Role of aldehyde oxidase in the hepatic in vitro metabolism of 3- methylindole in pigs

Journal of Agricultural and Food Chemistry

Volumn 48, Issue 3, 2000, Pages 833-837

  Diaz, Gonzalo J ^a,b   Squires, E James ^a  

^a UNIVERSITY OF GUELPH   (Canada)

^b UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

Author keywords

3 methylindole; Aldehyde oxidase; Metabolism; Pigs; Skatole

Indexed keywords

3 HYDROXY 3 METHYLOXINDOLE; ALDEHYDE DEHYDROGENASE; ALDEHYDE OXIDASE; FLAVOPROTEIN; MENADIONE; MEPACRINE; SKATOLE;

ANIMAL; ARTICLE; CATALYSIS; ENZYMOLOGY; LIVER; LIVER METABOLISM; MALE; METABOLISM; NONHUMAN; OXIDATION; SWINE;

ALDEHYDE OXIDASE; ALDEHYDE OXIDOREDUCTASES; ANIMALS; FLAVOPROTEINS; LIVER; MALE; SKATOLE; SWINE;

ANIMALIA; SUIDAE; SUS SCROFA;

EID: 0034113567     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf990805u     Document Type: Article

References (28)

1. Babol, J.; Squires, E. J. Quality of meat from entire male pigs. Food Res. Int. 1995, 28, 201-212.
2. Babol, J.; Squires, E. J.; Lundström, K. Relationship between oxidation and conjugation metabolism of skatole in pig liver and concentrations of skatole in fat. J. Anim. Sci. 1998, 76, 829-838.
3. Baek, C.; Hansen-Møller, J.; Friis, C.; Cornett, C.; Hansen, S. H. Identification of selected metabolites of skatole in plasma and urine from pigs. J. Agric. Food Chem. 1997, 45, 2332-2340.
4. Beedham, C. Molybdenum hydroxylases as drug-metabolizing enzymes. Drug Metab. Rev. 1985, 16, 119-156.
5. Beedham, C.; Peet, C. F.; Panoutsopoulos, G. I.; Carter, H.; Smith, J. A. Role of aldehyde oxidase in biogenic amine metabolism. Prog. Brain Res. 1995, 106, 345-353.
6. Diaz, G. J.; Skordos, K. W.; Yost, G. S.; Squires, E. J. Identification of Phase I metabolites of 3-methylindole produced by pig liver microsomes. Drug Metab. Dispos. 1999, 27, 1150-1156.
7. Fordtran, J. S.; Scroggie, W. B.; Polter, D. E. Colonie absorption of tryptophan metabolites in man. J. Lab. Clin. Med. 1964, 64, 125-132.
8. Jensen, M. T.; Cox, R. P.; Jensen, B. B. Microbial production of skatole in the hind gut of pigs given different diets and its relation to skatole deposition in backfat. Anim. Sci. 1995, 61, 293-304.
9. Johns, D. G. Human liver aldehyde oxidase: differential inhibition of oxidation of charged and uncharged substrates. J. Clin. Invest. 1967, 46, 1492-1505.
10. Kaye, B.; Rance, D. J.; Waring, L. Oxidative metabolism of carbazeran in vitro by liver cytosol of baboon and man. Xenobiotica 1985, 15, 237-242.
11. Krenitsky, T. A.; Tuttle, J. V.; Cattau, E. L., Jr.; Wang, P. A comparison of the distribution and electron acceptor specificities of xanthine oxidase and aldehyde oxidase. Comp. Biochem. Physiol. 1974, 49B, 687-703.
12. Lundström, K.; Bonneau, M. Off-flavour in meat with particular emphasis on boar taint. In Meat Quality and Meat Packaging; Taylor, S., Raimundo A., Severini, M., Smulders, F. J. M., Eds.; ECCEAMST: Utrecht, The Netherlands, 1996.
13. Lundström, K.; Malmfors, B.; Stern, S.; Rydhmer, L.; Eliasson-Selling, L.; Mortensen, A. B.; Mortensen, H. P. Skatole levels in pigs selected for high lean tissue growth rate on different dietary protein levels. Livestock Prod. Sci. 1995, 38, 125-132.
14. Mortensen, A. B.; Sørensen, S. E. Relationship between boar taint and skatole determination with a new analysis method. Proceedings of the 30th European Meeting of Meat Research Workers, Bristol, U.K., Sept 9-14, 1984; Paper 8-11, pp 394-396.
15. National Research Council. Vitamin Tolerance of Animals; National Academy Press: Washington, DC, 1987.
16. Patience, J. F.; Thacker, P. A.; de Lange, C. F. M. Swine Nutrition Guide, 2nd ed.; Prairie Swine Centre: Saskatoon, Canada, 1995.
17. Rajagopalan, K. V. Xanthine oxidase and aldehyde oxidase. In Enzymatic Basis of Detoxication; Jakoby, W. B., Ed.; Academic Press: New York, 1980; Vol. I.
18. Rajagopalan, K. V.; Handler, P. Hepatic aldehyde oxidase. III. The substrate binding site. J. Biol. Chem. 1964, 239, 2027-2035.
19. Rajagopalan, K. V.; Handler, P. Aldehyde oxidase. Methods Enzymol. 1966, 9, 364-368.
20. Rashidi, M. R.; Smith, J. A.; Clarke, S. E.; Beedham, C. In vitro oxidation of famciclovir and 6-deoxypenciclovir by aldehyde oxidase from human, guinea pig, rabbit, and rat liver. Drug Metab. Dispos. 1997, 25, 805-813.
21. Rodrigues, A. D. Comparison of levels of aldehyde oxidase with cytochrome P450 activities in human liver in vitro. Biochem. Pharmacol. 1994, 48, 197-200.
22. SAS. SAS System for Windows, release 6.11; SAS Institute: Cary, NC, 1995.
23. Skiles, G. L.; Adams, J. D., Jr.; Yost, G. S. Isolation and identification of 3-hydroxy-3-methyloxindole, the major murine metabolite of 3-methylindole. Chem. Res. Toxicol. 1989, 2, 254-259.
24. Skordos, K. W.; Skiles, G. L.; Laycock, J. D.; Lanza, D. L.; Yost, G. S. Evidence supporting the formation of 2,3-epoxy-3-methylindoline: a reactive intermediate of the pneumotoxin 3-methylindole. Chem. Res. Toxicol. 1998, 11, 741-749.
25. Smith, D. J.; Skiles, G. L.; Appleton, M. L.; Carlson, J. R.; Yost, G. S. Identification of goat and mouse urinary metabolites of the pneumotoxin, 3-methylindole. Xenobiotica 1993, 23, 1025-1044.
26. Smith, P. K.; Krohn, R. I.; Hermanson, G. T.; Mallia, A. K.; Gartner, F. H.; Provenzano, M. D.; Fujimoto, E. K.; Goeke, N. M.; Olson, B. J.; Klenk, D. C. Measurement of protein using bicinchoninic acid. Anal. Biochem. 1985, 150, 76-85.
27. Squires, E. J.; Lundström, K. Relationship between cytochrome P450IIE1 in liver and levels of skatole and its metabolites in intact male pigs. J. Anim. Sci. 1997, 75, 2506-2511.
28. Yokoyama, M. T.; Carlson, J. R. Microbial metabolites of tryptophan in the intestinal tract with special reference to skatole. Am. J. Clin. Nutr. 1979, 32, 173-178.