The effect of plant phenolics on the formation of 7,12-dimethylbenz[a]anthracene-DNA adducts and TPA-stimulated polymorphonuclear neutrophils chemiluminescence in vitro

Toxicology

Volumn 189, Issue 3, 2003, Pages 199-209

  Ignatowicz, Ewa ^c   Balana, Bartosz ^c   Vulimiri, Suryanarayana V ^b   Szaefer, Hanna ^c   Baer Dubowska, Wanda ^a  

^a POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

^b LORILLARD TOBACCO COMPANY   (United States)

^c NONE

Author keywords

7,12 Dimethylbenz a anthracene; Chemiluminescence; DNA adducts; Human neutrophils; Plant phenolics

Indexed keywords

3 METHYLCHOLANTHRENE; 7,12 DIMETHYLBENZ[A]ANTHRACENE; CHLOROGENIC ACID; DEOXYADENOSINE; DEOXYGUANOSINE; EPOXIDE; PHORBOL 13 ACETATE 12 MYRISTATE; PHOSPHORUS 32; PROTOCATECHUIC ACID; REACTIVE OXYGEN METABOLITE; RESVERATROL; TANNIN;

ARTICLE; CHEMOLUMINESCENCE; CONCENTRATION RESPONSE; COVALENT BOND; DNA ADDUCT; DRUG ACTIVITY; DRUG DNA BINDING; DRUG EFFECT; DRUG EFFICACY; HUMAN; HUMAN CELL; IN VITRO STUDY; INCUBATION TIME; NEUTROPHIL; PRIORITY JOURNAL; RESPIRATORY BURST;

EID: 0037784055     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0300-483X(03)00148-3     Document Type: Article

References (48)

1. Ashurst S.W., Cohen G.M. The formation of benzo[a]pyrene-deoxyribonucleoside adducts in vivo and in vitro. Carcinogenesis. 3:1982;267-273.
2. Athar M., Khan W.A., Mukhtar H. Effect of dietary tannic acid on epidermal, lung, and forestomach polycyclic aromatic hydrocarbon metabolism and tumorigenicity in Sencar mice. Cancer Res. 49:1989;5784-5788.
3. Babior B.M. NADPH oxidase: an update. Blood. 93:1999;1464-1476.
4. Baer-Dubowska W., Morris R.J., Gill R.D., DiGiovanni J. Distribution of covalent DNA adducts in mouse epidermal subpopulations after topical application of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene. Cancer Res. 50:1990;3048-3054.
5. Baer-Dubowska W., Gnojkowski J., Fenrych W. Effect of tannic acid on benzo[a]pyrene-DNA adduct formation in mouse epidermis: comparison with synthetic gallic acid esters. Nutr. Cancer. 29:1997;42-47.
6. Baer-Dubowska W., Szaefer H., Krajka-Kuzniak V. Inhibition of murine hepatic cytochrome P450 activities by natural and synthetic phenolic compounds. Xenobiotica. 28:1998;735-743.
7. Chun Y.J., Kim M.Y., Guengerich F.P. Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochem. Biophys. Res. Commun. 262:1999;20-24.
8. Ciolino H.P., Dascher P.J., Chao Yeh G. Resveratrol inhibits transcription of CYP1A1 in vitro by preventing activation of the aryl hydrocarbon receptor. Cancer Res. 58:1998;5707-5712.
9. Colapietro A.-M., Goodell A.L., Smart R.C. Characterization of benzo[a]pyrene-initiated mouse skin papillomas for Ha-ras mutations and protein kinase C levels. Carcinogenesis. 14:1993;2289-2295.
10. Cui H., He H., Zhao G. Determination of polyphenols by high-performance liquid chromatography with inhibited chemiluminescence detection. J. Chromatogr. A. 855:1999;171-179.
11. Das M., Mukhtar H., Bik D.P., Bickers D.R. Inhibition of epidermal xenobiotic metabolism in SENCAR mice by naturally occurring plant phenols. Cancer Res. 47:1987;760-766.
12. Das M., Khan W.A., Asokan P., Bickers D.R., Mukhtar H. Inhibition of polycyclic aromatic hydrocarbon-DNA adduct formation in epidermis and lungs of SENCAR mice by naturally occurring plant phenols. Cancer Res. 47:1987;767-773.
13. Desphande S.-S., Irani K. Oxidant signalling in carcinogenesis: a commentary. Hum. Exp. Toxicol. 21:2002;63-64.
14. DiGiovanni J., Beltrain L., Rupp A., Harvey R.G., Gill R.D. Further analysis of c-Ha-ras mutations in papillomas initiated by several polycyclic aromatic hydrocarbons and papillomas from uninitiated, promoter-treated skin in SENCAR mice. Mol. Carcinog. 8:1993;272-279.
15. -· generating NADPH oxidase pf phagocytes: structure and methods of detection. Methods. 9:1996;563-577.
16. Guengerich F.P. Metabolism of chemical carcinogens. Carcinogenesis. 21:2000;345-351.
17. Huang M.T., Chang R.L., Wood A.W., Newmark H.L., Sayer J.M., Yagi H., Jerina D.M., Conney A.H. Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by tannic acid, hydroxylated anthraquinones and hydroxylated cinnamic acid derivatives. Carcinogenesis. 6:1985;237-242.
18. Hursting S.D., Slaga T.J., Fischer S.M., DiGiovanni J. Mechanism-based cancer prevention approaches: targets, examples and the use of transgenic mice. JNCI. 91:1999;215-225.
19. Ignatowicz E., Szaefer H., Zielinska M., Korczowska I., Fenrych W. Silybin and silydianin diminish the oxidative metabolism of human polymorphonuclear neutrophils. Acta Biochem. Pol. 44:1997;127-130.
20. Izzotti A., Camoirano A., Cartagilia C., Grubbs C.J., Lubet R.A., Kellof G.J., De Flora S. Patterns of DNA adduct formation in liver and mammary epithelial cells of rats treated with 7,12-dimethylbenz[a]anthracene and selective effects of chemopreventive agents. Cancer Res. 59:1999;4285-4290.
21. Jang M., Cai L., Udeani G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., Fong H.H.S., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., Pezzuto J.M. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science. 275:1997;218-220.
22. Jang D.S., Kang B.S., Ryu S.Y., Chang I.M., Min K.R., Kim Y. Inhibitory effects of resveratrol analogs on unopsonized zymosan-induced oxygen radical production. Biochem. Pharmacol. 57:1999;705-712.
23. Katiyar S.K., Matsui M.S., Elmets C.A., Mukhtar H. Polyphenolic antioxidant (-)-epigallocatechin-3-gallate from green tea reduces UVB-induced inflammatory responses and infiltration of leucocytes in human skin. Photochem. Photobiol. 69:1991;148-153.
24. Kensler T.W., Trush M.A. Inhibition of phorbol ester-stimulated chemiluminescence in human polymorphonuclear leukocytes by retinoic acid and 5,6-epoxyretinoic acid. Cancer Res. 41:1981;216-222.
25. Kuhnau J. The flavonoids. A class of semi-essential food components: their role in human nutrition. World Rev. Nutr. Diet. 24:1976;117-191.
26. Kweon M.H., Hwang H.J., Sung H.C. Indentification and antioxidant activity of novel chlorogenic acid derivatives from bamboo (Phyllostachys edulis). J. Agri. Food Chem. 49:2001;4646-4655.
27. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193:1951;265-275.
28. Mukhtar H., Das M., Khan W.A., Wang Z.Y., Bik D.P., Bickers D. Exceptional activity of tannic acid among naturally occurring plant phenols in protecting against 7,12-dimethylbenz[a]anthracene-, benzo[a]pyrene-, 3-methylcholanthrene- and N-methyl-N-nitrosourea-induced skin tumorigenesis in mice. Cancer Res. 48:1988;2361-2365.
29. Nakamura H., Nishikawa A., Furukawa F., Kasahara K., Miyauchi M., Son H.-Y., Hirose M. Inhibitory effects of protocatechuic acid on the post-initiation phase of hamster pancreatic carcinogenesis induced by N-nitrosobis(2-oxopropyl)amine. Anticancer Res. 20:2000;3423-3427.
30. Newmark H. Plant phenolics as inhibitors of mutational and precarcinogenic events. Can. J. Physiol. Pharmacol. 65:1987;461-466.
31. Ohnishi M., Yoshimi N., Kawamori T., Ino N., Hirose Y., Tanaka T., Yamahara J., Miyata H., Mori H. Inhibitory effects of dietary protocatechuic acid and costunolide on 7,12-dimethylbenz[a]anthracene-induced hamster cheek pouch carcinogenesis. Jpn. J. Cancer Res. 88:1997;111-119.
32. Olas B., Wachowicz B., Saluk-Juszczak J., Zielinski T., Kaca W., Buczynski A. Antioxidant activity of resveratrol in endotoxin-stimulated blood platelets. Cell Biol. Toxicol. 17:2001;117-125.
33. Perchellet J.P., Perchellet E.M., Gali H.U., Gao X.M. Oxidant stress and multistage carcinogenesis. Mukhtar H. Skin Cancer: Mechanisms and Human Relevance. 1995;145-180 CRC Press, Boca Raton, FL.
34. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis. 11:1986;159-164.
35. Riedl K.M., Hagerman A.E. Tannin-protein complexes as radical scavengers and radical skins. J. Agric. Food Chem. 49:2001;4917-4923.
36. Ross J.A., Nesnow S. Polycyclic aromatic hydrocarbons: correlations between DNA adducts and ras oncogene mutations. Mutat. Res. 424:1999;155-166.
37. Rotondo S., Rajtar G., Manarini S., Celardo A., Rotillo D., de-Gaetano G., Evangelista V., Cerletti C. Effect of trans-resveratrol, a natural polyphenolic compound, on human polymorphonuclear leukocyte function. Br. J. Pharmacol. 123:1998;1691-1699.
38. Sayer J.M., Yagi H., Wood A.W., Conney A.H., Jerina D.M. Extremely facile reaction between the ultimate carcinogen benzo[a]pyrene-7,8-diol-9,10-epoxide and ellagic acid. J. Am. Chem. Soc. 104:1982;5562-5564.
39. 32P-postlabeling and high pressure liquid chromatographic analyses for 7,12-dimethylbenz[a]anthracene-DNA adducts. Carcinogenesis. 9:1988;633-638.
40. Simons J.M., Hart B.A., Ip Vai Ching T.R., Van Dijk H., Labadie R.P. Metabolic activation of natural phenols into selective oxidative burst agonists by activated human neutrophils. Free Rad. Biol. Med. 8:1990;251-258.
41. Smith W.A., Gupta R.C. Use of a microsome-mediated test system to assess efficacy and mechanisms of cancer chemopreventive agents. Carcinogenesis. 17:1996;1285-1290.
42. Subbaramaiah K., Chung W.J., Michaluart P., Telang N., Tanabe T., Inoue H., Jang M., Pezzuto J.M., Dannenberg A.J. Resveratrol inhibits cyclooxygenase-2 transcription and activity in phorbol ester-treated human mammary epithelial cells. J. Biol. Chem. 273:1998;21875-21882.
43. Tang M.-S., Vulimiri S.V., Viaje A., Chen J.X., Bilolikar D.S., Morris R., Harvey R.G., Slaga T.J., DiGiovanni J. Both (±) syn- and (±) anti-7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxides initiate tumors in mouse skin that possess CAA-to-CTA mutations at codon 61 of c-Ha-ras. Cancer Res. 60:2000;5688-5695.
44. Teel R.W., Huynh H. Modulation by phytochemicals of cytochrome P450 linked enzyme activity. Cancer Lett. 133:1998;135-141.
45. Teel R.W. Ellagic acid binding to DNA as a possible mechanism for its antimutagenic and anticarcinogenic action. Cancer Lett. 30:1986;329-336.
46. Toda S., Miyase T., Arichi T., Tanizawa H., Takino Y. Natural antioxidants III. Antioxidative components isolated from rizome of Curcuma longa. L. Chem. Pharm. Bull. 33:1985;1725-1728.
47. Vericat J., Cheng S., Dipple A. Absolute stereochemistry of the major 7,12-dimethylbenz[a]anthracene-DNA adducts formed in mouse cells. Carcinogenesis. 10:1989;567-570.
48. Vericat J., Cheng S., Dipple A. Absolute configuration of 7,12-dimethylbenz[a]anthracene-DNA adducts in mouse epidermis. Cancer Lett. 57:1991;237-242.