Mutagenic and Antimutagenic Property of 3-Hydroxymethylene-2-thioxopyrrolidine, a Major Product Generating from Pungent Principle of Radish

LWT

Volumn 33, Issue 1, 2000, Pages 37-43

  Uda, Yasushi ^a   Hayashi, Hiromi ^a   Takahashi, Asaka ^b   Shimizu, Atsushi ^a  

^a UTSUNOMIYA UNIVERSITY   (Japan)

^b Nagano Prefectural Junior College   (Japan)

Author keywords

Thioxopyrrolidine; antimutagenicity; 4 methylthio 3 butenyl isothiocyanate; radish root

Indexed keywords

EID: 0347999396     PISSN: 00236438     EISSN: None     Source Type: Journal    
DOI: 10.1006/fstl.1999.0614     Document Type: Article

References (33)

1. CARAGAY A. B. Cancer-preventive foods and ingredients. Food Technology. Apr. 1992;65-68.
2. Food, Nutrition and the Prevention of Cancer: a Global Perspective. 1997;World Cancer Research Fund and American Institute of Cancer Research, Washington.
3. SINGH A., SHUKLA Y. Antitumour activity of diallyl sulfide in two-stage mouse skin model of carcinogenesis. Biomedical and Environmental Sciences. 11:1998;258-263.
4. ZHANG Y., TALALAY P. Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanisms. Cancer Research. 54:1994;1976s-1981s.
5. HECHT S. S. Chemoprevention by isothiocyanates. Journal of Cellular Biochemistry. 22:1995;195-209.
6. 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. Chemico-Biological Interactions. 103:1997;79-129.
7. WATTENBERG L. W. Inhibitory effects of benzyl isothiocyanate administered shortly before diethylnitrosamine or benzo(a)pyrene on pulmonary and forestomach neoplasia in A/J mice. Carcinogenesis. 8:1987;1971-1973.
8. 6-methylguanine formation and metabolism of the tobaco-specific nitrosamine 4-(methylnitosamino)-1-(3-pyridyl)- 1-butanone in A/J mouse lung. Cancer Research. 49:1989;2894-2897.
9. TALALAY P. Mechanisms of induction of enzymes that protect against chemical carcinogenesis. Advances in Enzyme Regulation. 28:1989;237-250.
10. BOGGAARDS J. J. P., VAN OMMEN B., FALKE H. E., WILLEMS M. I., VAN BLADEREN P. J. Glutathione S-transferase subunit induction patterns of Brussels sprouts, allyl isothiocyanate and goitrin in rat liver and small intestinal mucosa: a new approach for the identification of inducing xenobiotics. Food and Chemical Toxicology. 28:1990;81-88.
11. ZHANG Y., TALALAY P., CHO C.-G., POSNER G. H. A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proceedings of the National Academy of Sciences of the USA. 89:1992;2399-2403.
12. GUO Z., SMITH T. J., WANG E., SADRIEH N., MA Q., THOMAS P., YANG C. S. Effects of phenethyl isothiocyanate, a carcinogenesis inhibitor, on xenobiotic-metabolizing enzymes and nitorosoamine metabolism in rats. Carcinogenesis. 13:1992;2205-2210.
13. BARCELO S., GARDINER J. M., GESCHER A., CHIPMAN J. K. CYP2E1-mediated mechanism of anti-genotoxicity of the broccoli constituent sulforaphane. Carcinogenesis. 17:1996;277-282.
14. HAMILTON S. M., TEEL R. W. Effects of isothiocyanates on cytochrome P-450 1A1 and 1A2 activity and on the mutagenicity of heterocyclic amines. Anticancer Research. 16:1996;3597-3602.
15. FRIIS P., KJAER A. 4-Methylthio-3-butenyl isothiocyanate, the Pungent principle of radish root. Acta Chemica Scandinavica. 20:1966;698-705.
16. KJAER A., MADSEN J. Ø., MAEDA Y., OZAWA Y., UDA Y. Volatiles in distillates of processed radish of Japanese origin. Agricultural and Biological Chemistry. 42:1978;1989-1996.
17. UDA Y., OZAWA Y., OHSHIMA T., KAWAKISHI S. Identification of enolated 2-thioxo-3-pyrrolidinecarbaldehyde, a new degradation product of 4-methylthio-3-butenyl isothiocyanate. Agricultural and Biological Chemistry. 54:1990;613-617.
18. KOSEMURA S., YAMAMURA S., HASEGAWA K. Chemical studies on 4-methylthio-3-butenyl isothiocyanate from roots of Japanese radish (Raphanus sativus L.) in connection with raphanusanins, phototropism-regulating substances of radish hypocotyls. Tetrahedron Letters. 34:1993;481-484.
19. MATSUOKA H., TODA Y., YONEYAMA K., UDA Y. Formation of Raphanusanins depends on extraction procedure and solvent. Phytochemistry. 47:1998;975-977.
20. MATSUOKA H., TODA Y., YANAGI K., TAKAHASHI A., YONEYAMA K., UDA Y. Formation of thioxopyrrolidines and dithiocarbamates from 4-methylthio-3-butenyl isothiocyanates, the pungent principle of radish, in aqueous media. Bioscience, Biotechnology and Biochemistry. 61:1997a;2109-2112.
21. UDA Y., MATSUOKA H., SHIMA H., KUMAGAMI H., MAEDA Y. Antimicrobial activity of water-soluble products derived from radish mustard oil and identification of an active component therein. Nippon Shokuhin Kogyo Gakkaishi (Journal of the Japanese Society for Food Science and Technology). 40:1993;801-806.
22. MATSUOKA, H. TAKAHASHI, A. YANAGI, K. UDA, Y. Antimicrobial action of 2-thioxo-3-pyrrolidinecarbaldehyde, a major Thiolactam compound generated from the pungent principle of radish in an aqueous medium, Food Science and Technology International, Tokyo, 3, 353, 356, 1997.
23. OZAWA Y., KAWAKISHI S., UDA Y., MAEDA Y. Isolation and identification of a novel β -carboline derivative in salted radish roots, Raphanus sativus L. Agricultural and Biological Chemistry. 54:1990;1241-1245.
24. TAKAHASHI A., MATSUOKA H., OZAWA Y., UDA Y. Antimutagenic properties of 3,5-disubstituted 2-thiohydantoins. Journal of Agricultural and Food Chemistry. 46:1998;5037-5042.
25. NOHMI T., MATSUI M., ISHIDATE M. JR. Method for the induced-mutation frequency test using bacterial tester strains. Toxicology Forum. 9:1986;189-198.
26. HATCH F. T., FELTON J. S., STUERMER D. H., BJELDANES L. F. Identification of mutagens from the cooking of food. DE SERRES F. J. Chemical Mutagens: Principles and Methods of their Detection. 1984;111-164 Plenum Press, New York.
27. JÄGERSTAD M., LASER-REUTERSWÄRD A., ÖSTE R., DAHLQVIST A., GRIVAS S., OLSSON K., NYHAMMAR T. Creatinine and Maillard reaction products as precursors of mutagenic compounds formed in fried beef. WALLER G. R., FEATHER M. S. The Maillard Reaction in Foods and Nutrition: ACS Symposium Series 215. 1983;507-519 American Chemical Society, Washington.
28. SPINGARN N. E., KASAI H., VUOLO L. L., NISHIMURA S., YAMAIZUMI Z., SUGIMURA T., MATSUSHIMA T., WEISBURGER J. H. Formation of mutagens in cooked foods. III. Isolation of a potent mutagen from beef. Cancer Letters. 9:1980;177-183.
29. ISHII K., YAMAZOE Y., KAMATAKI T., KATO R. Metabolic activation of mutagenic tryptophan pyrolysis products by rat liver microsomes. Cancer Research. 40:1980;2596-2600.
30. YAMAZOE U., SHIMADA M., KAMATAKI T., KATO R. Microsomal activation of 2-amino-3-methylimidazo(4,5-f) quinoline, a pyrolysate of sardine and beef extracts, to a mutagenic intermediate. Cancer Research. 43:1983;5768-5744.
31. SOUCEK P., GUT I. Cytochromes P-450 in rats: structures, functions, properties and relevant human forms. Xenobiotica. 22:1992;83-103.
32. KADA T., SHIMOI K. Desmutagens and bio-antimutagens: their modes of action. Bioassays. 7:1987;113-116.
33. WATTENBERG L. W. Inhibition of carcinogenesis by nonnutrient constituents of the diet. WALDRON K. W., JOHNSON I. T., FENWICK G. R. Food and Cancer Prevention: Chemical and Biological Aspects. 1993;12-23 Royal Society of Chemistry, Cambridge.