Document Detail

Arachidonate geometrical isomers generated by thiyl radicals: the relationship with trans lipids detected in biological samples.
MedLine Citation:
PMID:  12446209     Owner:  NLM     Status:  MEDLINE    
The presence of trans fatty acids in mammalians is attributed to exogenous sources; nevertheless, trans isomers could be easily formed by free radical-catalyzed isomerization processes in vivo. The isomerization of methyl arachidonate (all-cis isomer) catalyzed by thiyl radical is proposed as a methodology applicable in biochemical laboratories, which produces mono- and di-trans isomers. Carbon-13 nuclear magnetic resonance spectroscopy shows that the carbon atom in position 15 is characteristic for each mono- and di-trans isomer. Antioxidants, such as alpha-tocopherol and all-trans-retinol acetate, inhibited the isomerization process. Trans phospholipids are formed in erythrocyte membranes by exposing blood to gamma-irradiation in the presence of thiols, which is in contradiction with the known role of these compounds as radioprotectors. Trans isomers are also analyzed in tissues harvested from breast cancer patients and compared to the adipose breast tissue taken a few centimeters from the edge of the tumor from the same patient. This work is generally aimed at contributing to the debate on trans fatty acids and stimulating a reconsideration of the current view on the exclusive presence of cis double bonds in cell membranes by studying radical processes that could affect or protect this natural configuration.
Carla Ferreri; M Rosaria Faraone Mennella; Cesare Formisano; Laura Landi; Chryssostomos Chatgilialoglu
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Free radical biology & medicine     Volume:  33     ISSN:  0891-5849     ISO Abbreviation:  Free Radic. Biol. Med.     Publication Date:  2002 Dec 
Date Detail:
Created Date:  2002-11-26     Completed Date:  2003-05-28     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8709159     Medline TA:  Free Radic Biol Med     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1516-26     Citation Subset:  IM    
ISOF, Consiglio Nazionale delle Ricerche, Bologna, Italy.
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MeSH Terms
Adipose Tissue / metabolism
Arachidonic Acid / chemistry*,  metabolism
Breast Neoplasms / pathology
Carbon / chemistry
Chromatography, Gas
Chromatography, Thin Layer
Dose-Response Relationship, Radiation
Fatty Acids / chemistry,  metabolism
Free Radicals
Gas Chromatography-Mass Spectrometry
Lipid Metabolism
Lipids / chemistry
Magnetic Resonance Spectroscopy
Models, Biological
Models, Chemical
Protein Isoforms
Sulfhydryl Compounds / chemistry
Time Factors
Reg. No./Substance:
0/Fatty Acids; 0/Free Radicals; 0/Lipids; 0/Protein Isoforms; 0/Sulfhydryl Compounds; 506-32-1/Arachidonic Acid; 7440-44-0/Carbon

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