Antimutagenic effect of fruit and vegetable ethanolic extracts against N-nitrosamines evaluated by the Ames test

Journal of Agricultural and Food Chemistry

Volumn 47, Issue 8, 1999, Pages 3257-3264

  Ikken, Youssef ^a   Morales, Paloma ^a   Martínez, Adrián ^a   Marín, María L ^a   Haza, Ana Isabel ^a   Cambero, María Isabel ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Ames test; Fruits; Mutagenicity; N nitrosamines; Vegetables

Indexed keywords

ALCOHOL DERIVATIVE; ANTIMUTAGENIC AGENT; DIBUTYLNITROSAMINE; DIMETHYLNITROSAMINE; GLYCYRRHIZA; MUTAGENIC AGENT; N NITROSOPYRROLIDINE; NITROSAMINE; PIPERIDINE DERIVATIVE; PLANT EXTRACT;

AMES TEST; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; FRUIT; MUTAGEN TESTING; MUTAGENICITY; SALMONELLA TYPHIMURIUM; VEGETABLE;

ANTIMUTAGENIC AGENTS; FRUIT; MUTAGENICITY TESTS; MUTAGENS; NITROSAMINES; PLANT EXTRACTS; SALMONELLA TYPHIMURIUM; VEGETABLES;

ACTINIDIA CHINENSIS; ALLIUM CEPA; ALLIUM SATIVUM; ANANAS COMOSUS; BRASSICA OLERACEA VAR. BOTRYTIS; DAUCUS CAROTA; GLYCYRRHIZA; SALMONELLA TYPHIMURIUM; TYPHIMURIUM;

EID: 0032854344     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf990166n     Document Type: Article

References (95)

1. Agarwal, R.; Wang, Z. Y.; Mukhtar, H. Inhibition of mouse skin tumor-initiating activity of DMBA by chronic oral feeding of glycyrrhizin in drinking water. Nutr. Cancer 1991, 15, 187-193.
2. Ames, B. N.; Dietary carcinogens and anticarcinogens: oxygen radicals and degenerative diseases. Science 1983, 221, 1256-1263.
3. Ames, B. N.; McCann, J.; Yamasaki, E. Method for detecting carcinogens and mutagens with Salmonella/Mammalian microsome mutagenicity test. Mutat. Res. 1975, 31, 347-364.
4. Ames, B. N.; Shigena, M. K.; Hagen, T. M. Oxidants, antioxidants and the degenerative diseases of aging. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 7915-7922.
5. Armstrong, B.; Doll, R. Environmental factors and cancer incidence and mortality in different countries, with special reference to dietary practices. Int. J. Cancer 1975, 15, 617-624.
6. Ayanaba, A.; Alexander, M. Microbial formation of nitrosamines in vitro. Appl. Microbiol. 1973, 25, 862-864.
7. Bartsch, H.; Montesano, R. Relevance of nitrosamines to human cancer. Carcinogenesis 1984, 5, 1381-1393.
8. Bartsch, H.; Ohshima, H.; Pignatelli, B. Inhibitors of endogenous nitrosation. Mechanisms and implications in human cancer prevention. Mutat. Res. 1988, 202, 307-324.
9. Bingham, S. A. Mechanisms and experimental and epidemiological evidence relating dietary fibre (nonstarch polysaccharides) and starch to protection against large bowel cancer. Proc. Nutr. Soc. 1990, 49, 153-171.
10. Bors, W.; Werner, H.; Michel, C.; Saran, M. Flavonoids as antioxidants: determination of radical scavenging efficiencies. Methods Enzymol. 1990, 186, 343-355.
11. Bresnick, E.; Birt, D. P.; Wolterman, K.; Wheeler, M.; Markin, R. S. Reduction in mammary tumorigenesis in the rat by cabbage and cabbage residue. Carcinogenesis 1990, 11, 1159-1163.
12. Bronzetti, G. Antimutagens in food. Trends Food Sci. Technol. 1994, 5, 390-395.
13. Cozzi, R.; Ricordy, R.; Aglitti, T.; Gatta, V.; Perticone, P.; De Salvia, R. Ascorbic acid and β-carotene as modulators of oxidative damage. Carcinogenesis 1997, 18 (1), 223-228.
14. Demizu, S.; Kajiyama, K.; Takahashi, K.; Hiraga, Y.; Yamamoto, S.; Tamura, Y.; Okada, K.; Kinoshita, T. Antioxidant and antimicrobial constituents of licorice. Chem. Pharm. Bull. 1988, 36, 3474-3479.
15. Dion, M. E.; Agler, M.; Milner, J. A. S-allyl cysteine inhibits nitrosomorpholine formation and bioactivation. Nutr. Cancer 1997, 28 (1), 1-6.
16. Doll, R.; Peto, R. The causes of cancer: quantitative estimates of avoidable risks of cancer in the United States today. J. Natl. Cancer Inst. 1981, 66, 1191-1308.
17. Dorant, E.; van den Brandt, P. A.; Goldbohm, R. A. Allium vegetable consumption, garlic supplement intake, and female breast carcinoma incidence. Breast Cancer Res. Treat. 1995, 33, 163-170.
18. Dragsted, L. O.; Strube, M.; Larsen, J. C. Cancer-protective factors in fruits and vegetables: biochemical and biological background. Pharmacol. Toxicol. 1993, 72 (Suppl. 1), 116-135.
19. Duax, W. L.; Ghosh, D. Structure and function of steroid dehydrogenases involved in hypertension, fertility, and cancer. Steroids 1997, 62, 95-100.
20. Duthie, S. J.; Ma, A.; Ross, M. A.; Collins, A. R. Antioxidant supplementation decreases oxidative DNA damage in human lymphocytes. Cancer Res. 1996, 56 (6), 1291-1295.
21. Edenharder, R.; Kurz, P.; John, K.; Burgard, S.; Seeger, K. In vitro effect of vegetable and fruit juices on the mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline, 2-amino-3,4-dimethylimidazo[4,5-f]quinoline and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline. Food Chem. Toxicol. 1994, 32 (5), 453-459.
22. Ernst, E. Can Allium vegetables prevent cancer? Phytomedicine 1997, 4, 79-83.
23. Fenwick, G. R.; Lutomski, L.; Nieman, C. Liquorice, Glycyrrhiza glabra L. composition, uses and analysis. Food Chem. 1990, 38, 119-143.
24. Ferguson, L. R. Antimutagens as cancer chemopreventive agents in the diet. Mutat. Res. 1994, 307 (1), 395-410.
25. Frohlich, R. H.; Kunze, M.; Kiefer, I. Cancer preventive impact of naturally occurring, nonnutritive constituents in food. Acta Med. Aus. 1997, 96 (10), 1027-1039.
26. Gangolli, S. D.; Phillips, J. C. Carcinogenic NA: Absorption and metabolic activation. In Food Toxicology-Real or Imaginary Problems?; Gibson, G. G., Walker, R., Eds.; Taylor and Francis: London, 1985; pp 137-151.
27. Gey, K. F. The antioxidant hypothesis of cardiovascula disease: epidemiology and mechanisms. Biochem. Soc. Trans. 1990, 18, 1041-1045.
28. Gordon, M. H.; An, J. Antioxidant activity of flavonoids isolated from licorice. J. Agric. Food Chem. 1995, 43, 1784-1788.
29. Hanasaky, Y.; Ogawa, S.; Fukui, S. The correlation between active oxygen scavenging and antioxidative effects of flavonoids. Free Radical Biol. Med. 1994, 16, 845-850.
30. Hatono, S.; Jimenez, A.; Wargovich, M. J. Chemopreventive effect of S-allylcysteine and its relationship to the detoxification enzyme glutathione S-transferase. Carcinogenesis 1996, 17 (S), 1041-1044.
31. Havery, D. C.; Fazio, T. Human exposure to nitrosamines from foods. Food Technol. 1985, 39 (1), 80-83.
32. Heiser, M. A.; Hotchkiss, J. H.; Roe, D. A. Temporal influence of ascorbic acid dose on the endogenous formation of AT-nitrosoproline and N-nitrosothiazolidine-4-carboxylic acid in humans. J. Nutr. Biochem. 1991, 2, 268-273.
33. Helser, M. A.; Hotchkiss, J. H.; Roe, D. A. Influence of fruit and vegetable juices on the endogenous formation of N-nitrosoproline and N-nitrosothiazolidine-4-carboxylic acid in humans on controlled diets. Carcinogenesis 1992, 13 (12), 2277-2280.
34. Hotchkiss, J. A review of current literature on N-NC in foods. Adv. Food Res. 1987, 31, 53-115.
35. Ikken, Y.; Cambero, I.; Marin, M. L.; Martínez, A.; Haza, A. I.; Morales, P. Antimutagenic effect of fruit and vegetable aqueous extracts against N-Nitrosamines evaluated by the Ames test. J. Agric. Food Chem. 1998a, 46, 5194-5200.
36. Ikken, Y.; Morales, P.; Martínez, A.; Marin, M. L.; Haza, A. I.; Cambero, M. I. Mutagenic Activity of N-Nitrosamines evaluated by the Ames test when using different levels of lyophilized and frozen 89 fraction. Arch. Lebensmittelhyg. 1998b, 49, 35-38.
37. Ip, C.; Lisk, D. J. Enrichment of selenium in allium vegetables for cancer prevention. Carcinogenesis 1994, 15, 1881-1885,
38. Ishiwata, H.; Boriboon, P.; Nakamura, Y.; Harada, M.; Tanimura, A.; Ishidate, M. Studies on in vitro formation of nitroso compounds (2). Changes of nitrite and nitrate concentrations in human saliva after ingestion of vegetables or sodium nitrate. J. Food Hyg. Soc. 1975, 16, 19-21.
39. Ishikawa, K.; Naganawa, R.; Yoshida, H.; Iwata, N.; Fukuda, H.; Fujino, T.; Suzuki, A. Antimutagenic effect of ajoene, an organosulfur compound derived from garlic. Biosci. Biotech. Biochem. 1996, 60 (12), 2086-2088.
40. Kada, T.; Morita, K.; Inoue, T. Antimutagenic action of vegetable factor(s) on the mutagenic principle of tryptophan pyrolysate. Mutat. Res. 1978, 53, 351-353.
41. Knasmuller, S.; Friesen, M. D.; Holme, J. A.; Alexander, J.; Sanyal, R.; Kassie, F.; Barstsch, H. Effects of phenethyl isothiocyanate on metabolism and on genotoxicity of dimethylnitrosamine and 2-amino-1-methyl-6-phenylimidazo-[4,5-beta]pyridine (PhIP). Mutat. Res. 1996, 350 (1), 93-102.
42. Kobayashi, S.; Miyamoto, T.; Kimura, I.; Kimura, M. Inhibitory effect of issoliquiritin, a compound in licorice root, on angiogenesis in vivo and tube formation in vitro. Biol. Pharm. Bull. 1998, 18, 1382-1386.
43. Lea, M. A. Organosulfur compounds and cancer. Adv. Exp. Med. Biol. 1996, 401, 147-154.
44. Leaf, C. D.; Vecchio, A. J.; Roe, D. A.; Hotchkiss, J. H. Influence of ascorbic acid dose on N-nitrosoproline formation in humans. Carcinogenesis 1987, 8, 791-796.
45. Lijinsky, W. Chemistry and Biology of N-Nitroso Compounds; Cambridge University Press: Cambridge, U.K., 1992.
46. Lin, X.; Liu, J.; Wu, K. The blocking effect of garlic on the mold mediated formation of N-nitrosamines. Acta Nutr. Sin. 1986, 8, 262-265.
47. Liu, J.; Lin, R. I.; Milner, J. A. Inhibition of 7,12-dimethylbenz-[α]anthracene-induced mammary tumors and DNA adducts by garlic powder. Carcinogenesis 1992, 13 (10), 1847-1851.
48. Liu, J.; Lin, X.; Peng, S.; Song, P.; Hu, J. The blocking effect of garlic extract on the in vitro formation of N-nitrosamines. Acta Nutr. Sin. 1986, 8, 9-14.
49. Malaveille, C.; Hantefenille, A.; Pignatelli, B.; Talaska, G.; Vineis, P.; Bartsch, H. Dietary phenolics as antimutagens and inhibitors of tobacco-related DNA adduction in the urothelium of smokers. Carcinogenesis 1996, 17 (10), 2193-2200.
50. Maltzman, T. H.; Hurt, L. M.; Elson, C. E.; Tanner, M. A.; Gould, M. N. The prevention of nitrosomethylurea-induced mammary tumors by D-limonene and orange oil. Carcinogenesis 1989, 10, 781-783.
51. Maron, D. M.; Ames, B. N. Revised methods for Salmonella mutagenicity test. Mutat. Res. 1983, 113, 173-215.
52. Martínez, A.; Cambero, I.; Ikken, Y.; Marin, M. L.; Haza, A. I.; Morales, P. Protective effect of broccoli, Onion, Carrot, and Licorice Extracts against Cytotoxicity of N-Nitrosamines Evaluated by 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium Bromide Assay. J. Agric. Food Chem. 1998, 46, 585-589.
53. Martínez, A.; Ikken, Y.; Cambero, I.; Haza, A. I.; Marin, M. L.; Casas, C.; Morales, P. Mutagenicity and cytotoxicity of some fruits and vegetables in the Ames test and the MTT cell culture assay. Food Sci. Technol. Int. 1999b, in press.
54. Martínez, A.; Marin, M. L.; Cambero, I.; Ikken, Y.; Haza, A. I.; Morales, P. Protective effect of broccoli, onion, carrot, and licorice extracts against cytotoxicity of N-Nitrosamines evaluated by 5-bromo-2′-deoxy-uridine (BrdU) and determination of total cellular DNA content. Food Chem. Toxicol. 1999a, submitted for publication.
55. Mei, X.; Lin, X.; Liu, J.; Lin, R. I.; Song, P.; Hu, J.; Liang, X. The blocking effect of garlic on the formation of N-nitrosoproline in humans. Acta Nutr. Sin. 1989, 11, 141-145.
56. Mei, X.; Wang, M. L.; Han, N. Garlic and gastric cancer II - The inhibitory effect of garlic on the growth of nitrate reducing bacteria and on the production of nitrite. Acta Nutr. Sin. 1985, 7, 173-176.
57. Mirvish, S. S. Formation of N-nitrosocompounds: chemistry, kinetics, and in vivo occurrence. Toxicol. Appl. Pharmacol. 1975, 31, 325-351.
58. Mirvish, S. S. The etiology of gastric cancer. Intragastric nitrosoamide formation and other theories. J. Natl. Cancer Inst. 1983, 71, 630-647.
59. Newmark, H. L. A hypothesis of dietary components as a blocking agent of chemical carcinogenesis, plant phenolics and pyrrole pigments. Nutr. Cancer 1984, 6, 58-70.
60. Ohshima, H.; Bartsch, H. Quantitative estimation of endogenous nitrosation in humans by monitoring N-nitrosoproline excreted in the urine. Cancer Res. 1981, 41, 3658-3662.
61. Okuda, K.; Tamura, Y.; Yamamoto, M.; Lnoue, Y.; Takagaki, R.; Takahashi, K.; Demizu, S.; Kajiyama, K.; Hiraga, Y.; Kinoshita, T. Identification of antimicrobial and antioxidant constituents from licorice of Russian and Xinjing origin. Chem. Pharm. Bull. 1989, 37, 2528-2530.
62. Österdahl, B.-G. Occurrence of and exposure to N-nitrosamines in Sweden: A Review. IAAC 1991, 235-237.
63. PoolZobel, B. L.; Bub, A.; Muller, H.; Wollowski, I.; Rechkemmer, G. Consumption of vegetables reduces genetic damage in humans: first results of a human intervention trial with carotenoid-rich foods. Carcinogenesis 1997, 18 (9), 1847-1850.
64. Potter, J. D. β-carotene and the role of intervention studies. Cancer Lett. 1997, 114 (1-2), 329-331.
65. Potter, J. D.; Steimmetz, K. Vegetables, fruit and phytoestrogens as preventive agents. IARC Sci. Publ. 1996, 139, 61-90.
66. Rao, A. R.; Sadhana, A. S.; Goel, H. C. Inhibition of skin tumors in DMBA-induced complete carcinogenesis system in mice by garlic (Allium sativum). Indian J. Exp. Biol. 1990, 28, 405-408.
67. Riboli, E.; Slimani, N.; Kaaks, R. Identifiability of food components for cancer prevention. IARC Sci. Publ. 1996, 139, 23-31.
68. Sander, J. Nitrosaminsynthese durch Bakterien. Z. Physiol. Chem. 1968, 349, 429-432.
69. Scanlan, R. A. Formation and occurrence of nitrosamines in food. Cancer Res. 1983, 43 (5), 2435-2440.
70. Shenoy, N. R.; Choughuley, A. S. Inhibitory effect of diet related sulphydryl compounds on the formation of carcinogenic nitrosamines. Cancer Lett. 1992, 65, 227-232.
71. Soni, K. B.; Lahiri, M.; Chackradeo, P.; Bhide, S. V.; Kuttan, R. Protective effect of food additives on aflatoxin-induced mutagenicity and hepatocarcinogenicity. Cancer Lett. 1997, 115 (2), 129-133.
72. Sparnins, V. L.; Mott, A. W.; Barany, G.; Wattenberg, L. W. Effect of allyl methyl trisulfide on glutathione S-transferase activity and benzopyrene-induced neoplasia in the mouse. Nutr. Cancer. 1986, 8, 211-215.
73. Steinberg, D. Antioxidants and atherosclerosis: acurrent assessment. Circulation 1991, 84, 1420-1425.
74. Steinberg, D.; Parthasarathy, S.; Carew, T. E.; Khoo, J. C.; Witztum, J. L. Beyond cholesterol: modification of low-density lipoprotein that increase its atherogenicity. New Engl. J. Med. 1989, 320, 915-924.
75. Stoewsand, G. S.; Anderson, L. J.; Munson, L.; Lisk, D. J. Effect of dietary Brussels sprouts with increased selenium content on mammary carcinogenesis in the rat. Cancer Lett. 1989, 45, 43-48.
76. Sumiyoshi, H.; Wargovich, M. J. Chemoprevention of 1,2-dimethylhydrazine-induced colon cancer in mice by natural occurring organosulfur compounds. Cancer Res. 1990, 50, 5084-5087.
77. Surh, Y. J.; Lee, R. C.; Park, K. K.; Mayne, S. T.; Liem, A.; Miller, J. A. Chemoprotective effects of capsaicin and diallyl sulfide against mutagenesis or tumorigenesis by vinyl carbamate and N-nitrosodimethylamine. Carcinogenesis 1995, 16 (10), 2467-2471.
78. Tang, X.; Edenharder, R. Inhibition of the mutagenicity of 2-nitrofluorene, 3-nitrofluoranthene and 1-nitropyrene by vitamins, porphyrins and related compounds, and vegetables and fruit juices and solvent extracts. Food Chem. Toxicol. 1997, 35 (3-4), 373-378.
79. Teel, R. W.; Castonguay, A. Antimutagenis effects of polyphenolic compounds. Cancer Lett. 1992, 66, 107-113.
80. Tsai, S. J.; Jenq, S. N.; Lee, H. Naturally occurring diallyl disulfide inhibits the formation of carcinogenic heterocyclic aromatic amines in boiled pork juice. Mutagenesis 1996, 11 (3), 235-240.
81. Unnikrishnan, M. C.; Kuttan, R. Tumor reducing and anti-carcinogenic activity of selected spices. Cancer Lett. 1990, 51, 85-89.
82. USDA. Agriculture Handbook 8, Composition of foods; U.S. Government Printing office: Washington, DC, 1986.
83. van Poppel, G. Epidemiological evidence for β-carotene in prevention of cancer and cardiovascular disease. Eur. J. Clin. Nutr. 1996, 50, S57-61.
84. Verhoeven, D. T.; Goldbohm, R A.; van Poppel, G.; Verhagen, H.; van den Brandt, P. A. Epidemiological studies on brassica vegetables and cancer risk. Cancer Epidemiol. Biomark. Prevent. 1996, 5 (9), 733-748.
85. Verhoeven, D. T.; Verhagen, H.; Goldbohm, R. A.; van den Brandt, P. A.; van Poppel, G. A review of mechanisms underlying anticamnogenicity by brassica vegetables. Chem. Biol. Interact. 1997, 103, 79-129.
86. Wallum, E.; Stenberg, K.; Jenssen, D. Understanding cell toxicology, principles and practice; Ellis Horwood: Chichester, U.K., 1990.
87. Wanasundara, U. N.; Shahidi, F. Stabilization of canola oil with flavonoids. Food Chem. 1994, 50, 393-396.
88. Wang, H.; Cao, G.; Prior, R. L. Total antioxidant capacity of fruits. J. Agric. Food Chem. 1996, 44, 701-705.
89. Wang, Z. Y.; Agarwal, R.; Zhou, Z. C.; Bickers, D. R.; Mukhtar, H. Inhibition of mutagenicity in Salmonella typhimurium and skin tumor initiating and tumor promoting activities in SENCAR mice by glycyrrhetinic acid: comparison of 18 alpha- and 18 beta-steroisomers. Carcinogenesis 1991, 12 (2), 187-192.
90. Wargovich, M. J.; Woods, C.; Eng, V. W. S.; Stephens, L. C.; Gray, K. N. Chemoprevention of nitrosomethylbenzylamine-induced esophageal cancer in rats by the thioether, diallyl sulfide. Cancer Res. 1988, 48, 6872-6875.
91. Wattenberg, L. W. Inhibition of neoplasia by minor dietary constituents. Cancer Res. 1983, 43, 2448-2453.
92. Wattenberg, L. W.; Coccia, J. B. Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone Carcinogenesis in mice by D-limonene and citrus fruit oils. Carcinogenesis 1991, 12, 115-117.
93. Willet, C. W. Diet and health: what should we eat? Science 1994, 264, 532-537.
94. Yen, G.-C.; Duh, P.-D. Antimutagenic effect of methanolic extracts from peanut hulls. Biosci. Biotech. Biochem. 1996, 60 (10), 1698-1700.
95. You, W. C.; Blot, W. J.; Chang, Y. S.; Ershow, A. G.; Yang, Z. T.; An, Q.; Henderson, B.; Xu, G. W.; Fraumeni, J. F.; Wang, T. G. Allium vegetables and reduced risk of stomach cancer. J. Natl. Cancer Inst. 1989, 81, 162-164.