Metabolism of 4-n-nonylphenol by non-modified and CYP1A1- and CYP1A2-transgenic cell cultures of tobacco

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 60, Issue 11-12, 2005, Pages 883-892

  Berger, Angelika ^a   Ruß, Alexander S ^a   Schuphan, Ingolf ^a   Schmidt, Burkhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

4 n Nonylphenol; Oxidative Metabolic Profiling; Transgenic Plant Cell Culture

Indexed keywords

NICOTIANA TABACUM;

EID: 29744447537     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-2005-11-1211     Document Type: Article

References (26)

1. Bode M. (2004), Studien zum Metabolismus von Pestiziden und Xenobiotika durch humane Cytochrom P450-Monooxygenasen in transgenen Tabakzellkulturen. Thesis, RWTH Aachen University.
2. Bode M., Stöbe P., Thiede B., Schuphan I., and Schmidt B. (2004), Biotransformation of atrazine in transgenic tobacco cell culture expressing human P450. Pest Manag. Sci. 60, 49-58.
3. Bokern M. and Harms H. (1997), Toxicity and metabolism of 4-n-nonylphenol in cell suspension cultures of different plant species. Environ. Toxicol. Chem. 31, 1849-1854.
4. Bokern M., Nimtz M., and Harms H. (1996), Metabolites of 4-n-nonylphenol in wheat cell suspension cultures. J. Agric. Food Chem. 44, 1123-1127.
5. Coldham N. G., Sivapathasundaram S. D. M., Ashfield L. A., and Pottinger T. G. (1998), Biotransformation, tissue distribution, and persistence of 4-nonylphenol residues in juvenile rainbow trout (Oncorhynchus mykiss). Drug Metab. Dispos. 26, 347-354.
6. Doerge D. R., Twaddle N. C., Churchwell M. I., Chang H. C., Newbold R. R., and Delclos K. B. (2002), Mass spectrometric determination of p-nonylphenol metabolism and disposition following oral administration to Sprague-Dawley rats. Reprod. Toxicol. 16, 45-56.
7. Guenther K., Heinke V., Thiele B., Kleist E., Prast A., and Raecker T. (2002), Endocrine disrupting nonylphenols are ubiquitous in food. Environ. Sci. Technol. 36, 1676-1680.
8. Inui H. and Ohkawa H. (2005), Herbicide resistance in transgenic plants with mammalian P450 monooxygenase genes. Pest. Manag. Sci. 61, 286-291.
9. Inui H., Kodama T., Ohkawa Y., and Ohkawa H. (2000), Herbicide metabolism and cross-tolerance in transgenic potato plants co-expressing human CYP1A1, CYP2B6 and CYP2C19. Pestic. Biochem. Physiol. 66, 116-129.
10. Inui H., Shiota N., Motoi Y., Ido Y., Inoue T., Kodama T., Ohkawa Y., and Ohkawa H. (2001), Metabolism of herbicides and other chemicals in human cytochrome P450 species and in transgenic potato plants co-expressing human CYP1A1, CYP2B6 and CYP2C19. J. Pestic. Sci. 26, 28-40.
11. 14C-nonylphenol isomer in pond snails, Lymnaea stagnalis L. Aquat. Toxicol. 62, 305-319.
12. 14C-p-nonylphenol isomer in Lymnaea stagnalis L. Environ. Toxicol. Chem. 22, 1428-1436.
13. Lee P. C., Chakraborty-Patra C., Stelloh C. T., Lee W., and Struve M. (1996a), Interaction of nonylphenol and hepatic CYP1A in rats. Biochem. Pharmacol. 27, 885-889.
14. Lee P. C., Chakraborty-Patra S., and Struve M. (1996b), Modulation of rat hepatic CYP3A by nonylphenol. Xenobiotica 26, 831-838.
15. Lee P. C., Marquardt M., and Lech J. J. (1998), Metabolism of nonylphenol by rat and human microsomes. Toxicol. Lett. 99, 117-126.
16. Markham K. R. (1982), Techniques of Flavonoid Identification. Academic Press, London.
17. 14C-nonylphenol isomers in rainbow trout (Oncorhynchus mykiss): in vivo and in vitro microsomal metabolites. Xenobiotica 26, 1167-1180.
18. Nakagawa T., Sugaya N., Sakurai K., Nakagawa J., Usukura K., Onda N., and Oguma K. (2004), Simultaneous detection of endocrine disruptors of 4-nonyl phenols and 4-octyl phenols in commodity products using positive chemical ionization-gas chromatography/ mass spectrometry. Chromatographia 25, 25-32.
19. Parikh A., Gillam E. M. J., and Guengerich F. P. (1997), Drug metabolism by Escherichia coli expressing human cytochromes P450. Nature Biotechnol. 15, 784-788.
20. Ruß A. S., Vinken R., Schuphan I., and Schmidt B. (2005), Synthesis of branched para-nonylphenol isomers: Occurrence and quantification in two commercial mixtures. Chemosphere 60, 1624-1635.
21. th IUPAC International Congress on the Chemistry of Crop Protection, Basel, August 4-9. IUPAC, Basel, p. 34.
22. 14C]-4-n-nonylphenol by Agrostemma githago cell culture in a two-liquid-phase system. Biotechnol. Lett. 25, 1375-1381.
23. 14C]-4-(3′,5′-dimethyl- 3′-heptyl)-phenol by cell suspension cultures of Agrostemma githago and soybean. J. Environ. Sci. Health B 39, 533-549.
24. Staples C. A., Williams J. B., Blessing R. J., and Varineau P. T. (1999), Measuring the biodegradability of nonylphenol ether carboxylates, octylphenol ether carboxylates, and nonylphenol. Chemosphere 38, 2029-2039.
25. Thiele B., Günther K., and Schwuger M. J. (1997), Alkylphenol ethoxylates: trace analysis and environmental behaviour. Chem. Rev. 97, 3247-3272.
26. Wheeler T. F., Heim J. R., LaTorre M. R., and Janes A. B. (1997), Mass spectral characterization of p-nonylphenol isomers using high-resolution capillary GCMS. J. Chromatogr. Sci. 35, 19-30.