A glutathione S-transferase inducer from papaya: Rapid screening, identification and structure-activity relationship of isothiocyanates

Cancer Letters

Volumn 157, Issue 2, 2000, Pages 193-200

  Nakamura, Yoshimasa ^a   Morimitsu, Yasujiro ^b   Uzu, Tomoko ^a   Ohigashi, Hajime ^a   Murakami, Akira ^c   Naito, Yuko ^b   Nakagawa, Yoko ^b   Osawa, Toshihiko ^b   Uchida, Koji ^b  

^a KYOTO UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

^c Fac Biol Oriented Sci T   (Japan)

Author keywords

Fruit; Glutathione S transferase; Isothiocyanate; Papaya; Rat normal liver epithelial cell line

Indexed keywords

BENZYL ISOTHIOCYANATE; GLUTATHIONE TRANSFERASE; ISOENZYME; ISOTHIOCYANIC ACID DERIVATIVE; PHENETHYL ISOTHIOCYANATE;

ANIMAL CELL; ANIMAL MODEL; ARTICLE; CANCER CELL CULTURE; CANCER RISK; CHEMICAL CARCINOGENESIS; CONTROLLED STUDY; CYTOSOL; DETOXIFICATION; ENZYME ACTIVITY; FRUIT; LIVER CELL CARCINOMA; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN EXPRESSION; PROTEIN INDUCTION, SYNTHESIS AND MODIFICATION; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; BLOTTING, WESTERN; CELLS, CULTURED; ENZYME INDUCTION; EPITHELIAL CELLS; FLUORESCENCE; FRUIT; GLUTATHIONE TRANSFERASE; ISOTHIOCYANATES; LAURACEAE; LIVER; RATS; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA; CARICA PAPAYA; PERSEA AMERICANA;

EID: 0034285150     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0304-3835(00)00487-0     Document Type: Article

References (35)

1. Henderson C.J., Smith A.G., Ure J., Brown K., Bacon E.J., Wolf C.R. Increased skin tumorigenesis in mice lacking pi class glutathione S-transferases. Proc. Natl. Acad. Sci. USA. 95:1998;5275-5280.
2. Nakae D., Denda A., Kobayashi Y., Akai H., Kishida H., Tsujiuchi T., Konishi Y., Suzuki T., Muramatsu M. Inhibition of early-phase exogenous and endogenous liver carcinogenesis in transgenic rats harboring a rat glutathione S-transferase placental form gene. Jpn. J. Cancer Res. 89:1998;1118-1125.
3. Robertson I.G.C., Guthenberg C., Mannervik B., Jernström B. Differences in stereoselectivity and catalytic efficiency of three human glutathione transferases in the conjugation of glutathione with 7β,8α-dihydroxy-9α,10α-oxy-7,8,9,10-tetrahydrobenzo(a) pyrene. Cancer Res. 46:1986;2220-2224.
4. Robertson I.G.C., Jensson H., Mannervik B., Jernström B. Glutathione transferases in rat lung: the presence of transfer ase 7-7, highly efficient in the conjugation of glutathione with the carcinogenic (+)-7β,8α-dihydroxy-9α,10α-oxy-7,8,9,10- tetrahydrobenzo(a)pyrene. Carcinogenesis. 7:1986;295-299.
5. De Long M.J., Prochaska H.J., Talalay P. Induction of NAD(P)H:quinone reductase in murine hepatoma cells by phenolic antioxidants, azo dyes, and other chemoprotectors: a model system for the study of anticarcinogens. Proc. Natl. Acad. Sci. USA. 83:1986;787-791.
6. Prochaska H.J., Talalay P. Regulatory mechanisms of monofunctional and bifunctional anticarcinogenic enzyme inducers in murine liver. Cancer Res. 48:1988;4776-4782.
7. 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. USA. 85:1988;8261-8265.
8. Primiano T., Sutter T.R., Kensler T.W. Redox regulation of genes that protect against carcinogens. Comp. Biochem. Physiol. 118B:1998;487-497.
9. Aoki Y., Matsumoto M., Suzuki K.T. Expression of glutathione S-transferase P-form in primary cultured rat liver parenchymal cells by coplanar polychlorinated biphenyl congeners is suppressed by protein kinase inhibitors and dexamethasone. FEBS Lett. 333:1993;114-118.
10. Suzuki T., Morimura S., Diccianni M.B., Yamada R., Hochi S., Hirabayashi M., Yuki A., Nomura K., Kitagawa T., Imagawa M., Muramatsu M. Activation of glutathione transferase P gene by lead requires glutathione transferase P enhancer I. J. Biol. Chem. 271:1996;1626-1632.
11. Li G., Tajima H., Ohtani T. An improved procedure for the preparation of isothiocyanates from primary amines by using hydrogen peroxide as the dehydrosulfurization reagent. J. Org. Chem. 62:1997;4539-4540.
12. Murakami A., Kitazono Y., Jiwajinda S., Koshimzu K., Ohigashi H. Niaziminin, a thiocarbamate from the leaves of Moringa oleifera holds a strict structural requirement for inhibition of tumor-promoter-induced Epstein Barr virus activation. Planta Med. 64:1998;319-323.
13. Sato J., Namba M., Usui K., Nagao D. Carcinogenesis in tissue culture. 8, Spontaneous malignant transformation of rat liver cells long term culture. Jpn. J. Exp. Med. 38:1968;105-118.
14. Hoshika T. On the properties of five cell lines established from liver of rats fed on azo dyes. Okayama Igakkai Zasshi. 90:1978;1377-1391.
15. Yamada M., Okigaki T., Awai M. Adhesion and growth of rat liver epithelial cells on an extracellular matrix with proteins from fibroblast conditioned medium. Cell Struct. Funct. 12:1987;53-62.
16. Yamada M., Awai M., Okigaki T. Rapid in vitro transformation system for liver epithelial cells by iron chelate. Fe-NTA, Cytotechnology. 3:1990;149-156.
17. Fukuda A., Nakamura Y., Ohigashi H., Osawa T., Uchida K. Cellular response to the redox active lipid peroxidation products: induction of glutathione S-transferase P by 4-hydroxy-2-nonenal. Biochem. Biophys. Res. Commun. 236:1997;505-509.
18. Habig W.H., Pabst M.J., Jakoby W.B. Glutathione S-transferase. The first enzymatic step in mercapturic acid formation. J. Biol. Chem. 249:1974;7130-7139.
19. Nakamura Y., Ohigashi H., Masuda S., Murakami A., Morimitsu Y., Kawamoto Y., Osawa T., Imagawa M., Uchida K. Redox regulation of glutathione S-transferase induction by benzyl isothiocyanate: correlation of enzyme induction with the formation of reactive oxygen intermediates. Cancer Res. 60:2000;219-225.
20. Food, Nutrition and the Prevention of Cancer: a Global Perspective. 1997;The American Institute for Cancer Research, Washington DC.
21. Williamson G., DuPont M.S., Wanigatunga S., Heaney R.K., Musk S.R.R., Fenwick G.R., Rhodes M.J.C. Induction of glutathione S-transferase activity in hepG2 cells by extracts from fruits and vegetables. Food Chem. 60:1997;157-160.
22. Flath R.A., Forrey R.R. Volatile components of papaya (Carica papaya L. solo variety). J. Agric. Food Chem. 25:1977;103-109.
23. Huang M.-T., Ferraro T., Ho C.-T. Cancer chemoprevention by phytochemicals in fruits and vegetables an overview. Huang M.-T., Osawa T., Ho C.-T., Rosen R.T. Food Phytochemicals for Cancer Prevention I, ACS symposium series 546. 1994;2-16 American Chemical Society, Washington DC.
24. Sparnin 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.
25. Medesto R.R., Pesce A.J. Use of tolylene diisocyanate for the preparation of a peroxidase-labeled antibody conjugate: quantitation of the amount of diisocyanate bound. Biochim. Biophys. Acta. 295:1973;283-295.
26. Segal A., Solomon J.J., Li F. Isolation of methylcarbamoyl-adducts of adenine and cytosine following in vitro reaction methyl isocyanate with calf thymus DNA. Chem.-Biol. Interact. 69:1989;359-372.
27. Caspary W.J., Myhr B. Mutagenicity of methylisocyanate and its reaction products to cultured mammalian cells. Mutat. Res. 174:1986;285-293.
28. Podhradsky D., Drobnica L., Kristian P. Reactions of cysteine, its derivatives, glutathione, coenzyme A, and dihydrolipoic acid with isothiocyanates, Experientia. 35:1978;154-155.
29. Zhang Y., Talalay P. Mechanism of differential potencies of isothiocyanates as inducers of anticarcinogenic phase 2 enzymes. Cancer Res. 58:1998;4632-4639.
30. Bruggeman I.M., Temmink J.H.M., van Bladeren P.J. Glutathione- and cysteine-mediated cytotoxicity of alkyl and benzyl isothiocyanate. Toxicol. Appl. Pharm. 83:1986;349-359.
31. Sakai M., Okuda A., Muramatsu M. Multiple regulatory elements and phorbol 12-O-tetradecanoate 13-acetate responsiveness of the rat placental glutathione S-transferase. Proc. Natl. Acad. Sci. USA. 85:1988;9456-9460.
32. Okuda A., Imagawa M., Maeda Y., Sakai M., Muramatsu M. Structural and functional analysis of an enhancer GPE I having a phorbol 12-O-tetradecanoate 13-acetate responsive element-like sequence found in the rat glutathione transferase P gene. J. Biol. Chem. 264:1989;16919-16926.
33. Ogawa K., Futakuchi M., Hirose M., Boonyaphiphat P., Mizoguchi Y., Miki T., Shirai T. Stage and organ dependent effects of 1-O-hexyl-2,3,5-trimethylhydroquinone, ascorbic acid derivatives, N-heptadecane-8,10-dione and phenylethyl isothiocyanate in a rat multiorgan carcinogenesis model. Int. J. Cancer. 76:1998;851-856.
34. Hirose M., Yamaguchi T., Kimoto N., Ogawa K., Futakuchi M., Sano M., Shirai T. Strong promoting activity of phenylethyl isothiocyanate and benzyl isothiocyanate on urinary bladder carcinogenesis in F344 male rats. Int. J. Cancer. 77:1998;773-777.
35. 1 metabolism. Carcinogenesis. 18:1997;1729-1738.