Inhibitory effects of flavonoids on aldehyde oxidase activity

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 24, Issue 1, 2009, Pages 14-21

  Pirouzpanah, Saeed ^a   Hanaee, Jalal ^a   Razavieh, Seyed Vali ^a   Rashidi, Mohammad Reza ^b  

^a TABRIZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b TABRIZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Aldehyde oxidase; Flavonoids; Inhibition; Xanthine oxidase

Indexed keywords

AGLYCONE; ALDEHYDE OXIDASE; ALLOPURINOL; CARBOHYDRATE DERIVATIVE; CATECHIN; EPICATECHIN; FLAVAN; FLAVAN 3 OL; FLAVANONE; FLAVON 3 OL; FLAVONOID; FLAVONOL; HESPERETIN; HESPERIDIN; HYPERIN; MENADIONE; MORIN; MYRICETIN; NARINGENIN; NATURAL PRODUCT; PHENANTHRIDINE DERIVATIVE; QUERCETIN; RUTOSIDE; TAXIFOLIN; UNCLASSIFIED DRUG; VANILLIN; XANTHINE; XANTHINE OXIDASE;

ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME INHIBITION; ENZYME PURIFICATION; ENZYME SUBSTRATE; FOOD DRUG INTERACTION; IN VITRO STUDY; MALE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; SPECTROPHOTOMETRY;

ALDEHYDE OXIDASE; ANIMALS; BENZALDEHYDES; FLAVONOIDS; GUINEA PIGS; LIVER; PHENANTHRIDINES; QUERCETIN; XANTHINE OXIDASE;

CAVIA;

EID: 58949101051     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360701841301     Document Type: Article

References (38)

1. Beedham, C. (2002) Molybdenum hydroxylases. Enzyme systems that metabolites drugs and other xenobiotics, pp. 147-148. John Wiley, New York
2. Beedham, C. (1987) Molybdenum hydroxylases: Biological distribution and substrate-inhibitor specificity. Progress in medicinal chemistry, pp. 58-127. Elsevier Science Publishers (Biomedical Division), Amsterdam
3. Beedham, C. (1998) Molybdenum hydroxylase. Metabolism of xenobiotics, pp. 51-58. Taylor & Francis, London and New York
4. Stanulovic, M. and Chaykin, S. (1971) Aldehyde oxidase: Catalysis of the oxidation of N1-methylnicotinamide and pyridoxal. Arch Biochem Biophys, 145, pp. 27-34.
5. Ambroziak, W., Izaguirre, G. and Pietruszko, R. (1999) Metabolism of retinaldehyde and other aldehydes in soluble extracts of human liver and kidney. J Biol Chem, 274, pp. 33366-33373.
6. Moriwaki, Y., Yamamoto, T., Yamakita, J., Takahashi, S., Tsutsumi, Z. and Higashino, K. (1998) Zonal distribution of allopurinol-oxidizing enzymes in rat liver. Adv Exp Med Biol, 431, pp. 47-50.
7. Panoutsopoulos, G. (2005) Metabolism of homovanillamine to homovanillic acid in guinea pig liver slices. Cell Physiol Biochem, 15, pp. 225-232.
8. Rashidi, MR, Smith, JA, Clarke, SE and Beedham, C. (1997) In vitro oxidation of famciclovir and 6-deoxypenciclovir by aldehyde oxidase from human, guinea pig, rabbit, and rat liver. Drug Metab Dispos, 25, pp. 805-813.
9. Jordan, CG, Rashidi, MR, Laljee, H., Clarke, SE, Brown, JE and Beedham, C. (1999) Aldehyde oxidase-catalysed oxidation of methotrexate in the liver of guinea-pig, rabbit and man. J Pharm Pharmacol, 51, pp. 411-418.
10. Beedham, C., al-Tayib, Y. and Smith, JA (1992) Role of guinea pig and rabbit hepatic aldehyde oxidase in oxidative in vitro metabolism of cinchona antimalarials. Drug Metab Dispos, 20, pp. 889-895.
11. Critchley, DJ, Rance, DJ and Beedham, C. (1994) Biotransformation of carbazeran in guinea pig: Effect of hydralazine pretreatment. Xenobiotica, 24, pp. 37-47.
12. Lake, BG, Ball, SE, Kao, J., Renwick, AB, Price, RJ and Scatina, JA (2002) Metabolism of zaleplon by human liver: Evidence for involvement of aldehyde oxidase. Xenobiotica, 32, pp. 835-847.
13. Sugihara, K., Tayama, Y., Shimomiya, K., Yoshimoto, D., Ohta, S. and Kitamura, S. (2006) Estimation of aldehyde oxidase activity in vivo from conversion ratio of N1-methylnicotinamide to pyridines, and interspecies variation of the enzyme activity in rats. Drug Metab Dispos, 34, pp. 208-212.
14. Brandange, S. and Lindblom, L. (1979) The enzyme "aldehyde oxidase" is an iminium oxidase. Reaction with nicotine delta 1′(5′) iminium ion. Biochem Biophys Res Commun, 91, pp. 991-996.
15. Rochat, B., Kosel, M., Boss, G., Testa, B., Gillet, M. and Baumann, P. (1998) Stereoselective biotransformation of the selective serotonin reuptake inhibitor citalopram and its demethylated metabolites by monoamine oxidases in human liver. Biochem Pharmacol, 56, pp. 15-23.
16. Ruenitz, PC and Bai, X. (1995) Acidic metabolites of tamoxifen. Aspects of formation and fate in the female rat. Drug Metab Dispos, 23, pp. 993-998.
17. Kitamura, S., Ohashi, KNK, Sugihara, K., Hosokawa, R., Akagawa, Y. and Ohta, S. (2001) Extremely high drug-reductase activity based on aldehyde oxidase in monkey liver. Biol Pharm Bull, 24, pp. 856-859.
18. Lee, SC and Renwick, AG (1995) Sulphoxide reduction by rat and rabbit tissues in vitro. Biochem Pharmacol, 49, pp. 1557-1565.
19. Tatsumi, K., Yamada, H. and Kitamura, S. (1983) Evidence for involvement of liver aldehyde oxidase in reduction of nitrosamines to the corresponding hydrazine. Chem Pharm Bull, 31, pp. 764-767.
20. Tatsumi, K., Kitamura, S. and Yamada, H. (1983) Sulfoxide reductase activity of liver aldehyde oxidase. Biochem Biophys Acta, 747, pp. 86-92.
21. Obach, RS (2004) Potent inhibition of human liver aldehyde oxidase by raloxifene. Drug Metab Dispos, 32, pp. 89-97.
22. Hille, R. (2005) Molybdenum-containing hydroxylases. Arch Biochem Biophys, 433, pp. 107-116.
23. Nijveldt, RJ, van Nood, E., van Hoorn, DEC, Boelens, PG, van Norren, K. and van Leeuwen, PAM (2001) Flavonoids: A review of probable mechanisms of action and potential applications. Am J Clin Nutr, 74, pp. 418-425.
24. Van Hoorn, DE, Nijveldt, RJ, Van Leeuwen, PA, Hofman, Z., M'Rabet, L. De Bont, DB et al. (2002) Accurate prediction of xanthine oxidase inhibition based on the structure of flavonoids. Eur J Pharmacol, 451, pp. 111-118.
25. Aucamp, J., Gaspar, A., Hara, Y. and Apostolides, Z. (1997) Inhibition of xanthine oxidase by catechins from tea (Camellia sinensis). Anticancer Res, 17, pp. 4381-4385.
26. Lin, CM, Chen, CS, Chen, CT, Liang, YC and Lin, JK (2002) Molecular modeling of flavonoids that inhibits xanthine oxidase. Biochem Biophys Res Commun, 294, pp. 167-172.
27. Hanaee, J., Rashidi, MR, Delazar, A. and Pirouzpanah, S. (2004) Onion, a potent inhibitor of xanthine oxidase. Iran J Pharm Res, 4, pp. 243-247.
28. Nagao, A., Seki, M. and Kobayashi, H. (1999) Inhibition of xanthine oxidase by flavonoids. Biosci Biotechnol Biochem, 63, pp. 1787-1790.
29. Cotelle, N. (2001) Role of flavonoids in oxidative stress. Curr Top Med Chem, 1, pp. 569-590.
30. Kitamura, S., Sugihara, K. and Ohta, S. (2006) Drug-metabolizing ability of molybdenum hydroxylases. Drug Metab Pharmacokinet, 21, pp. 83-98.
31. Yu, Z., Fong, WP and Cheng, CH (2006) The dual actions of morin (3,5,7,2′,4′-pentahydroxyflavone) as a hypouricemic agent: Uricosuric effect and xanthine oxidase inhibitory activity. J Pharmacol Exp Ther, 316, pp. 169-175.
32. Pirouzpanah, S., Rashidi, MR, Delazar, A., Razavieh, SV and Hamidi, A. (2006) Inhibitory effects of Ruta graveolens L. Extract on guinea pig liver aldehyde oxidase. Chem Pharm Bull, 54, pp. 9-13.
33. Smith, PK, Krohn, RI, Hermanson, GT, Mallia, AK, Gartner, FH, Provenzano, MD, Fujimoto, EK, Goeke, NM, Olson, BJ and Klenk, DC (1985) Measurement of protein using bicinchoninic acid. Anal Biochem, 150, pp. 76-85.
34. Aziz, AA, Edwards, CA, Lean, MEJ and Crozier, A. (1998) Absorption and excretion of conjugated flavonols, including quercetin-4′-O-β-glucoside and isorhamnetin-4′-O-β-glucoside by human volunteers after the consumption of onions. Free Rad Res, 29, pp. 257-269.
35. McAnlis, GT, McEneny, J., Pearce, J. and Young, IS (1999) Absorption and antioxidant effects of quercetin from onions, in man. Eur J Clin Nutr, 53, pp. 92-96.
36. Zhang, Y., Zhang, Q., Li, L., Wang, B., Zhao, Y. and Guo, D. (2007) Simultaneous determination and pharmacokinetic studies of dihydromyricetin and myricetin in rat plasma by HPLC-DAD after oral administration of Ampelopsis grossedentata decoction. J Chromatogr B
37. Huh, K., Shin, US, Choi, JW and Lee, SI (1994) Effect of sex hormones on lipid peroxidation in rat liver. Arch Pharmacol Res, 17, pp. 109-114.
38. Lee, DU, Shin, US and Huh, K. (1998) Structure-activity relationships of gagaminine and its derivatives on the inhibition of hepatic aldehyde oxidase activity and lipid peroxidation. Arch Pharmacol Res, 21, pp. 273-277.