title: Cytochrome c catalyses the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide.
abstract: A reaction of 13-hydroperoxide octadecadienoic acid (13-HPODE) with cytochrome c was analysed using ESR, HPLC-ESR and HPLC-ESR-MS by the combined use of the spin-trapping technique. The ESR, HPLC-ESR and HPLC-ESR-MS analyses showed that cytochrome c catalyses formation of pentyl and octanoic acid radicals from 13-HPODE. On the other hand, only the alpha-(4-pyridyl-1-oxide)-N-t-butylnitrone/octanoic acid radical adduct was detected in the elution profile of HPLC-ESR for a mixture of 13-HPODE with haematin, indicating that haematin catalyses the formation of octanoic acid radical. In addition, the reaction of 13-HPODE with cytochrome c was inhibited by chlorogenic acid, caffeic acid and ferulic acid via two possible mechanisms, i.e. reducing cytochrome c (chlorogenic acid and caffeic acid) and scavenging the radical intermediates (chlorogenic acid, caffeic acid and ferulic acid).
authors.affiliation: Department of Chemistry, Wakayama Medical University, 811-1 Kimiidera, Wakayama 641-8509, Japan. chem1@wakayama-med.ac.jp
authors.forename: Hideo
authors.initials: H
authors.lastname: Iwahashi
authors.forename: Koji
authors.initials: K
authors.lastname: Nishizaki
authors.forename: Ichiro
authors.initials: I
authors.lastname: Takagi
mesh_terms: D000818:Animals; D002109:Caffeic Acids / Q000494:pharmacology; D002210:Caprylates / Q000737:chemistry / Q000378:metabolism*; D002726:Chlorogenic Acid / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003373:Coumaric Acids / Q000494:pharmacology; D003486:Cyanides / Q000494:pharmacology; D003574:Cytochrome c Group / Q000378:metabolism*; D004578:Electron Spin Resonance Spectroscopy; D005419:Flavonoids; D016166:Free Radical Scavengers / Q000494:pharmacology; D005609:Free Radicals / Q000378:metabolism; D006427:Hemin / Q000378:metabolism; D066298:In Vitro Techniques; D008041:Linoleic Acids / Q000378:metabolism*; D008054:Lipid Peroxides / Q000378:metabolism*; D013058:Mass Spectrometry; D008954:Models, Biological; D010084:Oxidation-Reduction; D010420:Pentanes / Q000737:chemistry / Q000378:metabolism*; D010636:Phenols / Q000494:pharmacology; D011108:Polymers / Q000494:pharmacology; D059808:Polyphenols; D013053:Spectrophotometry
chemical_list: D002109:Caffeic Acids; D002210:Caprylates; D003373:Coumaric Acids; D003486:Cyanides; D003574:Cytochrome c Group; D005419:Flavonoids; D016166:Free Radical Scavengers; D005609:Free Radicals; D008041:Linoleic Acids; D008054:Lipid Peroxides; D010420:Pentanes; D010636:Phenols; D011108:Polymers; D059808:Polyphenols; C038649:13-hydroperoxy-9,11-octadecadienoic acid; C008285:linoleic acid hydroperoxide; D002726:Chlorogenic Acid; C033353:pentane; D006427:Hemin; C004999:ferulic acid; C031492:octanoic acid; C040048:caffeic acid