|Neutrophil myeloperoxidase chlorinates and nitrates soy isoflavones and enhances their antioxidant properties.|
|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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|Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.|
|Title: Free radical biology & medicine Volume: 35 ISSN: 0891-5849 ISO Abbreviation: Free Radic. Biol. Med. Publication Date: 2003 Dec|
|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|
|Languages: eng Pagination: 1417-30 Citation Subset: IM|
|Department of Pharmacology and Toxicology, University of Alabama at Birmingham, Birmingham, AL 35294-2180, USA.|
|APA/MLA Format Download EndNote Download BibTex|
Chlorine / chemistry, metabolism*
Chromatography, High Pressure Liquid
Copper / chemistry
Dose-Response Relationship, Drug
Enzyme Inhibitors / chemistry, pharmacology
Genistein / chemistry, pharmacology
Isoflavones / chemistry, metabolism*, pharmacology
Lipoproteins, LDL / chemistry
Metmyoglobin / chemistry
Neutrophils / enzymology*
Nitrates / chemistry, metabolism*
Nitrites / chemistry
Nitrogen / chemistry
Oxygen / metabolism
Peroxidase / metabolism*
Reactive Nitrogen Species
Reactive Oxygen Species
|AA12613/AA/NIAAA NIH HHS; ES/DK11504/ES/NIEHS NIH HHS; HL 58031/HL/NHLBI NIH HHS; P30 CA13148-27/CA/NCI NIH HHS; P50 AT-00477/AT/NCCAM NIH HHS; S10RR06487/RR/NCRR NIH HHS|
|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 220.127.116.11/Peroxidase|
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