Cruciferous plants: Phytochemical toxicity versus cancer chemoprotection

Mini-Reviews in Medicinal Chemistry

Volumn 9, Issue 13, 2009, Pages 1470-1478

  Assayed, Mohamed E ^a,b   Abd El Aty, A M ^c  

^a Veterinary Dentistry and Oral Surgery   (United States)

^b MENOUFIA UNIVERSITY   (Egypt)

^c Cairo University   (Egypt)

Author keywords

Brassicaceae; Cancer chemoprotection; Cruciferae; Glucosinolates; GSLs; Isothiocyanate; ITC; Phytochemicals; Toxic

Indexed keywords

GLUCOSINOLATE; ISOTHIOCYANIC ACID; SULFORAPHANE;

ALLELOPATHY; BOVIDS; BRASSICACEAE; CABBAGE; CANCER RISK; CATTLE; CRUCIFERA; DRY WEIGHT; ECONOMIC ASPECT; ENZYME MECHANISM; FORAGE; HORSE; HYDROLYSIS; LIVESTOCK; NUTRITION; PHYTOCHEMISTRY; PLANT ROOT; POULTRY; RAPESEED; SHEEP; SHORT SURVEY; SWINE; WINTER;

ANIMAL FEED; ANIMALS; BRASSICACEAE; HUMANS; NEOPLASMS; PLANTS, TOXIC;

EID: 75449086987     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/138955709790361511     Document Type: Short Survey

References (102)

1. 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. Chem. Biol. Interact., 1997, 103, 79-129.
2. Matthäus, B.; Zubr, J. Variability of specific components in Camelina sativa oilseed cakes. Ind. Crops Prod., 2000, 12, 9-18.
3. Fahey, J.W.; Zalcmann, A.T.; Talalay, P. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry, 2001, 56, 5-51.
4. Beasley, V. In: Veterinary Toxicology, (Ed.) Publisher: International Veterinary Information Service (www.ivis.org), Ithaca, New York, USA, 1999.
5. Zhang, Y.; Talalay, P. Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanisms. Cancer Res. (suppl.) 1994, 54, 1976s-1981s.
6. Hecht, S.S. Chemoprevention by isothiocyanates. J. Cell. Biochem. Suppl., 1995, 22, 195-209.
7. Hecht, S.S. Chemoprevention by modifiers of carcinogen metabolism. In: "Phytochemicals as Bioactive Agents", Bidlack, W.R.; Omaye, S.T.; Meskin M.S.; Topham, D.K.W., Eds, Technomic Publishing Co.: Lancaster, PA, 2000, pp. 43-74.
8. Wattenberg, L.W.; Hanley, A.B.; Barany, G.; Sparnins, V.L.; Lam, L.K.T. and Fenwick, G.R. (1986): Inhibition of carcinogenesis by some minor dietary constituents. In: Diet, Nutrition and Cancer (Hayashi, Y.; Nagao, H.; Sugimura, T.; Tokayama, S.; Tomatis, L.; Wattenberg, L. W.; Wogan, G. N.; Eds, Japan Science Society Press: Tokyo, Japan, 1986, pp. 193-203
9. Talalay, P.; Zhang, Y. Chemoprotection against cancer by isothiocyanates and glucosinolates. Biochem. Soc. Trans., 1996, 24, 806-810.
10. Fahey, J.W.; Zhang, Y.; Talalay, P. Broccoli sprouts: an exceptionally rich source of inducers of enzymes that protect against chemical carcinogens. Proc. Natl. Acad. Sci. USA, 1997, 94, 10367-10372.
11. Rosa, E.A.S.; Heaney, R.K.; Fenwick, G.R.; Portas, C.A.M. Glucosinolates in crop plants. Hortic. Rev. 1997, 19, 99-215.
12. Shapiro, T.A.; Fahey, J.W.; Wade, K.L.; Stephenson, K.K.; Talalay, P. Chemoprotective glucosinolates and isothiocyanates of broccoli sprouts: metabolism and excretion in humans. Cancer Epidemiol. Biomarkers Prev., 2001, 10, 501-508.
13. Kliebenstein, D.J.; Kroymann, J.; Mitchell-Olds, T. The glucosinolate-myrosinase system in an ecological and evolutionary context. Curr. Opin. Plant Biol., 2005, 8, 264-271.
14. Eklind, K.I.; Morse, M.A.; Chung, F-L. Distribution and metabolism of the natural anticarcinogen phenethyl isothiocyanate in NJ mice. Carcinogenesis, 1990, 11, 2033-2036.
15. Mennicke, W.H.; Gorler, K.; Krumbiegel, G. Metabolism of some naturally occurring isothiocyanates in the rat. Xenobiotica 1983, 13, 203-207.
16. Chung, F-L.; Morse, M.A.; Eklind, K.I. New potential chemopreventive agents for lung carcinogenesis of tobacco-specific nitrosamine. Cancer Res. (Suppl.), 1992, 52, 2719s-2722s.
17. Gorler, K.; Krumbiegel, G.; Mennicke, W.H.; Siehl, H.U. The metabolism of benzyl isothiocyanate and its cysteine conjugate in ginea-pegs and rabbits. Xenobiotica, 1982, 12, 535-542.
18. Conaway, C.C.; Yang, Y.M.; Chung, F.L. Isothiocyanates as cancer chemopreventive agents: their biological activities and metabolism in rodents and humans. Curr.Drug Metab., 2002, 3, 233-255.
19. Bollard, M.; Stribbling, S.; Mitchell, S.; Caldwell, J. The disposition of allyl isothiocyanate in the rat and mouse. Food Chem. Toxicol., 1997, 35, 933-943.
20. Anderton, M.J.; Manson, M.M.; Verschoyle, R.D.; Gescher, A.; Lamb, J.H.; Farmer, P.B.; Steward, W.P.; Williams, M.L. Pharmacokinetics and tissue disposition of indole-3-carbinol and its acid condensation products after oral administration to mice. Clin. Cancer Res., 2004, 10, 5233-5241.
21. Duncan, A.J.; Milne, J.A. Effects of oral administration of brassica secondary metabolites, allyl cyanide, allyl isothiocyanate and dimethyl disulphide, on the voluntary food intake and metabolism of sheep. Br. J. Nutr., 1993, 70, 631-645.
22. Fenwick, G.R.; Heaney, R.K. Glucosinolates and their break-down products in cruciferous crops, foods and feeding stuffs. Food Chem. 1983, 11, 249-271.
23. Silver, E.H.; Kuttab, S.H.; Hasan, T. Structural considerations in the metabolism of nitriles to cyanide in vivo. Drug Metab. Dispos. 1982, 10, 495-498.
24. Srivastava, V.K.; Philbrick, D.J.; Hill, D.C. Responses of rats and chicks to rapeseed meal subjected to different enzymatic treatments. Can. J. Anim. Sci., 1975, 55, 331-335.
25. Nishie, K.; Daxenbichler, M.E. Toxicology of glucosinolates, related compounds (nitriles, R-goitrin, isothiocyanates) and vitamin U found in Cruciferae. Food Cosmet. Toxicol., 1980, 18, 159-172.
26. Gould, D.H.; Fettman, M.J.; Daxenbichler, M.E.; Bartuska, B.M. Functional and structural alterations of the rat kidney induced by the naturally occurring organonitrile, 2s-I-cyano-2-hydroxy-3, 4-epithiobutane. Toxicol. Appl. Pharmacol., 1985, 78, 190-201.
27. Willhite, C.C.; Smith, R.P. The role of cyanide liberation in the acute toxicity of aliphatic nitriles. Toxicol. Appl. Pharmacol., 1981, 59, 589-602.
28. Ahmed, P.; Farooqui, M.Y. Comparative toxicities of aliphatic nitriles. Toxicol. Lett., 1982, 12, 157-163.
29. Tanii, H.; Hashimoto, K. Studies on the mechanism of acute toxicity of nitriles in mice. Arch. Toxicol. 1984, 55, 47-54.
30. Langer, P. Study of the chemical representatives of the goitrogenic activity of raw cabbage. Physiologia Bohemoslovenica 1964, 3, 542-549.
31. Langer, P.; Stolc, V. Goitrogenic activity of allylisothiocyanate - a widespread natural mustard oil. Endocrinology, 1965, 76, 151-155.
32. Kawakishi, S.; Namiki, M. Oxidative cleavage of the disulfide bond of cystine by the action of ally1 isothiocyanate. J. Agric. Food Chem., 1982, 30, 618-620.
33. Kawakishi, S.; Goto, T.; Namiki, M. Oxidative scission of the disulphide bond of cystine and polypeptides by the action of allyl isothiocyanates. Agric. Biol. Chem., 1983, 47, 2071-2076.
34. Griffiths, D.W.; Birch, A.N.A.; Hillmann, J.R. Antinutritional compounds in the Brassicaceae -Analysis, biosynthesis, chemistry and dietary effects. J. Hortic. Sci. Biotechnol., 1998, 73, 1-18.
35. Halkier, B.A.; Gershenzon, J. Biology and biochemistry of glucosinolate. Annu. Rev. Plant Biol., 2006, 57, 303-333.
36. Mawson, R.; Heaney, R.K.; Zdunczyk, Z.; Kozlowska, H. Rapeseed meal glucosinolates and their antinutritional effects. Part 3. Animal growth and performance. Nahrung 1994a, 38, 167-177.
37. Mawson, R.; Heaney, R.K.; Zdunczyk, Z.; Kozlowska, H. Rape-seed meal glucosinolates and their antinutritional effects. Part 4. Goitrogenicity and internal organs abnormalities in animals. Nahrung 1994b, 38, 178-191.
38. Mithen, R.F.; Dekker, M.; Verkerk, R.; Rabot, S.; Johnson, I.T. The nutritional significance, biosynthesis and bioavailability of glucosinolates in human food. J. Sci. Food Agric. 2000, 80, 967-984.
39. Burel, C.; Boujard, T.; Kaushik, S.J.; Boeuf,G.; Mol, K.A.; Van der, G.S.; Darras, V.M.; Kuhn, E.R.; Pradet-Balade, B.; Querat, B.; Quinsac, A.; Krouti, M.; Ribaillier, D. Effects of rapeseed meal-glucosinolates on thyroid metabolism and feed utilization in rainbow trout. Gen. Comp. Endocrinol., 2001, 124, 343-358.
40. Spiegel, C.; Bestetti, G.E.; Rossi, G.L.; Blum, J.W. Normal circulating triiodothyronine concentrations are maintained despite severe hypothyroidism in growing pigs fed rapeseed presscake meal. J. Nutr. 1993, 123, 1554-1561.
41. Martland, M.F.; Butler, E.J.; Fenwick, G.R. Rapeseed induced liver haemorrhage reticulolysis and biochemical changes in laying hens: the effects of feeding high and low glucosinolate meals. Res. Vet. Sci. 1984, 63, 298-309.
42. Kloss, P.; Jeffrey, E.; Wallig, M.; Tumbleson, M.; Parsons, C.; Johnson, L.; Reuber, M. Efficacy of feeding glucosinolateextracted crambe meal to broiler chicks. Poult. Sci. 1994, 73, 1542-1551.
43. Schöne, F.; Rudolph, B.; Kirchheim, U.; Knapp, G. Counteracting the negative effects of rapeseed and rapeseed press cake in pig diets. Br. J. Nutr. 1997a, 78, 947-939.
44. Umemura, T.; Yamashiro, S.; Bhatnagar, M.K.; Moody, D.L.; Slinger, S.J. Liver fibrosis of the turkey on rapeseed products. Res. Vet. Sci. 1977, 23, 139-145.
45. Campbell, L.D. Incidence of liver haemorrhage among white leghorn strains fed on diets containing different types of rapeseed meals. Br. Poult. Sci., 1979, 20, 239-246.
46. Taljaard, T.L. Cabbage poisoning in ruminants. J. South African Vet. Assoc. 1993, 64, 96-100.
47. Ahlin, K.A.; Emanuelson, M.; Wiktorson, H. Rapeseed products from double- low cultivars as feed for dairy cows: effects of long term feeding on thyroid function, fertility and animal health. Acta Vet. Scand., 1994, 35, 37-53.
48. Schmid, A.; Schmid, H. Rapeseed poisoning of wild herbivores. Tierarzl. Prax. 1992, 20, 321-325.
49. Rodriguez, R.A.; Maciel, M.G.; de Ochoteco, M.B. Blindness in Holando Argentine calves due to ingestion of turnip (Brassica campestris). Vet. Arg., 1997, 14, 601-605.
50. Knight, A.P.; Stegelmeier, B.L.; Woods L.W.; Tiwary, A.K. 7th International Symposium on Poisonous Plants, Logan, UT (abstract) p. 95. http://ddr.nal.usda.gov/bitstream/10113/9257/1/-IND43954300.pdf 2005.
51. Dixon, P.M.; McGorum, B. Oilseed rape and equine respiratory disease. Vet Rec., 1990, 126, 585.
52. Gay, C.C. www.vetmed.wsu.edu/depts-fdiu/MustardFoalsReport.-pdf 2004.
53. Hines M.T. www.vetmed.wsu.edu/depts-fdiu/MustardFoals-Report. pdf 2004.
54. Mason, R.W.; Lucas, P. Acute poisoning in cattle after eating old non-viable seed of chou moellier (Brassica oleracea convar. Acephala). Aust. Vet. J. 1983, 60, 272-273.
55. Lardy, G.P.; Kerley, M.S. Effect of increasing the dietary level of rapeseed meal on intake by growing beef steers. J. Anim. Sci. 1994, 72, 1936-1942.
56. Morton, J.M.; Campbell, P.H. Disease signs reported in southeastern Australian dairy cattle while grazing Brassica species. Aust. Vet. J. 1997, 75, 109-113.
57. Hill, F.I.; Ebbett, P.C. Polioencephalomalacia in cattle in New Zealand fed chou moellier (Brassica oleracea). N. Z. Vet. J., 1997, 45, 37-39.
58. Katamoto, H.; Nishiguchi, S.; Harada, K.; Ueyama, I.; Fujita, T.; Watanabe, O. Suspected oriental mustard (Brassica juncea) intoxication in cattle. Vet. Rec., 2001, 149, 215-216.
59. Bush, R.S.; Ncholson, J.W.G.; MacIntyre, T.M.; McQueen, R.E. A comparison of Candle and Tower rapeseed meal in lamb, sheep and beef steer rations. Can. J. Anim. Sci., 1978, 58, 369-376.
60. Cox-Ganser, J.M.; Jung, G.A.; Pushkin, R.T.; Reid, R.L. Evaluation of Brassicas in grazing systems for sheeep: II. Blood composition and nutrient status. J Anim Sci., 1994, 72, 1832-1841.
61. Mandiki, S.N.M.; Derycke, G.; Bister, J.L.; Mabon, N.; Wathelet, J.P.; Marlier, M.; Paquay, R. Chemical changes and influence of rapeseed antinutritional factors on gestating and lactating ewes. Part1: Animal performance and plasma hormones and glucose. Anim. Feed Sci. Technol. 2002, 98, 25-35.
62. Stanford, K.; Wallins, G.L.; Smart,W.G.; McAllister, A.A. Effect of feeding canola screenings on apparent digestibility, growth performance and carcass characteristics of feedlot lambs. Can. J. Anim. Sci. 2000, 80, 355-365.
63. Mabon, N.; Mandiki, S.N.M.; Derycke, G.; Bister, J.-L.; Wathelet, J.P.; Paquay, R.; Marlier, M. Chemical changes and influence of rapeseed antinutritional factor on lamb physiology and performance. Part 3. Antinutritional factor in plasma and organ. Anim. Feed Sci. Technol. 2000, 85, 111-120.
64. Pattanaik, A.K.; Khan, S.A.; Mohanty D.N.; Vashaney, V.P. Nutritional performance, clinical chemistry and semen characteristics of goats fed mustard (Brassica juncea) cake based supplements with or without iodine. Small Rumin. Res. 2004, 54, 173-182.
65. Schöne, F.; Leiterer, M.; Jahreis, G.; Rudolph, B. Effect of rape-seed feedstuff with different glucosinolate conaten and iodine administration on gestating and lactating sow. Zentralbl. Veterinarmed. A, 1997, 44, 325-339.
66. Schöne, F.; Leiterer, M.; Hartung, H.; Jahreis, G.; Tischendorf, F. Rapeseed glucosinolates and iodine in sows affect the milk iodine concentration and the iodine status of piglets. Br. J. Nutr. 2001, 85, 659-670.
67. Opalka, M.; Dusza, L.; Koziorowski, M.; Staszkiewicz, J.; Lipinski, K.; Tywonczuk, J. Effect of long-term feeding with graded levels of low glucosinolate rapeseed meal on endocrine status of gilts and their piglets. Livestock Prod. Sci., 2001, 69, 233-243.
68. Ryhänen, E.-L.; Perttilä, S.; Tupasela, T.; Valaja, J.; Eriksson, C.; Larkka, K. Effect of Camelina sativa expeller cake on performance and meat quality of broilers. J. Sci. Food Agric., 2007, 87, 1489-1494.
69. Kassie, F.; Pool-Zobel, B.; Parzefall, W.; Knasmuller, S. Genotoxic effects of benzyl isothiocyanate, a natural chemopreventive agent. Mutagenesis, 1999, 14, 595-604.
70. NTP (National Toxicology Program). NTP carcinogenesis bioassay of allyl isothiocyanate (CAS No. 57-06-7) in F344N rats and B6C3F1 mice (gavage study). Technical Report Series No. 234. http://ntp.niehs.nih.gov/ntp/htdocs/LT- rpts/tr234.pdf 1982.
71. Chung, F-L.; Kelloff, G.; Steele, V.; Pittman, B.; Zang, E.; Jiao, D.; Rigotty, J.; Choi, C.I.; Rivenson, A. Chemopreventive efficacy of arylalkyl isothiocyanates and Nacetylcysteine for lung tumorigenesis in Fischer rats. Cancer Res., 1996, 56, 772-778.
72. Stoner, G.; Casto, B.; Ralston, S.; Roebuck, B.; Pereira, C.; Bailey, G. Development of a multi-organ rat model for evaluating chemo-preventive agents: efficacy of indole-3-carbinol. Carcinogenesis, 2002, 23, 265-272.
73. Adam-Rodwell, G.; Morse, M.A.; Stoner, G.D. The effects of phenethyl isothiocyanate on benzo[a]pyrene-induced tumors and DNA adducts in A/J mouse lung. Cancer Lett., 1993, 71, 35-42.
74. Rao, C.V.; Rivenson, A.; Simi, B.; Hamid, R.; Kelloff, G.J.; Steele, V.; Reddy, B.S. Enhancement of experimental colon carcinogenesis by dietary 6-phenylhexyl isothiocyanates. Cancer Res., 1995, 55, 4311-4318.
75. Guo, D.; Schut, H.A.; Davis, C.D.; Snyderwine, E.G.; Bailey, G.S.; Dashwood, R.H. Protection by chlorophyllin and indole-3-carbinol against 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-induced DNA adducts and colonic aberrant crypts in the F344 rat. Carcinognesis, 1995, 16, 2931-2937.
76. Kim D.J.; Lee, K.K.; Han, B.S.; Ahn, B.; Bae, J.H.; Jang, J.J. Biphasic modifying effect of indole-3-carbinol on diethylnitrosamine-induced preneoplastic glutathione S-transferase placenta form-positive liver cell foci in Sprague Dawley rat. Jpn. J. Cancer Res., 1994, 85, 578-583.
77. Yoshida, M.; Katashima, S.; Ando, J.; Tanaka, T.; Uematsu, F.; Nakae, D.; Maekawa, A. Dietary indole-3-carbinol promotes endometrial adenocarcinoma development in rats initiated with Nethyl-N'-nitro-N-nitrosoguanidine, with induction of cytochrome P450s in the liver and consequent modulation of estrogen metabolism. Carcinogenesis, 2004, 25, 2257-2264.
78. Higdon, J.V.; Delage, B.; Williams, D.E.; Dashwood, R.H. Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis. Pharmacol. Res., 2007, 55, 224-236.
79. Talalay, P. Chemoprotection against cancer by induction of phase 2 enzymes. Biofactors, 2000, 12, 5-11.
80. Khachik, F.; Bertram J.S.; Huang, M.T.; Fahey, J.W.; Talalay, P. Dietary carotenoids and their metabolites as potentially useful chemoprotective agents against cancer. In: "Antioxidant Food Sup- plements in Human Health"; Packer, L.; Hiramatsu, M.; Yoshikawa, T., Eds.; Academic Press: San Diego, CA, 1999, pp. 203-229.
81. Prochaska, H.J.; Talalay, P. Regulatory mechanisms of monofunctional and bifunctional anticarcinogenic enzyme inducers in murine liver. Cancer Res., 1988, 48, 4776-4782
82. Hayes, J.D.; McLellan, L.I. Glutathione and glutathione-dependent enzymes represent a coordinated regulated defense against oxidative stress. Free Radic. Res., 1999, 31, 273-300.
83. Steinmetz, K.A.; Potter, J.A. Vegetables, fruit, and cancer prevention: a review. J. Am. Diet Assoc. 1996, 96, 1027-1039.
84. Graham, S.; Dayal, H; Swanson, M.; Mittelman, A.; Wilkinson, G. Diet in the epidemiology of cancer of the colon and rectum. J. Natl. Cancer Inst., 1978, 61, 709-714
85. Verhoeven, D.T.H.; Goldbohm, R.A.; van Poppel, G.; Verhagen, H.; van den Brandt, P.A. Epidemiological studies on brassica vegetables and cancer risk. Cancer Epidemiol. Biomarkers Prev., 1996, 5, 733-748.
86. Jain, M.G.; Hislop, G.T.; Howe, G.R.; Ghadirian, P. Plant foods, antioxidants, and prostate cancer risk: findings from case-control studies in Canada. Nutr. Cancer, 1999, 34, 173-184.
87. Kolonel, L.N.; Hankin, J.H.; Whittemore, A.S.; Wu, A.H.; Gallagher, R.P.; Wilkens, L.R.; John, E.M.; Howe, G.R.; Dreon, D.M.; West, D.W.; Paffenberger, R.S., Jr. Vegetables, fruits, legumes and prostate cancer: a multiethnic case-control study. Cancer Epidemiol. Biomarkers Prev. 2000, 9, 795 - 804.
88. Terry, P.; Wolk, A.; Persson, I.; Magnusson, C. Brassica vegetables and breast cancer risk. JAMA, 2001, 285, 2975-2977.
89. Zhang, S.M.; Hunter, D.J.; Rosner, B.A.; Giovannucci, E.L.; Colditz, G.A.; Speizer, F.E.; Willett, W.C. Intakes of fruits, vegetables, and related nutrients and the risk of non-Hodgkin's lymphoma among women. Cancer Epidemiol. Biomarkers Prev., 2000, 9, 477-485.
90. Zhang, Y.; Kensler, T.W.; Cho, C.G.; Posner, G.H.; Talalay, P. Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc. Natl. Acad. Sci. USA, 1994, 91, 3147-3150.
91. Talalay, P.; Fahey, J.W. Phytochemicals from Cruciferous Plants Protect against Cancer by Modulating Carcinogen Metabolism. In: American Institute for Cancer Research 11th Annual Research Conference on Diet, Nutrition and Cancer held in Washington, DC, July, 16-17. 2001.
92. Nestle, M. Broccoli sprouts as inducers of carcinogen-detoxifying enzyme systems: clinical, dietary, and policy implications. Proc. Natl. Acad. Sci. USA, 1997, 94, 11149-11151.
93. Daxenbichler, M.E.; Spencer, G.F.; Carlson, D.G.; Rose, G.B.; Brinker, A.B.; Powell, R.G. Glucosinolate composition of seeds from 297 species of wild plants. Phytochemistry, 1991, 30, 2623-2638.
94. Guo, Z.; Smith, T.J.; Wang, E.; Eklind, K.I.; Chung, F-L.; Yang, C.S. Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis, 1993, 14, 1167-1173.
95. Chung, F-L.; Juchatz, A.; Vitarius, J.; Hecht, S.S. Effects of dietary compounds on alpha-hydroxylation of N-nitrosopyrrolidine and N'-nitrosonornicotine in rat target tissues. Cancer Res., 1984, 44, 2924-2928.
96. Chung, F-L.; Wang, M. Y.; Hecht, S.S. Effects of dietary indoles and isothiocyanates on N-nitrosodimethylamine and 4-(methylnitrosamino)-1-(3- pyridyl)-1-butanone alpha-hydroxylation and DNA methylation in rat liver. Carcinogenesis, 1985, 6, 539-543.
97. Morse, M.A.; Wang, C-X.; Amin, S.G.; Hecht, S.S.; Chung, F-L. Effects of dietary sinigrin or indole-3-carbinol on O6-methylguanine-DNA-transmethylase activity and 4-(methyllnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA methylation and tumorigenicity in F344 rats. Carcinogenesis, 1988, 9, 1891-1895.
98. Hasegawa, T.; Nishino, H.; Iwashima, A. Isothiocyanates inhibit cell cycle progression of HeLa cells at G2/M phase. Anticancer Drugs, 1993, 4, 273-279.
99. Bogaards, J.J.; van Ommen, B.; Falke, H.E.; Willems, M.I.; van Bladeren, P. 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 Chem. Toxicol., 1990, 28, 81-88.
100. Hara, A.; Sakai, N.; Yamada, H.; Tanaka, T.; Kato, K.; Mori, H.; Sato, K. Induction of glutathione S-transferase, placental type in T9 glioma cells by dibutyryladenosine 3′,5′-cyclic monophosphate and modification of its expression by naturally occurring isothiocyanates. Acta Neuropathol., 1989, 79, 144-148.
101. Posner, G.H.; Cho, C.G.; Green, J.V.; Zhang, Y.; Talalay, P. Design and synthesis of bifunctional isothiocyanate analogs of sulforaphane: correlation between structure and potency as inducers of anticarcinogenic detoxication enzymes. J. Med. Chem., 1994, 37, 170 - 176.
102. Dunnick, J.K.; Prejean, J.D.; Haseman, J.; Thomson, R.B.; Giles, H.D.; McConnell, E.E. Carcinogenesis bioassay of allyl isothiocyanates. Fundam. AppI. Toxicol., 1982, 2, 114-120.