title: Some polyphenols inhibit the formation of pentyl radical and octanoic acid radical in the reaction mixture of linoleic acid hydroperoxide with ferrous ions.
abstract: 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 alpha-(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.
authors.affiliation: Department of Chemistry, Wakayama Medical College, 811-1 Kimiidera, Wakayama 641-0012, Japan. chem1@wakayama-med.ac.jp
authors.forename: H
authors.initials: H
authors.lastname: Iwahashi
mesh_terms: D002851:Chromatography, High Pressure Liquid; D005296:Ferrous Compounds / Q000737:chemistry*; D005419:Flavonoids; D005609:Free Radicals / Q000737:chemistry; D008041:Linoleic Acids / Q000737:chemistry*; D015227:Lipid Peroxidation; D008054:Lipid Peroxides / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D059808:Polyphenols
chemical_list: D005296:Ferrous Compounds; D005419:Flavonoids; D005609:Free Radicals; D008041:Linoleic Acids; D008054:Lipid Peroxides; D010636:Phenols; D011108:Polymers; D059808:Polyphenols; C008285:linoleic acid hydroperoxide