Document Detail

Neutrophil myeloperoxidase chlorinates and nitrates soy isoflavones and enhances their antioxidant properties.
MedLine Citation:
PMID:  14642389     Owner:  NLM     Status:  MEDLINE    
Soy isoflavones and other polyphenolics have a number of potentially important beneficial effects on the pro-oxidant aspects of chronic inflammation. The impact of inflammatory cell-specific metabolism of polyphenolics, which can include halogenation and nitration, on the properties of these compounds has not been examined. Using either human neutrophils or differentiated human leukemia cells (HL-60) stimulated with phorbol ester to elicit a respiratory burst, the hypothesis that local generation of reactive oxygen and nitrogen species may metabolize and modify the biological properties of the soy isoflavones was examined. Coincubation of the stimulated cells with genistein or daidzein had no effect on the respiratory burst. Medium from stimulated cells in the presence of the isoflavones and NO(2)(-) increased the inhibition of copper-induced LDL oxidation. Mass spectrometry analysis of this medium revealed that monochlorinated, dichlorinated, and nitrated isoflavones, formed through a myeloperoxidase-dependent mechanism, were present. The consumption of genistein in the presence of cells was both extensive and rapid with > 95% of the genistein converted to either the chlorinated or nitrated metabolites within 30 min. Chemically synthesized 3'-chlorogenistein and 3'-chlorodaidzein increased the inhibition of LDL oxidation by approximately 4-fold and 2-fold over genistein and daidzein, respectively. These results lead to the hypothesis that inflammatory cell-specific metabolism of polyphenolics can modify the properties of these compounds at the local site of inflammation.
Brenda J Boersma; Tracy D'Alessandro; Matthew R Benton; Marion Kirk; Landon S Wilson; Jeevan Prasain; Nigel P Botting; Stephen Barnes; Victor M Darley-Usmar; Rakesh P Patel
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Free radical biology & medicine     Volume:  35     ISSN:  0891-5849     ISO Abbreviation:  Free Radic. Biol. Med.     Publication Date:  2003 Dec 
Date Detail:
Created Date:  2003-12-03     Completed Date:  2004-07-02     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  8709159     Medline TA:  Free Radic Biol Med     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1417-30     Citation Subset:  IM    
Department of Pharmacology and Toxicology, University of Alabama at Birmingham, Birmingham, AL 35294-2180, USA.
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MeSH Terms
Antioxidants / chemistry,  pharmacology*
Cell Differentiation
Cells, Cultured
Chlorine / chemistry,  metabolism*
Chromatography, High Pressure Liquid
Copper / chemistry
Dose-Response Relationship, Drug
Enzyme Inhibitors / chemistry,  pharmacology
Free Radicals
Genistein / chemistry,  pharmacology
HL-60 Cells
Isoflavones / chemistry,  metabolism*,  pharmacology
Lipoproteins, LDL / chemistry
Mass Spectrometry
Metmyoglobin / chemistry
Models, Chemical
Neutrophils / enzymology*
Nitrates / chemistry,  metabolism*
Nitrites / chemistry
Nitrogen / chemistry
Oxygen / metabolism
Peroxidase / metabolism*
Reactive Nitrogen Species
Reactive Oxygen Species
Respiratory Burst
Time Factors
Grant Support
Reg. No./Substance:
0/Antioxidants; 0/Enzyme Inhibitors; 0/Free Radicals; 0/Isoflavones; 0/Lipoproteins, LDL; 0/Nitrates; 0/Nitrites; 0/Reactive Nitrogen Species; 0/Reactive Oxygen Species; 12772-23-5/Metmyoglobin; 446-72-0/Genistein; 486-66-8/daidzein; 7440-50-8/Copper; 7727-37-9/Nitrogen; 7782-44-7/Oxygen; 7782-50-5/Chlorine; EC

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