Critical role of allyl groups and disulfide chain in induction of Pi class glutathione transferase in mouse tissues in vivo by diallyl disulfide, a naturally occuring chemopreventive agent in garlic

Carcinogenesis

Volumn 23, Issue 10, 2002, Pages 1661-1665

  Bose, Chhanda ^a   Guo, Jianxia ^b   Zimniak, Ludwika ^a   Srivastava, Sanjay K ^b   Singh, Sharda P ^a   Zimniak, Piotr ^a,c   Singh, Shivendra V ^b  

^a UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

^b UNIVERSITY OF PITTSBURGH CANCER INSTITUTE   (United States)

^c CENTRAL ARKANSAS VETERANS HEALTHCARE SYSTEM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLYL COMPOUND; ALLYL SULFIDE; BENZO[A]PYRENE; DISULFIDE; GLUTATHIONE TRANSFERASE; MESSENGER RNA; SULFIDE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER PREVENTION; CONTROLLED STUDY; ENZYME INDUCTION; FEMALE; FORESTOMACH; GARLIC; GENE EXPRESSION; GENE INDUCTION; IN VIVO STUDY; LIVER; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; STATISTICAL SIGNIFICANCE; STOMACH CARCINOGENESIS; STRUCTURE ACTIVITY RELATION;

ALLYL COMPOUNDS; ANIMALS; ANTICARCINOGENIC AGENTS; CARCINOGENS; DISULFIDES; FEMALE; GARLIC; GLUTATHIONE S-TRANSFERASE PI; GLUTATHIONE TRANSFERASE; ISOENZYMES; KINETICS; LIVER; MICE; MICE, INBRED A; PHYTOTHERAPY; RNA, MESSENGER; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTION, GENETIC;

EID: 0036801713     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (42)

1. Block,E. (1985) The chemistry of garlic and onions. Sci. Am., 252, 114-119.
2. Agarwal,K.C. (1996) Therapeutic actions of garlic constituents. Med. Res. Rev., 16, 111-124.
3. Lawson,L. D. (1998) Garlic: a review of its medicinal effects and indicated active compounds. In Lawson,L.D. and Bauer,R. (eds) Phytomedicines of Europe, Chemistry and Biological Activity. ACS Symposium Series 691, American Chemical Society, Washington, DC, pp. 176-209.
4. Dorant,E., van den Brandt,P.A., Goldbohm,R.A., Hermus,R.J.J. and Sturmans,F. (1993) Garlic and its significance for the prevention of cancer in humans: a critical review. Br. J. Cancer, 67, 424-429.
5. Wargovich,M.J., Uda,N., Woods,C., Velasco,M. and McKee,K. (1996) Allium vegetables: their role in prevention of cancer. Biochem. Soc. Trans., 24, 811-814.
6. You,W.C., Blot,W.J., Chang,Y.S., Ershow,A., Yang,Z.T., An,Q., Henderson,B.E., Fraumeni,J.F. Jr and Wang,T.G. (1989) Allium vegetables and reduced risk of stomach cancer. J. Natl Cancer Inst., 81, 162-164.
7. Buiatti,E., Palli,D., Decarli,A. et al. (1989) A case-control study of gastric cancer and diet in Italy. Int. J. Cancer, 44, 611-616.
8. Dausch,J.G. and Nixon,D.W. (1990) Garlic: a review of its relationship to malignant disease. Prev. Med., 19, 346-361.
9. Milner,J.A. (2001) A historical perspective on garlic and cancer. J. Nutr., 131, 1027S-1031S.
10. Sundaram,S.G. and Milner,J.A. (1996) Diallyl disulfide inhibits the proliferation of human tumor cells in culture. Biochim. Biophys. Acta, 1315, 15-20.
11. Pinto,J.T., Qiao,C., Xing,J., Rivlin,R.S., Protomastro,M.L., Weissler,M.L., Tao,Y., Thaler,H. and Heston,W.D. (1997) Effects of garlic thioallyl derivatives on growth, glutathione concentration and polyamine formation of human prostate carcinoma cells in culture. Am. J. Clin. Nutr., 66, 398-405.
12. Iciek,M.B., Rokita,H.B. and Wlodek,L.B. (2001) Effects of diallyl disulfide and other donors of sulfane sulfur on the proliferation of human hepatoma cell line (HepG2). Neoplasma, 48, 307-312.
13. Nakagawa,H., Tsuta,K., Kiuchi,K., Senzaki,H., Tanaka,K., Hioki,K. and Tsubura,A. (2001) Growth inhibitory effects of diallyl disulfide on human breast cancer cell lines. Carcinogenesis, 22, 891-897.
14. Sundaram,S.G. and Milner,J.A. (1996) Diallyl disulfide induces apoptosis of human colon tumor cells. Carcinogenesis, 17, 669-673.
15. 2/M phase arrest induced by diallyl disulfide in HCT-15 cells. Nutr Cancer, 30, 169-174.
16. cdc2 kinase activity through changes in complex formation and phosphorylation. Carcinogenesis, 21, 1129-1134.
17. Robert,V., Mouille,B., Mayeur,C., Michaud,M. and Blachier,F. (2001) Effects of the garlic compound diallyl disulfide on the metabolism, adherence and cell cycle of HT-29 colon carcinoma cells: evidence of sensitive and resistant sub-populations. Carcinogenesis, 22, 1155-1161.
18. H-ras processing. Biochem. Biophys. Res. Commun., 225, 660-665.
19. Sundaram,S.G. and Milner,J.A. (1996) Diallyl disulfide suppresses the growth of human colon tumor cell xenografts in athymic nude mice. J. Nutr., 126, 1355-1361.
20. Wattenberg,L.W., Sparnins,V.L. and Barany,G. (1989) Inhibition of N-nitrosodiethylamine carcinogenesis in mice by naturally occurring organosulfur compounds and monoterpenes. Cancer Res., 49, 2689-2692.
21. Takàhashi,S., Hakoi,K., Yada,H., Hirose,M., Ito,N. and Fukushima,S. (1992) Enhancing effects of diallyl sulfide on hepatocarcinogenesis and inhibitory actions of the related diallyl disulfide on colon and renal carcinogenesis in rats. Carcinogenesis, 13, 1513-1518.
22. Dwivedi,C., Rohlfs,S., Jarvis,D. and Engineer,F.N. (1992) Chemoprevention of chemically induced skin tumor development by diallyl sulfide and diallyl disulfide. Pharmaceut. Res., 9, 1668-1670.
23. Reddy,B.S., Rao,C.V., Rivenson,A. and Kelloff,G. (1993) Chemoprevention of colon carcinogenesis by organosulfur compounds. Cancer Res., 53, 3493-3498.
24. Schaffer,E.M., Liu,J.-Z, Green,J., Dangler,C.A. and Milner,J.A. (1996) Garlic and associated allyl sulfur components inhibit N-methyl-N-nitrosourea induced rat mammary carcinogenesis. Cancer Lett., 102, 199-204.
25. Suzui,N., Sugie,S., Rahman,K.M., Ohnishi,M., Yoshimi,N., Wakabayashi,K. and Mori,H. (1997) Inhibitory effects of diallyl disulfide or aspirin on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced mammary carcinogenesis in rats. Jpn. J. Cancer Res., 88, 705-711.
26. Hu X, Benson,P.J., Srivastava,S.K., Xia,H., Bleicher,R.J., Zaren,H.A., Awasthi,S., Awasthi,Y.C. and Singh,S.V. (1997) Induction of glutathione S-transferase π as a bioassay for the evaluation of potency of inhibitors of benzo(a)pyrene-induced cancer in a murine model. Int. J. Cancer, 73, 897-902.
27. Hu,X., Benson,P.J., Srivastava,S.K., Mack,L.M., Xia,H., Gupta,V., Zaren,H.A. and Singh,S.V. (1996) Glutathione S-transferases of female A/J mouse liver and forestomach and their differential induction by anti-carcinogenic organosulfides from garlic. Arch. Biochem. Biophys., 336, 199-214.
28. Singh,S.V., Mack,L.M., Xia,H., Srivastava, S.K., Hu,X., Benson,P.J., Murthy,M., McFadden,E., Gupta,V. and Zaren,H.A. (1997) Differential induction of glutathione redox-cycle enzymes by anti-carcinogenic organosulfides from garlic. Clin. Chem. Enzymol. Commun., 7, 287-297.
29. Srivastava,S.K., Hu,X, Zaren,H.A., Chatterjee,M.L., Agarwal,R. and Singh,S.V. (1997) Mechanism of differential efficacy of garlic organosulfides in preventing benzo(a)pyrene-induced cancer in mice. Cancer Lett., 118, 61-67.
30. Chomczynski,P. and Mackey,K. (1995) Modification of the TRI reagent procedure for isolation of RNA from polysaccharide- and proteoglycan-rich sources. Biotechniques, 19, 942-945.
31. Xu,X. and Stambrook,P.J. (1994) Two murine GSTpi genes are arranged in tandem and are differentially expressed. J. Biol. Chem., 269, 30268-30273.
32. Sparnins,V.L., Barany,G. and Wattenberg,L.W. (1988) Effects of organosulfur compounds from garlic and onions on benzo[a]pyrene-induced neoplasia and glutathione S-transferase activity in the mouse. Carcinogenesis, 9, 131-134.
33. Buening,M.K., Wislocki,P.G., Levin,W., Yagi,H., Thakker,D.R., Akagi,H., Koreeda,M., Jerina,D.M. and Conney,A.H. (1978) Tumorigenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene-7,8-diol-9,10-epoxides in newborn mice: exceptional activity of (+)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobe nzo[a]pyrene. Proc. Natl Acad. Sci. USA, 75, 5358-5361.
34. Slaga,TT, Bracken,W.J., Gleason,G., Levin,W., Yagi,H., Jerina,D.M. and Conney,A.H. (1979) Marked differences in the skin tumor-initiating activities of the optical enantiomers of the diastereomeric benzo(a)pyrene 7,8-diol-9,10-epoxides. Cancer Res., 39, 67-71.
35. Gelboin,H.V. (1980) Benzo(a)pyrene metabolism, activation and carcinogenesis: role and regulation of mixed-function oxidases and related enzymes. Physiol. Rev., 60, 1107-1166.
36. Thakker,D.R., Yagi,H., Levin,W., Wood,A.W., Conney,A.H. and Jerina,D.M. (1985) Polycyclic aromatic hydrocarbons: metabolic activation to ultimate carcinogens. In Anders,M.W. (ed.) Bioactivation of Foreign Compounds. Academic Press, New York, NY, pp. 177-242.
37. Robertson,I.G.C., Jensson,H., Mannervik,B. and Jernstrom,B. (1986) Glutathione transferases in rat lung: the presence of transferase 7-7, highly efficient in the conjugation of glutathione with the carcinogenic (+)-7β,8α-dihydroxy-9α,10α-oxy-7,8,9,10-tetrahydrobenz o(a)pyrene. Carcinogenesis, 7, 295-299.
38. Jernstrom,B., Funk,M., Frank,H., Mannervik,B. and Seidel,A. (1996) Glutathione S-transferase A1-1-catalysed conjugation of bay and fjord region diol epoxides of polycyclic aromatic hydrocarbons with glutathione. Carcinogenesis, 17, 1491-1498.
39. Sundberg,K., Widersten,M., Seidel,A., Mannervik,B. and Jernstrom,B. (1997) Glutathione conjugation of bay- and fjord-region diol epoxides of polycyclic aromatic hydrocarbons by glutathione transferases M1-1 and P1-1. Chem. Res. Toxicol., 10, 1221-1227.
40. Fields,W.R., Morrow,C.S., Doss,A.J., Sundberg,K., Jernstrom,B. and Townsend,A.J. (1998) Overexpression of stably transfected human glutathione-S-transferase P1-1 protects against DNA damage by benzo[a]pyrene diol-epoxide in human T47D cells. Mol. Pharmacol., 54, 298-304.
41. Hu,X., Herzog,C., Zimniak,P. and Singh,S.V. (1999) Differential protection against benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide-induced DNA damage in HepG2 cells stably transfected with allelic variants of π class human glutathione S-transferase. Cancer Res., 59, 2358-2362.
42. Henderson,C.J., Smith,A.G., Ure,J., Brown,K., Bacon,E.J. and Wolf,C.R. (1998) Increased skin tumorigenesis in mice lacking pi class glutathione S-transferases. Proc. Natl Acad. Sci. USA, 95, 5275-5280.