Skip to main content
Log in

Anti-carcinogenic activity of 6-methylsulfinylhexyl isothiocyanate-, an active anti-proliferative principal of wasabi (Eutrema wasabi Maxim.)

  • Published:
Cytotechnology Aims and scope Submit manuscript

Abstract

Synthetic 4-methylsulfinylhexyl isothiocyanate (MITC)(a potent inducer of phase 2 detoxification enzymes from broccoli) and 6-MITC(a potent anti-proliferative principal from wasabi) slightly inhibited the induction of mouse skin tumor in a two-stage process of carcinogenesis (initiator, 9,10-dimethyl-1,2-benzanthracene; promotor,12-o-tetradecanoylphorbol-13-acetate), but the effect was not significant. Both compounds, however, significantly inhibited the mutation of skin resulting from topical applications of the carcinogens. When a murine hepatoma cell line, Hepa 1c1c7, was treated with 2-,4-,6- and 8-MITCs, they augmented the induction of its quinone reductase, one of the phase 2 detoxification enzymes in a concentration dependent manner, and the 4- and 6-MITCs were much more potent on the reduction of the enzyme than the 2- and 8-MITCs. All 2-, 4-, 6- and 8-MITCs suppressed the growth of murine tumor cells, their suppressive activities being proportional to the length of their methyl residue. They were also cytotoxic to mouse peritoneal exudate macrophages which were not proliferating in vitro, indicating that the cellular targets of isothiocyanate may not be dependent upon the cell cycle. In addition, all the 2-, 4-, 6- and 8-MITCs inhibited the production of nitric oxide (a potent radical carcinogen) by peritoneal macrophages.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Camichael J, DeGraff WG, Gazdar AF, Minna JD and Mitchell JB (1987) Evaluation of a tetrazorium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res 47: 936–942.

    Google Scholar 

  • Constantinou A and Huberman E (1995) Genistein as an inducer of tumor cell differentiation: possible mechanisms of action. Exp Biol Med 208: 109–115.

    CAS  Google Scholar 

  • De Long MJ, Prochaska HJ and Talalay P (1986) Induction of NAD(P)H:quinone reductase in murine hepatoma cells by phenolic antioxidants, azo dyes, and other chemoprotector: a model system for the study of anticarcinogens. Proc Natl Acad Sci USA 83: 787–791.

    Article  PubMed  CAS  Google Scholar 

  • Esumi H, Ogura T, Kuvashima Y, Adachi H, Hokari A and Weisz A (1995) Implication of nitric oxide synthase in carcinogenesis analysis of the human inducible nitric oxide synthase gene. Pharmacogenetics 5: 5166–5170.

    Google Scholar 

  • Etoh H, Nishimura A, Takasawa R, Yagi A, Saito K, Sakata K, Kishima I and Ina K (1990) ω-methylsulfinylalkyl isothiocyanates in wasabi, Wsabia japonica Matsum. Agric Biol Chem 54: 1587–1589.

    CAS  Google Scholar 

  • Fuke Y, Oishi Y, Iwashita K, Ono H and Shinohara K (1994) Growth suppression of MKN-28 human stomach cancer cells by wasabi (Eutrema wasabi Maxim.). Nippon Shokuhin Kogyo Gakkaishi 41: 709–711.

    Google Scholar 

  • Gilbert RS and Herschmsann HR (1993) ‘Macrophage’ nitric oxide synthase is a glucocorticoid-inhibitable primary response gene in 3T3 cells. J Cell Physiol 157: 128–132.

    Article  PubMed  CAS  Google Scholar 

  • Hortelano S, Genaro AM and Bosca L (1993) Phorbol esters induce nitric oxide synthase and increase arginine influx in cultured peritoneal macrophages. FEBS Lett 320: 135–139.

    Article  PubMed  CAS  Google Scholar 

  • Huang M-T and Ferraro T (1992) Phenolic compounds in food and cancer prevention: Phenolic compounds in food and their effects on health II. (pp. 8–34) American Chemical Society.

  • Isshiki K and Tokuoka K (1993) Allyl isothiocyanate and wholesomeness of food. Jap. J Food Microbiology 12: 1–6.

    Google Scholar 

  • Jackson PE, Hall CN, Badaf AF, O'Conner PJ and Povey AC (1996) Frequency of Ki-ras mutations and DNA alkylation in colorectal tissue from individuals living in Manchester. Mol Carcino 16: 12–19.

    Article  CAS  Google Scholar 

  • Kojima M (1988) Pungent components and functional ingredient of wasabi. Food processing 23: 32–35.

    Google Scholar 

  • Kumagai H, Kashima N, Seki T, Sakurai H, Ishii K and Ariga T (1994) Analysis of components in essential oil of upland wasabi and their inhibitory effects on platelet aggregation. Biosci. Biotech. Biochem. 58: 2131–2135.

    Article  CAS  Google Scholar 

  • Ono H, Adachi K, Fuke Y and Shinohara K (1996) Purification and structural analysis of substances in wasabi (Eutrema wasabi Maxim.) that suppress the growth of MKN-28 human stomach cancer cells. J Jap Food Sci Technol 43: 1092–1097.

    CAS  Google Scholar 

  • Osawa T (1995) Recent development of food phytochemical for cancer prevention. CMC Co., Ltd., Tokyo.

    Google Scholar 

  • Prochaska HJ, De Long MJ and Talalay P (1985) On the mechanisms of induction of cancer protective enzymes: a unifying protocoal. Proc Natl Acad Sci USA, 82: 8232–8236.

    Article  PubMed  CAS  Google Scholar 

  • Prochaska HJ, Santamaria AB and Talalay P (1992) Rapid detection of inducers of enzymes that protect against carcinogens. Proc Natl Acad Sci USA 89: 2394–2398.

    Article  PubMed  CAS  Google Scholar 

  • Ryoyama K, Nomura T and Nakamura S (1993) Inhibition of macrophage nitric oxide production by arachidonate-cascade inhibitors. Cancer Immuno Immunother 37: 385–391.

    Article  CAS  Google Scholar 

  • Spencer S R, Wilczak C A and Talalay P (1990) Induction of glitathione transferases and NAD(P)H:quinone reductase by fumaric acid derivatives in rodent cells and tissues. Cancer Res 50: 7871–7875.

    PubMed  CAS  Google Scholar 

  • Talalay P, De Long MJ and Prochaska HJ (1988) Identification of a common signal regulating the induction of enzymes that protect against chemical carcinogenesis. Pro. Natl. Acad. Sci. USA 85: 8261–8265.

    Article  CAS  Google Scholar 

  • Zhang Y, Talalay P, CHO C-G and Posner GH (1992) A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure. Proc Natl Acad Sci USA 89: 2399–2403.

    Article  PubMed  CAS  Google Scholar 

  • Zhang Y, Kensler TW, Cho C-G, Posner GH and Talalay P (1994) Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc Natl Acad Sci USA 91: 3147–3150.

    Article  PubMed  CAS  Google Scholar 

Download references

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fuke, Y., Haga, Y., Ono, H. et al. Anti-carcinogenic activity of 6-methylsulfinylhexyl isothiocyanate-, an active anti-proliferative principal of wasabi (Eutrema wasabi Maxim.). Cytotechnology 25, 197–203 (1997). https://doi.org/10.1023/A:1007918508115

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1007918508115

Navigation