Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by phenolic plant flavonoids

Carcinogenesis

Volumn 4, Issue 12, 1983, Pages 1631-1637

  Huang, Mou Tuan ^a   Wood, Alexander W ^a   Newmark, Harold L ^a   Sayer, Jane M ^b   Yagi, Haruhiko ^b   Jerina, Donald M ^b   Conney, Allan H ^a  

^a Hoffmann La Roche ^*  (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOHIPPURIC ACID; DIOL EPOXIDE; FLAVONOID; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL MODEL; ETIOLOGY; HEREDITY; HIGHER PLANT; MUTAGENESIS; NONHUMAN; PLANT;

ANIMALS; BIOTRANSFORMATION; FLAVONOIDS; HISTIDINE; LUTEOLIN; MICROSOMES, LIVER; MUTAGENS; MUTATION; PLANTS, MEDICINAL; POLYCYCLIC COMPOUNDS; RATS; SALMONELLA TYPHIMURIUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0021052055     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/4.12.1631     Document Type: Article

References (39)

1. Locki, P.G., Wood, A.W., Chang, R.L., Levin, W., and Conney, A.H. (1976), Mutagenicity of benzo[a]pyrene derivatives and the description of a quantum mechanical model which predicts the ease of carbonium ion formation from diol epoxides, in de Serres.F.J., Fouts.J.R., Bend.J.R. and Philpot.R.M. (eds.), Metabolic Activation in Mutagenesis Testing, ElsevierNorth Holland Biomedical Press, Amsterdam, pp. 159-177.
2. Conney, A.H. (1982), Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G.H.A.Clowes Memorial Lecture, Cancer Res., 42, 4875-4917.
3. Dipple, A., Moschel, R.C., and Bigger, C.A.H. (1983), Polynuclear aromatic carcinogens, in Searle.C.E. (ed.), Chemical Carcinogens (Revised), American Chemical Society, Washington, DC, in press.
4. Sims, P., and Grover, P.L. (1981), Involvement of dihydrodiols and diol epoxides in the metabolic activation of polycyclic hydrocarbons other than benzo[a]pyrene, in Gelboin.H.V. and Ts’O.P.O.P. (eds.), Polycyclic Hydrocarbons and Cancer, Vol. 3, Academic Press, New York, pp. 117-181.
5. Kapitulnik, J., Wislocki, P.G., Levin, W., Yagi, H., Jerina, D.M., and Conney, A.H. (1978), Tumorigenicity studies with diol-epoxides of benzo[a]pyrene which indicate that (±)-r<7ts-73, 8a-dihydroxy 9a, 10a-epoxy-7, 8, 9, 10-tetra- hydrobenzo[a]pyrene is an ultimate carcinogen in newborn mice, Cancer Res., 38, 354-358.
6. Nordqvist, M., Thakker, D.R., Yagi, H., Lehr, R.E., Wood, A.W., Levin, W., Conney, A.H., and Jerina, D.M. (1980), Evidence in support of the bay region theory as a basis for the carcinogenic activity of polycyclic aromatic hydrocarbons, in Bhatnagar.R.S. (ed.), Molecular Basis of Environmental Toxicity, Ann Arbor Science Publishers, Ann Arbor, Michigan, pp. 329-357.
7. Wood, A.W., Levin, W., Chang, R.L., Yagi, H., Thakker, D.R., Lehr, R.E., Jerina, D.M., and Conney, A.H. (1979), Bay-region activation of carcinogenic polycyclic hydrocarbons, in Jones, P.W. and Leber, P. (eds.), Polynuclear Aromatic Hydrocarbons, Third International Symposium on Chemistry and Biology-Carcinogenesis and Mutagenesis, Ann Arbor Science Publishers, Ann Arbor, Michigan, pp. 531-551.
8. Sayer, J.M., Yagi, H., CroisyDelcey, M., and Jerina, D.M. (1981), Novel bay-region diol epoxides from benzo[c]phenanthrene, J. Am. Chem. Soc.
9. Whalen, D.L., Montemarano, J.A., Thakker, D.R., Yagi, H. (1977), Changes of mechanism and product distributions in the hydrolysis of benzo[a)pyrene-7, 8-diol-9, 10-epoxide metabolites induced by changes in pH, J. Am. Chem. Soc., 99, 5522-5524.
10. Whalen, D.L., Ross, A.M., Montemarano, J.A., Thakker, D.R., Yagi, H., and Jerina, D.M. (1979), General acid catalysis in the hydrolysis of benzo[a]pyrene 7, 8-diol-9, 10-epoxides, J. Am. Chem. Soc., 101, 5086-5088.
11. Whalen, D.L., Ross, A.M., Yagi, H., Karle, J.M., and Jerina, D.M. (1978), Stereoelectronic factors in the solvolysis of bay region diol epoxides of polycyclic aromatic hydrocarbons, J. Am. Chem. Soc., 100, 5218-5221.
12. Yagi, H., Hernandez, O., and Jerina, D.M. (1975), Synthesis of (±> 73, 8or-dihydroxy-93, 103-epoxy-7, 8, 9, 10-tetrahydrobenzo[a]pyrene, a potential metabolite of the carcinogen benzo[a]pyrene with stereochemistry related to the antileukemic triptolides, J. Am. Chem. Soc., 97, 6881-6883.
13. Yagi, H., Thakker, D.R., Hernandez, O., Koreeda, M., and Jerina, D.M. (1977), Synthesis and reactions of the highly mutagenic 7, 8-diol 9, 10-epoxides of the carcinogen benzo[a]pyrene, J. Am. Chem. Soc., 99, 1604-1611.
14. Wood, A.W., Huang, M.T., Chang, R.L., Newmark, H.L., Lehr, R.E., Yagi, H., Sayer, J.M., Jerina, D.M., and Conney, A.H. (1982), Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: exceptional activity of ellagic acid, Proc. Natl. Acad. Sci., 79, 5513-5517.
15. Wood, A.W., Sayer, J.M., Newmark, H.L., Yagi, H., Michaud, D.P., Jerina, D.M., and Conney, A.H. (1982), Mechanism of the inhibition of mutagenicity of a benzo[a]pyrene 7, 8-diol 9, 10-epoxide by riboflavin 5'-phosphate, Proc. Natl. Acad. Sci. USA, 79, 5122-5126.
16. Sayer, J.M., Yagi, H., Wood, A.W., Conney, A.H., and Jerina, D.M. (1982), Extremely facile reaction between the ultimate carcinogen benzo[a]pyrene-7, 8-diol 9, 10-epoxide and ellagic acid, J. Am. Chem. Soc. 5562-5564.
17. Lehr, R.E., Kumar, S., Cohenour, P.T., and Jerina, D.M. (1979), Dihydrodiols and diol epoxides of dibenzo[a, iand [a.hjpyrene, Tetrahedron Lett., 3819-3822.
18. Lehr, R.E., Ridder, M., and Jerina, D.M. (1977), Synthesis and reactivity of diol epoxides derived from non-K-regjon trans-dihydrodiols of benzo[a]anthracene, Tetrahedron Lett., 539-542.
19. Yagi, H., Vyas, K.P., Tada, M., Thakker, D.R., and Jerina, D.M. (1982), Synthesis of the enantiomeric bay-region diol epoxides of benz[a]anthracene and chrysene, J. Org. Chem., 47, 1110-1117.
20. Yagi, H., Holder, J.M., Dansette, P., Hernandez, O., Yeh, H.J.C., LeMahieu, R.A., and Jerina, D.M. (1976), Synthesis and spectral properties of the isomeric hydroxybenzo[a]pyrenes, J. Org. Chem., 41, 977-985.
21. Dansette, P.M., and Jerina, D.M. (1974), A facile synthesis of arene oxides at the K regions of polycyclic hydrocarbons, J. Am. Chem. Soc., 96, 1224-1225.
22. Gibson, D.T., Mahadevan, V., Jerina, D.M., Yagi, H., and Yeh, H.J.C. (1975), Oxidation of the carcinogens benzo[a]pyrene and benzo[a]anthracene to dihydrodiols by bacteria, Science, 189, 295-297.
23. Wood, A.W., Chang, R.L., Levin, W., Lehr, R.E., Schaeffer, M., Karle, J.M., Jerina, D.M., and Conney, A.H. (1977), Mutagenicity and cytotoxicity of benzfajanthracene diol epoxides and tetrahydroepoxides: exceptional activity of the bay region 1, 2-epoxides, Proc. Natl. Acad. Sci. USA, 74, 2746-2750.
24. Ames, B.N., McCann, J., and Yamasaki, E. (1975), Methods for detecting carcinogens and mutagens with the Salmonellamammalian microsome mutagenicity test, Mutat. Res., 31, 347-364.
25. Levin, W., Wood, A.W., Yagi, H., Dansette, P.M., Jerina, D.M., and Conney, A.H. (1976), Carcinogenicity of benzo[a]pyrene 4, 5-, 7, 8-, and 9, 10-oxides on mouse skin, Proc. Natl. Acad. Sci. USA, 73, 243-247.
26. Wislocki, P.G., Kapitulnik, J., Levin, W., Yagi, H., Jerina, D.M., and Conney, A.H. (1978), Tumorigenicity of benzofajpyrene 4, 5-, 7, 8-, 9, 10- and 11, 12-oxides in newborn mice, Cancer Lett., 5, 191-197.
27. Wood, A.W., Goode, R.L., Chang, R.L., Levin, W., Conney, A.H., Yagi, H., Dansette, P.M., and Jerina, D.M. (1975), Mutagenic and cytotoxic activity of benzo[a]pyrene 4, 5-, 7, 8-, and 9, 10-oxides and the six corresponding phenols, Proc. Natl. Acad. Sci. USA, 72, 3176-3180.
28. Grisebach, H. (1979), Selected topics in flavonoid biosynthesis, in Swain, T., Harbone.J.B. and Van Sumere.C.F. (eds.), Recent Advances in Photochemistry, Vol. 12, Plenum, New York, pp. 221-248.
29. Harbome, J.B. (1977), Flavonoids and the evolution of the angiosperms, Biochem. Syst. Ecoi, 5, 7-12.
30. Harbome, J.B., Mabry, T.J., and Mabry, H. (eds.) (1975) Flavonoids, published by Academic Press, New York.
31. Brown, J.P. (1980), A reivew of the genetic effects of naturally occurring flavonoids, anthraquinolines and related compounds, Mutat. Res., 75, 243-277.
32. Buening, M.K., Chang, R.L., Huang, M.-T., Fortner, J.G., Wood, A.W., and Conney, A.H. (1981), Activation and inhibition of benzo[a]pyrene and aflatoxin B metabolism in human liver microsomes by naturally occurring flavonoids, Cancer Res., 41, 67-72.
33. Wiebel, F.J., Gelboin, H.V., BuuHoi, N.P., Stout, M.G., and Bum ham, W.S. (1974), Flavones and polycyclic hydrocarbons as modulators of aryl hydrocarbon [benzo[a]pyrene] hydroxylase, in Ts’o.P.O.P. and Dipaolo.J.A. (eds.), Chemical Carcinogenesis, Marcel Dekker Inc., New York, NY, pp. 249-270.
34. Bjeldanes, I.F., and Chang, G.W. (1977), Mutagenic activity of quercetin and related compounds, Science, 197, 577-578.
35. Brown, J.P., and Dietrich, P.S. (1979), Mutagenicity of plant flavonols in the Salmonellamammalian microsomes test: activation of flavonol glycosides by mixed glycosidases from rat cecal bacteria and other sources, Mutat. Res., 66, 223-240.
36. MacGregor, J.T., and Jurd, L. (1978), Mutagenicity of plant flavonoids: structural requirements for mutagenic activity in Salmonella typhimurium, Mutat. Res., 54, 297-309.
37. Nagao, M., Morita, N., Yahagi, T., Shimisu, M., Kuroyanagi, M., Fukuoka, M., Yoshihira, K., Natori, S., Fujino, T. and Sugimura, T. (1981), Mutagenicities of 61 flavonoids and 11 related compounds, Environ. Mutagenesis, 3, 401-419.
38. Sugmiura, T., Nagao, M., Matsushima, T., Yahagi, T., Scino, Y., Shirai, A., Sawamura, M., Natori, S., Yoshihira, K., Fukuoka, M., and Kuroyanagi, M. (1977), Mutagenicity of flavone derivatives, Proc. Jap. Acad., 53, 194-197.
39. Pamukcu, A.M., Yalciner, S., Hatcher, J.F., and Bryan, G.T. (1980), Quercetin, a rat intestinal and bladder carcinogen present in bracken fern (Pteridion aquilinum), Cancer Res., 40, 3468-3472.