Document Detail


Fragmentation of a linoleate-derived γ-hydroperoxy-α,β-unsaturated epoxide to γ-hydroxy- and γ-oxo-alkenals involves a unique pseudo-symmetrical diepoxycarbinyl radical.
MedLine Citation:
PMID:  22155057     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Many of the pathological effects of lipid peroxidation are mediated by aldehydes generated through fragmentation of lipid peroxides. Among these aldehydes, the γ-hydroxy- and γ-oxo-α,β-alkenals, e.g., 4-hydroxy-2-nonenal (HNE) and 4-oxo-2-nonenal (ONE), are especially prone to modifying proteins and DNA through covalent adduction. In addition the "mirror image" γ-hydroxy- and γ-oxo-α,β-alkenal phospholipids can serve as high-affinity ligands for biological receptors triggering pathology. Therefore, the mechanisms by which these aldehydes are generated in vivo are under intense scrutiny. We now report observations supporting the intermediacy of a unique pseudo-symmetrical diepoxycarbinyl radical that accounts for the coproduction of HNE, ONE, and their mirror image analogues 9-hydroxy-12-oxo-10(E)-dodecenoic acid and 9-keto-12-oxo-10-dodecenoic acid upon fragmentation of 13-hydroperoxy-cis-9,10-epoxyoctadeca-11-enoic acid.
Authors:
Xiaodong Gu; Robert G Salomon
Related Documents :
14708087 - Goitrogenic activity of p-coumaric acid in rats.
6858197 - Hydrolysis of the biliary glucuronic acid conjugate of phenol by the intestinal mucus/f...
21691107 - Biliary bicarbonate secretion constitutes a protective mechanism against bile acid- ind...
24166667 - Identification of unknown impurity of azelaic acid in liposomal formulation assessed by...
4054517 - Polydispersity of acidic glycosaminoglycan components in human liver and the changes at...
20045147 - Endogenous red blood cell membrane fatty acids and sudden cardiac arrest.
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2011-12-01
Journal Detail:
Title:  Free radical biology & medicine     Volume:  52     ISSN:  1873-4596     ISO Abbreviation:  Free Radic. Biol. Med.     Publication Date:  2012 Feb 
Date Detail:
Created Date:  2012-01-27     Completed Date:  2012-05-17     Revised Date:  2013-08-15    
Medline Journal Info:
Nlm Unique ID:  8709159     Medline TA:  Free Radic Biol Med     Country:  United States    
Other Details:
Languages:  eng     Pagination:  601-6     Citation Subset:  IM    
Copyright Information:
Copyright © 2011 Elsevier Inc. All rights reserved.
Affiliation:
Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Aldehydes / chemistry
Epoxy Compounds / chemical synthesis,  chemistry*
Free Radicals / chemistry*
Hydrolysis
Iron / chemistry
Linoleic Acids / chemical synthesis,  chemistry*
Lipid Peroxidation
Oxidation-Reduction
Tandem Mass Spectrometry
Grant Support
ID/Acronym/Agency:
EY016813/EY/NEI NIH HHS; GM021249/GM/NIGMS NIH HHS; HL053315/HL/NHLBI NIH HHS; R01 EY016813/EY/NEI NIH HHS; R01 GM021249/GM/NIGMS NIH HHS; R01 HL053315/HL/NHLBI NIH HHS
Chemical
Reg. No./Substance:
0/4-oxo-2-nonenal; 0/Aldehydes; 0/Epoxy Compounds; 0/Free Radicals; 0/Linoleic Acids; 29343-52-0/4-hydroxy-2-nonenal; 7439-89-6/Iron
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Sulforaphane attenuates hepatic fibrosis via NF-E2-related factor 2-mediated inhibition of transform...
Next Document:  Biochemical and biological characterization of Escherichia coli STb His(12) to Asn variant.