Dietary role of glucosinolate derivatives: A review

Journal of Food Science and Technology

Volumn 43, Issue 1, 2006, Pages 8-17

  Anilakumar, K R ^a   Khanum, Farhath ^a   Bawa, A S ^a  

^a DEFENCE FOOD RESEARCH LABORATORY   (India)

Author keywords

Anticarcinogenic; Biotransformation enzymes; Brassica; Glucosinolate products; Glucosinolates; Goitrogenic

Indexed keywords

CARCINOGENS; ENZYMES; GLUCOSE; HYDROLYSIS; NUTRITION; PHYSIOLOGY;

ENDOMETRIAL CANCER CELLS; GLUCOSINOLATES (GS); LUNG CANCER; PROSTATE CANCER;

DERIVATIVES;

ANIMALIA; BRASSICA; BRASSICACEAE; ONCORHYNCHUS MYKISS; ORYCTOLAGUS CUNICULUS;

EID: 29244463834     PISSN: 00221155     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (107)

1. Abraham S K 1991. Inhibitory effects of coffee on the genotoxicity of carcinogens in mice. Mutat Res 262:109-114
2. Agrawal RC, Kumar S 1998. Prevention of cyclophosphamide-induced micronucleus formation in mouse bone narrow by indole 3-carbinol. Food Chem Toxicol 36:975-977
3. Agrawal RC, Mehrotra NK 1997. Assessment of mutagenic potential of propoxur and its modulation by indole-3-carbinol. Food Chem Toxicol 35:1081-1084
4. Astwood EB 1943. The chemical nature of compounds which inhibit function of the thyroid gland. J Pharm Exp Therap 78:79-89
5. Astwood EB, Greer MA, Ettlinger MG 1949. L-5-vinyl-2-thiooxazolidone, an antithyroid compound from yellow turnip and from Brassica seeds. J Biol Chem 81:121-130
6. Bablish JG, Stoewsand GS 1978. Effect of dietary indole-3-carbinol on the induction of the mixed-function oxidases of rat tissue. Food Cosmet Toxicol 16:151-155
7. Bachmann M, Theus R, Luthy J, Schlatter CL 1985. Vkorkommen von Goitrogen Stoffen in Milch. Zeitschrift Lebensmitteluntersuchung Forschung 181:375-378
8. Bailey GS, Hendricks JD, Shelton DW, Nixon JE, Pawlowski NE 1987. Enhancement of carcinogenesis by the natural anticarcinogen indole-3-carbinol. J Nat Cancer Inst 78:931-942
9. Bailey GS, Hendricks JD, Dashwood RH 1992. Anticarcinogenesis in fish. Mutat Res 267:243-250
10. Betz JM, Fox WD 1994. High performance liquid Chromatographic determination of glucosinolates in Brassica vegetables. In: Food phytochemical for cancer prevention. I. Fruits and vegetables. Huang M-T, Osawa T, Ho C-T, Rosen RT (eds). American Chemical Society, Washington DC, p 181-196
11. Birt DF, Walker B, Tibels MG, Brensnick E 1986. Antimutagenesis and antipromotion by epigenin, robenetin and indole-3-carbinol. Carcinogenesis 7:959-963
12. Bjeldanes LF, Kim J-Y, Grose KR, Bartholomew JC, Bradfield CA 1991. Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: comparison with 2,3,7,8-tetrachloro dibenzo-p-dioxin. Proc Nat Acad Sci USA 88:9547-9558
13. Bjorkman R 1976. Properties and function of plant myrosinase. In: The Biology and Chemistry of the Cruciferae. Vaughan JG, Macleod AJ, Jones BMG (eds). Academic Press, London, p 191-215
14. Bollard N, Stribbling S, Mitchell S, Caldwell J 1997. The disposition of allyl isothiocyanate in the rat and mouse. Food Chem Toxicol 35:933-943
15. 1-induced rat plasma α-foetoprotein elevation, hepatic tumorigenesis and mutagenicity of urine. Food Chem Toxicol 20:47-52
16. Bradfield CA, Bjeldanes LF 1984. Effect of dietary indole-3-carbinol on intestinal and hepatic monooxygenase, glutathione S-transferase and epoxide hydrolase activities in the rat. Food Chem Toxicol 22:977-980
17. Carlson DG, Daxenbichler ME, Van Etten CH, Tookey HL, Williaams PH 1982. Glucosinolates in crucifer crops. Turnips and rutabagas. J Agric Food Chem 29:1235-1239
18. Chang Y, Bjeldanes LF 1985. Effects of dietary R-goitrin on hepatic and intestinal GS-transferase, microsomal epoxide hydratase and ethoxy coumarin O-deethylase activities in the rat. Food Chem Toxicol 23:905-911
19. Chaloner C, Sandle LN, Mohan V, Suchalatha C, Viswanatha M, Braganza JM 1990. Evidence for induction of cytochrome P-4501 in patients with tropical chronic pancreatitis. Int J Clin Pharmacol Therap Toxicol 28:235-244
20. Cha Y-N, Thompson DC, Heine HS, Chung J-H 1985. Differential effects of indole, indole-3-carbinol and benzofuran on several microsomal and cytosolic enzyme activities in mouse liver. Korean J Pharmacol 21:1-6
21. Chen OZ, Qi M, Auborn KJ, Carter TH 2001. Indole-3-carbinol and dindolylmethane induce apoptosis of human cervical cancer cells and in murine HPV 16-transgenic preneoplastic cervical epithilium. J Nutr 131:3294-3302
22. Chesney AM, Clawson TA, Webster B 1928. Endemic goitre in rabbits. 1. Incidence and characteristics. Bull John Hopkins Hosp 43:261-277
23. Chinni SR, Liy, Upadhay SK, Sarkar FH 2001. Indole-3-carbinol induced cell growth inhibition, G cell cycle arrest apoptosis in prostate cancer cells. Oncogene 20:2927-2936
24. Clandinin DR, Robblec AR 1981. Rapeseed meal in animal nutrition. Non-ruminant animal. J Am Oil Chem Soc 58:682-686
25. Cohen JH, Kristal AR, Stanford JL 2000. High consumption of vegetables associated with reduced risk of prostate cancer. Evid Based Oncology 1:69-70
26. Cole RA 1980. Volatile components produced during ontogeny of some cultivated crucifers. J Sci Food Agric 31:549-557
27. 1 carcinogen dose, indole-3-carbinol anticarcinogen dose, target organ DNA adduction and final tumor response. Carcinogenesis 10:175-181
28. 1 carcinogenesis by the natural tumour modulator indole-3-carbinol: influence of dose, duration and intermittent exposure on indole-3-carbinol promotional potency. Cancer Res 51:2362-2365
29. Daxenbichler ME, van Ettan CH, Williams PH 1979. Glucosinolates and derived products in cruciferous vegetables: Analysis of fourteen varieties of Chinese cabbage. J Agric Food Chem 27:34-37
30. Deby C, Goutier R 1990. New perspectives on the biochemistry of Superoxide anion and the efficacy of Superoxide dismutase. Biochem Pharmacol 39:399-405
31. De Groot AP, Willems MI, De Vos RH 1991. Effects of high levels of Brussels sprouts in the diet of rats. Food Chem Toxicol 29:829-837
32. Dornberger K, Bockel V, Heyer J, Schonfeld CL, Tonew E 1975. Untersuchungen uber die Isothiocyanate Erysolin und Sulphoraphan an Cardaria draba L. Pharmazie 30:792-796
33. Dunnick JK, Psejean JD, Haseman J, Thomson RB, Giles HD, McConnel EE 1982. Carcinogenesis bioassay of allyl isothiocyanate. Fundament Appl Toxicol 2:114-120
34. Elliot MC, Stowe BB 1971. Indole compounds related to auxins and goitrogens of wood (Isatis tuctorial L.). Plant Physiol 47:366-372
35. Fahey JW, Zalcmann AT, Talalaly P 2001. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochem 56:5-51
36. Fenwick GR, Heaney TK, 1983. Glucosinolate and their breakdown products in Cruciferous crops, food and feeding stuffs. Food Chem 11:249-271
37. Fenwick GR, Heaney RK, Mawson R 1989. Glucosinolates. In: Toxicants of plant origin. Cheeke PR (ed), CRC Press, Florida, p 1-41
38. Foster JR, Idle JR, Hardwick JP, Bars R, Scoot P, Braganza JM 1993. Induction of drug metabolizing enzymes in human pancreatic cancer and chronic pancreatitis. J Pathol 169:457-463.
39. Gmelin R, Virtanen AL 1961. Glucobrassicin, the precursor of 3-indolyl acetonitrile, ascorbigen, and SCN in Brassica oleracea species. Suomen Kemistilehti B34:15-18
40. Gmelin R 1964. Occurrence, isolation and properties of glucobrassicin and neoglucorassicin. Colloq Int CNRS Paris, p 123
41. Graham S 1983. Results of case control studies of diet and cancer in Buffalo, New York. Cancer Res 43:2409-2416
42. Greer MA 1962. The isolation and identification of progoitrin from Brassica seed Arch Biochem Biophys 99:369-371
43. Greer MA 1957. Goitrogenic substances in food. Am J Clin Nutr 5:440-444
44. Heaney RK, Fenwick GR 1980. Glucosinolates in Brassica vegetables. Analysis of twenty two varieties of Brussels sprout (Brassica oleracea L. var gemmifera). J Scei Food Agric 31:785-793
45. Heddle JA, Hite M, Kirkhat B, Mavournin K, MacGregor JT, Newell GW, Salamone MF 1983. The induction of micronuclei as a measure of genotoxicity: a report of the U S Environmental protection Agency Gene-Tox Program. Mutat Res 123:61-118
46. Hirayama T 1986. Diet and cancer, feasibility and importance of prospective cohort study. In: Diet and human carcinogenesis. Jossens JV, Hill MJ, Geboers J (eds), Proceedings of the Second ECP Symposium, Excerpta Media, Arhus Denmark Amsterdam, p 191-194
47. Jellinck PH, Forkert PG, Riddick DS, Okey AB, Michnovicz JJ, Bradlow HL 1993. Ah receptor binding properties of indole carbinols and induction of hepatic estradiol hydroxylation. Biochem Pharmacol 45:1129-1136
48. Jiao D, Ho CT, Foils P, Chung FL 1994. Identification and quantification of the Nacetylcysteine conjugate of allyl isothiocyanate in human urine after ingestion of mustard. Cancer Epidemiol Biomarkers Prevent 3:487-492
49. Jongen WMF, Topp RJ, Wienk KJK, Homan EC 1989. Modulating effects of naturally occurring indoles on SCE induction depend largely on the type of mutagen. Mutat Res 222:263-269
50. Kin DJ, Han BS, Aim B, Hsegawa R, Shirai T, Ito N, Tsuda N 1997. Enhancement by indole-3-carbinol of liver and thyroid gland neoplastic development in a rat medium term multi organ carcinogenesis model. Carcinogenesis 7:371-386.
51. Kjaer A 1974. The natural distribution of glucosinolates, A uniform class of sulphur containing glucosides. In: Chemistry in Botanical Classification. Bends G, Santesson G (eds). Academic Press, London, p 229-234
52. Kurilich AC, Jeffery EH, Juvik JA, Walig MA, Klein BP 2003. Broccoli extracts protect agianst reactive oxygen species in HepG2 cells. J Nutraceut Functional Med Food 4:5-16
53. Lang H, Firestone GL, Bjeldanes LF 2001. Cytostatic effects of 3,3′-diindolylmethane in human endometrial cancer cells result from an restrogen receptor-mediated increase in transforming growth factor aexpression. Carcinogenesis 22:1809-1817
54. 1 polymorphism and lung-cancer risk: a prospective study of men in Shanghai, China. Lancet 356:724-729
55. Loub WD, Wallenberg LW, Davis DW 1975. Aryl hydrocarbon hydroxylase induction in rat tissues by naturally occurring indoles of cruciferae pramb. J Nat Cancer Inst 54:985-999
56. Luthy J, Garden B, Friederich U, Bachmann M 1984. Goitrin-a nitrosatable constituent of plant food stuffs. Experientia 40:452-453
57. Marks HS, Anderson JL, Stoewsand GS 1992. Inhibition of benzo (a) pyrene-induced bone narrow micronuclei formation by diallyl thioethers in mice. J Toxicol Environ Health 37:1-9
58. Mason HS 1970. Mechanisms of oxygen metabolism. Adv Enzymol 19:79-99
59. Matsumoto Y 1970. Volatile organic sulphur compounds as insects attractants with special reference to host selection. In: Control of Insect's Behaviour by Natural Products. Wood DL, Silverstein RM, Nakayima M (eds), Academic press, London, p 133-158
60. McDanell RE, Mclean AEM, Hanley AB, Heaney RK, Fenwick GR 1987. Differential induction of mixed function oxidase (MFO) activity in rat liver and intestine by diets containing processed cabbage: Correlation of the cabbage levels of glucosinolates and glucosinolate hydrolysis products. Food Chem Toxicol 25:365-368
61. McDanell R, McLean AEM, Hanley AB, Heaney RK, Fenwick GR 1998. Chemical and biological properties of indole glucosinolates (glucobrassicins). A review. Food Chem Toxicol 26:59-70
62. Michajlovskij, Langer P 1967. Identity of the goitrogenic effect of glucobrassicin and the equivalent amount of thiocyanate in rats. Endocr Exp 1:229-240
63. Michnovicz JJ, Bradlow HL 1994. Dietary cytochrome P-450 modifiers in the control of estrogen metabolism. In: Food Phytochemicals for Cancer Prevention: Fruits and Vegetables. Huang M-T, Osawa T, Ho C-T, Rosen RT (eds). Am Chem Soc, Washington DC. p 282-293
64. Nachshon-Kedmi M, Yanni S, Haj A, Fares FA 2003. Indole-3-carbinol and 3,3-′ diindolyl methane induce apoptosis in human prostate cancer cells. Food Chem Toxicol 41:745-752
65. Nash SL, Oehme FW 1984. A review of acetaminophens effect on methemoglobin, glutathione and some related enzymes. Veter Human Toxicol 2:123-132
66. Pantuck EJ, Hariao KC, Loub WD, Wattenberg LW, Kuntxman R, Conney AH 1976. Stimulatory effect of vegetables on intestinal drug metabolism in the rat. J Pharm Exp Ther 198:277-288
67. Pantuck EJ, Pantuck CB, Garland WA, Min BH, Wattenberg LW, Anderson KE, Kappas A, Conney AH 1979. Stimulatory effect of Brussels sprouts and cabbage on human drug metabolism. Clin Pharmac Ther 25:88
68. Pence BC, Buddingh F, Yang SP 1986. Multiple dietary factors in the enhancement of dimethyl hydrazine carcinogenesis: main effect of indole-3-carbinol. J Natl Cancer Inst 77:269-276
69. Queinnec Y 1967. Etude des facteurs psychophysiologiques permettant ladecouverte de la plante hot for les larves neonates de I' Altise d' Liver due Colza (Phylliodes chrysocephala L.). Ann Epiphyt 18:5-15
70. Schrandolf H, Bergman F 1965. Metabolism of indole derivatives of Sinapis alba L. Planta 67:75-84
71. Searle LM, Chamberlain K, Riush T, Butcher DN 1982. The conversion of 3-indomethyl glucosinolate to 3-indolylacetonitrile by myrosinase and its relevance to the club root disease of cruciferae. J Exp Bot 33:935-942
72. Shertzer HG 1978. Indole-3-carbinol protects against covalent binding of benzo(a)pyrene and N-introsodimethylamine metabolites to mouse liver macromolecules. ChemicoBiol Inter 48:82-90
73. Shertzer HG, Sainsbury M 1991a. Intrinsic acute toxicity and hepatic enzyme inducing properties of the chemo protectants indole-3-carbinol and 5,10-dihydroindeno (1,2-b) indole in mice. Food Chem Toxicol 29:237-247
74. Shertzer HG, Sainsbury M 1991b. Mechanisms of chemical mediated cytotoxicity and chemoprevention in isolated rat hepatocytes. Chemico-Biol Interactions 78:123-141
75. Shertzer HG, Tabor MW 1988. Nucleophilic carbinol from N-nitrosodimethylamine cyto and genotoxicity in mouse liver. J Appl Toxicol 8:105-110
76. Sones K, Heaney RK, Fenwick GR 1984a. The glucosionate content of UK vegetables-cabbage (Brassica oleracea) swede (B. napus) and turnip (B. campestris). Food Add Contam 1:289-298
77. Sones K, Heaney RK, Fenwick GR 1984b. Glucosinolates in Brassica vegetables. Analysis of twenty seven cauliflower cultivars (Brassica oleracea L. var. botrytis subvar. Cauliflora DC). J Sci Food Agric 35:762-769
78. Sorensen M, Jonsen BR, Poulsen HE, Deng XS, Tygstrup N, Dalholff K, Loft S 2001. Brussels sprouts extract induced oxidative DNA damage and metabolizing enzymes in rat liver. Food Chem Toxicol 39:533-540
79. Sparnis VL, Wattenberg LW 1982. Glutathione-S-transferase activity: enhancement by compounds inhibiting chemical carcinogenesis and by dietary constituents. J Nat Cancer Inst 68:493
80. Stanely GS, York JL, Benson AM 1992. Nitroreductases and glutathione transferases that act on 4-nitroquinoline-1-oxide and their differential induction by butylated hydroxyanisole in mice. Cancer Res 52:58-63
81. 1 in rats fed cauliflower. J Environ Pathol Toxicol 2:399-409
82. Stoner GD, Galati AJ, Schmidt CJ, Morse MA 1994. Inhibition of esophageal tumorigenesis by phenethyl isothiocyanate. In: Food Phytochemicals for Cancer Prevention: 1. Fruits and Vegetables. Huang MT, Osawa T, Ho C-T, Rosen RT (eds). American Chemical Society, Washington, p 173-180
83. 1 metabolism and cytochrome P-450 associated with bio activation and detoxification of aflatoxin B in the rat. Drug Metab Disp 22:383-391
84. 1-DNA adduction and mutagenesis by 13C acid condensation products. Food Chem Toxicol 33:851-857
85. Tanii H, Takayasu T, Higashi T, Leng S, Saijoh K 2004. Allylnitrile: generation from cruciferous vegetables and behavioural effects on mice of repeated exposure. Food Chem Toxicol 42:453-458
86. Tolonen M, Taipale M, Viander B, Pihlava JM, Korhonen H, Ryhanen EL 2002. Plantderived biomolecules in fermented cabbage. J Agric Food Chem 50:6798-6803
87. Tookey HL, van Etten CH, Daxenbichler ME 1980. Glucosinolates. In: Toxic Constituents of Plant Food Stuffs. 2nd edn, Liener JE (ed), Academic Press, New York, p 103-142
88. Underhill EW, Wetter LR, Chishohn MD 1973. Biosynthesis of glucosinolates. Biochem Soc Symp 38:303-326
89. van Etten CH, Daxenbichler ME, Tookey HI, Kwolek WF, Williams PH, Yoder OC 1980. Glucosinolates: Potential toxicants in cabbage cultivars. J Am Soc Hort Sci 105:710-714
90. Virtanen AI, Kreunla M, Kiesvaara M 1963. Investigations on the alleged goitrogenic properties of milk. Ernahrungswiss (suppl) 3:23-37
91. Viswanathan KR, Anilakumar KR, Farhath Khanum, Sudarshanakrishna KR 1998. Modulatory effect of dehydrated cabbage on the detoxifying enzymes of rats with a carcinogen treatment. Nutr Res 18:1733-1741
92. Wakabyashi K, Nagao M, Ochiai M, Tahira T, Yamaiznmi Z, Sugimura T 1985. A mutagen precursor in Chinese cabbage, indole-3-acetonitrile, which becomes mutagenic on nitrite treatment. Mutat Res 143:17-27
93. Wallig MA, Kingston S, Staack T, Jeffery EH 1998. Induction of rat pancreatic glutathione-S-transferase and quinone reductase activities by a mixture of glucosinolate breakdown derivatives found in Brussels sprouts. Food Chem Toxicol 36:365-373
94. Warterlboer HM, deKruif CA, Van Lersel AAA, Falke HE, Noordhoek J, Blaauboer BJ 1992a. Acid reaction products of indole-3-carbinol and their effect on cytochrome P-450 and phase II enzymes in rat and monkey hepatocytes. Biochem Pharmacol 43:1439-1447
95. Wartelboer HM, Van der Linden ECM, de Kruif CA, Noordoek J, Blaauboer BJ, uan Bladeren PJ, Falke HE 1992b. Effects of indole-3-carbinol on biotransformation enzymes in the rat: in vivo changes in liver and small intestinal mucosa in comparison with primary hepatocyte cultures. Food Chem Toxicol 30:589-599
96. Wattenberg L W 1971. Studies on polycyclic hydrocarbon hydroxylases of the intestine possibly related to cancer. Cancer 28:99-110
97. Wattenberg LW 1983. Inhibition of neoplasia by minor dietary constituents. Cancer Res 43:2448-2455
98. Watternberg LW 1990. Inhibition of carcinogenesis by minor antinurtrient constituents of the diet. Proc Nutr Soc 49:173-183
99. Wattenberg LW, Loub WD 1978. Inhibition of polycyclic aromatic hydrocarbon induced neoplasia by naurally occurring indoles. Cancer Res 38:1410-1422
100. Wattenberg LW, Loub WD, Lam LK, Speier JL 1976. Dietary constituents altering the response to chemical carcinogens. Fed Proc 35:241-253
101. Welch RM 1979. Toxicological implications of drug metabolism. Pharmac Rev 30:457468
102. West LG, Badenhop AF, McLaughlin JL 1977. Allyl isothiocyanate and allyl cyanide production in cell-free cabbage leaf extracts, shredded cabbage and cole slaw. J Agric Food Chem 25:1234-1238
103. Williams RT 1978. Nutrients in drug detoxification reactions. In: Nutrition and Drug Interrelations. Hathcock JN, Coon J (eds), Academic Press, New York, p 303-320
104. Zhu C-Y, Poulson E, Loft S 2000. Inhibition of oxidative DNA damage in vitro by extract of Brussels sprouts. Free Rad Res 33:187-196
105. Zhu C-Y, Loft S 2001. Effect of Brussels sprouts extract on hydrogen peroxide-induced DNA strand breaks in human lymphocytes. Food Chem Toxicol 39:1191-1197
106. Zhu C-Y, Loft S 2003. Effect of chemopreventive compounds from Brassica vegetables on NAD(P)H: quinone reductase and induction of DNA strand breaks in murine hepa1c1c7 cells. Food Chem Toxicol 41:455-462
107. Zsolnai T 1966. Die Antimikrobielle Wirkung von thiocyanates und isothiocyanates. Arzneim Forschung 16:870-876