Induction of detoxication enzymes in mice by naturally occurring allyl nitrile

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 23, 2005, Pages 8993-8996

  Tanii, Hideji ^a   Higashi, Tomomi ^a   Nishimura, Fusae ^a   Higuchi, Yoshihiro ^a   Saijoh, Kiyofumi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Allyl nitrile; Glutathione; Glutathione S transferase; Mice; Quinone reductase

Indexed keywords

ALLYL CYANIDE; GLUTATHIONE TRANSFERASE; NITRILE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE);

ANIMAL; ARTICLE; BIOSYNTHESIS; BRASSICACEAE; CHEMISTRY; DRUG EFFECT; ENZYME INDUCTION; ENZYMOLOGY; LUNG; MALE; MOUSE; STOMACH;

ANIMALS; BRASSICACEAE; ENZYME INDUCTION; GLUTATHIONE TRANSFERASE; LUNG; MALE; MICE; NAD(P)H DEHYDROGENASE (QUINONE); NITRILES; STOMACH;

EID: 28444471665     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0516282     Document Type: Article

References (37)

1. Graham, S.; Dayal, H.; Swanson, M.; Mittelman, A.; Wilkinson, G. Diet in the epidemiology of cancer of the colon and rectum. J. Natl. Cancer Inst. 1978, 61, 709-714.
2. Haenszel, W.; Locke, F. B.; Segi, M. A case-control study of large bowel cancer in Japan. J. Natl. Cancer Inst. 1980, 64, 17-22.
3. Verhoeven, D. T.; 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. 1996, 9, 733-748.
4. Fahey, J. W.; Zelcmann, A. T.; Talalay, P. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 2001, 56, 5-51.
5. Fenwick, G. R.; Heaney, R. K.; Mullin, W. J. Glucosinolates and their breakdown products in food and food plants. CRC Crit. Rev. Food Sci. Nutr. 1983, 18, 123-201.
6. Lampe, J. W.; Peterson, S. Brassica, biotransformation and cancer risk: genetic polymorphism alter the preventive effects of cruciferous vegetables. J. Nutr. 2002, 132, 2991-2994.
7. Ettlinger, M. G.; Dateo, G. P.; Harrison, B. R., Jr.; Mabry, T. J.; Thompson, C. P. Vitamin C as a coenzyme: the hydrolysis of mustard oil glucosides. Proc. Natl. Acad. Sci. U.S.A. 1961, 47, 1875-1880.
8. Guo, Z.; Smith, T. J.; Wang, E.; Sadrieh, N.; Ma, Q.; Thomas, P. E.; Yang, C. S. Effects of phenethylisothiocyanate, a carcinogenesis inhibitor, on xenobiotic-metabolizing enzymes and nitrosamine metabolism in rats. Carcinogenesis 1992, 13, 2205-2210.
9. Zhang, Y.; Talalay, P.; Cho, C.-G.; Posner, G. H. A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2399-2403.
10. Kensler, T. W. Chemoprotection by inducers of carcinogen detoxication enzymes. Environ. Health Perspect. 1997, 105 (Suppl. 4), 965-970.
11. Begleiter, A.; Leith, M. K.; Curphey, T. J.; Doherty, G. P. Induction of DT-diaphorase in cancer chemoprevention and chemotherapy. Oncol. Res. 1997, 9, 371-382.
12. Talalay, P. Chemoprotection against cancer by induction of phase 2 enzymes. BioFactors 2000, 12, 5-11.
13. Wallig, M. A.; Kore, A. M.; Crawshaw, J.; Jeffery, E. H. Separation of the toxic and glutathione-enhancing effects of the naturally occurring nitrile, cyanohydroxybutene. Fundam. Appl. Toxicol. 1992, 19, 598-606.
14. Nho, C. W.; Jeffery, E. The synergistic upreguration of phase II detoxication enzymes by glucosinolate breakdown products in cruciferous vegetables. Toxicol. Appl. Pharmacol. 2001, 174, 146-152.
15. Matusheski, N. V.; Jeffery, E. H. Comparison of the bioactivity of two glucoraphanin hydrolysis products found in broccoli, sulforaphane and sulforaphane nitrile. J. Agric. Food Chem. 2001, 49, 5743-5749.
16. West, L. G.; Badenhop, A. F.; McLaughlin, J. L. Allylisothiocyanate and allyl cyanide production in cell-free cabbage leaf extracts, shredded cabbage, and cole slaw. J. Agric. Food Chem. 1977, 25, 1234-1238.
17. Tolonen, M.; Taipale, M.; Viander, B.; Pihlava, J. M.; Korhonen, H.; Ryhanen, E. L. Plant-derived biomolecules in fermented cabbage. J. Agric. Food Chem. 2002, 50, 6798-6803.
18. Tanii, H.; Takayasu, T.; Higashi, T.; Leng, S.; Saijoh, K. Allylnitrile: generation from cruciferous vegetables and behavioral effects on mice of repeated exposure. Food Chem. Toxicol. 2004, 42, 453-458.
19. Shapiro, T. A.; Fahey, J. W.; Wade, K. L.; Stephenson, K. K.; Talalay, P. Human metabolism and excretion of cancer chemopreventive glucosinolates and isothiocyanates of cruciferous vegetables. Cancer Epidemiol. Biomarkers Prev. 1998, 12, 1091-1100.
20. Elfoul, L.; Rabot, S.; Khelifa, N.; Quinsac, A.; Duguay, A; Rimbault, A. Formation of allyl isothiocyanate from sinigrin in the digestive tract of rats monoassociated with a human colonic strain of Bacteroides thetaiotaomicron. FEMS Microbiol. Lett. 2001, 197, 99-103.
21. Krul, C.; Humblot, C.; Philippe, C.; Vermeulen, M.; van Nuenen, M.; Havenaar, R.; Rabot, S. Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model. Carcinogenesis 2002, 23, 1009-1016.
22. Cheng, D.-L.; Hashimoto, K.; Uda, Y. In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products. Food Chem. Toxicol. 2004, 42, 351-357.
23. Tanii, H.; Kurosaka, Y.; Hayashi, M.; Hashimoto, K. Allylnitrile: a compound which induces long-term dyskinesia in mice following a single administration. Exp. Neurol. 1989, 103, 64-67.
24. Tanii, H.; Hayashi, M.; Hashimoto, K. Nitrile-induced behavioral abnormalities in mice. Neurotoxicology 1989, 10, 157-166.
25. Tanii, H.; Hayashi, M.; Hashimoto, K. Behavioral syndrome induced by allylnitrile, crotononitrile or 2-pentenenitrile in rats. Neuropharmacology 1991, 30, 887-892.
26. 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. 1997, 103, 79-129.
27. Wallig, M. A.; Jeffery, E. H. Enhancement of pancreas and hepatic glutathione levels in rats during cyanohydroxybutene intoxication. Fundam. Appl. Toxicol. 1990, 14, 144-159.
28. 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. 1998, 149, 17-23.
29. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein dye binding. Anal. Biochem. 1976, 72, 248-254.
30. Habig, W. H.; Pabst, M. J.; Jakoby, W. B. Glutathione S-transferases. J. Biol. Chem. 1974, 249, 7130-7139.
31. Ernster, L. DT diaphorase. Methods Enzymol. 1967, 10, 309-317.
32. Jaeger, R. J.; Conolly, R. B.; Murphy, S. D. Effect of 18 HR fast and glutathione depletion on 1,1-dichloroethylene-induced hepatotoxicity and lethality in rats. Exp. Mol. Pathol. 1974, 20, 187-198.
33. Munday, R.; Munday, C. M. Selective induction of phase II enzymes in the urinary bladder of rats by allyl isothiocyanate, a compound derived from Brassica vegetables. Nutr. Cancer 2002, 44, 52-59.
34. Munday, R.; Munday, C. M. Induction of phase II detoxification enzymes in rats by plant-derived isothiocyanates: comparison of allyl isothiocyanate with sulforaphane and related compounds. J. Agric. Food Chem. 2004, 52, 1867-1871.
35. Nakamura, Y.; Iwahashi, T.; Tanaka, A.; Koutani, J.; Matsuo, T.; Okamoto, S.; Sato, K.; Otsuki, K. 4-(Methylthio)-3-butenyl isothiocyanate, a principal antimutagen in daikon (Raphanus sativus; Japanese white radish). J. Agric. Food Chem. 2001, 49, 5755-5760.
36. Silver, E. H.; Kuttab, S. H.; Hasan, T.; Hassan, M. Structural considerations in the metabolism of nitriles to cyanide in vivo. Drug Metab. Dispos. 1982, 10, 495-498.
37. Talalay, P.; De Long, M. J.; Prochaska, H. J. Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8261-8265.