Inhibition of benzo[a]pyrene-induced mouse forestomach neoplasia and reduction of H2O2 concentration in human polymorphonuclear leucocytes by flavour components of Japanese-style fermented soy sauce

Food and Chemical Toxicology

Volumn 35, Issue 5, 1997, Pages 449-457

  Kataoka, S ^a   Liu, W ^a   Albright, K ^a   Storkson, J ^a   Pariza, M ^a  

^a UNIVERSITY OF WISCONSIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; BENZO[A]PYRENE; FLAVORING AGENT; FURANONE DERIVATIVE; HYDROGEN PEROXIDE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; FEMALE; FOOD; FORESTOMACH; HUMAN; HUMAN CELL; MOUSE; NEUTROPHIL; NONHUMAN; ORAL DRUG ADMINISTRATION; STOMACH TUMOR;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZO(A)PYRENE; CELLS, CULTURED; FEMALE; FOOD ADDITIVES; FORMAMIDES; FURANS; GLUTATHIONE TRANSFERASE; HUMANS; HYDROGEN PEROXIDE; IRON; MICE; NEUTROPHILS; REACTIVE OXYGEN SPECIES; SOYBEANS; STOMACH NEOPLASMS;

EID: 0030970433     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0278-6915(97)00009-4     Document Type: Article

References (48)

1. Badwey J. A., Curnutte J. T., Robinson J. M., Berde C. B., Karnovsky M. J. and Karnovsky M. L. (1984) Effects of free fatty acids on release of superoxide and on change of shape by human neutrophils. Reversibility by albumin. Journal of Biological Chemistry 259, 7870-7877.
2. Benjamin H., Storkson J., Nagahara A. and Pariza M. W. (1991) Inhibition of benzo(a)pyrene-induced mouse forestomach neoplasia by dietary soy sauce. Cancer Research 52, 2940-2942.
3. Benjamin H., Storkson J., Tallas P. G. and Pariza M. W. (1988) Reduction of benzo[a]pyrene-induced forestomach neoplasms in mice given nitrite and dietary soy sauce. Food and Chemical Toxicology 26, 671-678.
4. 2 production and oxidative DNA damage in HeLa cells by (-).epigallocatechin gallate (EGCG). Proceedings of the American Association for Cancer Research 32, 126.
5. Fenton H. J. H. (1894) Oxidation of tartaric acid in presence of iron. Journal of the Chemical Society 65, 899-910.
6. Filipic V. J., Underwood J. C. and Willits C. O. (1965) The identification of methylcyclopentenolone and other compounds in maple syrup flavour extract. Journal of Food Science 30, 1008-1015.
7. 2 formation by activated human polymorphonuclear leucocytes. Carcinogenesis 8, 1207-1212.
8. Frenkel K., Chrzan K., Troll W., Teebor G. W. and Steinberg J. J. (1986) Radiation-like modification of bases on DNA exposed to tumour promoter-activated polymorphonuclear leucocytes. Cancer Research 46, 5533-5540.
9. Gianturco M. A. and Friedel P. (1963) The synthesis of some cyclic diketones isolated from coffee. Tetrahedron 19, 2039-2049.
10. Habig W. H., Pabst M. J. and Jakoby W. B. (1974) Glutathione S-transferase, the first enzymatic step in mercapturic acid formation. Journal of Biological Chemistry 249, 7130-7139.
11. Haenszel W. (1958) Variation in incidence of and mortality from stomach cancer, with particular reference to the United States. Journal of the National Cancer Institute 21, 213-262.
12. Halliwell B. and Gutteridge J. M. C. (1985) Free Radicals in Biology and Medicine. Clarendon Press, Oxford.
13. Harman D. (1987) The free-radical theory of ageing. In Modern Biological Theories of Ageing. Edited by H. R. Warner, R. N. Butler, R. L. Sprott and E. L. Schneider. pp. 81-87. Raven Press, New York.
14. Hashiba H. (1976) Participation of amadori rearrangement products and carbonyl compounds in oxygen-dependent brewing of soy sauce. Journal of Agricultural and Food Chemistry 24, 70-73.
15. Hicks K. B. and Feather M. S. (1975) Studies on the mechanism of formation of 4-hydroxy-5-methyl-3(2H)-furanone, a component of beef flavour, from amadori products. Journal of Agricultural and Food Chemistry 23, 957-960.
16. Heyworth P. G. and Badwey J. A. (1990) Protein phosphorylation associated with the stimulation of neutrophils. Modulation of superoxide production by protein kinase C and calcium. Journal of Bioenergetics and Biomembranes 22, 1-26.
17. Hodge J. E., Mill F. D. and Fisher B. E. (1972) Compounds of browned flavour derived from sugar-amine reactions. Cereal Science Today 17, 34-38.
18. Hodge J. E. and Nelson E. C. (1961) Preparation and properties of galactosylisomaltol and isomaltol. Cereal Chemistry 38, 207-228.
19. Honkanen E., Pyysalo T. and Hirvi T. (1980) The aroma of Finnish wild raspberries, Rubus idaeus, 1. Zeitschrift für Lebensmittel-Untersuchung und -Forschung 171, 180-182.
20. Huang M.-T., Ho C.-T., Wang Z.-Y., Ferraro T., Finnegan-Olive T., Lou Y.-R., Mitchell J. M., Laskin J. D., Newmark H., Yang C. S. and Conney A. H. (1992) Inhibitory effect of topical application of a green tea polyphenol fraction on tumour initiation and promotion in mouse skin. Carcinogenesis 13, 947-954.
21. Huang M.-T., Smart R. C., Wong C.-O. and Conney A. H. (1988) Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumour promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Cancer Research 48, 5941-5946.
22. Kharasch E. D. and Novak R. F. (1985) Mitoxantrone and ametantrone inhibit hydroperoxide-dependent initiation and propagation reactions in fatty acid peroxidation. Journal of Biological Chemistry 260, 10645-10652.
23. Kikkawa U., Takai Y., Tanaka Y., Miyake R. and Nishizuka Y. (1983) Protein kinase C as a possible receptor protein of tumour-promoting phorbol esters. Journal of Biological Chemistry 285, 11442-11445.
24. Lim J. S., Frenkel K. and Troll W. (1992) Tamoxifen suppresses tumour promoter-induced hydrogen peroxide formation by human neutrophils. Cancer Research 52, 4969-4972.
25. Lowry O. H., Rosebrough N. J., Farr A. L. and Randall R. J. (1951) Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry 193, 265-275.
26. Nagahara A., Benjamin H., Storkson J., Krewson J., Sheng K., Liu W. and Pariza M. W. (1992) Inhibition of benzo(a)pyrene-induced mouse forestomach neoplasia by a principal flavour component of Japanese-style fermented soy sauce. Cancer Research 52, 1754-1756.
27. NRC (1985) Guide for the Care and Use of Laboratory Animals. Publ. no. 85-23 (rev.). National Institutes of Health, Bethesda, MA.
28. Nilsson R., Merkel P. B. and Kearns D. R. (1972) Unambiguous evidence for the participation of singlet oxygen in photodynamic oxidation of amino acids. Photochemistry and Photobiology 16, 117-124.
29. Nunomura N., Sasaki M., Asao Y. and Yokotsuka T. (1976a) Identification of volatile components in shoyu (soy sauce) by gas chromatography-mass spectrometry. Agricultural and Biological Chemistry 40, 485-490.
30. Nunomura N., Sasaki M., Asao Y. and Yokotsuka T. (1976b) Isolation and identification of 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone, as a flavour component in Shoyu (soy sauce). Agricultural and Biological Chemistry 40, 491-495.
31. Nunomura N., Sasaki M. and Yokotsuka T. (1979) Isolation of 4-hydroxy-5-methyl-3(2H)-furanone in shoyu (soy sauce). Agricultural and Biological Chemistry 43, 1361-1363.
32. Nunomura N., Sasaki M. and Yokotsuka T. (1980) Shoyu (soy sauce) flavour components: acidic fractions and the characteristic flavour components. Agricultural and Biological Chemistry 44, 339-351.
33. Perchellet J.-P., Owen M. D., Posey T. D., Orten D. K. and Schneider B. A. (1985) Inhibitory effects of glutathione level-raising agents and D-α-tocopherol on ornithine decarboxylase induction and mouse skin tumour promotion by 12-O-tetradecanoylphorbol-13-acetate. Carcinogenesis 6, 567-573.
34. Re L., Mauere B. and Ohloff G. (1973) Ein einfacher zugang zu 4-hydroxy-2,5-dimethyl-3(2H)-furanon (furaneol), einem aromabestandteil von ananas und erdbeere. Helvetica Chimica Acta 56, 1882-1894.
35. Rodin J. O., Himel C. M., Silverstein R. M., Leeper R. W. and Gortner W. A. (1965) Volatile flavour and aroma components of pineapple. 1. Isolation and tentative identification of 2,5-dimethyl-4-hydroxy-3(2H)-furanone. Journal of Food Science 30, 280-285.
36. Sasaki M., Nunomura N. and Matsudo T. (1991) Biosynthesis of 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone by yeasts. Journal of Agricultural and Food Chemistry 39, 934-938.
37. Saul R. L., Gee P. and Ames B. N. (1987) Free radicals, DNA damage, and ageing. In Modern Biological Theories of Ageing. Edited by H. R. Warner, R. N. Butler, R. L. Sprott and E. L. Schneider. pp. 113-129. Raven Press, New York.
38. Sirak A., Beavis A.-H. and Robertson F. M. (1991) Enhanced hydroperoxide production by peripheral blood leucocytes following exposure of murine epidermis to 12-O-tetradecanoylphorbol-13-acetate. Carcinogenesis 12, 91-95.
39. Smart R. C., Huang M.-T., Han Z. T., Kaplan M. C., Focella A. and Conney A. H. (1987) Inhibition of 12-O-tetradecanoylphorbol-13-acetate induction of ornithine decarboxylase activity, DNA synthesis, and tumour promotion in mouse skin by ascorbic acid and ascorbic palmitate. Cancer Research 47, 6633-6638.
40. Suwa K., Kimura T. and Schaap A. P. (1977) Reactivity of singlet molecular oxygen with cholesterol in a phospholipid membrane matrix. A model for oxidative damage of membranes. Biochemical and Biophysical Research Communications 75, 785-792.
41. Tonsbeek C. H. T., Plancken A. J. and Weerdhof T. (1968) Components contributing to beef flavour: isolation of 4-hydroxy-5-methyl-3(2H)-furanone and its 2,5-dimethyl homolog from beef broth. Journal of Agricultural and Food Chemistry 16, 1016-1021.
42. Tsen C. C. (1961) An improved spectrophotometric method for the determination of tocopherols using 4-7-diphenyl-1,10-phenanthroline. Analytical Chemistry 33, 849-851.
43. Wakabayashi K., Ochiai M., Saito H., Tsuda M., Suwa Y., Nagao M. and Sugimura T. (1983) Presence of 1-methyl-1,2,3,4-tetrahydro-3-carboxylic acid, a precursor of a mutagenic nitroso compound, in soy sauce. Proceedings of the National Academy of Sciences of the U.S.A. 80, 2912-2916.
44. Wattenberg L. W. (1993) Prevention-therapy-basic science on the resolution of the cancer problem: Presidential Address. Cancer Research 53, 5890-5896.
45. Wei H. and Frenkel K. (1992a) Relationship of oxidative events and DNA damage to in vivo tumour promoting activity. Proceedings of the American Association for Cancer Research 33, 179.
46. Wei H. and Frenkel K. (1992b) Suppression of tumour promoter-induced oxidative events and DNA damage in vivo by sarcophytol A: a possible mechanism of anti-promotion. Cancer Research 52, 2298-2303.
47. Witz G., Goldstein B. D., Amoruso M., Stone D. S. and Troll W. (1980) Retinoid inhibition of superoxide anion radical production by human polymorphe-nuclear leucocytes stimulated with tumour promoter. Biochemical and Biophysical Research Communications 97, 883-888.
48. Yokotsuka T., Sasaki M., Nunomura N. and Asao Y. (1980) Flavour constituents in soy sauce (in Japanese). Nippon Zyozokyokai Shi 75, 717-728.