Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: Glutathione oxidation and conjugation

Free Radical Biology and Medicine

Volumn 30, Issue 4, 2001, Pages 370-382

  Galati, Giuseppe ^a   Moridani, Majid Y ^b   Chan, Tom S ^b   O'Brien, Peter J ^a,b  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

Flavonoids; Free radicals; GSH conjugates; Oxidation; Peroxidase; Thiyl radicals

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; APIGENIN; BOROHYDRIDE POTASSIUM; FLAVONOID; GLUTATHIONE; HYDROGEN PEROXIDE; KAEMPFEROL; LUTEOLIN; NARINGENIN; PEROXIDASE; PHENOL DERIVATIVE; PHENOXYL; POTASSIUM DERIVATIVE; QUERCETIN; QUINONE DERIVATIVE; QUINONE METHIDE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; ELECTRON SPIN RESONANCE; GLUTATHIONE METABOLISM; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PH; PRIORITY JOURNAL; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION;

APIGENIN; CATALASE; ELECTRON SPIN RESONANCE SPECTROSCOPY; FLAVANONES; FLAVONOIDS; FREE RADICALS; GLUTATHIONE; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; LUTEOLIN; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; QUERCETIN; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0035865879     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(00)00481-0     Document Type: Article

References (25)

1. Solid-phase extraction and gas chromatography-mass spectrometry determination of kaempferol and quercetin in human urine after consumption of Ginkgo biloba tablets
2. Antioxidant properties of phenolic compounds
3. Plasma metabolites of quercetin and their antioxidant properties
4. Glutathione-dependent generation of reactive oxygen species by the peroxidase-catalyzed redox cycling of flavonoids
5. Thiyl radicals in biological systems: Significant or trivial?
6. Tissue sulfhydryl groups
7. The fate of the oxidizing tyrosyl radical in the presence of glutathione and ascorbate: Implications for the radical sink hypothesis
8. Generation of superoxide and tyrosine peroxide as a result of tyrosyl radical scavenging by glutathione
9. Phenoxyl radical-induced thiol-dependent generation of reactive oxygen species: Implications for benzene toxicity
10. The toxicology of benzene
11. Potential role of free radicals in benzene-induced myelotoxicity and leukemia
12. Peroxidase-catalyzed pro- versus antioxidant effects of 4- hydroxy-tamoxifen: Enzyme specificity and biochemical sequelae
13. Myeloperoxidase catalyzed cooxidative metabolism of methimazole: Oxidation of glutathione and NADH by free radical intermediates
14. Characterization of one- and two-electron oxidations of glutathione coupled with lactoperoxidase and thyroid peroxidase reactions
15. Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product
16. Molecular mechanisms of quinone cytotoxicity
17. Redox potential of some sulfur containing radicals
18. 2+ ions: Implications for their antioxidant properties
19. Mutagenicity of plant flavonoids: Structural requirements for mutagenic activity in Salmonella typhimurium
20. Evidence that 4-allyl-o-quinones spontaneously rearrange to their more electrophilic quinone methides: Potential bioactivation mechanism for the hepatocarcinogen safrole
21. Regioselectivity and reversibility of the glutathione conjugation of quercetin quinone methide
22. Peroxidase-catalyzed formation of quercetin quinone methide-glutathione adducts
23. In vitro metabolism of 3-t-butyl-4-hydroxyanisole and its irreversible binding to proteins
24. Initial mushroom tyrosinase-catalyzed oxidation product of 4-hydroxyanisole is 4-methoxy-ortho-benzoquinone
25. Oxidation of 4-alkylphenols and catechols by tyrosinase: ortho-substituents alter the mechanism of quinoid formation