Metabolism of 12(R)-hydroxyeicosatetraenoic acid by rat liver microsomes

Hemant K. Jajoo; Jorge H. Capdevila; J. R. Falck; R. K. Bhatt; Ian A. Blair

doi:10.1016/0005-2760(92)90177-W

Metabolism of 12(R)-hydroxyeicosatetraenoic acid by rat liver microsomes

Hemant K. Jajoo, Jorge H. Capdevila, J. R. Falck, R. K. Bhatt, Ian A. Blair

Biochemistry

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

The in vitro metabolism of 12(R)-hydroxyeicosatetraenoic acid was studied using freshly isolated rat liver microsomes. Ten metabolites were isolated and identified by a combination of ultraviolet spectroscopy and gas chromatography/mass spectrometry. The two major metabolites were dihdroxyeicosatetraenoic acids generated by ω /ω - 1 hydroxylation. Oxidation at C-5 resulted in the formation of four leukotriene-like compounds, two of which differed from leukotriene B₄ in double-bond geometry alone. The other two differed from leukotriene B₄ in olefin geometry and C-5 configuration. Epoxidation at the 14,15-olefin resulted in the formation of two diastereomeric epoxy alcohols, while C-16 hydroxylation gave two diastereomeric dihydroxyeicosatetraenoic acids.

Original language	English (US)
Pages (from-to)	110-116
Number of pages	7
Journal	Biochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism
Volume	1123
Issue number	1
DOIs	https://doi.org/10.1016/0005-2760(92)90177-W
State	Published - Jan 3 1992

Keywords

Cytochrome P-450
Eicosanoid
Epoxygenase
Metabolism
Rat liver microsome

ASJC Scopus subject areas

Biophysics
Biochemistry
Endocrinology

Access to Document

10.1016/0005-2760(92)90177-W

Cite this

@article{8d5ebd05f29d4857a5a12aad044893c5,

title = "Metabolism of 12(R)-hydroxyeicosatetraenoic acid by rat liver microsomes",

abstract = "The in vitro metabolism of 12(R)-hydroxyeicosatetraenoic acid was studied using freshly isolated rat liver microsomes. Ten metabolites were isolated and identified by a combination of ultraviolet spectroscopy and gas chromatography/mass spectrometry. The two major metabolites were dihdroxyeicosatetraenoic acids generated by ω /ω - 1 hydroxylation. Oxidation at C-5 resulted in the formation of four leukotriene-like compounds, two of which differed from leukotriene B4 in double-bond geometry alone. The other two differed from leukotriene B4 in olefin geometry and C-5 configuration. Epoxidation at the 14,15-olefin resulted in the formation of two diastereomeric epoxy alcohols, while C-16 hydroxylation gave two diastereomeric dihydroxyeicosatetraenoic acids.",

keywords = "Cytochrome P-450, Eicosanoid, Epoxygenase, Metabolism, Rat liver microsome",

author = "Jajoo, {Hemant K.} and Capdevila, {Jorge H.} and Falck, {J. R.} and Bhatt, {R. K.} and Blair, {Ian A.}",

note = "Funding Information: This work was supported by National Institutes of Health Grant DK 38226. We acknowledge the invaluable advice given by Dr Alan R. Brash.",

year = "1992",

month = jan,

day = "3",

doi = "10.1016/0005-2760(92)90177-W",

language = "English (US)",

volume = "1123",

pages = "110--116",

journal = "Biochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism",

issn = "0005-2760",

publisher = "Elsevier",

number = "1",

}

TY - JOUR

T1 - Metabolism of 12(R)-hydroxyeicosatetraenoic acid by rat liver microsomes

AU - Jajoo, Hemant K.

AU - Capdevila, Jorge H.

AU - Falck, J. R.

AU - Bhatt, R. K.

AU - Blair, Ian A.

N1 - Funding Information: This work was supported by National Institutes of Health Grant DK 38226. We acknowledge the invaluable advice given by Dr Alan R. Brash.

PY - 1992/1/3

Y1 - 1992/1/3

N2 - The in vitro metabolism of 12(R)-hydroxyeicosatetraenoic acid was studied using freshly isolated rat liver microsomes. Ten metabolites were isolated and identified by a combination of ultraviolet spectroscopy and gas chromatography/mass spectrometry. The two major metabolites were dihdroxyeicosatetraenoic acids generated by ω /ω - 1 hydroxylation. Oxidation at C-5 resulted in the formation of four leukotriene-like compounds, two of which differed from leukotriene B4 in double-bond geometry alone. The other two differed from leukotriene B4 in olefin geometry and C-5 configuration. Epoxidation at the 14,15-olefin resulted in the formation of two diastereomeric epoxy alcohols, while C-16 hydroxylation gave two diastereomeric dihydroxyeicosatetraenoic acids.

AB - The in vitro metabolism of 12(R)-hydroxyeicosatetraenoic acid was studied using freshly isolated rat liver microsomes. Ten metabolites were isolated and identified by a combination of ultraviolet spectroscopy and gas chromatography/mass spectrometry. The two major metabolites were dihdroxyeicosatetraenoic acids generated by ω /ω - 1 hydroxylation. Oxidation at C-5 resulted in the formation of four leukotriene-like compounds, two of which differed from leukotriene B4 in double-bond geometry alone. The other two differed from leukotriene B4 in olefin geometry and C-5 configuration. Epoxidation at the 14,15-olefin resulted in the formation of two diastereomeric epoxy alcohols, while C-16 hydroxylation gave two diastereomeric dihydroxyeicosatetraenoic acids.

KW - Cytochrome P-450

KW - Eicosanoid

KW - Epoxygenase

KW - Metabolism

KW - Rat liver microsome

UR - http://www.scopus.com/inward/record.url?scp=0026565623&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0026565623&partnerID=8YFLogxK

U2 - 10.1016/0005-2760(92)90177-W

DO - 10.1016/0005-2760(92)90177-W

M3 - Article

C2 - 1730042

AN - SCOPUS:0026565623

SN - 0005-2760

VL - 1123

SP - 110

EP - 116

JO - Biochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism

JF - Biochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism

IS - 1

ER -

Metabolism of 12(R)-hydroxyeicosatetraenoic acid by rat liver microsomes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this