In vitro cytotoxic activity of some glucosinolate-derived products generated by myrosinase hydrolysis

Journal of Agricultural and Food Chemistry

Volumn 44, Issue 4, 1996, Pages 1014-1021

  Nastruzzi, Claudio ^a   Cortesi, Rita ^a   Esposito, Elisabetta ^a   Menegatti, Enea ^a   Leoni, Onofrio ^b   Iori, Renato ^b   Palmieri, Sandro ^b,c  

^a UNIVERSITY OF FERRARA   (Italy)

^b ISTITUTO NAZIONALE DELLA NUTRIZIONE   (Italy)

^c NONE   (Italy)

Author keywords

Antitumor activity; Crucifers; Glucosinolates; Isothiocyanates; Myrosinase

Indexed keywords

HUMAN IMMUNODEFICIENCY VIRUS 1; MURINAE;

EID: 0001036863     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9503523     Document Type: Article

References (42)

1. Bell, J. M. Nutrients and toxicants in rapeseed meal: a review. J. Anim. Sci. 1984, 58, 996-1010.
2. Bjorkman, R. Properties and function of plant myrosinases. In The Biology and Chemistry of the Cruciferae; Vaugham, J. G., MacLeod, A. J., Jones, B. M. G., Eds.; Academic Press: London, 1976; pp 191-205.
3. Caputo, A.; Balboni, P. G.; Manservigi, R.; Bozzini, R.; Marconi, P. C.; Rossi, C.; Zucchini, S.; Barbanti-Brodano, G.; Grossi, M. P. Possible approaches of gene therapy of AIDS. Minerva Biotecnol. 1993, 5, 322-325.
4. Cohen, L. A. Diet and cancer. Sci. Am. 1987, 257, 42-48.
5. Gil, V.; MacLeod, A. J. The effects of pH on glucosinolate degradation by a thioglucoside glucohydrolase preparation. Phytochemistry 1980, 19, 2547-2551.
6. Graham, S.; Mettlin, C. Fiber and other constituents of vegetables in cancer epidemiology. In Nutrition and Cancer. Aetiology and Treatment; Newell, G. R., Ellison, N. M., Eds.; Raven Press: New York, 1981; pp 189-198.
7. Graham, S.; Dayal, H.; Swanson, M.; Mittleman, A.; Wilkinson, G. Diet in the epidemiology of cancer in the colon and rectum. J. Natl. Cancer Inst. 1978, 61, 709-714.
8. Greer, M. A. The natural occurrence of goitrogenic agents. Recent Prog. Horm. Res. 1962, 18, 187-212.
9. Greer, M. A.; Deeney, J. M. Antithyroid activity elicited by the ingestion of pure progoitrin, a naturally occurring thioglucoside of the turnip family. J. Clin. Invest. 1959, 38, 1465-1474.
10. Fenwick, G. R.; Heaney, R. K.; Mullin, W. J. Glucosinolates and their breakdown products in food and food plants. CRC Crit. Rev. Food Sci. 1983, 18, 123-201.
11. Haensezel, W.; Locke, F. B.; Segi, M. A case-control study of large bowel cancer in Japan. J. Cancer Inst. 1980, 64, 17-22.
12. Iori, R.; Leoni, O.; Palmieri, S. A polarographic method for the rapid determination of total glucosinolates and free glucose of cruciferous material. Anal. Biochem. 1983, 134, 195-198.
13. Kjaer, A.; Skrydstrup, T. Selenoglucosinolates synthesis and enzymatic hydrolysis. Acta Chem. Scand. 1987, B41, 29-33.
14. Kore, A. M.; Gayland, F. S.; Matthew, A. W. Purification of the ω-(methylsulfinyl)alkyl glucosinolate hydrolysis products: 1-isothiocyanate-3-(methylsulfinyl)propane, 1-isothiocyanato-4-(methylsulfinyl)butane, 4-(methylsulfinyl)butanenitrile and 5-(methylsulfinyl)pentanenitrile from broccoli and Lesquerella fendleri. J. Agric. Food Chem. 1993, 41, 89-95.
15. Lambert, J. W. Modelling oil-water portioning and membrane permeation using reverse-phase chromatography. J. Chromatogr. A 1993, 656, 469-484.
16. Lanzani, A.; Piana, G.; Piva, G.; Cardillo, M.; Rastelli, A.; Jacini, G. Changes in Brassica napus progoitrin induced by sheep rumen fluid. J. Am. Chem. Soc. 1974, 96, 517-518.
17. Larsen, P. O. Glucosinolates. In The Biochemistry of Plants; Conn, E. E., Stumpf, P. K., Eds.; Academic Press: New York, 1981; Vol. 26, pp 59-70.
18. Lazzeri, L.; Tacconi, R.; Palmieri, S. In vitro activity of some glucosinolate and their reaction products toward a population of the nematode Heterodera schactii. J. Agric. Food Chem. 1993, 41, 825-829.
19. Lee, H. P.; Gourley, L.; Duffy, S. W.; Esteve, J.; Lee, J.; Day, N. E. Colorectal cancer and diet in the asian population - a case-control study among Singapore Chinese. Int. J. Cancer 1989, 43, 1007-1016.
20. Leoni, O.; Iori, R.; Palmieri, S. Immobilization of myrosinase on membrane for determining the glucosinolate content of cruciferous material. J. Agric. Food Chem. 1991, 39, 2322-2326.
21. Leoni, O.; Felluga, F.; Palmieri, S. The formation of 2-hydroxybut-3-enyl cyanide from (2S)-2-hydroxybut-3-enyl glucosinolate using immobilized myrosinase. Tetrahedron Lett. 1993, 49, 7967-7970.
22. Leoni, O.; Marot, C.; Rollin, P.; Palmieri, S. Preparation of (5R)-5-vinyloxazolidine-2-thione from natural epi-progoitrin using immobilized myrosinase. Tetrahedron Asymm. 1994, 5, 1157-1160.
23. Manousos, O.; Day, N. E.; Trichopoulos, D.; Gerevassilis, F.; Tzonou, A.; Polychronopoulou, A. Diet and colorectal cancer: a case-control study in Greece. Int. J. Cancer 1983, 32, 1-5.
24. Marangosa, A.; Hill, R. The hydrolysis and absorption of tbioglucosides of rapeseed meal. Proc. Nutr. Soc. 1974, 33, 90A.
25. Marx, J. How cells cycle toward cancer. Science 1993, 263, 319-321.
26. Nugon-Baudon, L.; Szylit, O.; Raibaud, P. Production of toxic glucosinolate from rapeseed meal by intestinal microflora of rat and chicken. J. Sci. Food Agric. 1988, 43, 299-308.
27. Nugon-Baudon, L.; Rabot, S.; Szylit, O.; Raibaud, P. Glucosinolates toxicity in growing rats: interactions with the hepatic detoxification system. Xenobiotica 1990, 20, 223-230.
28. Official Journal of the European Community. Regulation (EEC) 1864/90, June Enclosure VIII, J. O. n. L170. 1990, 27-34.
29. Palmieri, S. Bioactivity of some glucosinolates and their derived breakdown products obtained using immobilized myrosinase. Proceedings of the International Euro Food Tox IV Conference; 1994; pp 40-45.
30. Palmieri, S.; Leoni, O.; Iori, R. A steady state kinetics studies of myrosinase with direct ultraviolet spectrophotometric assay. Anal. Biochem. 1982, 123, 320-324.
31. Palmieri, S.; Iori, R.; Leoni, O. Myrosinase from Sinapis alba L.: a new method of purification for glucosinolate analyses. J. Agric. Food Chem. 1986, 34, 138-140.
32. Pessina, A.; Thomas, R. M.; Palmieri, S.; Luisi, P. L. An improved method for the purification of myrosinase and its physicochemical characterization. Arch. Biochem. Biophys. 1990, 280, 383-389.
33. Stoewsand, G. S.; Babish, J. B.; Munson, L. Protective effect of dietary Brussels sprouts against mammary carcinogenesis in Sprague-Dawley rats. Cancer Lett. 1988, 39, 199-207.
34. Streicher, H.; Thiem, J.; Rollin, P.; Iori, R.; Palmieri, S. Influence of the substrate sugar structure on myrosinase activity demonstrated by using native and synthetic glucotropaeolins. Proceedings, 9th International Rapeseed Congress, Cambridge, U.K.; 1995; Vol. 3, pp 958-960.
35. Thies, W. Isolation of sinigrin and glucotropaeolin from cruciferous seed. Fat Sci. Technol. 1988, 8, 311-314.
36. Tookey, H. L.; Van Etten, C. H.; Daxenbichler, M. E. Glucosinolates. In Toxic Constitutents of Plants Foodstuff, 2nd ed.; Liener, I. E., Ed.; Academic Press: New York, 1980; pp 103-142.
37. Uda, Y.; Kurata, T.; Arakawa, N. Effects of pH and ferrous ion on the degradation of glucosinolates by myrosinase. Agric. Biol. Chem. 1986a, 50, 2735-2740.
38. Uda, Y.; Kurata, T.; Arakawa, N. Effects of thiol compounds on the formation of nitriles from glucosinolates. Agric. Biol. Chem. 1986b, 50, 2741-2746.
39. Visentin, M.; Tava, A.; Iori, R.; Palmieri, S. Isolation and identification of trans-4-(methylthio)-3-butenyl glucosinolate from radish roots (Raphanus sativus). J. Agric. Food Chem. 1992, 40, 1687-1691.
40. Wattemberg, L. W. Inhibition of carcinogenic effects of polycyclic hydrocarbons by benzyl isothiocyanate and related compounds. J. Natl. Cancer Inst. 1977, 58, 395-398.
41. Wattemberg, L. W. Inhibition of carcinogenesis by minor dietary constituents. Cancer Res. 1992, 52 (Suppl.), 2085s-2091s.
42. Zhang, G. Y.; Talalay, P.; Cho, C.; Posner, G. H. A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2399-2403.