Identification of the metabolites of the antioxidant flavonoid 7-mono-O-(β-hydroxyethyl)-rutoside in mice

Drug Metabolism and Disposition

Volumn 39, Issue 5, 2011, Pages 750-756

  Jacobs, Hilde ^a,c   Peters, Ron ^b   Den Hartog, Gertjan J M ^a   Van Der Vijgh, Wim J F ^a   Bast, Aalt ^a   Haenen, Guido R M M ^a  

^a MAASTRICHT UNIVERSITY   (Netherlands)

^b DSM RESOLVE   (Netherlands)

^c MAASTRICHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

7 DI O (BETA HYDROXYETHYL)RUTOSIDE; 7 DI O (BETA HYDROXYETHYL)RUTOSIDE DIMETHYL ESTER; 7 DI O (BETA HYDROXYETHYL)RUTOSIDE METHYL ESTER; 7 MONO O (BETA CARBOXYETHYL)RUTOSIDE; 7 MONO O (BETA CARBOXYETHYL)RUTOSIDE DIMETHYL ESTER; 7 MONO O (BETA CARBOXYETHYL)RUTOSIDE GLUCURONIDE; 7 MONO O (BETA CARBOXYETHYL)RUTOSIDE GLUCURONIDE METHYL ESTER; 7 MONO O (BETA CARBOXYETHYL)RUTOSIDE METHYL ESTER; 7 MONO O (BETA HYDROXYETHYL)GLUCOSIDE; 7 MONO O (BETA HYDROXYETHYL)GLUCOSIDE DIMETHYL ESTER; 7 MONO O (BETA HYDROXYETHYL)GLUCOSIDE METHYL ESTER; 7 MONO O (BETA HYDROXYETHYL)RUTOSIDE; 7 MONO O (BETA HYDROXYETHYL)RUTOSIDE DIGLUCURONIDE; 7 MONO O (BETA HYDROXYETHYL)RUTOSIDE GLUCURONIDE; 7 MONO O (BETA HYDROXYETHYL)RUTOSIDE GLUCURONIDE METHYL ESTER; 7 MONO O (BETA HYDROXYETHYL)RUTOSIDE METHYL ESTER; 7 TETRA O (BETA HYDROXYETHYL)RUTOSIDE; 7 TRI O (BETA HYDROXYETHYL)RUTOSIDE; ANTIOXIDANT; DISACCHARIDE; DOXORUBICIN; DRUG METABOLITE; FLAVONOID; GLUTATHIONE; GLUTATHIONE 7 MONO O (BETA HYDROXYETHYL)RUTOSIDE; RUTOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CARDIOTOXICITY; CONTROLLED STUDY; DIODE ARRAY DETECTION TIME OF FLIGHT MASS SPECTROMETRY; DRUG BILE LEVEL; DRUG CLEARANCE; DRUG CONJUGATION; DRUG GLUCURONIDATION; DRUG HYDROLYSIS; DRUG IDENTIFICATION; DRUG METABOLISM; DRUG OXIDATION; DRUG STRUCTURE; DRUG UPTAKE; GALLBLADDER; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; METHYLATION; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTECTION;

ANIMALS; ANTIOXIDANTS; BILE; CARDIOTONIC AGENTS; DOXORUBICIN; GLUCURONIDES; GLUTATHIONE; HYDROXYETHYLRUTOSIDE; MALE; METHYLATION; MICE; MICE, INBRED BALB C;

MUS;

EID: 79954992768     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.110.036525     Document Type: Article

References (30)

1. Abou El Hassan MA, Kedde MA, Zwiers UT, Bast A, and van der Vijgh WJ (2003a) The cardioprotector monoHER does not interfere with the pharmacokinetics or the metabolism of the cardiotoxic agent doxorubicin in mice. Cancer Chemother Pharmacol 51:306-310. (Pubitemid 36629808)
2. Abou El Hassan MA, Kedde MA, Zwiers UT, Tourn E, Haenen GR, Bast A, and van der Vijgh WJ (2003b) Bioavailability and pharmacokinetics of the cardioprotecting flavonoid 7-monohydroxyethylrutoside in mice. Cancer Chemother Pharmacol 52:371-376. (Pubitemid 37363609)
3. Barrow A and Griffiths LA (1974) Metabolism of the hydroxyethylrutosides. II. Excretion and metabolism of 3',4',7-tri-O-(β- hydroxyethyl) rutoside and related compounds in laboratory animals after parenteral administration. Xenobiotica 4:1-16.
4. Bast A, Haenen GR, Bruynzeel AM, and Van der Vijgh WJ (2007) Protection by flavonoids against anthracycline cardiotoxicity: From chemistry to clinical trials. Cardiovasc Toxicol 7:154-159. (Pubitemid 47339864)
5. Breinholt VM, Offord EA, Brouwer C, Nielsen SE, Brøsen K, and Friedberg T (2002) In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids. Food Chem Toxicol 40:609-616. (Pubitemid 34310426)
6. Doroshow JH, Locker GY, and Myers CE (1980) Enzymatic defenses of the mouse heart against reactive oxygen metabolites: Alterations produced by doxorubicin. J Clin Invest 65:128-135. (Pubitemid 10214339)
7. Forester SC and Waterhouse AL (2009) Metabolites are key to understanding health effects of wine polyphenolics. J Nutr 139:1824S-1831S.
8. Gescher AJ and Steward WP (2003) Relationship between mechanisms, bioavailability, and preclinical chemopreventive efficacy of resveratrol: A conundrum. Cancer Epidemiol Biomarkers Prev 12:953-957. (Pubitemid 37310248)
9. Hackett AM and Griffiths LA (1977a) The disposition and metabolism of 3',4',7-tri-O-(β- hydroxyethyl)rutoside and 7-mono-O-(β- hydroxyethyl)rutoside in the mouse. Xenobiotica 7:641-651. (Pubitemid 8176858)
10. Hackett AM and Griffiths LA (1977b) Enterohepatic cycling of O-(β- hydroxyethyl) rutosides and their biliary metabolites in the rat. Experientia 33:161-163. (Pubitemid 8039971)
11. Haenen GR, Jansen FP, and Bast A (1993) The antioxidant properties of five O-(-β- hydroxyethyl)-rutosides of the flavonoid mixture Venoruton. Phlebology Suppl 1:10-17. (Pubitemid 24064735)
12. Horenstein MS, Vander Heide RS, and L'Ecuyer TJ (2000) Molecular basis of anthracyclineinduced cardiotoxicity and its prevention. Mol Genet Metab 71:436-444.
13. Huang S and Czech MP (2007) The GLUT4 glucose transporter. Cell Metab 5:237-252. (Pubitemid 46477860)
14. Iarussi D, Indolfi P, Galderisi M, and Bossone E (2000) Cardiac toxicity after anthracycline chemotherapy in childhood. Herz 25:676-688.
15. Jacobs H, Moalin M, Bast A, van der Vijgh WJ, and Haenen GR (2010) An essential difference between the flavonoids monoHER and quercetin in their interplay with the endogenous antioxidant network. PLoS One 5:e13880.
16. Jacobs H, van der Vijgh WJ, Koek GH, Draaisma GJ, Moalin M, van Strijdonck GP, Bast A, and Haenen GR (2009) Characterization of the glutathione conjugate of the semisynthetic flavonoid monoHER. Free Radic Biol Med 46:1567-1573.
17. Julicher RH, Sterrenberg L, Haenen GR, Bast A, and Noordhoek J (1988) The effect of chronic adriamycin treatment on heart kidney and liver tissue of male and female rat. Arch Toxicol 61:275-281. (Pubitemid 18058436)
18. Lipshultz SE, Lipsitz SR, Sallan SE, Dalton VM, Mone SM, Gelber RD, and Colan SD (2005) Chronic progressive cardiac dysfunction years after doxorubicin therapy for childhood acute lymphoblastic leukemia. J Clin Oncol 23:2629-2636. (Pubitemid 46179451)
19. Passamonti S, Terdoslavich M, Franca R, Vanzo A, Tramer F, Braidot E, Petrussa E, and Vianello A (2009) Bioavailability of flavonoids: A review of their membrane transport and the function of bilitranslocase in animal and plant organisms. Curr Drug Metab 10:369-394.
20. Petruzzellis V, Troccoli T, Candiani C, Guarisco R, Lospalluti M, Belcaro G, and Dugall M (2002) Oxerutins (Venoruton): Efficacy in chronic venous insufficiency-a double-blind, randomized, controlled study. Angiology 53:257-263. (Pubitemid 34525862)
21. Singal PK and Iliskovic N (1998) Doxorubicin-induced cardiomyopathy. N Engl J Med 339: 900-905. (Pubitemid 28446849)
22. Spencer JP, Abd-el-Mohsen MM, and Rice-Evans C (2004) Cellular uptake and metabolism of flavonoids and their metabolites: Implications for their bioactivity. Arch Biochem Biophys 423:148-161. (Pubitemid 38198224)
23. Spencer JP, Kuhnle GG, Williams RJ, and Rice-Evans C (2003) Intracellular metabolism and bioactivity of quercetin and its in vivo metabolites. Biochem J 372:173-181. (Pubitemid 36609619)
24. Strobel P, Allard C, Perez-Acle T, Calderon R, Aldunate R, and Leighton F (2005) Myricetin, quercetin and catechin-gallate inhibit glucose uptake in isolated rat adipocytes. Biochem J 386:471-478. (Pubitemid 40445871)
25. van Acker FA, van Acker SA, Kramer K, Haenen GR, Bast A, and van der Vijgh WJ (2000) 7-Monohydroxyethylrutoside protects against chronic doxorubicin-induced cardiotoxicity when administered only once per week. Clin Cancer Res 6:1337-1341. (Pubitemid 30226217)
26. van Acker SA, Boven E, Kuiper K, van den Berg DJ, Grimbergen JA, Kramer K, Bast A, and van der Vijgh WJ (1997) Monohydroxyethylrutoside, a dose-dependent cardioprotective agent, does not affect the antitumor activity of doxorubicin. Clin Cancer Res 3:1747-1754. (Pubitemid 27444713)
27. Walle T (2009) Methylation of dietary flavones increases their metabolic stability and chemopreventive effects. Int J Mol Sci 10:5002-5019.
28. Willems AM, Bruynzeel AM, Kedde MA, van Groeningen CJ, Bast A, and van der Vijgh WJ (2006) A phase I study of monohydroxyethylrutoside in healthy volunteers. Cancer Chemother Pharmacol 57:678-684.
29. Xu MF, Tang PL, Qian ZM, and Ashraf M (2001) Effects by doxorubicin on the myocardium are mediated by oxygen free radicals. Life Sci 68:889-901. (Pubitemid 32168065)
30. Zhu BT (2002) Catechol-O-methyltransferase (COMT)-mediated methylation metabolism of endogenous bioactive catechols and modulation by endobiotics and xenobiotics: Importance in pathophysiology and pathogenesis. Curr Drug Metab 3:321-349. (Pubitemid 34625043)