Action of pyrroloquinolinequinol as an antioxidant against lipid peroxidation in solution.
The activities of pyrroloquinoline quinone (PQQ), a coenzyme of methanol dehydrogenase and amine oxidase, and its reduced form pyrroloquinoline quinol (PQQH2) as an antioxidant have been measured in solution. PQQH2 was stable in the absence of oxygen but rapidly auto-oxidized to PQQ in the presence of oxygen in water. PQQH2 was stable in an aprotic solvent such as acetonitrile, even in air. PQQ did not exert appreciable antioxidant activity, whereas PQQH2 exerted higher reactivity than alpha-tocopherol toward galvinoxyl radical and peroxyl radical. PQQH2 acted as a potent antioxidant against the oxidation of methyl linoleate in acetonitrile induced by azo compound and produced a clear induction period, from which the apparent stoichiometric number was obtained as 1.1. PQQH2 reduced the alpha-tocopheroxyl radical and spared alpha-tocopherol in the oxidation of methyl linoleate. These results suggest that PQQH2 may act as a potent antioxidant, particularly in combination with alpha-tocopherol.
Research Center for Advanced Science and Technology, The University of Tokyo, Japan.
K
K
Miyauchi
T
T
Urakami
H
H
Abeta
H
H
Shi
N
N
Noguchi
E
E
Niki
D000818:Animals; D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D001559:Benzhydryl Compounds / Q000378:metabolism; D004578:Electron Spin Resonance Spectroscopy; D005609:Free Radicals / Q000378:metabolism; D006801:Humans; D008041:Linoleic Acids / Q000737:chemistry / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D045542:PQQ Cofactor; D010545:Peroxides / Q000378:metabolism; D015363:Quinolones / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D011809:Quinones / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D012996:Solutions; D013053:Spectrophotometry; D014810:Vitamin E / Q000494:pharmacology; D014867:Water / Q000737:chemistry
D000975:Antioxidants; D001559:Benzhydryl Compounds; D005609:Free Radicals; D008041:Linoleic Acids; D010545:Peroxides; D015363:Quinolones; D011809:Quinones; D012996:Solutions; D014867:Water; D014810:Vitamin E; C005575:methyl linoleate; C049375:perhydroxyl radical; D045542:PQQ Cofactor; C020338:galvinoxyl