Evaluation of the mutagenic activity of chrysin, a flavonoid inhibitor of the aromatization process

Journal of Toxicology and Environmental Health - Part A: Current Issues

Volumn 75, Issue 16-17, 2012, Pages 1000-1011

  Oliveira, G A R ^a   Ferraz, E R A ^a   Souza, A O ^a   Lourenco R A ^a   Oliveira, D P ^a   Dorta, D J ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CHRYSIN; FLAVONOID; SULFORHODAMINE B;

APOPTOSIS; AROMATIZATION; CELL CYCLE; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL STRUCTURE; COLORIMETRY; CONCENTRATION (PARAMETERS); CONFERENCE PAPER; CONTROLLED STUDY; CYTOTOXICITY; DNA DETERMINATION; DRUG ACTIVITY; HUMAN; HUMAN CELL; MICRONUCLEUS; MUTAGENIC ACTIVITY; NONHUMAN; PRIORITY JOURNAL; SALMONELLA TYPHIMURIUM; SUBSTITUTION REACTION;

AROMATASE INHIBITORS; CELL CYCLE; CELL PROLIFERATION; ESTRADIOL; FLAVONOIDS; HEP G2 CELLS; HEPATOCYTES; HUMANS; MICRONUCLEUS TESTS; MOLECULAR STRUCTURE; MUTAGENESIS; SALMONELLA; TESTOSTERONE;

EID: 84864879372     PISSN: 15287394     EISSN: 10872620     Source Type: Journal    
DOI: 10.1080/15287394.2012.696517     Document Type: Conference Paper

References (38)

1. Bernstein, L., Kaldor, J., McCann, J., and Pike, M. C. 1982. An empirical approach to the statistical analysis of mutagenesis data from Salmonella test. Mutation Res. 97: 267-81. (Pubitemid 12099663)
2. Bjeldanes, L. F., and Chang, G. W. 1977. Mutagenic activity of quercetin and related compounds. Science 197: 577-78. (Pubitemid 8150855)
3. Braylan, R. C., Benson, N. A., Norse, V. Kruth, H. S. 1982. Correlated analysis of cellular DNA membrane antigens, and light scatter of human lymphoid cells. Cytometry. 2: 337-43. (Pubitemid 12116979)
4. Crissman, H. A., and Steinkamp, J. A. 1973. Rapid simultaneous measurement of DNA, protein, and cell volume in single cell from large mammalian cell populations. J. Cell Biol. 59: 766.
5. Czeczot, H., Tudek, B., Kusztelak, J., Szymczyk, T., Dobrowolska, B., Glinkowska, G., Malinowski, J., and Strzelecka, H. 1990. Isolation and studies of the mutagenic activity in the Ames test of flavonoids naturally occurring in medical herbs. Mutat. Res. 240: 209-16. (Pubitemid 20075452)
6. Dhawan, K., Kumar, S., and Sharma A. 2002. Beneficial effects of chrysin and benzoflavone on virility in 2-year-old male rats. J. Med. Food 5: 43-48. (Pubitemid 34462800)
7. Fenech, M., Chang, W.P., Kirsch-Volders, M., Holland, N., Bonassi, S., and Zeiger, E. 2003. Human project: Detailed description of the scoring criteria for the cytokinesisblock micronucleus assay using isolated human lymphocyte cultures. Mutat Res. 534: 65-75. (Pubitemid 36015839)
8. Fujimoto, K., Hosotani, R., Doi, R., Wada, M., Lee, J., Koshiba, T., Miyamoto,Y., Tsuji, S., Sakajima, S., and Imamura, M. 1999. Induction of cell-cycle arrest and apoptosis by novel retinobenzoic-acid derivative, TAC-101 in human pancreatic-cancer cell. Int. J. Cancer 81: 634-44.
9. Gambelunghe, C., Rossi, R., Sommavilla, M., Ferranti, C., Ciculi, C., Gizzi, S Micheletti, A., and Rufini, S. 2003. Effects of chrysin on urinary testosterone levels in human males. J. Med. Food 6: 387-90. (Pubitemid 38114332)
10. Hartmann, A., Elhajouji, A., Kiskinis, E., Poetter, F., Marins, H., Fjallman, A., Frieau, W., and Suter, W. 2001. Use of the alkaline comet assay for industrial genotoxicity screening: Comparative investigation with the micronucleus test. Food Chem. Toxicol. 39: 843-58. (Pubitemid 32575252)
11. Hong, T. B., Rahumatullah, A., Yogarajah, T., Ahmad, M., and Yin, K. B. 2010. Potential effects of chrysin on MDA-MB-231 cells. Int. J. Mol. Sci. 11: 1057-69.
12. Johnson, P. A., Clements, P., Hudson, K., and Caldecott, K. W. 1999. A mitotic spindle requirement for DNA damage-induced apoptosis in Chinese hamster ovary cells. Cancer Res. 59: 2696-700. (Pubitemid 29269118)
13. Kao, Y., Zhou, C., Sherman, M., Laughton, C. A., and Chen, S. 1998. Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study. Environ. Health Perspect. 106: 85-92 (Pubitemid 28143862)
14. Kessel, D., and Luo,Y. 2000. Cell in cryptophycin-induced cell cycle arrest are susceptible to apoptosis. Cancer Cell. 151: 25-29. (Pubitemid 30155581)
15. Khoo, B. Y., Chua, S. L., and Balaram, P. 2010. Apoptotic effects of chrysin in human cancer cell lines. Int. J. Mol. Sci. 11: 2188-99.
16. Knasmuller, S., Parzefall, W., Sanyal, R., Ecker, S., Schwab, C., Uhl, M., Mersch-Sundermann, V., Williamson, G., Hietsch, G., Langer, T., Darroudi, F., and Adayapalam, A. T. 1998. Use of metabolically competent human hepatoma cells for the detection of mutagens and antimutagens. Mutat. Res. 402: 185-202. (Pubitemid 28440274)
17. Lautraite, S., Musonda, A. C., Doehmer, J., Edwards, G. O, and Chipman, J. K. 2002. Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1. Mutagenesis 17: 45-53. (Pubitemid 34083385)
18. Lin, Z. X., Hoult, J. R. S., and Raman, A. 1999. Sulphorhodamine B assay for measuring proliferation of a pigmented melanocyte cell line and its application to the evaluation of crude drugs used in the treatment of vitiligo. J. Ethnopharmacol. 66: 141-50. (Pubitemid 29307912)
19. Lorge, E., Hayashi, M., Albertini, S., and Kirkland, D. 2008. Comparison of different methods for an accurate assessment of cytotoxicity in the in vitro micronucleus test. I. Theoretical aspects. Mutat. Res. 655: 1-38.
20. MacGregor, J. T., and Jurd, L. 1978. Mutagenicity of plant flavonoids: structural requirements for mutagenic activity in Salmonella typbimurium. Mutat. Res. 54: 297-309. (Pubitemid 9040997)
21. Majer, B. J., Mersch-Sundermann, V., Darroudi, F., Laky, B.,Wit, K., and Knasmuller, S. 2004. Genotoxic effects of dietary and lifestyle related carcinogens in human derived hepatoma (HepG2, Hep3B) cells. Mutat. Res. 551: 153-66. (Pubitemid 38833505)
22. Maron, D. M., and Ames, B. N. 1983. Revised methods for the Salmonella mutagenicity test. Mutat. Res. 113: 173-214.
23. Mortelmans, K., and Zeiger, E. 2000. The Ames Salmonella/microsome mutagenicity assay. Mutat. Res. 455: 29-60.
24. Natarajan, A. T., and Darroudi, F. 1991. Use of human hepatoma cells for in vitro metabolic activation of chemical mutagen/carcinogens. Mutagenesis 6: 399-403.
25. Oren, D. K., Petersen, L. N., and Bohr, V. A. 1997. Persistent DNA damage inhibits S-phase and G2 progression and results in apoptosis. Mol. Biol. Cell. 8: 1129-42. (Pubitemid 27276331)
26. Purohit, A., Hejas, H., Walden, L., MacCartthy-Morrong, L., Packham, G., Potter, B. V. L., and Reed, M. J. 2000.The effect of 2-methoxioestrone 3-sulphamate on the growth of breast cancer cell and induced mammary tumor. Int. J. Cancer 85: 584-90.
27. Sanderson, J. T., Hordijk, J., Denison, M. S., Springsteel, M. F., Nantz, M. H., and Van den Berg, M. 2004. Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells. Toxicol. Sci. 82: 70-79. (Pubitemid 39485321)
28. Silva, I. D., Rodrigues, A. S., Gaspar, J.,Maia, R., Laires, A., and Rueff, J. 1997. Involvement of rat cytochrome 1A1 in the biotransformation of kaempferol to quercetin: Relevance to the genotoxicity of kaempferol. Mutagenesis 12: 383-90. (Pubitemid 27417579)
29. Simons, A. L., Renouf, M., Hendrich, S., and Murphy, P. A. 2005. Human gut microbial degradation of flavonoids: Structure-function relationships. J. Agric. Food Chem. 53: 4258-63. (Pubitemid 40936793)
30. Skehan, P., Storeng, R., Scudiero, D, Monks, A., Mcmahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, R. M. 1990. New colorimetric cytotocity assay for anticancer-drug screening. J. Natl. Cancer Inst. 82: 1107-12. (Pubitemid 20213250)
31. Surrallés, J., Xamena, N., Creus, A., Catalán, J., Norppa, H., and Marcos, R. 1995. Induction of micronuclei by five pyrethroid insecticides in whole-blood and isolated human lymphocyte cultures. Mutat. Res. 341: 169-84.
32. Ta, N., and Walle, T. 2007. Aromatase inhibition by bioavailable methylated flavones. J. Steroid Biochem. Mol. Biol. 107: 127-29. (Pubitemid 47362668)
33. Tsuji, P. A., andWalle, T. 2008. Cytotoxic effects of the dietary flavones chrysin and apigenin in a normal trout liver cell line. Chem-Biol. Interact. 171: 37-44. (Pubitemid 350191840)
34. Walle, T., Otake, Y., Brubaker, J. A., Walle, U. K., and Halushka, P. V. 2001. Disposition and metabolism of the flavonoid chrysin in normal volunteers. Br. J. Clin.Pharmacol. 51: 143-46. (Pubitemid 32216062)
35. Weinberg, O. K., Marquez-Garban, D. C., Fishbein, M. C., Goodglick, L., Garban, H. J., Dubinett, S. M., and Pietras, R. J. 2005. Aromatase inhibitors in human lung cancer therapy. Cancer Res. 65: 11287-91. (Pubitemid 41821684)
36. Weng, M. S., Ho, Y. S., and Lin, J. K. 2005. Chrysin induces G1 phase cell cycle arrest in C6 glioma cells through inducing p21Waf1/Cip1 expression: Involvement of p38 mitogen-activated protein kinase. Biochem. Pharmacol 69: 1815-27.
37. XinWu, Y., and Fang, X. 2010. Apigenin, chrysin, and luteolin selectively inhibit chymotrypsin-like and trypsin-like proteasome catalytic activities in tumor cells. Planta. Med. 76: 128-32.
38. Yao, R., Yasuoka, A., Kamei, A., Kitagawa, Y., Tateishi, N., Tsuruoka, N., Kiso, Y., Sueyoshi, T., Negishi, M., Misaka, T., and Abe, K. 2010. Dietary flavonoids activate the constitutive androstane receptor CAR. J. Agric. Food Chem. 58: 2168-73.