Recent results in the organosulfur and organoselenium chemistry of genus Allium and Brassica plants: Relevance for cancer prevention

Advances in Experimental Medicine and Biology

Volumn 401, Issue , 1996, Pages 155-163

  Block, Eric ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHANESULFINOTHIOIC ACID S ETHYL ESTER; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE; ORGANOSELENIUM DERIVATIVE; ORGANOSULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; BRASSICA; CANCER INHIBITION; CANCER PREVENTION; CONFERENCE PAPER; GARLIC; NONHUMAN; PRIORITY JOURNAL;

ALLIUM; ALLIUM SATIVUM; BRASSICA;

EID: 0029836409     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4613-0399-2_13     Document Type: Conference Paper

References (77)

1. Weisberger, A.S. and J. Pensky, Tumor-inhibiting effects derived from an active principle of garlic (Allium sativum), Science 126:1112 (1957).
2. You, W.C., W.J. Blot, Y.S. Chang, A. Ershow, Z.T. Yang, Q. An, B.E. Henderson, J.F. Fraumeni Jr., and T.G. Wang, Allium vegetables and reduced risk of stomach cancer. J. Natl. Cancer Inst. 81:162 (1989).
3. Reuter, H.D. and H.P. Koch. Therapeutic effects and applications of garlic and its preparations, in "Garlic: The Science and Therapeutic Applications of Allium sativum L. and Related Species;" H.P. Koch and L.D. Lawson, ed.; Williams and Wilkins, Baltimore, (1995).
4. Steinmetz, K.A., L.H. Kushi, R.M. Bostick, A.R. Folsom, and J.D. Potter, Vegetables, fruit, and colon cancer in the Iowa's Women's Health Study, Am. J. Epidemiol. 139:1 (1994).
5. Mei, X., M.C. Wang, H.X. Xu, X.P. Pan, C.Y. Gao, N. Han, and M.Y. Fu, Garlic and gastric cancer: The effect of garlic on nitrite and nitrate in gastric juice, Acta Nutrimenta Sinica 4:53 (1982).
6. Ip, C., D.J. Lisk, and G.S. Stoewsand, Mammary cancer prevention by regular garlic and selenium-enriched garlic, Nutr. Cancer 17:279 (1992).
7. Ip, C. and D. Lisk, Bioavailability of selenium from selenium-enriched garlic. Nutr. Cancer 20:129 (1993).
8. Ip, C. and D. Lisk, Enrichment of selenium in allium vegetables for cancer prevention. Carcinogenesis 15:1881 (1994).
9. Gebhardt, R., H. Beck, and K.G. Wagner, Inhibition of cholesterol biosynthesis by allicin and ajoene in rat hepatocytes and DepG2 cells, Biochim. Biophys. Acta 1213:57 (1994).
10. Hong, J.Y.; T. Smith, M.J. Lee, W.S. Li, B.L. Ma, S.M. Ning, J.F. Brady, P.E. Thomas, and Yang, C.S., Metabolism of carcinogenic nitrosamines by rat nasal mucosa and the effect of diallyl sulfide, Cancer Res. 51:1509 (1991).
11. Block, E., The organosulfur chemistry of the genus Allium - Implications for the organic chemistry of sulfur. Angew. Chem., Int. Ed. Engl. 31:1135 (1992).
12. Morris, V.C. and O.A. Levander, Selenium content of foods, J. Nutr. 100:1383 (1970).
13. C.-G. Spare and A.I. Virtanen, On the occurrence of free selenium-containing amino acids in onion (Allium Cepa), Acta Chem. Scand. 18: 280 (1964).
14. Young, V.R., Selenium: A case for its essentiality in man, N. Engl. J. Med. 304: 1228 (1981).
15. Sathe, S.K., A.C. Mason, R. Rodibaugh, and C.M. Weaver, Chemical form of selenium in soybean (Glycine max L.) lectin, J. Agric. Food Chem. 40:2084 (1992).
16. Axley, M.J., A. Böck, and T.C. Stadtman, Catalytic properties of an Escherichia coli formate dehydrogenase mutant in which sulfur replaces selenium. Proc. Natl. Acad. Sci. U.S.A. 88:8450 (1991).
17. Söll, D., Enter a new amino acid, Nature 331:662 (1988).
18. Burk, R.F., and K.E. Hill, and Selenoprotein P. A selenium-rich extracellular glycoprotein, J. Nutr. 124:1891 (1994).
19. Wang, W., J. Tang, and A. Peng, The isolation, identification and bioactivities of selenoproteins in selenium-rich garlic.Shengwu Huaxue Zazhi 5:229 (1989) [Chem. Abstr. 111:95847d (1989)].
20. Wang, W., J. Tang, and A. Peng, The isolation, identification and bioactivities of selenoproteins in selenium-rich garlic.Shengwu Huaxue Zazhi 5:229 (1989) [Chem. Abstr. 111:95847d (1989)].
21. Yang, M., K. Wang, L. Gao, Y. Han, J. Lu, and T. Zou, Exploration for a natural seleni- um supplement - characterization and bioactivities of Se-containing polysaccharide from garlic. J. Chin. Pharm. Sci. 1:28 (1992) [Chem. Abstr. 118:77092u (1993)].
22. Yang, M., K. Wang, L. Gao, Y. Han, J. Lu, and T. Zou, Exploration for a natural seleni- um supplement - characterization and bioactivities of Se-containing polysaccharide from garlic. J. Chin. Pharm. Sci. 1:28 (1992) [Chem. Abstr. 118:77092u (1993)].
23. Bañuelos, G.S., D. Dyer, R. Ahmad, S. Ismail, R.N. Raut, and J.C. Dagar, In search of Brassica germplasm in saline semiarid and arid regions of India and Pakistan for reclamation of selenium-laden soils in the U.S., J. Soil Water Cons. 48:530 (1993).
24. Hamilton, J.W., Chemical examination of seleniferous cabbage Brassica oleracea capitata, J. Agric. Food Chem. 23:1150 (1975).
25. Uden, P.C., Atomic specific chromatographic detection: An overview, in "Element- Specific Chromatographic Detection by Atomic Emission Spectroscopy," ACS Symp. Ser. 479, American Chemical Society, Washington, DC, 1992.
26. Cai, X.-J., P.C. Uden, J.J. Sullivan, B.D. Quimby, and E. Block, Headspace-gas chromatography with atomic emission and mass selective detection for the determination of organoselenium compounds in elephant garlic., Anal. Proc., 31:325 (1994).
27. Cai, X.-J., P.C. Uden, E. Block, X. Zhang, B.D. Quimby, and J.J. Sullivan, Allium chemistry: Identification of natural abundance organoselenium volatiles from garlic, elephant garlic, onion, and Chinese chive using headspace gas chromatography with atomic emission detection, J. Agric. Food Chem. 42:2081 (1994).
28. Deruaz, D., F. Soussan-Marchal, I. Joseph, M. Desage, A. Bannier, and J.L. Brazier, Analytical strategy by coupling headspace gas chromatography, atomic emission spectrometric detection and mass spectrometry. Application to sulfur compounds from garlic. J. Chromatogr. A. 677:345 (1994).
29. Ryan, M.D. and D. Harpp, The first selenium transfer reagent: Preparation, and mechanism of formation, Tetrahedron Lett. 33:2129 (1992).
30. Potapov, V.A., S.V. Amosova, P.A. Petrov, L.S. Romanenko, and V.V. Keiko, Exchange reactions of dialkyl dichalcogenides, Sulfur Lett. 15:121 (1992).
31. Soda, K., H. Tanaka, and N. Esaki, Biochemistry of physiologically active selenium compounds, in "The Chemistry of Organic Selenium and Tellurium Compounds" (ed. S. Patai), Vol. 2, (John Wiley, Chichester, 1987).
32. Evans, C.S., C.J. Asher, and C.M. Johnson, Isolation of dimethyl diselenide and other volatile selenium compounds from Astragalus racemosus (Pursh.). Aust. J. Biol. Sci. 21:13(1968).
33. Chasteen, T.G., G.M. Silver, J.W. Birks, and R. Fall, Fluorine-induced chemiluminescence detection of phosphine, alkyl phosphines and monophosphinate esters. Chromatographia 30:181 (1990).
34. Chasteen, T.G. Confusion between dimethyl selenenyl sulfide and dimethyl selenone released by bacteria. Appl. Organomet. Chem. 7:335 (1993).
35. Husek, P., Rapid derivatization and gas chromatographic determination of amino acids, J. Chromatogr. 552:289 (1991).
36. Wang, J., Z.-H. Huang, D.A. Gage, and J.T. Watson, Analysis of amino acids by gas chromatography-flame ionization detection and gas chromatography-MS: simultaneous derivatization of functional groups by an aqueous phase chloroformate-mediated reaction.J. Chromatogr. A 663:71 (1994).
37. Janák, J., H.A.H. Billiet, J. Frank, K.C.A.M. Luyben, and P. Husek, Separation of selenium analogues of sulphur-containing amino acids by high performance liquid chromatography and high resolution gas chromatography, J. Chromatogr. A 677:192 (1994).
38. Cai, X.-J., E. Block, P.C. Uden, X. Zhang, B.D. Quimby, and J.J. Sullivan, Allium chemistry: identification of selenoamino acids in ordinary and selenium-enriched garlic, onion and broccoli using gas chromatography with atomic emission detection. J. Agric. Food Chem., 43:1754 (1995).
39. Marks, H.S., J.A. Hilson, H.C. Leichtweis, and G.S. Stoewsand, S-Methylcysteine sulfoxide in Brassica vegetables and formation of methyl methanethiosulfinate from Brussels sprouts, J. Agric. Food Chem. 40:2098 (1992).
40. Vadhanavikit, S., C. Ip, and H.E. Ganther, Metabolites of sodium selenite and methylated selenium compounds administered at cancer chemoprevention levels in the rat. Xenobiotica 23:731 (1993).
41. 3-N bond cleavage of 2-amino-3- (N-substituted-amino)propionic acids catalyzed by L-methionine γ-lyase, Agric. Biol. Chem. 52:2897 (1988).
42. Kamitani, H., N. Esaki, H. Tanaka, and K. Soda, Thermostable S-alkylcysteine α,β-lyase from a thermophile: purification and properties, Agric. Biol. Chem. 54:2069 (1990).
43. Cai, X.-J., E. Block, P.C. Uden, B.D. Quimby, and J.J. Sullivan, Allium chemistry: identification of natural abundance organoselenium compounds in human breath after ingestion of garlic using gas chromatography with atomic emission detection, J. Agric. Food Chem. 43:1751 (1995).
44. Ruth, J.H. Odor thresholds and irritation levels of several chemical substances: A review, Am. Ind. Hyg. Assoc. J. 47:A142 (1986).
45. Buchan, R.F., Garlic breath odor, JAMA 227:559 (1974).
46. Ballard-Barbash, R., S. Krebs-Smith, and A.F. Subar, Re: Vegetables, fruit, and colon cancer in the Iowa's Women's Health Study, Am. J. Epidemiol. 141:84 (1995).
47. Dorant, E., P.A. van den Brandt, and R.A. Goldbohm, A prospective cohort study on AIlium vegetable consumption, garlic supplement use, and the risk of lung carcinoma in the Netherlands, Cancer Res. 54: 6148 (1994).
48. Dorant, E., P.A. van den Brandt, and R.A. Goldbohm, Allium vegetable consumption, garlic supplement intake and female breast carcinoma incidence, Breast Cancer Research and Treatment 33:163 (1995).
49. Dorant, E., P.A. van den Brandt, R.A. Goldbohm. R.J.J. Hermus, and F. Sturmans, Garlic and its significance for the prevention of cancer in humans: A critical view, British Journal of Cancer 67:424 (1993).
50. Shenoy, N.R., and A.S.U. Choughuley, Inhibitory effect of diet related sulphydryl compounds on the formation of carcinogenic nitrosamines, Cancer Lett. 65:227 (1992).
51. Takada, N., T. Matsuda, T. Otoshi, Y. Yano, S. Otani, T. Hasegawa, D. Nakae, Y. Konishi, and S. Fukushima, Enhancement by organosulfur compounds from garlic and onion of diethylnitrosamine-induced glutathione S-transferase positive foci in the rat liver, Cancer Res. 54:2895 (1994).
52. Scharfenberg, K., R. Wagner, and K.G. Wagner, The cytotoxic effect of ajoene, a natural product from garlic, investigated with different cell lines, Cancer Letters 53:103 (1990).
53. Marks, H.S.; J.A. Anderson, and G.S. Stoewsand, Effect of S-methyl cysteine sulphoxide and its metabolite methyl methanethiosulfinate, both occurring naturally in Brassica vegetables, on mouse genotoxicity, Food Chem. Toxicol. 31:491 (1993).
54. Sundaram, S.G., and J.A. Milner, Organosulfur compounds in processed garlic alter the in vitro growth of human tumor cell lines, FASEB J. 8:A426 (1994).
55. Sundaram, S.G., and J.A. Milner, Diallyl disulfide present in garlic oil inhibits both in vitro and in vivo growth of human colon tumor cells, FASEB J. 9:A869 (1995).
56. Ip, C. 1995, personal communication.
57. El Bayoumy, K., C. Ip, Y.H. Chae, P. Upadhyaya, D. Lisk, and B. Prokopczyk, Mammary cancer prevention by diallyl selenide, a novel organoselenium compound, Proc. Am. Assoc. Cancer Res. 34:A3322 (1993).
58. Sparnins, V.L., A.W. Mott, and L.W. Wattenberg, Effects of allyl methyl trisulfide on glutathione S-transferase activity and PB-induced neoplasia in the mouse, Nutr. Cancer 8:211 (1986).
59. Sparnins, V.L., G. Barany, and L.W. Wattenberg, Effects of organosulfur compounds from garlic and onions on benzo[a]pyrene-induced neoplasia and glutathione S-transferase activity in the mouse, Carcinogenesis 9:131-4 (1988).
60. Feng, Z.H., G.M. Zhang, T.L. Hao, B. Zhou, H. Zhang, and Z.Y. Jiang, Effect of diallyl trisulfide on the activation of T cell and macrophage-mediated cytotoxicity, J. Tongji Med. Univ. 14:142 (1994).
61. Sundaram, S.G., and J.A. Milner, Impact of organosulfur compounds in garlic on canine mammary tumor cells in culture, Cancer Lett. 74:85 (1993).
62. Belman, S.; J. Solomon, A. Segal, E. Block, and G. Barany, Inhibition of soybean lipoxygenase and mouse skin tumor promotion by onion and garlic components, J. Biochem. Toxicol. 4:151 (1989).
63. Dwivedi, C., S. Rohlfs, D. Jarvis, and F.N. Engineer, Chemoprevention of chemically- induced skin tumor development by diallyl sulfide and diallyl disulfide, Pharm. Res. 9:1668 (1992).
64. Wargovich, M.J., and M.T. Goldberg, Diallyl sulfide: a naturally occurring thioether that inhibits carcinogen induced damage to colon epithelial cells in vivo, Mutation Res. 143:127 (1985).
65. Yang, G.C., P.M. Yasaei, and S.W. Page, Garlic as anti-oxidants and free radical scavengers, J. Food Drug. Anal. 1:357 (1993).
66. Popov, I., A. Blumstein, and G. Lewin, Antioxidant effects of aqueous garlic extracts: 1st communication: direct detection using the photochemiluminescence, Arzneimittel- Forschung 44:602 (1994).
67. ++-initiated oxidation of low density lipoproteins, Arzneimittel-Forschung 44:604 (1994).
68. Rekka, E.A., and P.N. Kourounakis, Investigation of the molecular mechanism of the antioxidant activity of some Allium sativum ingredients, Pharmazie 49:539 (1994).
69. Toeroek, B., J. Belagyi, B. Rietz, and R. Jacob, Efectiveness of garlic on the radical activity in radical generating systems, Arzneimittel-Forschung 44:608 (1994).
70. Imai, J., N. Ide, S. Nagae, T. Moriguchi, H. Matsuura, and Y. Itakura, Antioxidant and radical scavenging effects of aged garlic extract and its constituents, Planta Med. 60:417 (1994).
71. Gwilt, P.R., C.L. Lear, M.A. Tempero, D.D. Birt, A.C. Grandjean, R.W. Ruddon, and D.L. Nagel, The effect of garlic extract on human metabolism of acetaminophen, Cancer Epidemiology, Biomarkers and Prevention 3:155 (1994).
72. Yellin, S.A., B.J. Davidson, J.T. Pinto, P.G. Sacks, C. Qiao, and S.P. Schantz, Relationship of glutathione and glutathione-S-transferase to cisplatin sensitivity in human head and neck squamous carcinoma cell lines, Cancer Lett. 85:223 (1994).
73. Belman, S., A. Sellakumar, M.C. Bosland, K. Savarese, and R.D. Estensen, papilloma and carcinoma production in DMBA-initiated, onion oil-promoted mouse skin, Nutr. Cancer 14:141 (1990).
74. Hong, J.-Y., T.J. Smith, W. Huang, Y. Wang, and C.S. Yang, Enhancement of 4- (methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumorigenesis in mice by oral administration of fresh garlic homogenate, Poster Abstract 63, American Institute for Cancer Research 1995 Research Conference.
75. Klopman, G., personal communication.
76. Munday, R., and E. Manns, Comparative toxicity of prop(en)yl disulfides derived from Alliaceae: Possible involvement of 1-propenyl disulfides in onion-induced hemolytic anemia, J. Agric. Food Chem. 42: 959 (1994).
77. Herbert, V. Antioxidants, Pro-oxidants and Their Effects, JAMA 272: 1659 (1994).