Cytochrome P450/NADPH-dependent formation of trans epoxides from trans-arachidonic acids
- PMID: 15013014
- DOI: 10.1016/j.bmcl.2003.11.054
Cytochrome P450/NADPH-dependent formation of trans epoxides from trans-arachidonic acids
Abstract
Trans-arachidonic acids (trans-AA) are products of cis-trans isomerization of arachidonic acid by nitrogen dioxide radical (NO(2)), and occur in vivo, but their metabolism is unknown. We found that hepatic microsomes oxidized trans-AA via cytochrome P450/NADPH system to epoxides, which were hydrolyzed by epoxide hydrolase to diols (DiHETEs). 14,15-trans-AA produced one erythro diol and three threo diols each having one trans double bond.
Similar articles
-
Cytochrome P450/NADPH-dependent biosynthesis of 5,6-trans-epoxyeicosatrienoic acid from 5,6-trans-arachidonic acid.Biochem J. 2005 Sep 15;390(Pt 3):719-27. doi: 10.1042/BJ20050681. Biochem J. 2005. PMID: 15916533 Free PMC article.
-
Novel metabolic pathways for linoleic and arachidonic acid metabolism.Biochim Biophys Acta. 1996 Aug 13;1290(3):327-39. doi: 10.1016/0304-4165(96)00037-2. Biochim Biophys Acta. 1996. PMID: 8765137
-
Biochemical characterization of the human liver cytochrome P450 arachidonic acid epoxygenase pathway.Arch Biochem Biophys. 1996 Jun 1;330(1):87-96. doi: 10.1006/abbi.1996.0229. Arch Biochem Biophys. 1996. PMID: 8651708
-
The CYP P450 arachidonic acid monooxygenases: from cell signaling to blood pressure regulation.Biochem Biophys Res Commun. 2001 Jul 20;285(3):571-6. doi: 10.1006/bbrc.2001.5167. Biochem Biophys Res Commun. 2001. PMID: 11453630 Review.
-
Cytochrome P450-dependent metabolism of arachidonic acid.Biochemistry (Mosc). 1999 Jul;64(7):725-37. Biochemistry (Mosc). 1999. PMID: 10424895 Review.
Cited by
-
Cytochrome P450/NADPH-dependent biosynthesis of 5,6-trans-epoxyeicosatrienoic acid from 5,6-trans-arachidonic acid.Biochem J. 2005 Sep 15;390(Pt 3):719-27. doi: 10.1042/BJ20050681. Biochem J. 2005. PMID: 15916533 Free PMC article.
-
Trans fatty acids and atopic eczema/dermatitis syndrome: the relationship with a free radical cis-trans isomerization of membrane lipids.Lipids. 2005 Jul;40(7):661-7. doi: 10.1007/s11745-005-1428-7. Lipids. 2005. PMID: 16196416
-
An epoxide hydrolase involved in the biosynthesis of an insect sex attractant and its use to localize the production site.Proc Natl Acad Sci U S A. 2008 Jul 1;105(26):8914-9. doi: 10.1073/pnas.0801559105. Epub 2008 Jun 25. Proc Natl Acad Sci U S A. 2008. PMID: 18579785 Free PMC article.
-
Enzymatic and free radical formation of cis- and trans- epoxyeicosatrienoic acids in vitro and in vivo.Free Radic Biol Med. 2017 Nov;112:131-140. doi: 10.1016/j.freeradbiomed.2017.07.015. Epub 2017 Jul 19. Free Radic Biol Med. 2017. PMID: 28734877 Free PMC article.
-
Trans-arachidonic acids generated during nitrative stress induce a thrombospondin-1-dependent microvascular degeneration.Nat Med. 2005 Dec;11(12):1339-45. doi: 10.1038/nm1336. Epub 2005 Nov 27. Nat Med. 2005. PMID: 16311602 Free PMC article.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources