Uptake and transformation of phenols by duckweed (Lemna gibba)
Uptake and transformation of phenol and its five derivatives each labeled with 14C were examined in duckweed (Lemna gibba). A kinetic analysis on uptake and metabolic transformation was conducted using the assumed compartments. Positive correlation was observed between log P and the logarithm value...
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| Published in | Journal of Pesticide Science Vol. 35; no. 4; pp. 456 - 463 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
Pesticide Science Society of Japan
01.01.2010
Japan Science and Technology Agency |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1348-589X 1349-0923 1349-0923 |
| DOI | 10.1584/jpestics.G10-42 |
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| Abstract | Uptake and transformation of phenol and its five derivatives each labeled with 14C were examined in duckweed (Lemna gibba). A kinetic analysis on uptake and metabolic transformation was conducted using the assumed compartments. Positive correlation was observed between log P and the logarithm value of relative uptake rate constant with respect to phenol, and an even higher correlation was obtained against the physico-chemical index, EffTox, where the undissociated fraction of phenol was incorporated. No significant correlation was observed between any of the electronic parameters of the phenol derivatives and the transformation rate. These analyses showed that the uptake of phenols by duckweed is mainly controlled by the hydrophobic profile of the undissociated form. For the metabolic profile, the glycoside conjugate was detected as a typical major metabolite for all phenols and the glutathione conjugate as a unique metabolite for 4-chlorophenol. |
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| AbstractList | Uptake and transformation of phenol and its five derivatives each labeled with super(14)C were examined in duckweed (Lemna gibba). A kinetic analysis on uptake and metabolic transformation was conducted using the assumed compartments. Positive correlation was observed between log P and the logarithm value of relative uptake rate constant with respect to phenol, and an even higher correlation was obtained against the physico-chemical index, EffTox, where the undissociated fraction of phenol was incorporated. No significant correlation was observed between any of the electronic parameters of the phenol derivatives and the transformation rate. These analyses showed that the uptake of phenols by duckweed is mainly controlled by the hydrophobic profile of the undissociated form. For the metabolic profile, the glycoside conjugate was detected as a typical major metabolite for all phenols and the glutathione conjugate as a unique metabolite for 4-chlorophenol. Uptake and transformation of phenol and its five derivatives each labeled with 14C were examined in duckweed (Lemna gibba). A kinetic analysis on uptake and metabolic transformation was conducted using the assumed compartments. Positive correlation was observed between log P and the logarithm value of relative uptake rate constant with respect to phenol, and an even higher correlation was obtained against the physico-chemical index, EffTox, where the undissociated fraction of phenol was incorporated. No significant correlation was observed between any of the electronic parameters of the phenol derivatives and the transformation rate. These analyses showed that the uptake of phenols by duckweed is mainly controlled by the hydrophobic profile of the undissociated form. For the metabolic profile, the glycoside conjugate was detected as a typical major metabolite for all phenols and the glutathione conjugate as a unique metabolite for 4-chlorophenol. (C)Pesticide Science Society of Japan Uptake and transformation of phenol and its five derivatives each labeled with 14C were examined in duckweed (Lemna gibba). A kinetic analysis on uptake and metabolic transformation was conducted using the assumed compartments. Positive correlation was observed between log P and the logarithm value of relative uptake rate constant with respect to phenol, and an even higher correlation was obtained against the physico-chemical index, EffTox, where the undissociated fraction of phenol was incorporated. No significant correlation was observed between any of the electronic parameters of the phenol derivatives and the transformation rate. These analyses showed that the uptake of phenols by duckweed is mainly controlled by the hydrophobic profile of the undissociated form. For the metabolic profile, the glycoside conjugate was detected as a typical major metabolite for all phenols and the glutathione conjugate as a unique metabolite for 4-chlorophenol. |
| Author | Fujisawa, Takuo Katagi, Toshiyuki Ichise-Shibuya, Keiko |
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| Cites_doi | 10.1002/1521-3838(200211)21:5<457::AID-QSAR457>3.0.CO;2-5 10.1897/02-649 10.1021/es00166a009 10.1021/jf061301g 10.1111/j.1365-313X.2005.02344.x 10.1897/1552-8618(1994)13[325:TAMODB]2.0.CO;2 10.1016/j.chemosphere.2006.04.091 10.1061/(ASCE)0733-9372(2007)133:10(955) 10.1002/ps.2780130506 10.1002/jlcr.2580130306 10.1006/eesa.1998.1688 10.1007/BF00210732 10.1016/j.chemosphere.2004.02.017 10.1104/pp.008334 10.1002/jlcr.2580130305 10.1016/S0031-9422(00)00116-3 10.1016/0045-6535(95)00205-M 10.1038/sj.emboj.7600970 10.1016/j.chemosphere.2005.12.025 10.1002/jlcr.2580160314 10.1104/pp.42.11.1553 10.1021/ja01231a055 10.1105/tpc.105.035055 10.13031/2013.22269 10.1016/0041-008X(85)90262-5 10.1897/1552-8618(1994)13[763:PEKAMI]2.0.CO;2 10.1016/S0379-6779(98)00127-1 10.1042/bj1330089 |
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| References_xml | – reference: 34) X. Liu, J. Chen, H. Yu, J. Zhao, J. P. Giesy and X. Wang: Chemosphere 64, 1619–1626 (2006). – reference: 11) A. Yoshitake, F. Shono, T. Kamada and I. Nakatsuka: J. Labelled Compd. Radiopharm. 13, 333–338 (1977). – reference: 31) C. Schrenk, S. Pflugmacher, R. Brugemann. H., Jr. Sandermann and C. E. W. Steinberg and A. Kettrup: Ecotoxicol. Environ. Saf. 40, 226–233 (1998). – reference: 7) T. Fujisawa, M. Kurosawa and T. Katagi: J. Agric. Food Chem. 54, 6286–6293 (2006). – reference: 16) C. F. Cleland and W. R. Briggs: Plant Physiol. 42, 1553–1561 (1967). – reference: 6) J. M. Tront and F. M. Saunders: Chemosphere 64, 400–407 (2006). – reference: 33) R. P. Schwarzenbach, R. Stierli, B. R. Folsom and J. Zeyer: Environ. Sci. Technol. 22, 83–92 (1988). – reference: 32) C. Pietsch, E. Krause, B. K. Burnison and C. E. W. Steinberg: J. Appl. Bot. Food Qual. 80, 25–30 (2006). – reference: 21) T. Fujita: “Structure–Activity Relationships-Quantitative Approaches; Applications to Drug Design and Mode-of-Action Studies,” ed. by T. Fujita, Nankodo, Tokyo, 1982. – reference: 15) E. Landolt and R. Kandeln: “The Family of Lemnaceae: A monographic study, Vol. 2”, Geobotanischen Institutes der ETH, Stiftung Rubel: Zurich, Switzerland, p. 638, 1987. – reference: 1) H. E. Ensley, H. A. Sharma, J. T. Barber and M. A. Polito: “Metabolism of Chlorinated Phenols by Lemna gibba, Duckweed (ACS Symposium Series 664),” Chap. 17, ed. by E. L. Kruger, T. A. Anderson and J. R. Coats, American Chemical Society, Washington D.C., pp. 238–253, 1997. – reference: 19) W. Offen, C. Martinez-Fleites, M. Yang, E. Kiat-Lim, B. G. Davis, C. A. Tarling, C. M. Ford, D. J. Bowles and G. J. Davies: EMBO J. 25, 1396–1405 (2006). – reference: 13) M. L. Sinnot and I. J. L. Souchard: Biochem. J. 133, 89–98 (1973). – reference: 36) OECD SID Initial Assessment Report, 3-Methyl-4-nitro-phenol (1994). – reference: 26) L. Achnine, D. V. Huhman, M. A. Farag, L. W. Sumner, J. W. Blount and R. A. Dixon: Plant J. 41, 875–887 (2005). – reference: 10) A. Yoshitake, K. Kawahara, T. Kamada and M. Endo: J. Labelled Compd. Radiopharm. 13, 323–331 (1977). – reference: 2) J. T. Barber, H. A. Sharma, H. E. Ensley, M. A. Polito and D. A. Thomas: Chemosphere 31, 3567–3574 (1995). – reference: 27) D. M. Bartholomew, D. E. van Dyk, S. C. Lau, D. P. O'Keefe and P. A. Rea: Plant Physiol. 130, 1562–1572 (2002). – reference: 30) S. Roy and O. Hänninen: Environ. Toxicol. Chem. 13, 763–773 (1994). – reference: 24) P. Smejtek and S. Wang: Arch. Environ. Contam. Toxicol. 25, 394–404 (1993). – reference: 23) G. G. Briggs, R. H. Bromilow and A. A. Evans: Pestic. Sci. 13, 495–504 (1982). – reference: 37) B. G. Tehan, E. J. Lloyd, M. G. Wong, W. R. Pitt, J. G. Montana and E. Gancia: Quant. Struc.-Act. Relat. 21, 457–472 (2002). – reference: 17) T. Shishido and H. Ohkawa: “Methods in Pesticide Science,” Chap. 1, ed. by J. Fukami, Y. Uesugi, K. Ishizuka and C. Tomizawa, Soft Science, Tokyo, pp. 3–67, 1981 (in Japanese). – reference: 3) H. E. Ensley, J. T. Barber, M. A. Polito and A. I. Oliver: Environ. Toxicol. Chem. 13, 325–331 (1994). – reference: 35) S. Taj, S. Sankarapapavinsam and M. F. Armed: Synth. Met. 97, 205–209 (1998). – reference: 12) A. Yoshitake, H. Kanamaru, F. Shono and I. Nakatsuka: J. Labelled Compd. Radiopharm. 16, 477–482 (1979). – reference: 18) J. M. McKim, P. Schmeider and G. Veith: Tox. App. Pharm. 77, 1–10 (1985). – reference: 5) V. Ugrekhelidze: J. Bio. Phys. Chem. 2, 38–41 (2002). – reference: 28) G. L. Lamoureux and D. G. Rusness: “Xenobiotic Conjugation in Higher Plants (ACS Symposium Series 299),” Chap. 4, ed. by G. D. Paulson, J. Cardwell, D. H. Hutson and J. J. Menn, American Chemical Society, Washington D.C., pp. 62–105, 1986. – reference: 8) J. M. Tront, D. M. Reinhold, A. W. Bragg and F. M. Saunders: J. Environ. Eng. 133, 955–961 (2007). – reference: 22) S. Pflugmacher, P. Schröder and H. Sandermann Jr.: Phytochemistry 54, 267–273 (2000). – reference: 29) J. A. Days and F. M. Saunders: Environ. Toxicol. Chem. 23, 613–620 (2004). – reference: 4) S. Pascal-Lorber, E. Rathahao, J.-P. Cravedi and F. Laurent: Chemosphere 56, 275–284 (2004). – reference: 14) E. Mitts and R. M. Hixon: J. Am. Chem. Soc. 66, 483–486 (1944). – reference: 25) H. Shao, X. He, L. Achnine, J. W. Blount, R. A. Dixon and X. Wang: Plant Cell 17, 3141–3154 (2005). – reference: 20) C. Hansch and A. Leo: “Exploring QSAR: Fundamentals and applications in Chemistry and Biology,” American Chemical Society, Washington D.C., 1995. – reference: 9) D. M. Reinhold and F. M. Saunders: Trans. ASABE 49, 2077–2083 (2006). – volume: 21 start-page: 457 issn: 1346-8014 year: 2002 ident: 37 publication-title: Quant. Struc.-Act. Relat. doi: 10.1002/1521-3838(200211)21:5<457::AID-QSAR457>3.0.CO;2-5 – ident: 29 doi: 10.1897/02-649 – ident: 33 doi: 10.1021/es00166a009 – ident: 7 doi: 10.1021/jf061301g – start-page: 62 issn: 0097-6156 year: 1986 ident: 28 publication-title: Xenobiotic Conjugation in Higher Plants" ed. by G. D. Paulson, J. Cardwell, D. H. Hutson and J. J. Menn, ACS Symp. Ser. 299, American Chemic – volume: 41 start-page: 875 issn: 0960-7412 year: 2005 ident: 26 publication-title: Plant J. doi: 10.1111/j.1365-313X.2005.02344.x – ident: 3 doi: 10.1897/1552-8618(1994)13[325:TAMODB]2.0.CO;2 – ident: 34 doi: 10.1016/j.chemosphere.2006.04.091 – ident: 8 doi: 10.1061/(ASCE)0733-9372(2007)133:10(955) – ident: 23 doi: 10.1002/ps.2780130506 – ident: 11 doi: 10.1002/jlcr.2580130306 – ident: 31 doi: 10.1006/eesa.1998.1688 – ident: 20 – start-page: 3 issn: 0031-613X year: 1981 ident: 17 publication-title: Methods in Pesticide Science – ident: 24 doi: 10.1007/BF00210732 – ident: 4 doi: 10.1016/j.chemosphere.2004.02.017 – ident: 5 – ident: 27 doi: 10.1104/pp.008334 – ident: 10 doi: 10.1002/jlcr.2580130305 – ident: 22 doi: 10.1016/S0031-9422(00)00116-3 – ident: 2 doi: 10.1016/0045-6535(95)00205-M – ident: 19 doi: 10.1038/sj.emboj.7600970 – ident: 6 doi: 10.1016/j.chemosphere.2005.12.025 – ident: 12 doi: 10.1002/jlcr.2580160314 – volume: 42 start-page: 1553 issn: 0032-0889 year: 1967 ident: 16 publication-title: Plant Physiol. doi: 10.1104/pp.42.11.1553 – ident: 36 – volume: 66 start-page: 483 issn: 0002-7863 year: 1944 ident: 14 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01231a055 – ident: 15 – ident: 25 doi: 10.1105/tpc.105.035055 – ident: 9 doi: 10.13031/2013.22269 – ident: 18 doi: 10.1016/0041-008X(85)90262-5 – ident: 30 doi: 10.1897/1552-8618(1994)13[763:PEKAMI]2.0.CO;2 – ident: 21 – start-page: 238 issn: 0026-0495 year: 1997 ident: 1 publication-title: Metabolism of Chlorinated Phenols by Lemna gibba, Duckweed – volume: 80 start-page: 25 issn: 1613-9216 year: 2006 ident: 32 publication-title: J. Appl. Bot. Food Qual. – ident: 35 doi: 10.1016/S0379-6779(98)00127-1 – volume: 133 start-page: 89 issn: 0264-6021 year: 1973 ident: 13 publication-title: Biochem. J. doi: 10.1042/bj1330089 |
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| Snippet | Uptake and transformation of phenol and its five derivatives each labeled with 14C were examined in duckweed (Lemna gibba). A kinetic analysis on uptake and... Uptake and transformation of phenol and its five derivatives each labeled with super(14)C were examined in duckweed (Lemna gibba). A kinetic analysis on uptake... |
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| SubjectTerms | Aquatic plants Chlorophenol duckweed (Lemna gibba) Floating plants glucose and glutathione conjugate Lemna gibba Metabolites phenol and its derivatives Phenols uptake and transformation |
| Title | Uptake and transformation of phenols by duckweed (Lemna gibba) |
| URI | https://www.jstage.jst.go.jp/article/jpestics/35/4/35_G10-42/_article/-char/en http://mol.medicalonline.jp/en/journal/download?GoodsID=cy3jpesc/2010/003504/007&name=0456-0535u https://www.proquest.com/docview/1444586336 https://www.proquest.com/docview/851471071 |
| Volume | 35 |
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| ispartofPNX | Journal of Pesticide Science, 2010/11/25, Vol.35(4), pp.456-463 |
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