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Journal of Environmental Science and Health, Part B
Pesticides, Food Contaminants, and Agricultural Wastes
Volume 39, 2004 - Issue 4
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Original Articles

Metabolism of the Nonylphenol Isomer [Ring-U-14c]-4-(3′,5′-Dimethyl-3′-Heptyl)-Phenol by Cell Suspension Cultures of Agrostemma githago and Soybean

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Pages 533-549 | Received 13 Feb 2004, Published online: 24 Jun 2011

References

  • Staples , C.A. , Williams , J.B. , Blessing , R.L. and Varineau , P.T. 1999 . Measuring the biodegradability of nonylphenol ether carboxylates, octylphenol ether carboxylates, and nonylphenol . Chemosphere , 38 ( 9 ) : 2029 – 2039 .
  • Thiele , B. , Günther , K. and Schwuger , M.J. 1997 . Alkylphenol ethoxylates: trace analysis and environmental behaviour . Chem. Rev. , 97 ( 8 ) : 3247 – 3272 .
  • 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 GC-MS . J. Chromatogr. Sci. , 35 ( 1 ) : 19 – 30 .
  • Meldahl , A.C. , Nithipatikom , K. and Lech , J.J. 1996 . Metabolism of several 14C-nonylphenol isomers by rainbow trout (Oncorhynchus mykiss): in vivo and in vitro Metabolites . Xenobiotica , 26 ( 11 ) : 1167 – 1180 .
  • Kim , Y.-S. , Katase , T. , Sekine , S. , Inoue , T. , Makino , M. , Uchiyama , T. , Fujimoto , Y. and Yamashita , N. 2004 . Variation in estrogenic activity among fractions of a commercial nonylphenol by high performance liquid chromatography . Chemosphere , 54 ( 8 ) : 1127 – 1134 .
  • Giger , W. , Stephanou , E. and Schaffner , C. 1981 . Persistent organic chemicals in sewage effluents: 1 . Identification of nonylphenols and nonylphenolethoxylates by capillary gas chromatography/mass spectrometry. Chemosphere , 10 ( 11–1 ) : 1253 – 1263 .
  • Giger , W. , Brunner , P.H. and Schaffner , C. 1984 . 4-Nonylphenol in sewage sludge: accumulation of toxic metabolites from nonionic surfactants . Science , 225 ( 4662 ) : 623 – 625 .
  • Jobst , H. 1995 . Chlorophenols an nonylphenols in sewage sludges. 1. Occurrence in sewage sludges of Western German treatment plants from 1987–1989 . Acta Hydrochim. Hydrobiol , 23 ( 1 ) : 20 – 25 .
  • 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 ( 4 ) : 347 – 354 .
  • Lee , P.C. , Marquardt , M. and Lech , J.J. 1998 . Metabolism of nonylphenol by rat and human microsomes . Toxicol. Lett. , 99 ( 7 ) : 117 – 126 .
  • Bokern , M. and Harms , H.H. 1997 . Toxicity and metabolism of 4-n-nonylphenol in cell suspension cultures of different plant species . Environ. Sci. Technol. , 31 ( 7 ) : 1849 – 1854 .
  • Bokern , M. , Nimtz , M. and Harms , H.H. 1996 . Metabolites of 4-n-nonylphenol in wheat cell suspension cultures . J. Agric. Food Chem. , 44 ( 4 ) : 1123 – 1127 .
  • Guenther , K. , Heinke , V. , Thiele , B. , Kleist , E. , Prast , H. and Raecker , T. 2002 . Endocrine disrupting nonylphenols are ubiquitous in food . Environ. Sci. Technol. , 36 ( 8 ) : 1676 – 1680 .
  • Soto , A.M. , Justicia , H. , Wray , J.W. and Sonnenschein , C. 1991 . p-Nonylphenol: an estrogenic xenobiotic released from “modified” polystyrene . Environ. Health Perspect. , 92 : 167 – 173 .
  • Degen , D.H. and Bolt , H.M. 2003 . Comments on “endocrine disrupting nonylphenols are ubiquitous in food.” . Envirn. Sci. Technol. , 37 ( 11 ) : 2622 – 2623 .
  • Vinken , R. , Schmidt , B. and Schäffer , A. 2002 . Synthesis of tertiary 14C-labelled nonylphenol isomers . J. Label. Compd. Radiopharm. , 45 ( 14 ) : 1253 – 1263 .
  • Lalah , J.O. , Lenoir , D. , Henkelmann , B. , Hertkorn , N. , Günther , K. , Schramm , K.-W. and Kettrup , A. 2001 . Synthesis of ring-14C-labelled 4(3′,6′-dimethyl-3′-heptyl)-phenol . J. Label. Compd. Radiopharm. , 44 ( 6 ) : 459 – 463 .
  • Lalah , J.O. , Schramm , K.-W. , Henkelmann , B. , Lenoir , D. , Behechti , A. , Günther , K. and Kettrup , A. 2003 . The dissipation, distribution and fate of a branched 14C-nonylphenol isomer in lake water/sediment systems . Environ. Pollut. , 122 ( 2 ) : 195 – 203 .
  • Lalah , J.O. , Schramm , K.-W. , Severin , G.F. , Lenoir , D. , Henkelmann , B. , Behechti , A. , Günther , K. and Kettrup , A. 2003 . In vivo metabolism and organ distribution of a branched 14C-nonylphenol isomer in pond snails, Lymnaea stagnalis L . Aquat. Toxicol. , 62 ( 4 ) : 305 – 319 .
  • Lalah , J.O. , Behechti , A. , Severin , G.F. , Lenoir , D. , Günther , K. , Kettrup , A. and Schramm , K.-W. 2003 . The Bioaccumulation and fate of a branched 14C-p-nonylphenol isomer in Lymnaea stagnalis L . Environ. Toxicol. Chem. , 22 ( 7 ) : 1428 – 1436 .
  • Schmidt , B. 2001 . “ Metabolic profiling using plant cell suspension cultures ” . In Pesticide Transformation in Plants and Microorganisms Edited by: Hall , J.C. , Hoagland , R.E. and Zablotowicz , R.M. 40 – 56 . Washington, DC : American Chemical Society .
  • Komoßa , D. , Langebartels , C. and Sandermann , H. 1995 . “ Metabolic processes for organic chemicals in plants ” . In Plant Contamination—Modeling and Simulation of Organic Chemical Processes Edited by: Trapp , S. and Mc Farlane , J.C. 69 – 103 . Boca Raton : Lewis Publishers .
  • Schmidt , B. and Schuphan , I. Metabolism of the Xenoestrogens 4-n-nonylphenol and bisphenol A in plant cell suspension cultures . 10th IUPAC International Congress on the Chemistry of Crop Protection . August 4–9 , Basel . Book of Abstracts , Vol. 2 , pp. 34 Basel : IUPAC .
  • Schmidt , B. , Patti , H. , Niewersch , C. and Schuphan , I. 2003 . Biotransformation of [ring-U-14C]4-n-nonylphenol by Agrostemma githago cell culture in a two-liquid-phase system . Biotechnol. Lett. , 25 ( 16 ) : 1375 – 1381 .
  • Murashige , T. and Skoog , F. 1962 . Revised medium for rapid growth and bio assay with tobacco tissue cultures . Physiol. Plant. , 15 : 473 – 497 .
  • Gamborg , O.L. , Miller , R.A. and Ojima , K. 1968 . Nutrient requirements of suspension cultures of soybean root cells . Exp. Cell Res. , 50 : 151 – 158 .
  • Schmidt , B. and Schuphan , I. 2002 . Metabolism of the environmental estrogen bisphenol A by plant cell suspension cultures . Chemosphere , 49 ( 1 ) : 51 – 59 .
  • Diekman , J. , Thomson , J.B. and Djerassi , C. 1968 . Mass spectrometry and stereochemical problems . CLV. Electron impact induced fragmentations and rearrangements of some trimethylsilyl ethers of aliphatic glycols and related compounds. J. Org. Chem. , 33 ( 6 ) : 2271 – 2284 .
  • Diekman , J. , Thomson , J.B. and Djerassi , C. 1967 . Mass spectrometry and stereochemical problems. CXLI. Electron impact induced fragmentations and rearrangements of trimethylsilyl ethers, amines and sulfides . J. Org. Chem. , 32 ( 12 ) : 3904 – 3919 .
  • Odham , G. 1980 . “ Fatty acids ” . In Biochemical Applications of Mass Spectrometry Edited by: Waller , G.R. and Dermer , O.C. First Supplementary Volume , 153 – 171 . New York : Wiley-Interscience .
  • Stolzenberg , G.E. , Olson , P.A. , Zaylskie , R.G. and Mansager , E.R. 1982 . Behavior and fate of ethoxylated alkylphenol nonionic surfactant in barley plants . J. Agric. Food Chem. , 30 ( 4 ) : 637 – 644 .
  • Tanghe , T. , Dhooge , W. and Verstraete , W. 1999 . Isolation of a bacterial strain able to degrade branched nonylphenol . Appl. Environ. Microbiol. , 65 ( 2 ) : 746 – 751 .
  • Corvini , P.F.X. , Vinken , R. , Hommes , G. , Schmidt , B. and Dohmann , M. 2003 . Degradation of the radioactive and non-labelled branched 4(3′,5′-dimethyl-3′-heptyl)-phenol nonylphenol isomer by Sphingomonas TTNP3 . Biodegradation , 15 ( 1 ) : 1 – 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 ( 1 ) : 28 – 40 .

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