Effects of some polyphenols and their related compounds (chlorogenic acid, caffeic acid, quinic acid, ferulic acid, gallic acid, D-(+)-catechin, D-(-)-catechin, 4-hydroxy-3-methoxybenzoic acid, salicylic acid, L-dopa, dopamine, L-adrenaline, L-noradrenaline, o-dihydroxybenzene, m-dihydroxybenzene, and p-dihydroxybenzene) on the formation of 13-hydroperoxide octadecadienoic (13-HPODE) acid-derived radicals (pentyl radical and octanoic acid radical) were examined. The ESR spin trapping showed that chlorogenic acid, caffeic acid, gallic acid, D-(+)-catechin, D-(-)-catechin, L-dopa, dopamine, L-adrenaline, L-noradrenaline, and o-dihydroxybenzene inhibited the overall formation of 13-HPODE acid-derived radicals in the reaction mixture of 13-HPODE with ferrous ions. The ESR peak heights of α-(4-pyridyl-1-oxide)-N-tert-butylnitrone (4-POBN)/13-HPODE-derived radical adducts decreased to 46±4% (chlorogenic acid), 54±2% (caffeic acid), 49±2% (gallic acid), 55±1% [D-(+)-catechin], 60±3% [D-(-)-catechin], 42±1% (L-dopa), 30±2% (dopamine), 49±2% (L-adrenaline), 24±2% (L-noradrenaline), and 54±5% (o-dihydroxybenzene) of the control, respectively. The high performance liquid chromatography-electron spin resonance (HPLC-ESR) and high performance liquid chromatography-electron spin resonance-mass spectrometries (HPLC-ESR-MS) showed that caffeic acid inhibited the formation of octanoic acid radical and pentyl radical to 42±2% and 52±7% of the control, respectively. On the other hand, the polyphenols and their related compounds had few inhibitory effects on the radical formation in the presence of EDTA. Visible absorbance measurement revealed that all the polyphenols exhibiting the inhibitory effect chelate ferrous ions. Above results indicated that the chelation of ferrous ion is essential to the inhibitory effects of the polyphenols.
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Research Article|
February 22 2000
Some polyphenols inhibit the formation of pentyl radical and octanoic acid radical in the reaction mixture of linoleic acid hydroperoxide with ferrous ions
Hideo IWAHASHI
Hideo IWAHASHI
1
1Department of Chemistry, Wakayama Medical College, 811-1 Kimiidera, Wakayama 641-0012, Japan
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Publisher: Portland Press Ltd
Received:
September 17 1999
Revision Received:
November 22 1999
Accepted:
December 22 1999
Online ISSN: 1470-8728
Print ISSN: 0264-6021
The Biochemical Society, London © 2000
2000
Biochem J (2000) 346 (2): 265–273.
Article history
Received:
September 17 1999
Revision Received:
November 22 1999
Accepted:
December 22 1999
Citation
Hideo IWAHASHI; Some polyphenols inhibit the formation of pentyl radical and octanoic acid radical in the reaction mixture of linoleic acid hydroperoxide with ferrous ions. Biochem J 1 March 2000; 346 (2): 265–273. doi: https://doi.org/10.1042/bj3460265
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