Novel maltotriose esters enhance biodegradation of Aroclor 1242 by Burkholderia cepacia LB400

  • M. Ferrer
  • P. Golyshin
  • K.N. Timmis


The objective of this research was to evaluate the effect of enzymatically synthesized maltotriose fatty acid monoesters (Ferrer, M., et al. 2000 Tetrahedron56, 4053–4061) on Aroclor 1242 solubilization and biodegradation. Three forms of the surfactant, laurate, palmitate and stearate monoester, were tested. Potential enhancement of solubilization of hydrophobic substances mediated by these non-ionic surfactants was exploited in this study. A polychlorinated biphenyl (PCB) degrading organism, Burkholderia cepacia LB400, was also selected. It was found that all surfactants were effective in solubilizing Aroclor 1242 but the rate of Aroclor 1242 biodegradation proceeded rapidly only in the presence of 6′′-O-palmitoylmaltotriose. For example, the addition of 48 mg 6′′-O-palmitoylmaltotriose/l increased the apparent solubility from 140 to 305 μg/l. As a result, only 8% of the Aroclor remained at the end of 24 h incubation. In contrast, 49.2% of the Aroclor 1242 remained in the absence of surfactant. It appears that maltotriose fatty acid monoesters can significantly increase the bioavailability, and thereby accelerate the biodegradation of highly chlorinated PCBs, particularly Aroclor 1242, by Burkholderia cepacia LB400. The possibility of obtaining these biodegradable surfactants with high yield, easy recovery and high purity by using a new enzymatic methodology, makes maltotriose esters available for bioremediation purposes.

Aroclor 1242 bioremediation Burkholderia cepacia LB400 lipase sugar esters 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Aoki, Y. 2001 Polychlorinated biphenyls, polychlorinated dibenzo-p-dioxins, and polychlorinated dibenzofurans as endocrine disrupters-what we have learned from Yusho disease. Environmental Research 86, 2–11.PubMedGoogle Scholar
  2. Bardi, L., Mattei, A., Steffan, S. & Marzona, M. 2000 Hydrocarbon degradation by a soil microbial population with beta-cyclodextrin as surfactant to enhance bioavailability. Enzyme and Microbial Technology 27, 709–713.PubMedGoogle Scholar
  3. Barkay, T., Navon-Venezia, S., Ron, E.Z. & Rosenberg, E. 1999 Enhancement of solubilization and biodegradation of polyaromatic hydrocarbons by the bioemulsifier alasan. Applied and Environmental Microbiology 65, 2697–2702.PubMedGoogle Scholar
  4. Beaudette, L.A., Ward, O.P., Pickard, M.A. & Fedorak, P.M. 2000 Low surfactant concentration increases fungal mineralization of a polychlorinated biphenyl congener but has no effect on overall metabolism. Letters in Applied Microbiology 30, 155–160.PubMedGoogle Scholar
  5. Billingsley, K.A., Backus, S.M. & Ward, O.P. 1999 Effect of surfactant solubilization on biodegradation of polychlorinated biphenyl congeners by Pseudomonas LB400. Applied Microbiology and Biotechnology 52, 255–260.PubMedGoogle Scholar
  6. Chen, W., Bruhlmann, F., Richins, R.D. & Mulchandani, A. 1999 Engineering of improved microbes and enzymes for bioremediation. Current Opinion in Biotechnology 10, 137–141.PubMedGoogle Scholar
  7. Fava, F. & Di Gioia, D. 1998 Effects of Triton X-100 and Quillaya Saponin on the ex situ bioremediation of a chronically polychlorobiphenyl-contaminated soil. Applied Microbiology and Biotechnology 50, 623–630.Google Scholar
  8. Fava, F. & Di Gioia, D. 2001 Soya lecithin effects on the aerobic biodegradation of polychlorinated biphenyls in an artificially contaminated soil. Biotechnology and Bioengineering 72, 177–184.PubMedGoogle Scholar
  9. Ferrer, M., Comelles, F., Plou. F.J., Cruces, M.A., Fuentes, G., Parra, J.L. & Ballesteros, A. 2001 Comparative surface activities of diand trisaccharide fatty acid esters. Langmuir 18, 667–673.Google Scholar
  10. Ferrer, M., Cruces, M.A., Plou, F.J., Bernabé, M. & Ballesteros, A. 2000 A simple procedure for the regioselective synthesis of fatty acid esters of maltose, leucrose, maltotriose and n-dodecyl maltosides. Tetrahedron 56, 4053–4061.Google Scholar
  11. Ferrer, M., Plou, F.J., Fuentes, G., Cruces, M.A., Andersen, L., Kirk, O., Christensen, M. & Ballesteros, A. 2002 Immobilization by granulation of lipase from Thermomyces lanuginosus for the acylation of sucrose in two solvent mixture. Biocatalysis and Biotransformation 20, 63–71.Google Scholar
  12. Ghosh, U., Weber, S., Jensen, J.N. & Smith, J.R. 1998 Dissolved PCB congener distribution in generator column solutions. Water Research 32, 1373–1382.Google Scholar
  13. Gilbert, E.S. & Crowly, D.E. 1998 Repeated application of carvoneinduced bacteria to enhance biodegradation of polychlorinated biphenyls in soil. Applied Microbiology and Biotechnology 50, 489–494.PubMedGoogle Scholar
  14. Golyshin, P.M., Fredrickson, H.L., Giuliano, L., Rothmel, R., Timmis, K.N. & Yakimov, M.M. 1999 Effect of novel biosurfactants on biodegradation of polychlorinated biphenyls by pure and mixed bacterial cultures. Microbiologica 22, 257–267.PubMedGoogle Scholar
  15. Kim, S.H., Limm, E.J., Lee, S.O., Lee, J.D. & Lee, T.H. 2002 Purification and characterization of biosurfactants from Nocardia sp. L-417. Biotechnology and Applied Biochemistry 31, 249–253.Google Scholar
  16. Lajoie, C.A., Layton, A.C., Easter, J.P., Menn, F.M. & Sayler, C.S. 1997 Degradation of nonionic surfactants and polychlorinated biphenyls by recombinant field application vectors. Journal of Industrial Microbiology and Biotechnology 19, 252–262.PubMedGoogle Scholar
  17. Lin, S.C., Chen, Y.C. & Lin, Y.M. 1998 General approach for the development of high-performance liquid chromatography methods for biosurfactant analysis and purification. Journal of Chromatography A 825, 149–159.Google Scholar
  18. Maltseva, O.V., Tsoi, T.V., Quensen III, J.F., Fukuda, M. & Tiedje, J.M. 1999 Degradation of anaerobic reductive dechlorination products of Aroclor 1242 by four aerobic bacteria. Biodegradation 10, 363–371.PubMedGoogle Scholar
  19. Mayes, B.A., McConnell, E.E., Neal, B.H., Brunner, M.J., Hamilton, S.B., Sullivan, T.M., Peters, A.C., Ryan, M.J., Toft, J.D., Singer, A.W., Brown, J.F., Menton, R.G. & Moore, J.A. 1998 Comparative carcinogenicity in Sprague-Dawley rats of the polychlorinated biphenyl mixtures Aroclors 1016, 1242, 1254, and 1260. Fundamental and Applied Toxicology 41, 62–76.Google Scholar
  20. Mondello, F.J. 1989 Cloning and expression in Escherichia coli of Pseudomonas strain LB400 genes encoding polychlorinated biphenyl degradation. Journal of Bacteriology 171, 1725–1732.PubMedGoogle Scholar
  21. Murerjee-Dhar, G., Shimura, M. & Kimbara, K. 1998 Degradation of polychlorinated biphenyl by cells of Rhodococcus opacus strain TSP203 immobilized in alginate and in solution. Enzyme and Microbial Technology 23, 34–41.Google Scholar
  22. Na, K., Lee, Y., Huh, Y., Lee, J., Lee, J., Kubo, M. & Chung, S. 2000 Characterization of PCB-Degrading Bacteria Immobilized in Polyurethane Foam. Journal of Bioscience and Bioengineering 90, 368–373.Google Scholar
  23. Nakamura, S. 1997 Using sucrose esters as food emulsifiers. Oleochemicals 8, 866–874.Google Scholar
  24. Potrawfke, T., Löhnert, T.-H., Timmis, K.N. & Wittich, R.-M. 1998 Mineralization of low-chlorinated biphenyls by Burkholderia sp. strain LB400 and by a two-membered consortium upon directed interspecies transfer of chlorocatechol pathway genes. Applied Microbiology and Biotechnology 50, 440–446.Google Scholar
  25. Rentel, C.O., Bouwstra, J.A., Naisbett, B. & Junginger, H.E. 1999 Niosomes as a novel peroral vaccine delivery system. International Journal of Pharmaceutics 186, 161–167.PubMedGoogle Scholar
  26. Schilderman, P.A.E.L., Maas, L.M., Pachen, D.M.F.A., de Kok, T.M.C.M., Kleinjans, J.C.S. & van Schooten, F.J. 2000 Induction of DNA adducts by several polychlorinated biphenyls. Environmental and Molecular Mutagenesis 36, 79–86.PubMedGoogle Scholar
  27. Schwartz, A. & Bar, R. 1995 Cyclodextrin-enhanced degradation of toluene and p-toluic acid by Pseudomonas putida. Applied Environmental Microbiology 61, 2727–2731.Google Scholar
  28. Singer, A.C., Gillbert, E.S., Luepromchai, E. & Crowly, D.E. 2000 Bioremediation of polychlorinated biphenyl-contaminated soil using carvone and surfactant-grown bacteria. Applied Microbiology and Biotechnology 54, 838–843.PubMedGoogle Scholar
  29. Timmis, K.N. & Pieper, D.H. 1999 Bacteria designed for bioremediation. Trends in Biotechnology 17, 201–204.Google Scholar
  30. Wang, J-M., Marlowe, E.M., Miller-Maier, R.M. & Brusseau, M.L. 1998 Cyclodextrin-enhanced biodegradation of phenanthrene. Environmental Science and Technology 32, 1907–1912.Google Scholar
  31. Zhang, Y., Maier, W.J. & Miller, R.M. 1997 Effect of rhamnolipids on the dissolution, bioavailability, and biodegradation of phenanthrene. Environmental Science and Technology 31, 2211–2217.Google Scholar

Copyright information

© Kluwer Academic Publishers 2003

Authors and Affiliations

  • M. Ferrer
    • 1
  • P. Golyshin
    • 1
  • K.N. Timmis
    • 1
  1. 1.Department of MicrobiologyGBF – German Research Center for Biotechnology, Mascheroder Weg 1, D-BraunschweigGermany; Tel.:

Personalised recommendations