Glucosinolates, isothiocyanates and human health

Phytochemistry Reviews

Volumn 8, Issue 1, 2009, Pages 269-282

  Traka, Maria ^a   Mithen, Richard ^a  

^a INSTITUTE OF FOOD RESEARCH   (United Kingdom)

Author keywords

Brassica; Cancer; Epidemiology; GST; Intervention studies

Indexed keywords

GLUCOSINOLATE; GLUTATHIONE TRANSFERASE; ISOTHIOCYANIC ACID DERIVATIVE;

ABSORPTION; CANCER PREVENTION; CRUCIFERA; DIETARY INTAKE; ENZYME ACTIVITY; HEART PROTECTION; HUMAN; MAMMAL CELL; METABOLISM; NONHUMAN; PLANT HERBIVORE INTERACTION; PRIORITY JOURNAL; REVIEW; RISK REDUCTION; VEGETABLE;

BRASSICA; MAMMALIA;

EID: 58149327483     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-008-9103-7     Document Type: Review

References (141)

1. CB Ambrosone SE McCann JL Freudenheim 2004 Breast cancer risk in premenopausal women is inversely associated with consumption of broccoli, a source of isothiocyanates, but is not modified by GST genotype J Nutr 134 1134 1138
2. M Asakage NH Tsuno J Kitayama 2006 Sulforaphane induces inhibition of human umbilical vein endothelial cells proliferation by apoptosis Angiogenesis 9 83 91
3. S Barcelo JM Gardiner A Gescher 1996 CYP2E1-mediated mechanism of anti-genotoxicity of the broccoli constituent sulforaphane Carcinogenesis 17 277 282
4. GP Basten Y Bao G Williamson 2002 Sulforaphane and its glutathione conjugate but not sulforaphane nitrile induce UDP-glucuronosyl transferase (UGT1A1) and glutathione transferase (GSTA1) in cultured cells Carcinogenesis 23 1399 1404
5. E Bertl H Bartsch C Gerhauser 2006 Inhibition of angiogenesis and endothelial cell functions are novel sulforaphane-mediated mechanisms in chemoprevention Mol Cancer Ther 5 575 585
6. JJ Bogaards H Verhagen MI Willems 1994 Consumption of Brussels sprouts results in elevated alpha-class glutathione S-transferase levels in human blood plasma Carcinogenesis 15 1073 1075
7. C Bonnesen IM Eggleston JD Hayes 2001 Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines Cancer Res 61 6120 6130
8. JD Brooks VG Paton G Vidanes 2001 Potent induction of phase 2 enzymes in human prostate cells by sulforaphane Cancer Epidemiol Biomarkers Prev 10 949 954
9. G Brusewitz BD Cameron LF Chasseaud 1977 The metabolism of benzyl isothiocyanate and its cysteine conjugate Biochem J 162 99 107
10. DG Carlson ME Daxenbichler HL Tookey 1987 Glucosinolates in turnip tops and roots-cultivars grown for greens and or roots J Am Soc Hortic Sci 112 179 183
11. DG Carlson ME Daxenbichler CH Vanetten 1987 Glucosinolates in crucifer vegetables-broccoli, brussels- sprouts, cauliflower, collards, kale, mustard greens, and kohlrabi J Am Soc Hortic Sci 112 173 178
12. DL Cheng K Hashimoto Y Uda 2004 In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products Food Chem Toxicol 42 351 357
13. JW Chiao FL Chung R Kancherla 2002 Sulforaphane and its metabolite mediate growth arrest and apoptosis in human prostate cancer cells Int J Oncol 20 631 636
14. JW Chiao H Wu G Ramaswamy 2004 Ingestion of an isothiocyanate metabolite from cruciferous vegetables inhibits growth of human prostate cancer cell xenografts by apoptosis and cell cycle arrest Carcinogenesis 25 1403 1408
15. FL Chung D Jiao SM Getahun 1998 A urinary biomarker for uptake of dietary isothiocyanates in humans Cancer Epidemiol Biomarkers Prev 7 103 108
16. FL Chung CC Conaway CV Rao 2000 Chemoprevention of colonic aberrant crypt foci in Fischer rats by sulforaphane and phenethyl isothiocyanate Carcinogenesis 21 2287 2291
17. JH Cohen AR Kristal JL Stanford 2000 Fruit and vegetable intakes and prostate cancer risk J Natl Cancer Inst 92 61 68
18. CC Conaway SM Getahun LL Liebes 2000 Disposition of glucosinolates and sulforaphane in humans after ingestion of steamed and fresh broccoli Nutr Cancer 38 168 178
19. CC Conaway CX Wang B Pittman 2005 Phenethyl isothiocyanate and sulforaphane and their N-acetylcysteine conjugates inhibit malignant progression of lung adenomas induced by tobacco carcinogens in A/J mice Cancer Res 65 8548 8557
20. MC Cornelis A El-Sohemy H Campos 2007 GSTT1 genotype modifies the association between cruciferous vegetable intake and the risk of myocardial infarction Am J Clin Nutr 86 752 758
21. SC Cotton L Sharp J Little 2000 Glutathione S-transferase polymorphisms and colorectal cancer: a HuGE review Am J Epidemiol 151 7 32
22. EL Dahl RT Mulcahy 2001 Cell-type specific differences in glutamate cysteine ligase transcriptional regulation demonstrate independent subunit control Toxicol Sci 61 265 272
23. M Dey D Ribnicky AG Kurmukov 2006 In vitro and in vivo anti-inflammatory activity of a seed preparation containing phenethylisothiocyanate J Pharmacol Exp Ther 317 326 333
24. DA Dickinson AL Levonen DR Moellering 2004 Human glutamate cysteine ligase gene regulation through the electrophile response element Free Radic Biol Med 37 1152 1159
25. AT Dinkova-Kostova WD Holtzclaw RN Cole 2002 Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants Proc Natl Acad Sci USA 99 11908 11913
26. AT Dinkova-Kostova JW Fahey KL Wade 2007 Induction of the phase 2 response in mouse and human skin by sulforaphane-containing broccoli sprout extracts Cancer Epidemiol Biomarkers Prev 16 847 851
27. L Elfoul S Rabot N Khelifa 2001 Formation of allyl isothiocyanate from sinigrin in the digestive tract of rats monoassociated with a human colonic strain of Bacteroides thetaiotaomicron FEMS Microbiol Lett 197 99 103
28. JW Fahey AT Zalcmann P Talalay 2001 The chemical diversity and distribution of glucosinolates and isothiocyanates among plants Phytochemistry 56 5 51
29. JW Fahey X Haristoy PM Dolan 2002 Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors Proc Natl Acad Sci U S A 99 7610 7615
30. K Faulkner R Mithen G Williamson 1998 Selective increase of the potential anticarcinogen 4-methylsulphinylbutyl glucosinolate in broccoli Carcinogenesis 19 605 609
31. C Fimognari M Nusse R Cesari 2002 Growth inhibition, cell-cycle arrest and apoptosis in human T-cell leukemia by the isothiocyanate sulforaphane Carcinogenesis 23 581 586
32. JH Fowke FL Chung F Jin 2003 Urinary isothiocyanate levels, brassica, and human breast cancer Cancer Res 63 3980 3986
33. MV Galan AA Kishan AL Silverman 2004 Oral broccoli sprouts for the treatment of Helicobacter pylori infection: a preliminary report Dig Dis Sci 49 1088 1090
34. L Gamet-Payrastre P Li S Lumeau 2000 Sulforaphane, a naturally occurring isothiocyanate, induces cell cycle arrest and apoptosis in HT29 human colon cancer cells Cancer Res 60 1426 1433
35. AV Gasper A Al-Janobi JA Smith 2005 Glutathione S-transferase M1 polymorphism and metabolism of sulforaphane from standard and high-glucosinolate broccoli Am J Clin Nutr 82 1283 1291
36. AV Gasper M Traka JR Bacon 2007 Consuming broccoli does not induce genes associated with xenobiotic metabolism and cell cycle control in human gastric mucosa J Nutr 137 1718 1724
37. C Gerhauser M You J Liu 1997 Cancer chemopreventive potential of sulforamate, a novel analogue of sulforaphane that induces phase 2 drug-metabolizing enzymes Cancer Res 57 272 278
38. SM Getahun FL Chung 1999 Conversion of glucosinolates to isothiocyanates in humans after ingestion of cooked watercress Cancer Epidemiol Biomarkers Prev 8 447 451
39. D Gingras M Gendron D Boivin 2004 Induction of medulloblastoma cell apoptosis by sulforaphane, a dietary anticarcinogen from Brassica vegetables Cancer Lett 203 35 43
40. E Giovannucci EB Rimm Y Liu 2003 A prospective study of cruciferous vegetables and prostate cancer Cancer Epidemiol Biomarkers Prev 12 1403 1409
41. LE Hansson O Nyren R Bergström 1993 Diet and risk of gastric cancer. A population-based case-control study in Sweden Int J Cancer 55 181 189
42. X Haristoy K Angioi-Duprez A Duprez 2003 Efficacy of sulforaphane in eradicating Helicobacter pylori in human gastric xenografts implanted in nude mice Antimicrob Agents Chemother 47 3982 3984
43. JD Hayes RC Strange 2000 Glutathione S-transferase polymorphisms and their biological consequences Pharmacology 61 154 166
44. JD Hayes JU Flanagan IR Jowsey 2005 Glutathione transferases Annu Rev Pharmacol Toxicol 45 51 88
45. AJ Heidel MJ Clauss J Kroymann 2006 Natural variation in MAM within and between populations of Arabidopsis lyrata determines glucosinolate phenotype Genetics 173 1629 1636
46. E Heiss C Herhaus K Klimo 2001 Nuclear factor kappa B is a molecular target for sulforaphane-mediated anti-inflammatory mechanisms J Biol Chem 276 32008 32015
47. CB Hill PH Williams DG Carlson 1987 Variation in glucosinolates in oriental Brassica vegetables J Am Soc Hortic Sci 112 309 313
48. F Hong ML Freeman DC Liebler 2005 Identification of sensor cysteines in human Keap1 modified by the cancer chemopreventive agent sulforaphane Chem Res Toxicol 18 1917 1926
49. R Hu BR Kim C Chen 2003 The roles of JNK and apoptotic signaling pathways in PEITC-mediated responses in human HT-29 colon adenocarcinoma cells Carcinogenesis 24 1361 1367
50. R Hu TO Khor G Shen 2006 Cancer chemoprevention of intestinal polyposis in ApcMin/+ mice by sulforaphane, a natural product derived from cruciferous vegetable Carcinogenesis 27 2038 2046
51. C Huang WY Ma J Li 1998 Essential role of p53 in phenethyl isothiocyanate-induced apoptosis Cancer Res 58 4102 4106
52. K Itoh KI Tong M Yamamoto 2004 Molecular mechanism activating Nrf2-Keap1 pathway in regulation of adaptive response to electrophiles Free Radic Biol Med 36 1208 1213
53. K Itoh N Wakabayashi Y Katoh 1999 Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amino-terminal Neh2 domain Genes Dev 13 76 86
54. SJ Jackson KW Singletary 2004 Sulforaphane inhibits human MCF-7 mammary cancer cell mitotic progression and tubulin polymerization J Nutr 134 2229 2236
55. SJ Jackson KW Singletary 2004 Sulforaphane: a naturally occurring mammary carcinoma mitotic inhibitor, which disrupts tubulin polymerization Carcinogenesis 25 219 227
56. SJ Jackson KW Singletary RC Venema 2006 Sulforaphane suppresses angiogenesis and disrupts endothelial mitotic progression and microtubule polymerization Vascul Pharmacol 46 77 84
57. Jeffery EH, Araya M (2008) Broccoli and health: a growing benefit. Phytochemistry Reviews
58. ZQ Jiang C Chen B Yang 2003 Differential responses from seven mammalian cell lines to the treatments of detoxifying enzyme inducers Life Sci 72 2243 2253
59. MA Joseph KB Moysich JL Freudenheim 2004 Cruciferous vegetables, genetic polymorphisms in glutathione S-transferases M1 and T1, and prostate cancer risk Nutr Cancer 50 206 213
60. N Juge RF Mithen M Traka 2007 Molecular basis for chemoprevention by sulforaphane: a comprehensive review Cell Mol Life Sci 64 1105 1127
61. S Karmakar MS Weinberg NL Banik 2006 Activation of multiple molecular mechanisms for apoptosis in human malignant glioblastoma T98G and U87MG cells treated with sulforaphane Neuroscience 141 1265 1280
62. TW Kensler JG Chen PA Egner 2005 Effects of glucosinolate-rich broccoli sprouts on urinary levels of aflatoxin-DNA adducts and phenanthrene tetraols in a randomized clinical trial in He Zuo township, Qidong, People's Republic of China Cancer Epidemiol Biomarkers Prev 14 2605 2613
63. TO Khor YS Keum W Lin 2006 Combined inhibitory effects of curcumin and phenethyl isothiocyanate on the growth of human PC-3 prostate xenografts in immunodeficient mice Cancer Res 66 613 621
64. Khor TO, Cheung WK, Prawan A et al (2007) Chemoprevention of familial adenomatous polyposis in Apc(Min/+) mice by phenethyl isothiocyanate (PEITC). Mol Carcinog
65. VA Kirsh U Peters ST Mayne 2007 Prospective study of fruit and vegetable intake and risk of prostate cancer J Natl Cancer Inst 99 1200 1209
66. DJ Kliebenstein J Gershenzon T Mitchell-Olds 2001 Comparative quantitative trait loci mapping of aliphatic, indolic and benzylic glucosinolate production in Arabidopsis thaliana leaves and seeds Genetics 159 359 370
67. RH Kolm UH Danielson Y Zhang 1995 Isothiocyanates as substrates for human glutathione transferases: structure-activity studies Biochem J 311 453 459
68. J Kroymann S Textor JG Tokuhisa 2001 A gene controlling variation in arabidopsis glucosinolate composition is part of the methionine chain elongation pathway Plant Physiol 127 1077 1088
69. MM Kushad AF Brown AC Kurilich 1999 Variation of glucosinolates in vegetable crops of Brassica oleracea J Agric Food Chem 47 1541 1548
70. HJ Lin NM Probst-Hensch AD Louie 1998 Glutathione transferase null genotype, broccoli, and lower prevalence of colorectal adenomas Cancer Epidemiol Biomarkers Prev 7 647 652
71. SJ London JM Yuan FL Chung 2000 Isothiocyanates, glutathione S-transferase M1 and T1 polymorphisms, and lung-cancer risk: a prospective study of men in Shanghai, China Lancet 356 724 729
72. C Lopez-Berenguer M Carvajal DA Moreno 2007 Effects of microwave cooking conditions on bioactive compounds present in broccoli inflorescences J Agric Food Chem 55 10001 10007
73. K Maheo F Morel S Langouet 1997 Inhibition of cytochromes P-450 and induction of glutathione S-transferases by sulforaphane in primary human and rat hepatocytes Cancer Res 57 3649 3652
74. NV Matusheski EH Jeffery 2001 Comparison of the bioactivity of two glucoraphanin hydrolysis products found in broccoli, sulforaphane and sulforaphane nitrile J Agric Food Chem 49 5743 5749
75. NV Matusheski JA Juvik EH Jeffery 2004 Heating decreases epithiospecifier protein activity and increases sulforaphane formation in broccoli Phytochemistry 65 1273 1281
76. M McMahon K Itoh M Yamamoto 2003 Keap1-dependent proteasomal degradation of transcription factor Nrf2 contributes to the negative regulation of antioxidant response element-driven gene expression J Biol Chem 278 21592 21600
77. GK McWalter LG Higgins LI McLellan 2004 Transcription factor Nrf2 is essential for induction of NAD(P) H:quinone oxidoreductase 1, glutathione S-transferases, and glutamate cysteine ligase by broccoli seeds and isothiocyanates J Nutr 134 3499S 3506S
78. DJ Meyer DJ Crease B Ketterer 1995 Forward and reverse catalysis and product sequestration by human glutathione S-transferases in the reaction of GSH with dietary aralkyl isothiocyanates Biochem J 306 565 569
79. R Mithen K Faulkner R Magrath 2003 Development of isothiocyanate-enriched broccoli, and its enhanced ability to induce phase 2 detoxification enzymes in mammalian cells Theor Appl Genet 106 727 734
80. PL Moseley 1997 Heat shock proteins and heat adaptation of the whole organism J Appl Physiol 83 1413 1417
81. H Motohashi F Katsuoka JD Engel 2004 Small Maf proteins serve as transcriptional cofactors for keratinocyte differentiation in the Keap1-Nrf2 regulatory pathway Proc Natl Acad Sci U S A 101 6379 6384
82. SR Musk TK Smith IT Johnson 1995 On the cytotoxicity and genotoxicity of allyl and phenethyl isothiocyanates and their parent glucosinolates sinigrin and gluconasturtiin Mutat Res 348 19 23
83. MC Myzak PA Karplus FL Chung 2004 A novel mechanism of chemoprotection by sulforaphane: inhibition of histone deacetylase Cancer Res 64 5767 5774
84. MC Myzak K Hardin R Wang 2006 Sulforaphane inhibits histone deacetylase activity in BPH-1, LnCaP and PC-3 prostate epithelial cells Carcinogenesis 27 811 819
85. T Nguyen HC Huang CB Pickett 2000 Transcriptional regulation of the antioxidant response element. activation by Nrf2 and repression by MafK J Biol Chem 275 15466 15473
86. ML Palop JP Smiths B Tenbrink 1995 Degradation of sinigrin by Lactobacillus-Agilis Strain R16 Int J Food Microbiol 26 219 229
87. G Parnaud P Li G Cassar 2004 Mechanism of sulforaphane-induced cell cycle arrest and apoptosis in human colon cancer cells Nutr Cancer 48 198 206
88. EJ Patten MJ DeLong 1999 Temporal effects of the detoxification enzyme inducer, benzyl isothiocyanate: activation of c-Jun N-terminal kinase prior to the transcription factors AP-1 and NFkappaB Biochem Biophys Res Commun 257 149 155
89. S Rabot L Nugon-Baudon P Raibaud 1993 Rape-seed meal toxicity in gnotobiotic rats: influence of a whole human faecal flora or single human strains of Escherichia coli and Bacteroides vulgatus Br J Nutr 70 323 331
90. P Rose K Faulkner G Williamson 2000 7-Methylsulfinylheptyl and 8-methylsulfinyloctyl isothiocyanates from watercress are potent inducers of phase II enzymes Carcinogenesis 21 1983 1988
91. P Rose YK Won CN Ong 2005 Beta-phenylethyl and 8-methylsulphinyloctyl isothiocyanates, constituents of watercress, suppress LPS induced production of nitric oxide and prostaglandin E2 in RAW 264.7 macrophages Nitric Oxide 12 237 243
92. G Rouzaud SA Young AJ Duncan 2004 Hydrolysis of glucosinolates to isothiocyanates after ingestion of raw or microwaved cabbage by human volunteers Cancer Epidemiol Biomarkers Prev 13 125 131
93. G Sarikamis J Marquez R MacCormack 2006 High glucosinolate broccoli: a delivery system for sulforaphane Molecular Breeding 18 219 228
94. A Seow CY Shi FL Chung 1998 Urinary total isothiocyanate (ITC) in a population-based sample of middle-aged and older Chinese in Singapore: relationship with dietary total ITC and glutathione S-transferase M1/T1/P1 genotypes Cancer Epidemiol Biomarkers Prev 7 775 781
95. A Seow JM Yuan CL Sun 2002 Dietary isothiocyanates, glutathione S-transferase polymorphisms and colorectal cancer risk in the Singapore Chinese Health Study Carcinogenesis 23 2055 2061
96. TA Shapiro JW Fahey KL Wade 1998 Human metabolism and excretion of cancer chemoprotective glucosinolates and isothiocyanates of cruciferous vegetables Cancer Epidemiol Biomarkers Prev 7 1091 1100
97. G Shen TO Khor R Hu 2007 Chemoprevention of familial adenomatous polyposis by natural dietary compounds sulforaphane and dibenzoylmethane alone and in combination in ApcMin/+ mouse Cancer Res 67 9937 9944
98. AV Singh D Xiao KL Lew 2004 Sulforaphane induces caspase-mediated apoptosis in cultured PC-3 human prostate cancer cells and retards growth of PC-3 xenografts in vivo Carcinogenesis 25 83 90
99. SV Singh A Herman-Antosiewicz AV Singh 2004 Sulforaphane-induced G2/M phase cell cycle arrest involves checkpoint kinase 2-mediated phosphorylation of cell division cycle 25C J Biol Chem 279 25813 25822
100. TK Smith EK Lund ML Parker 2004 Allyl-isothiocyanate causes mitotic block, loss of cell adhesion and disrupted cytoskeletal structure in HT29 cells Carcinogenesis 25 1409 1415
101. IE Sønderby BG Hansen N Bjarnholt 2007 A systems biology approach identifies a R2R3 MYB gene subfamily with distinct and overlapping functions in regulation of aliphatic glucosinolates PLoS ONE 2 e1322
102. MR Spitz CM Duphorne MA Detry 2000 Dietary intake of isothiocyanates: evidence of a joint effect with glutathione S-transferase polymorphisms in lung cancer risk Cancer Epidemiol Biomarkers Prev 9 1017 1020
103. R Staack S Kingston MA Wallig 1998 A comparison of the individual and collective effects of four glucosinolate breakdown products from brussels sprouts on induction of detoxification enzymes Toxicol Appl Pharmacol 149 17 23
104. SE Steck MD Gammon JR Hebert 2007 GSTM1, GSTT1, GSTP1, and GSTA1 polymorphisms and urinary isothiocyanate metabolites following broccoli consumption in humans J Nutr 137 904 909
105. S Sugie K Okamoto A Okumura 1994 Inhibitory effects of benzyl thiocyanate and benzyl isothiocyanate on methylazoxymethanol acetate-induced intestinal carcinogenesis in rats Carcinogenesis 15 1555 1560
106. L Tang Y Zhang 2004 Dietary isothiocyanates inhibit the growth of human bladder carcinoma cells J Nutr 134 2004 2010
107. L Tang Y Zhang 2005 Mitochondria are the primary target in isothiocyanate-induced apoptosis in human bladder cancer cells Mol Cancer Ther 4 1250 1259
108. L Tang G Li L Song 2006 The principal urinary metabolites of dietary isothiocyanates, N-acetylcysteine conjugates, elicit the same anti-proliferative response as their parent compounds in human bladder cancer cells Anticancer Drugs 17 297 305
109. N Tani M Ohtsuru T Hata 1974 Studies on bacterial myrosinase.1. Isolation of myrosinase producing microorganism Agric Biol Chem 38 1617 1622
110. N Tani M Ohtsuru T Hata 1974 Studies on bacterial myrosinase.2. Purification and general characteristics of bacterial myrosinase produced by enterobacter-cloacae Agric Biol Chem 38 1623 1630
111. R Thapliyal GB Maru 2001 Inhibition of cytochrome P450 isozymes by curcumins in vitro and in vivo Food Chem Toxicol 39 541 547
112. P Thejass G Kuttan 2007 Allyl isothiocyanate (AITC) and phenyl isothiocyanate (PITC) inhibit tumour-specific angiogenesis by downregulating nitric oxide (NO) and tumour necrosis factor-alpha (TNF-alpha) production Nitric Oxide 16 247 257
113. PJ Thornalley 2002 Isothiocyanates: mechanism of cancer chemopreventive action Anticancer Drugs 13 331 338
114. D Toroser CE Thormann TC Osborn 1995 Rflp mapping of quantitative trait loci controlling seed aliphatic-glucosinolate content in oilseed rape (Brassica napus L.) Theor Appl Genet 91 802 808
115. M Traka AV Gasper JA Smith 2005 Transcriptome analysis of human colon Caco-2 cells exposed to sulforaphane J Nutr 135 1865 1872
116. E Tseng A Kamath ME Morris 2002 Effect of organic isothiocyanates on the P-glycoprotein- and MRP1-mediated transport of daunomycin and vinblastine Pharm Res 19 1509 1515
117. F Vallejo FA Tomas-Barberan C Garcia-Viguera 2002 Glucosinolates and vitamin C content in edible parts of broccoli florets after domestic cooking Eur Food Res Technol 215 310 316
118. H Verhagen HE Poulsen S Loft 1995 Reduction of oxidative DNA-damage in humans by brussels sprouts Carcinogenesis 16 969 970
119. DT Verhoeven H Verhagen RA Goldbohm 1997 A review of mechanisms underlying anticarcinogenicity by brassica vegetables Chem Biol Interact 103 79 129
120. JM Visanji SJ Duthie L Pirie 2004 Dietary isothiocyanates inhibit Caco-2 cell proliferation and induce G2/M phase cell cycle arrest, DNA damage, and G2/M checkpoint activation J Nutr 134 3121 3126
121. L Wang D Liu T Ahmed 2004 Targeting cell cycle machinery as a molecular mechanism of sulforaphane in prostate cancer prevention Int J Oncol 24 187 192
122. LI Wang EL Giovannucci D Hunter 2004 Dietary intake of cruciferous vegetables, glutathione S-transferase (GST) polymorphisms and lung cancer risk in a Caucasian population Cancer Causes Control 15 977 985
123. LG Wang A Beklemisheva XM Liu 2007 Dual action on promoter demethylation and chromatin by an isothiocyanate restored GSTP1 silenced in prostate cancer Mol Carcinog 46 24 31
124. AM Wentzell HC Rowe BG Hansen 2007 Linking metabolic QTLs with network and cis-eQTLs controlling biosynthetic pathways PLoS Genet 3 1687 1701
125. A Wierinckx J Breve D Mercier 2005 Detoxication enzyme inducers modify cytokine production in rat mixed glial cells J Neuroimmunol 166 132 143
126. D Xiao SV Singh 2002 Phenethyl isothiocyanate-induced apoptosis in p53-deficient PC-3 human prostate cancer cell line is mediated by extracellular signal-regulated kinases Cancer Res 62 3615 3619
127. D Xiao SV Singh 2007 Phenethyl isothiocyanate inhibits angiogenesis in vitro and ex vivo Cancer Res 67 2239 2246
128. D Xiao SK Srivastava KL Lew 2003 Allyl isothiocyanate, a constituent of cruciferous vegetables, inhibits proliferation of human prostate cancer cells by causing G2/M arrest and inducing apoptosis Carcinogenesis 24 891 897
129. D Xiao CS Johnson DL Trump 2004 Proteasome-mediated degradation of cell division cycle 25C and cyclin-dependent kinase 1 in phenethyl isothiocyanate-induced G2-M-phase cell cycle arrest in PC-3 human prostate cancer cells Mol Cancer Ther 3 567 575
130. D Xiao KL Lew Y Zeng 2006 Phenethyl isothiocyanate-induced apoptosis in PC-3 human prostate cancer cells is mediated by reactive oxygen species-dependent disruption of the mitochondrial membrane potential Carcinogenesis 27 2223 2234
131. C Xu G Shen C Chen 2005 Suppression of NF-κB and NF-κB-regulated gene expression by sulforaphane and PEITC through IκBα, IKK pathway in human prostate cancer PC-3 cells Oncogene 24 4486 4495
132. YM Yang CC Conaway JW Chiao 2002 Inhibition of benzo(a) pyrene-induced lung tumorigenesis in A/J mice by dietary N-acetylcysteine conjugates of benzyl and phenethyl isothiocyanates during the postinitiation phase is associated with activation of mitogen-activated protein kinases and p53 activity and induction of apoptosis Cancer Res 62 2 7
133. L Ye Y Zhang 2001 Total intracellular accumulation levels of dietary isothiocyanates determine their activity in elevation of cellular glutathione and induction of Phase 2 detoxification enzymes Carcinogenesis 22 1987 1992
134. Y Zhang 2000 Role of glutathione in the accumulation of anticarcinogenic isothiocyanates and their glutathione conjugates by murine hepatoma cells Carcinogenesis 21 1175 1182
135. Y Zhang EC Callaway 2002 High cellular accumulation of sulphoraphane, a dietary anticarcinogen, is followed by rapid transporter-mediated export as a glutathione conjugate Biochem J 364 301 307
136. DD Zhang M Hannink 2003 Distinct cysteine residues in Keap1 are required for Keap1-dependent ubiquitination of Nrf2 and for stabilization of Nrf2 by chemopreventive agents and oxidative stress Mol Cell Biol 23 8137 8151
137. Y Zhang TW Kensler CG Cho 1994 Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates Proc Natl Acad Sci USA 91 3147 3150
138. Y Zhang RH Kolm B Mannervik 1995 Reversible conjugation of isothiocyanates with glutathione catalyzed by human glutathione transferases Biochem Biophys Res Commun 206 748 755
139. R Zhang S Loganathan I Humphreys 2006 Benzyl isothiocyanate-induced DNA damage causes G2/M cell cycle arrest and apoptosis in human pancreatic cancer cells J Nutr 136 2728 2734
140. B Zhao A Seow EJ Lee 2001 Dietary isothiocyanates, glutathione S-transferase -M1, -T1 polymorphisms and lung cancer risk among Chinese women in Singapore Cancer Epidemiol Biomarkers Prev 10 1063 1067
141. H Zhao J Lin HB Grossman 2007 Dietary isothiocyanates, GSTM1, GSTT1, NAT2 polymorphisms and bladder cancer risk Int J Cancer 120 2208 2213