New metabolic pathways for flavanones catalyzed by rat liver microsomes

Drug Metabolism and Disposition

Volumn 32, Issue 4, 2004, Pages 387-397

  Nikolic, Dejan ^a   Van Breemen, Richard B ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3' HYDROXYFLAVANONE; 4' HYDROXYFLAVANONE; ALCOHOL DERIVATIVE; CARBON; CARBONYL DERIVATIVE; CHROMONE DERIVATIVE; CYTOCHROME P450 ISOENZYME; DRUG METABOLITE; FLAVAN 4 OL DERIVATIVE; FLAVAN DERIVATIVE; FLAVANONE; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; LIQUIRITIGENIN; NARINGENIN; PIGMENT; PINOCEMBRINE; QUINOL DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CATALYSIS; CONTROLLED STUDY; DIET; DRUG ACTIVITY; DRUG METABOLISM; DRUG STRUCTURE; ENZYME INDUCTION; ENZYME INHIBITION; ENZYME SUBSTRATE; FEMALE; FRUIT; HYDROXYLATION; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RAT; REDUCTION; STANDARD; TANDEM MASS SPECTROMETRY; VEGETABLE;

ANIMALS; BIOTRANSFORMATION; CHROMATOGRAPHY, LIQUID; FLAVANONES; MASS SPECTROMETRY; MICROSOMES, LIVER; MOLECULAR STRUCTURE; QUINONES; RATS;

ANIMALIA;

EID: 1842432471     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.32.4.387     Document Type: Article

References (31)

1. Awad HM, Boersma MG, Boeren S, van der Woude H, van Zanden J, van Bladeren PJ, Vervoort J, and Rietjens IMCM (2002) Identification of o-quinone/quinone methide metabolites of quercetin in a cellular in vitro system. FEBS Lett 520:30-34.
2. Breinholt VM, Offord EA, Brouwer C, Nielsen SE, Brosen K, and Friedberg T (2002) In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids, Food Chem Toxicol 40:609-616.
3. Canivenc-Lavier MC, Bentejac M, Miller ML, Leclerc J, Siess MH, Latruffe N, and Suschetet M (1996) Differential effects of nonhydroxylated flavonoids as inducers of cytochrome P450 1A and 2B isozymes in rat liver. Toxicol Appl Pharmacol 136:348-353.
4. Ciolino HP, Wang TTY, and Yeh GC (1998) Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity. Cancer Res 58:2754-2760.
5. Erlund I, Silaste ML, Alfthan G, Rantala M, Kasäiniemi YA, and Aro A (2002) Plasma concentration of the flavonoids hesperetin, naringenin and quercetin in human subjects following their habitual diets and diets high or low in fruit and vegetables. Eur J Clin Nutr 56:891-898.
6. Fabre N, Rustan I, deHofmann E, and Quetin-Leclerq J (2001) Determination of flavone, flavonol and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry. J Am Soc Mass Spectrom 12:707-715.
7. Fahey JW and Stephenson KK (2002) Pinostrobin from honey and Thai ginger (Boesenbergia pandurata): a potent flavonoid inducer of mammalian phase 2 chemoprotective and antioxidant enzymes. J Agric Food Chem 50:7472-7476.
8. Foti M, Piatelli M, Baratta MT, and Ruberto G (1996) Flavonoids, coumarins and cinnamic acids as antioxidants in a micellar system. Structure-activity relationship. J Agric Food Chem 44:497-501.
9. Guengerich P (2001) Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem Res Toxicol 14:612-655.
10. Havsteen BH (2002) The biochemistry and medical significance of the flavonoids. Pharmacol Ther 96:67-202.
11. Hertog MGL, Hollman PCH, Katan MB, and Kromhout D (1993) Intake of potentially anticarcinogenic flavonoids and their determinants in adults in The Netherlands. Nutr Cancer 20:21-29.
12. Hodek P, Trefil P, and Stiborova M (2002) Flavonoids - potent and versatile biologically active compounds interacting with cytochromes P450. Chem-Biol Interact 139.1-21.
13. Ibrahim AR and Abdul-Hajj YJ (1990) Aromatase inhibition by flavonoids. J Steroid Biochem Mol Biol 37:257-260.
14. Kuhnau J (1976) The flavonoids. A class of Semiessential food components: their role in human nutrition. World Rev Nutr Diet 24:117-191.
15. Ma YL, Li QM, van den Heuvel H, and Claeys M (1997) Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry. Rapid Commun Mass Spectrom 11:1357-1364.
16. Manthey J and Guthrie N (2002) Antiproliferative activities of citrus flavonoids against six human cancer cell lines. J Agric Food Chem 50:5837-5843.
17. Miketova P, Schram KH, Whitney J, Li M, Huang R, Kerns E, Valcic S, Timmermann BN, Rourick R, and Klohr S (2000) Tandem mass spectrometry studies of green tea catechins. Identification of three minor components in the polyphenolic extract of green tea. J Mass Spectrom 35:860-869.
18. Milligan SR, Kalita JC, Heyerick A, Rong H, De Cooman L, and De Keukeleire D (1999) Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer. J Clin Endocrinol Metab 84:2249-2252.
19. Miksicek RJ (1993) Commonly occurring plant flavonoids have estrogenic activity. Mol Pharmacol 44:37-43.
20. Nielsen SE, Breinholt V, Justesen U, Cornett C, and Dragsted LO (1998) In vitro biotransformation of flavonoids by rat liver microsomes. Xenobiotica 28:389-401.
21. Nikolic D, Li Y, Chadwick LR, Grubjesic S, Schwab P, Metz P, and van Breemen RB (2004) Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus L.) by human liver microsomes. Drug Metab Dispos 32:272-279.
22. Ohe T, Hirobe M, and Mashino T (2000) Novel metabolic pathway of estrone and 17β-estradiol catalyzed by cytochrome P-450. Drug Metab Dispos 28:110-112.
23. Ohe T, Mashino T, and Hirobe M (1994) Novel metabolic pathway of arylethers by cytochromes P450: cleavage of the oxygen-aromatic ting bond accompanying ipso-substitution by the oxygen atom of the active species in cytochromes P450 models and cytochromes P450. Arch Biochem Biophys 310:402-409.
24. Otake Y and Walle T (2002) Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2 and CYP2C9. Drug Metab Dispos 30:103-105.
25. Patzlaff M and Barz W (1978) Peroxidatic degradation of flavanones, Z Naturforsch 33:675-684.
26. Ross JA and Kasum C (2002) Dietary flavonoids: bioavailability, metabolic effects, and safety. Annu Rev Nutr 22:19-34.
27. Solaja BA, Milic, D, and Gasic MJ (1996) A novel m-CPBA oxidation: p-quinols and epoxyquinols from phenols. Tetrahedron Lett 37:3765-3768.
28. Testa B (1995) Biochemistry of Redox Reactions, p. 244, Academic Press, London.
29. Thompson JA, Malkinson AM, Wand MD, Mastovich SL, Mead EW, Schullek KM, and Laudenschlager WG (1987) Oxidative metabolism of butylated hydroxytoluene by hepatic and pulmonary microsomes from rats and mice. Drug Metab Dispos 15:833-840.
30. Wang W and Goodman MT (1999) Antioxidant property of dietary phenolic agents in a human LDL-oxidation ex vivo model: interaction of protein binding activity. Nutr Res 19:191-202.
31. Zhou L, Voyksner RD, Thakker D, Stephens CE, Anbazhagan M, Boykin DW, Hall JE, and Tidwell RR (2000) Characterizing the fragmentation of 2,5-bis (4-amidinophenyl) furan-bis-O-methylamidoxime and selected metabolites using ion trap mass spectrometry. Rapid Commun Mass Spectrom 16:1078-1085.