Organic pollutants associated with macromolecular soil organic matter: Mode of binding

Organic Geochemistry

Volumn 26, Issue 11-12, 1997, Pages 745-758

  Richnow, H H ^a   Seifert, R ^a   Hefter, J ^a   Link, M ^a   Francke, W ^a   Schaefer, G ^b   Michaelis, W ^c  

^a UNIVERSITY OF HAMBURG   (Germany)

^b HAMBURG UNIVERSITY OF TECHNOLOGY   (Germany)

^c NONE

Author keywords

Bioremediation; Ether bond cleavage; High temperature hydrolysis; Humic substances; Pollutant binding; Polycyclic aromatic pollutants; Soil organic matter

Indexed keywords

BIOREMEDIATION; HUMIC SUBSTANCES; POLYCYCLIC AROMATIC HYDROCARBONS;

ALCOHOLS; AROMATIC HYDROCARBONS; CHEMICAL BONDS; DEGRADATION; ENZYMES; GAS CHROMATOGRAPHY; HIGH TEMPERATURE APPLICATIONS; HYDROLYSIS; MACROMOLECULES; MASS SPECTROMETRY; MOLECULAR STRUCTURE; SOIL POLLUTION;

ANALYTICAL GEOCHEMISTRY;

CONTAMINATION; ORGANIC COMPOUND; PAH; SOIL;

EID: 0031179710     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0146-6380(97)00054-5     Document Type: Article

References (44)

1. Berghausen, M. and Goetz, D. (1993) Change of soil physical values through oil contaminations. In Contaminated Soils 1993, eds. F. Arend, G. J. Annokkee, R. Bosman and W. J. van den Brink, pp. 907-910. Kluwer, Dordrecht.
2. Berry, D. F. and Boyd, S. A. (1984) Oxidative coupling of phenols and anilines by peroxidase: structure-activity relationships. Journal of the Soil Science Society of America 48, 565-569.
3. Berry, D. F. and Boyd, S. A. (1985) Decontamination of soil through enhanced formation of bound residues. Environmental Science and Technology 19, 1132-1133.
4. Bollag, J. M. (1983) Cross-coupling of humus constituents and xenobiotic substances. In Aquatic and Terrestrial Humic Material, eds. R. F. Christman and E. T. Gjessing, pp. 127-141. Ann Arbor Publishers, Michigan.
5. Bollag, J. M. (1992) Decontaminating soils with enzymes. Environmental Science and Technology 26, 1877-1881.
6. Bollag, J. M., Shuttleworth, K. L. and Anderson, D. H. (1988) Laccase-mediated detoxification of phenolic compounds. Applied Environmental Microbiology 54, 3086-3091.
7. Burns, R. G. (1989) Microbial and enzyme activities in soil biofilms. In Structure and Function of Biofilms, eds. W. G. Characklis and P. A. Wilderer, pp. 333-349. Wiley, Chichester.
8. Claus, H. and Filip, Z. (1990a) Effects of clays and other solids on the activity of phenoloxidases produced by some fungi and actinomycetes. Soil Biology and Biochemistry 22, 483-488.
9. Claus, H. and Filip, Z. (1990b) Enzymatic oxidation of some substituted phenols and aromatic amines, and the behaviour of some phenoleoxidase in the presence of soil related adsorbents. Water Science and Technology 22, 69-77.
10. Dagley, J. W., Jerina, D. M. and Witkop, B. (1972) Arene oxides and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds. Experientia 28, 1129-1149.
11. Efroymson, R. A. and Alexander, M. (1995) Reduced mineralization of low concentration of phenanthrene because of sequestering in nonaqueous-phase lipids. Environmental Science and Technology 29, 515-521.
12. Eisenbrand, G. and Metzler, M. (1994) Toxikologie für Chemiker - Stoffe, Mechanismen, Prüfverfahren. Georg Thieme, Stuttgart.
13. Filip, Z. and Preusse, T. (1985) Phenoloxidierende Enzyme - ihre Eigenschaften und Wirkungen im Boden. Pedobiologica 28, 133-142.
14. Führ, F. (1987) Non-extractable pesticide residues in soil. In Pesticide Science and Biotechnology, eds. R. Greenhalgh and T. R. Roberts, pp. 381-389. Blackwell Scientific Publications, Oxford.
15. Gibson, D. T. and Subramanian, V. (1984) Microbial degradation of aromatic hydrocarbons. In Microbial Degradation of Organic Compounds, ed. D. T. Gibson, pp. 1281-252. Marcel Dekker, New York.
16. Grabbe, K., Koenig, R. and Haider, K. (1968) Die Bildung der Phenoloxydase und die Stoffwechselbeeinflussung durch Phenole bei Polystictus versicolor. Archives of Microbiology 63, 133-153.
17. Hammel, K. E., Gai, W. Z., Green, B. and Moen, M. (1992) Oxidative degradation of phenanthrene by the ligninolytic fungus Phanerochaete chrysosporium. Applied Environmental Microbiology 58, 1832-1838.
18. 13C-labelled 2,4 dichlorophenol to humic substances. Environmental Science and Technology 27, 2089-2103.
19. Hatcher, P. G., Lerch, H. E., Kotra, R. K. and Verheyen, T. V. (1988) Pyrolysis GC-MS of a series of degraded wood and coalifled logs that increase in rank from peat to subbituminous coal. Fuel 67, 1069-1075.
20. Hatzinger, P. B. and Alexander, M. (1995) Effect of aging of chemicals in soil on their biodegradability and extractability. Environmental Science and Technology 29, 537-545.
21. Heitkamp, M. A., Freeman, J. P., Miller, D. W. and Cerniglia, C. E. (1988) Pyrene degradation by a Mycobacterium sp. - Identification of ring oxidation and ring fission products. Applied Environmental Microbiology 54, 2549-2555.
22. Hempfling, R. and Schulten, H. R. (1990) Chemical characterisation of organic matter in forest soils by Curie Point pyrolysis - GC/MS and pyrolysis-field ionisation mass spectrometry. Organic Geochemistry 15, 131-145.
23. 14C-labelled anthracene and hexadecane in compost manured soils. Applied Microbiology and Biotechnology 43, 1128-1135.
24. Katritzky, A., Murugan, R., Balasubramanian, M. and Siskin, M. (1991) Aqueous high-temperature chemistry of carbo- and heterocycles. 10. Aquathermolysis of acyclic and cyclic phenol ethers in the presence of sodium bisulfite or phosphoric acid. Energy and Fuels 5, 543-564.
25. Klibanov, A. M., Tsu, M. T. and Scott, K. P. (1983) Peroxidase-catalyzed removal of phenols from coal-conversion waste waters. Science 221, 259-261.
26. Livingston, D. (1993) Biotechnology and pollution monitoring: use of molecular biomarkers in the aquatic environment. Journal of Chemical Technology and Biotechnology 57, 195-211.
27. Luthy, R. G., Ramaswarmi, A., Ghoshal, S. and Merke, W. (1993) Interfacial films in coal tar nonaqueous-phase liquid-water system. Environmental Science and Technology 27, 2914-2918.
28. Martin, J. P. and Haider, K. (1980) A comparison of the use of phenolase and peroxidase for the synthesis of model humic acid-type polymers. Journal of the Soil Science Society of America 44, 983-988.
29. Michaelis, W., Richnow, H. H. and Seifert, R. (1995) Chemically bound chlorinated aromatics in humic substances. Naturwissenschaften 82, 139-142.
30. Mulder, G. J. (ed.) (1990) Conjugation Reaction in Drug Metabolism - An Integrated approach. Substrates, Cosubstrates, Enzymes and their Interaction in Vivo and in Vitro. Taylor and Francis, London.
31. Mycke, B. and Michaelis, W. (1986) Molecular fossils from chemical degradation of macromolecular organic matter. Organic Geochemistry 10, 847-858.
32. Nissenbaum, A. and Serban, A. (1987) Enzyme activity associated with humic substances in deep sediments from the Cariaco Trench and Walvis Ridge. Geochimica et Cosmochimica Acta 51, 373-378.
33. Richnow, H. H., Seifert, R., Hefter, J., Kästner, M., Mahro, B. and Michaelis, W. (1994) Metabolites of xenobiotica and mineral oil constituents linked to macromolecular organic matter in polluted environments. Organic Geochemistry 22, 671-681.
34. Roberts, T. R. (1984) Non-extractable pesticide residues in soil and plants. Pure and Applied Chemistry 56, 946-956.
35. Saiz-Jimenez, C. (1994) Production of alkylbenzenes and alkylnaphthalenes upon pyrolysis of unsaturated fatty acids. Naturwissenschaften 81, 451-453.
36. Sarkar, J. M. and Bollag, J. M. (1987) Inhibitory effect of humic and fulvic acids on oxidoreductases as measured by the coupling of 2,4-dichlorophenol to humic substances. The Science of the Total Environment 62, 367-377.
37. Sarkar, J. M., Malcolm, R. L. and Bollag, J. M. (1988) Enzymatic coupling of 2,4 dichlorophenol to stream fulvic acid in the presence of oxidoreductase. Journal of the Soil Science Society of America 52, 688-694.
38. Schnöder, F., Mittelstaedt, M. and Führ, F. (1993) Das Verhalten von Benzo(a)pyrene und Fluoranthen in einer Parabraunerde - Lysimeter und Laborabbaustudien. Biologische Abwasserreinigung 4, 217-230.
39. Siskin, M., Brons, G., Vaughn, S. N., Katritzky, A. R. and Balasubramania, M. (1990) Aqueous organic chemistry. 3.1,2 Aquathermolysis: reactivity of ethers and esters. Energy & Fuels 4, 488-492.
40. Siskin, M., Katritzky, A. R. and Balasubramania, M. (1991) Aqueous organic chemistry, 4. Cleavage of diaryl ethers. Energy & Fuels 5, 770-771.
41. Sutherland, J. B., Freeman, J. P., Selby, A. L., Fu, P. P., Miller, D. W. and Cerniglia, C. E. (1990) Stereoselective formation of a K-region dihydrodiol from phenanthrene by Stretomyces flavoviens. Archives of Microbiology 154, 260-266.
42. Weißenfels, W. D., Klewer, H. J. and Berger, F. (1993) Mikrobielle Abbaubarkeit und Biotoxizität von polyzyklischen Kohlenwasserstoffen (PAK) in Böden. Bioengineering 4, 29-34.
43. Yang, S. K. (1988) Metabolism and activation of benz(a)anthracene and methylbenz(a)anthracene. In Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships, eds. S. K. Yang and B. D. Silverman. CRC Press, Boca Raton, FL.
44. Yu, Y., Wade, T. L., Fang, J., McDonald, S. and Brooks, J. M. (1995) Gas Chromatographic-mass spectrometric analysis of polycyclic aromatic hydrocarbon metabolites in Antarctic fish (Notothenia gibberifrons) injected with diesel fuel. Archives of Environmental Contamination and Toxicology 29, 241-246.