The formation of 20-OH-LXB4 is inhibited solely by substrates of P-450LTBω such as LTB4 and leukotriene B5 among various fatty acids including prostaglandins. The order of the inhibitory potencies of these substances on the LXB4 ω-hydroxylation is the same as that of their affinities for LTB4 ω-hydroxylase. LTB4 inhibits the reaction in a competitive manner with the Ki value of 0.2 μM, which agrees with the Km value for the LTB4 ω-hydroxylation (0.3 μM).",
author = "Mizukami Yoichi and Hideki Sumimoto and Isobe Ryuichi and Minakami Shigeki",
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T1 - ω-Hydroxylation of lipoxin B4 by human neutrophil microsomes

T2 - Identification of ω-hydroxy metabolite of lipoxin B4 and catalysis by leukotriene B4 ω-hydroxylase (cytochrome P-450LTBω)

AU - Yoichi, Mizukami

AU - Sumimoto, Hideki

AU - Ryuichi, Isobe

AU - Shigeki, Minakami

PY - 1993/5/20

Y1 - 1993/5/20

N2 - Lipoxin B4 (LXB4) is metabolized either by human neutrophils or by the neutrophil microsomes to a polar compound on a reverse-phase high-performance liquid chromatography. The metabolite is identified as 20-hydroxy-lipoxin B4 (20-OH-LXB4), a novel member in the arachidonic acid cascade, on the basis of ultraviolet spectrometry and gas chromatography-mass spectrometry. The neutrophil microsomes convert LXB4 to its 20-hydroxy derivative under aerobic condition in the presence of NADPH. The reaction is inhibited by carbon monoxide, an inhibitor of cytochrome P-450 (P-450), and by antibodies raised against NADPH-P-450 reductase. A P-450 is thus involved in the ω-hydroxylation of LXB4. The P-450 appears to be the one responsible for leukotriene B4 (LTB4) ω-hydroxylation, P-450LTBω, based on the following observations. The formation of 20-OH-LXB4 is inhibited solely by substrates of P-450LTBω such as LTB4 and leukotriene B5 among various fatty acids including prostaglandins. The order of the inhibitory potencies of these substances on the LXB4 ω-hydroxylation is the same as that of their affinities for LTB4 ω-hydroxylase. LTB4 inhibits the reaction in a competitive manner with the Ki value of 0.2 μM, which agrees with the Km value for the LTB4 ω-hydroxylation (0.3 μM).

AB - Lipoxin B4 (LXB4) is metabolized either by human neutrophils or by the neutrophil microsomes to a polar compound on a reverse-phase high-performance liquid chromatography. The metabolite is identified as 20-hydroxy-lipoxin B4 (20-OH-LXB4), a novel member in the arachidonic acid cascade, on the basis of ultraviolet spectrometry and gas chromatography-mass spectrometry. The neutrophil microsomes convert LXB4 to its 20-hydroxy derivative under aerobic condition in the presence of NADPH. The reaction is inhibited by carbon monoxide, an inhibitor of cytochrome P-450 (P-450), and by antibodies raised against NADPH-P-450 reductase. A P-450 is thus involved in the ω-hydroxylation of LXB4. The P-450 appears to be the one responsible for leukotriene B4 (LTB4) ω-hydroxylation, P-450LTBω, based on the following observations. The formation of 20-OH-LXB4 is inhibited solely by substrates of P-450LTBω such as LTB4 and leukotriene B5 among various fatty acids including prostaglandins. The order of the inhibitory potencies of these substances on the LXB4 ω-hydroxylation is the same as that of their affinities for LTB4 ω-hydroxylase. LTB4 inhibits the reaction in a competitive manner with the Ki value of 0.2 μM, which agrees with the Km value for the LTB4 ω-hydroxylation (0.3 μM).

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