The metabolisms of agaritine, a mushroom hydrazine in mice

Food and Chemical Toxicology

Volumn 46, Issue 3, 2008, Pages 854-862

  Kondo, Kazunari ^a   Watanabe, Asako ^a   Akiyama, Hiroshi ^a   Maitani, Tamio ^a  

^a NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

Author keywords

Agaritine; LC MS MS; Metabolism; Mushroom; Phenylhydrazine; Plasma; Urine

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; AGARITINE; HYDRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DEGRADATION; DNA DAMAGE; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; METABOLITE; NONHUMAN; OXIDATIVE STRESS; POISONOUS MUSHROOM; TOXICITY TESTING; URINALYSIS;

AGARICALES; ANIMALS; CHROMATOGRAPHY, LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICE; OXIDATIVE STRESS; PHENYLHYDRAZINES; TANDEM MASS SPECTROMETRY;

BASIDIOMYCOTA; MUS;

EID: 38649132322     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2007.10.022     Document Type: Article

References (26)

1. Chauhan Y., Nagel D., Gross M., Cerny R., and Toth B. Isolation of N2-[gamma-l-(+)-glutamyl]-4-carboxyphenylhydrazine in the cultivated mushroom Agaricus bisporus. J. Agric. Food Chem. 33 (1985) 817-820
2. Ferrali M., Signorini C., Sugherini L., Pompella A., Lodovici M., Caciotti B., Ciccoli L., and Comporti M. Release of free, redox-active iron in the liver and DNA oxidative damage following phenylhydrazine intoxication. Biochem. Pharmacol. 53 (1997) 1743-1751
3. Gannett P.M., Shi X., Lawson T., Kolar C., and Toth B. Aryl radical formation during the metabolism of arylhydrazines by microsomes. Chem. Res. Toxicol. 10 (1997) 1372-1377
4. Gigliotti H.J., and Levenberg B. Isolation and structure of agaritine, a gamma-glutamyl-substituted arylhydrazine derivative from Agaricaceae. J. Biol. Chem. 239 (1964) 2267-2273
5. Hashida C., Hayashi K., Jie L., Haga S., Sakurai M., and Shimizu H. Quantities of agaritine in mushrooms (Agaricus bisporus) and the carcinogenicity of mushroom methanol extracts on the mouse bladder epithelium. Nippon. Koshu. Eisei. Zasshi. 37 (1990) 400-405
6. Hiramoto K., Kaku M., Sueyoshi A., Fujise M., and Kikugawa K. DNA base and deoxyribose modification by the carbon-centered radicals generated from 4-(hydroxymethyl)benzenediazonium salt, a carcinogen in mushroom. Chem. Res. Toxicol. 8 (1995) 356-362
7. Hiramoto K., Kaku M., Kato T., and Kikugawa K. DNA strand breaking by the carbon-centered radicals generated from 4-(hydroxymethyl)benzenediazonium salt, a carcinogen in mushroom Agaricus bisporus. Chemico-Biol. Interact. 94 (1995) 21-36
8. Hoesch L., and Datta S. Novel synthesis of agaritine, a 4-hydrazinobenzyl-alcohol derivatives occurring in Agaricaceae. Helv. Chim. Acta. 70 (1987) 1261-1267
9. Kelly R.B., Daniels E.G., and Hinman J.W. Agaritine: isolation, degradation, and synthesis. J. Chem. Soc. 27 (1962) 3229-3231
10. Kondo K., Watanabe A., Iwanaga Y., Abe I., Tanaka H., Nagaoka M.H., Akiyama H., and Maitani T. Analysis of agaritine in mushrooms and in agaritine-administered mice using liquid chromatography-tandem mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 834 (2006) 55-61
11. Kondo K., Watanabe A., Iwanaga Y., Abe I., Tanaka H., Nagaoka M.H., Akiyama H., and Maitani T. Determination of genotoxic phenylhydrazine agaritine in mushrooms using liquid chromatography-electrospray ionization tandem mass spectrometry. Food Addit. Contam. 23 (2006) 1179-1186
12. Lawson T., Gannett P.M., Yau W.-M., Dalal N.S., and Toth B. Different patterns of mutagenicity of arenediazonium ions in V79 cells and Salmonella typhimurium TA102: evidence for different mechanisms of action. J. Agric. Food Chem. 43 (1995) 2627-2635
13. Ross A.E., Nagel D.L., and Toth B. Evidence for the occurrence and formation of diazonium ions in the Agaricus bisporus mushroom and its extracts. J. Agric. Food. Chem. 30 (1982) 521-525
14. Ross A.E., Nagel D.L., and Toth B. Occurrence, stability and decomposition of beta-N [gamma-l(+)-glutamyl]-4-hydroxymethylphenylhydrazine (agaritine) from the mushroom Agaricus bisporus. Food Chem. Toxicol. 20 (1982) 903-907
15. Singh R., and Farmer P.B. Liquid chromatography-electrospray ionization-mass spectrometry: the future of DNA adduct detection. Carcinogenesis 27 (2006) 178-196
16. Toth B., and Erickson J. Cancer induction in mice by feeding of the uncooked cultivated mushroom of commerce Agaricus bisporus. Cancer Res. 46 (1986) 4007-4011
17. Toth B., and Nagel D. Studies of the tumorigenic potential of 4-substituted phenylhydrazines by the subcutaneous route. J. Toxicol. Environ. Health 8 (1981) 1-9
18. Toth B., Nagel D., Patil K., Erickson J., and Antonson K. Tumor induction with the N′-acetyl derivative of 4-hydroxymethyl-phenylhydrazine, a metabolite of agaritine of Agaricus bisporus. Cancer Res. 38 (1978) 177-180
19. Toth B., Patil K., and Jae H.S. Carcinogenesis of 4-(hydroxymethyl)benzenediazonium ion (tetrafluoroborate) of Agaricus bisporus. Cancer Res. 41 (1981) 2444-2449
20. Toth B., Erickson J., Gannett P.M., and Patil K. Carcinogenesis by the cultivated baked Agaricus bisporus mushroom in mice. Oncol. Rep. 4 (1997) 913-936
21. Toth B., Gannett P., Visek W.J., and Patil K. Carcinogenesis studies with the lyophilized mushroom Agaricus bisporus in mice. In Vivo 12 (1998) 239-244
22. von Wright A., Knnutinen J., Lindroth S., Pellinen M., Winden K.-G., and Seppa E.L. The mutagenicity of some edible mushrooms in the Ames test. Food Chem. Toxicol. 20 (1982) 265-267
23. Wallcave R., Nagel D.L., Raha C.R., Hwan-Soo J., Bronczyk S., Kupper R., and Toth B. An improved synthesis of agaritine. J. Org. Chem. 44 (1979) 3752-3755
24. Walton K., Coombs M.M., Walker R., and Ioannides C. Bioactivation of mushroom hydrazines to mutagenic products by mammalian and fungal enzymes. Mutat. Res. 381 (1997) 131-139
25. Walton K., Coombs M.M., Catterall F.S., Walker R., and Ioannides C. Bioactivation of the mushroom hydrazine, agaritine, to intermediates that bind covalently to proteins and induce mutations in the Ames test. Carcinogenesis 18 (1997) 1603-1608
26. Walton K., Coombs M.M., King L.J., Walker R., and Ioannides C. Fate of the mushroom hydrazine agaritine in the rat and mouse. Nutr. Cancer 37 (2000) 55-64