In vitro and in vivo inhibition of human flavin-containing monooxygenase form 3 (FMO3) in the presence of dietary indoles

Biochemical Pharmacology

Volumn 58, Issue 6, 1999, Pages 1047-1055

  Cashman, John R ^a   Xiong, Yeng ^a   Lin, Jing ^a   Verhagen, Hans ^b   Van Poppel, Geert ^b   Van Bladeren, Peter J ^b   Larsen Su, Shelley ^c   Williams, David E ^c  

^a HUMAN BIOMOLECULAR RESEARCH INSTITUTE   (United States)

^b TNO   (Netherlands)

^c OREGON STATE UNIVERSITY   (United States)

Author keywords

Dietary indoles; Human flavin containing monooxygenase; Indole 3 carbinol related inhibitors; Trimethylamine N oxygenation inhibitors

Indexed keywords

3 INDOLEMETHANOL; COMPLEMENTARY DNA; FLAVIN CONTAINING MONOOXYGENASE 3; GLUCOSINOLATE; HYDROCHLORIC ACID; INDOLE DERIVATIVE; ISOENZYME; TRIMETHYLAMINE; TRIMETHYLAMINE OXIDE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ADULT; ARTICLE; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; DIETARY INTAKE; ENZYME ACTIVITY; ENZYME INHIBITION; GAS CHROMATOGRAPHY; GASTROINTESTINAL TRACT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN EXPERIMENT; MALE; MASS SPECTROMETRY; NORMAL HUMAN; ORAL DRUG ADMINISTRATION; POLYMERIZATION; PRIORITY JOURNAL; RANDOMIZED CONTROLLED TRIAL; VOLUNTEER; XENOBIOTIC METABOLISM;

ADULT; ANTIOXIDANTS; BRASSICA; CARRIER PROTEINS; CROSS-OVER STUDIES; DIET; HUMANS; INDOLES; MALE; METHYLAMINES; OXYGENASES;

EID: 0032802490     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(99)00166-5     Document Type: Article

References (49)

1. Bradlow H.L., Michnovicz J.J., Telang N.T., Osborne M.P. Effects of dietary indole-3-carbinol on estradiol metabolism and spontaneous tumors in mice. Carcinogenesis. 12:1991;1571-1574.
2. Grubbs C.J., Steele V.E., Casebolt T., Juliana M.M., Eto I., Whitaker L.M., Dragnev K.H., Kelloff G.J., Lubet R.L. Chemoprevention of chemically-induced mammary carcinogenesis by indole-3-carbinol. Anticancer Res. 15:1995;709-716.
3. 1 carcinogenesis in rainbow trout by flavone and indole compounds. Carcinogenesis. 5:1984;615-619.
4. Wattenberg L.W., Loub W.D. Inhibition of polycyclic aromatic hydrocarbon-induced neoplasia by naturally occurring indoles. Cancer Res. 38:1978;1410-1413.
5. Kojima T., Tamaka T., Mori M. Chemoprevention of spontaneous endometrial cancer in female Donryu rats by dietary indole-3-carbinol. Cancer Res. 54:1994;1446-1449.
6. Verhoeven D.T.H., Goldbohm R.A., van Poppel G., Verhagen H., van den Brandt P.A. Epidemiological studies on brassica vegetables and cancer risk. Cancer Epidemiol Biomarkers Prev. 5:1996;733-748.
7. Verhoeven D.T.H., Verhagen H., Goldbohm R.A., van den Brandt P.A., van Poppel G. A review of mechanisms underlying anticarcinogenicity by brassica vegetables. Chem Biol Interact. 103:1997;79-129.
8. Graham S. Results of case-control studies of diet and cancer in Buffalo, New York. Cancer Res. 43:(Suppl):1983;2409s-2413s.
9. Medso B., Barrell V., Lubin M., Modan R.A., Greensberg R.A., Graham S. Low-fiber intake as an etiologic factor in cancer of the colon. J Natl Cancer Inst. 55:1975;15-18.
10. Bailey G.S., Hendricks J.D., Shelton D.W., Nixon J.E., Pawlowski N.E. Enhancement of carcinogenesis by the natural anti-carcinogen indole-3-carbinol. J Natl Cancer Inst. 78:1987;931-934.
11. Preobrazhenshaya M.N., Korolev A.M. Indole-3-carbinol. J Natl Cancer Inst. 84:1994;1210-1211.
12. McDanell R., McLean A., Hanley A., Heaney R., Fenwick G. Chemical and biological properties of indole glucosinolates (glucobrassicins) A review . Food Chem Toxicol. 26:1988;59-70.
13. Wall M.E., Taylor H., Perera P., Wani M.C. Indoles in edible members of the Cruciferae. J Nat Prod. 51:1988;129-135.
14. Chung F.-L., Wang M., Hecht S. Effects of dietary indoles and isothiocyanates on N-nitrosodimethylamine and 4-(methylnitrosomanio)-1-(3-pyridyl)-4-butanone α-hydroxylation and DNA methylation in rat liver. Carcinogenesis. 6:1985;539-543.
15. Stoewsand G.S., Anderson J.L., Munson L. Protective effect of dietary Brussels sprouts against mammary carcinogenesis in Sprague-Dawley rats. Cancer Lett. 39:1988;199-207.
16. Tanaka T., Mori Y., Morishita Y., Hara A., Ohuo T., Kojima T., Mori H. Inhibitory effect of siniquin and indole-3-carbinol on diethylnitrosoamine-induced hepatocarcinogenesis in male ACI/N rats. Carcinogenesis. 11:1990;1403-1406.
17. Bjeldanes L.F., Kim J.-Y., Grouse K.R., Bartholomew J.C., Bradfield C.A. Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo Comparisons with 2,3,7,8-tetrachlorodibenzo-p-dioxin . Proc Natl Acad Sci USA. 88:1991;9543-9547.
18. Bradfield C.A., Bjeldanes L.F. Structure-activity relationships of dietary indoles A proposed mechanism of action as modifiers of xenobiotic metabolism . J Toxicol Environ Health. 21:1987;311-323.
19. Liu H., Wormke M., Safe S.H., Bjeldanes L.F. Indolo[3,2-b]carbazole A dietary-derived factor that exhibits both antiestrogenic and estrogenic activity . J Natl Cancer Inst. 86:1994;1758-1765.
20. Sparnins V.L., Venegas P.L., Wattenberg L.W. Glutathione S-transferase activity Enhancement by compounds inhibiting chemical carcinogenesis and by dietary constituents . J Natl Cancer Inst. 68:1982;493-496.
21. 1 in the rat. Drug Metab Dispos. 22:1994;383-391.
22. Michnovicz J.J., Adlercreutz H., Bradlow H.L. Changes in levels of urinary estrogen metabolites after oral indole-3-carbinol treatment in humans. J Natl Cancer Inst. 89:1997;718-723.
23. Pantuck E.J., Pantuck C.B., Garland W.A., Min B.H., Wattenberg L.W., Anderson K.E., Kappas A., Conney A.H. Stimulatory effect of Brussels sprouts and cabbage on human drug metabolism. Clin Pharmacol Ther. 25:1979;88-95.
24. Pantuck E.J., Pantuck C.B., Anderson K.E., Wattenberg L.W., Conney A.H., Kapas A. Effect of Brussels sprouts and cabbage on drug conjugation. Clin Pharmacol Ther. 35:1984;161-169.
25. Bogaards J.J.P., Verhagen H., Willems M.I., van Poppel G., van Bladeren P.J. Consumption of Brussels sprouts results in elevated α-class glutathione S-transferase levels in human blood plasma. Carcinogenesis. 15:1994;1073-1075.
26. Verhagen H., Poulsen H.E., Loft S., van Poppel G., Willems M.I., van Bladeren P.J. Reduction of oxidative DNA-damage in humans by Brussels sprouts. Carcinogenesis. 16:1995;969-970.
27. Verhagen H and van Poppel G, Research on functional foods: Brussels sprouts for your health? Food Ingredients in Europe: Conference Proceedings 1996, pp. 65-68. Miller Freeman Plc., Maarssen, The Netherlands, 997.
28. 1 exo-epoxide Association with reduced levels of hepatic aflatoxin-DNA adducts in vivo . Drug Metab Dispos. 22:1994;392-399.
29. Larsens-Su S., Williams D.E. Dietary indole-3-carbinol inhibits the activity and expression of flavin-containing monooxygenase form 1 in rat liver and intestine. Drug Metab Dispos. 24:1996;927-931.
30. Staack R., Kingston S., Wallig M.A., Jeffery E.H. A comparison of the individual and collective effects of four glucosinolate breakdown products from Brussels sprouts on induction of detoxification enzymes. Toxicol Appl Pharmacol. 149:1998;17-23.
31. Stresser D.M., Williams D.E., Griffin D.A., Bailey G.S. Mechanisms of tumor modulation by indole-3-carbinol. Disposition and excretion in male Fischer 344 rats. Drug Metab Dispos. 23:1995;965-975.
32. Treacy E.P., Akerman B.R., Chow L.M.L., Youil R., Bibeau C., Lin J., Bruce A.G., Knight M., Danks D.M., Cashman J.R., Forrest S.M. Mutations of the flavin-containing monooxygenase gene (FMO3) cause trimethylaminuria, a defect in detoxication. Human Mol Genet. 7:1998;839-845.
33. Lomri N., Yang Z., Cashman J.R. Regio- and stereoselective oxygenations by adult human liver flavin-containing monooxygenase Comparison with forms 1 and 2 . Chem Res Toxicol. 6:1993;800-807.
34. Brunelle A., Bi Y.A., Lin J., Russell B., Lu Y.C., Berkman C.E., Cashman J.R. Characterization of two human flavin-containing monooxygenase (form 3) enzymes expressed in Escherichia coli as maltose binding fusions. Drug Metab Dispos. 25:1997;1001-1007.
35. Sokal RR and Rohlf FJ, Biometry, pp. 226-231. Freeman Publishing, San Francisco, CA, 1981.
36. Cochran WG and Cox GM, Experimental Designs, pp. 100-102. John Wiley, New York, NY, 1975.
37. Steinmetz K.A., Potter J.D. Vegetables, fruit, and cancer. I. Epidemiology. Cancer Causes Control. 2:1991;325-357.
38. Ames B.N., Gold L.S. The prevention of cancer. Drug Metab Rev. 30:1998;201-223.
39. Verhagen H., Rompelberg C.J.M., Strube M., van Poppel G., van Bladeren P.J. Cancer prevention by dietary constituents in toxicological perspective. J Environ Pathol Toxicol Oncol. 16:1997;343-360.
40. Wattenberg L.W. Chemoprevention of cancer. Cancer Res. 45:1985;1-8.
41. Cashman J.R. Structural and catalytic properties of the mammalian flavin-containing monooxygenase. Chem Res Toxicol. 8:1995;165-181.
42. Ziegler D.M. Flavin-containing monooxygenase catalytic mechanism and substrate specificities. Drug Metab Rev. 19:1988;1-32.
43. Akerman B.R., Chow L., Forrest S., Youil R., Cashman J.R., Treacy E.P. Mutations in the flavin-containing monooxygenase form 3 (FMO3) gene cause trimethylaminuria, fish odor syndrome. Am J Hum Genet. 61:(Suppl):1997;281.
44. 14C-labeled trimethylamine and its N-oxide in man. Xenobiotica. 17:1987;551-558.
45. Dolphin C.T., Janhmohmed C., Smith R.L., Shephard E.A., Phillips I.R. Missense mutation in flavin-containing monooxygenase 3 gene, FMO3, underlies fish-odour syndrome. Nat Genet. 17:1997;491-494.
46. Treacy E., Johnson D., Pitt J.J., Danks D.M. Trimethylaminuria, fish odor syndrome A new method of detection and response to treatment with metronidazole . J Inherit Metab Dis. 18:1995;306-312.
47. Larsen-Su S, Developmental and dietary regulation of flavin-containing monooxygenase. Ph.D. Thesis, Oregon State University, Corvallis, OR, 1998.
48. Leete E., Marion L. The hydrogenolysis of 3-hydroxymethyl indole and other indole derivatives with lithium aluminum hydride. Can J Chem. 31:1953;775-784.
49. Clement B., Weide M., Ziegler D.M. Inhibition of purified and membrane-bound flavin-containing monooxygenase 1 by (N,N-dimethylamino)stilbene carboxylates. Chem Res Toxicol. 9:1996;599-604.