title: Effects of quinones and flavonoids on the reduction of all-trans retinal to all-trans retinol in pig heart.
abstract: We have recently purified a tetrameric carbonyl reductase from the cytosolic fraction of pig heart (pig heart carbonyl reductase). Since pig heart carbonyl reductase efficiently reduces all-trans retinal as the endogenous substrate, it probably plays an important role in retinoid metabolism in the heart. The purpose of the present study was to evaluate the inhibitory effects of quinones and flavonoids on the reduction of all-trans retinal to all-trans retinol catalyzed by pig heart carbonyl reductase, using pig heart cytosol. Of quinones tested, 9,10-phenanthrenequinone, a component of diesel exhaust particles, was the most potent inhibitor for the all-trans retinal reduction, and a significant inhibition was also observed for plumbagin and menadione. The order of the inhibitory potencies for flavonoids was kaempferol > quercetin > genistein > myricetin = apigenin = daidzein. However, the inhibitory potencies of flavonoids were much lower than that of 9,10-phenanthrenequinone. 9,10-Phenanthrenequinone competitively inhibited the all-trans retinal reduction, whereas kaempferol exhibited a mixed-type inhibition. It is likely that 9,10-phenanthrenequinone strongly inhibits the reduction of all-trans retinal to all-trans retinol by acting as the substrate inhibitor of pig heart carbonyl reductase present in pig heart cytosol.
authors.affiliation: Faculty of Education, Kumamoto University, 2-40-1, Kurokami, Kumamoto 860-8555, Japan. hshimada@gpo.kumamoto-u.ac.jp
authors.forename: Hideaki
authors.initials: H
authors.lastname: Shimada
authors.forename: Takaomi
authors.initials: T
authors.lastname: Hirashima
authors.forename: Yorishige
authors.initials: Y
authors.lastname: Imamura
mesh_terms: D000429:Alcohol Oxidoreductases / Q000378:metabolism*; D000818:Animals; D047310:Apigenin / Q000494:pharmacology; D001462:Barbital / Q000494:pharmacology; D003600:Cytosol / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology*; D019833:Genistein / Q000494:pharmacology; D007529:Isoflavones / Q000494:pharmacology; D044949:Kaempferols / Q000494:pharmacology; D007700:Kinetics; D015394:Molecular Structure; D009206:Myocardium / Q000166:cytology / Q000201:enzymology / Q000378:metabolism; D009285:Naphthoquinones / Q000494:pharmacology; D010084:Oxidation-Reduction / Q000187:drug effects; D010616:Phenanthrenes / Q000494:pharmacology; D011794:Quercetin / Q000494:pharmacology; D011809:Quinones / Q000737:chemistry / Q000494:pharmacology*; D012172:Retinaldehyde / Q000378:metabolism*; D013552:Swine; D014801:Vitamin A / Q000378:metabolism*; D024483:Vitamin K 3 / Q000494:pharmacology
chemical_list: D005419:Flavonoids; D007529:Isoflavones; D044949:Kaempferols; D009285:Naphthoquinones; D010616:Phenanthrenes; D011809:Quinones; D014801:Vitamin A; C005399:9,10-phenanthrenequinone; D001462:Barbital; C004742:daidzein; D024483:Vitamin K 3; C006552:kaempferol; C040015:myricetin; D047310:Apigenin; D011794:Quercetin; D019833:Genistein; D000429:Alcohol Oxidoreductases; D012172:Retinaldehyde; C014758:plumbagin