Skip to main content
SpringerLink
Log in

Degradation of N-phenyl-2-naphthylamine by Rhizobium leguminosarum bv. viciae, Pseudomonas syringae pv. pisi, and Clavibacter michiganensis sps. sepedonicus Bacteria

  • Published:
Applied Biochemistry and Microbiology Aims and scope Submit manuscript

Abstract

The composition of aromatic compounds in the liquid culture medium and the cells of the Rhizobium leguminosarum bv. viciae, Pseudomonas syringae pv. pisi, and Clavibacter michiganensis sps. sepedonicus bacteria grown in the presence of the negative allelopathic compound N-phenyl-2-naphthylamine (N-PNA) found in the root exudates of legume plants is analyzed. It is demonstrated that phthalates are the main products of N-PNA degradation. Bacteria can actively secrete them into the environment and convert phthalates of one type into other types by changing the alkyl groups linked to the o-phthalic acid via the ester bond in their molecules. The analyzed bacteria differed in the rate of N-PNA degradation (10 and 100 µM), which exerted different effects on their growth and viability. The proposed mechanisms could potentially be used to control the bacterial composition and number in the rhizosphere of legume plants with N-PNA and phthalates secreted by plant roots into the exudates, as well as the phthalates produced in the course of N-PNA degradation in the bacterial cells.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.

Similar content being viewed by others

REFERENCES

  1. D'Arcy-Lameta, A., Plant Soil., 1986, vol. 92, no. 1, pp. 113–123.

    Article  CAS  Google Scholar 

  2. Shaw, L.J., Morris, P., and Hooker, J.E., Environ. Micro-biol., 2006, vol. 8, no. 11, pp. 1867–1880.

    Article  CAS  Google Scholar 

  3. Makoi, J.H.J.R. and Ndakidemi, P.A., Afr. J. Biotechnol., 2007, vol. 6, no. 12, pp. 1358–1368.

    CAS  Google Scholar 

  4. Kuzmicheva, Yu.V., Shaposhnikov, A.I., Azarova, T.S., Petrova, S.N., Naumkina, T.S., Borisov, A.Yu., Belimov, A.A., Kravchenko, L.V., Parakhin, N.V., and Tikhonovich, I.A., Russ. J. Plant Physiol., 2014, vol. 61, no. 1, pp. 112–118.

    Article  CAS  Google Scholar 

  5. Hassan, S. and Mathesius, U., J. Exp. Bot., 2012, vol. 63, no. 9, pp. 3429–3444.

    Article  CAS  Google Scholar 

  6. Brack, W., Altenburger, R., Ensenbach, U., Moder, M., Segner, H., and Schuurmann, G., Arch. Inviron. Contam. Toxicol., 1999, vol. 37, no. 2, pp. 164–174.

    Article  CAS  Google Scholar 

  7. Hauser, R. and Calafat, A.M., Occup. Environ. Med., 2005, vol. 62, no. 11, pp. 806–818.

    Article  CAS  Google Scholar 

  8. Altenburger, R., Brak, W., Greco, W.R., Groot, M., Jung, K., Ovari, A., Riedl, J., Schwab, K., and Koster, E., Environ. Sci. Technol., 2006, vol. 40, no. 19, pp. 6163–6169.

    Article  CAS  Google Scholar 

  9. Mankidy, R., Wiseman, S., Ma, H., and Giesy, J.P., Toxicol. Lett., 2013, vol. 217, pp. 50–58.

    Article  CAS  Google Scholar 

  10. Ma, T., Teng, Y., Christie, P., and Luo, Y., Front. Environ. Sci. Eng., 2015, vol. 9, no. 2, pp. 259–268.

    Article  CAS  Google Scholar 

  11. Paul, L. and Schiff, Jr., Alkaloids: Chemical and Biological Perspectives, New York: Pergamon Press, 1996, vol. 11, pp. 1–236.

    Google Scholar 

  12. Yu, R., Li, B.-G., Ye, Q., and Zhang, G.-L., Nat. Prod. Res., 2005, vol. 19, no. 4, pp. 359–362.

    Article  CAS  Google Scholar 

  13. Sultankhodzhaev, M.N. and Tadzhibaev, M.M., Khim. Prir. Soedin., 1976, vol. 12, no. 3, p. 406.

    Google Scholar 

  14. Evstratova, R.I. and Zapesochnaya, G.G., Khim. Prir. Soedin., 1977, no. 4, p. 582.

  15. Zhanaeva, T.A., Krivoshchekova, O.E., Semenov, A.A., and Minaeva, V.G., Khim. Prir. Soedin., 1989, vol. 25, no. 3, p. 377.

    Google Scholar 

  16. Shi, D.Y., Han, L.J., Sun, J., Wang, Y., Yang, Y.C., Shi, J.G., and Fan, X., Zhongguo Zhong Yao Za Zhi, 2005, vol. 30, no. 5, pp. 347–350.

    CAS  PubMed  Google Scholar 

  17. Wu, Z.B., Zhang, S.H., Wu, X.H., Cheng, S.P., and He, F., Allelopathy J., 2007, vol. 20, no. 2, pp. 327–338.

    Google Scholar 

  18. Makarova, L.E., Smirnov, V.I., Klyba, L.V., Petrova, I.G., and Dudareva, L.V., Appl. Biochem. Microbiol., 2012, vol. 48, no. 4, pp. 355-362.

    Article  CAS  Google Scholar 

  19. Lomovatskaya, L.A., Makarova, L.E., Kuzakova, O.V., Romanenko, A.S., and Goncharova, A.M., Appl. Biochem. Microbiol., 2016, vol. 52, no. 3, pp. 287–292.

    Article  CAS  Google Scholar 

  20. Lomovatskaya, L.A., Goncharova, A.M., Makarova, L.E., Filinova, N.V., and Romanenko, A.S., Appl. Biochem. Microbi-ol., 2018, vol. 54, no. 3, pp. 331–336.

    Article  CAS  Google Scholar 

  21. Weiss, T., Bolt, H.M., Schluter, G., Koslitz, S., Taeger, D., Welge, P., and Bruning, T., Arch. Toxicol., 2013, vol. 87, no. 7, pp. 1265–1272.

    Article  CAS  Google Scholar 

  22. Marek, E.V., Koslitz, S., Weiss, T., Fartasch, M., Schluter, G., Kafferlein, H.U., and Bruning, T., Arch. Toxicol., 2017, vol. 91, no. 11, pp. 3587–3596.

    Article  CAS  Google Scholar 

  23. Makarova, L.E. and Morits, A.S., Phenolic compounds: functional role in plants, in Sb. nauchn. statei po materialam X mezhd. simpoziuma “Fenol’nye soedineniya: fundamental’nye i prikladnye aspekty” (Collection of Scientific Articles Based on the Proceedings of X international Symposium “Phenolic Compounds: Fundamental and Applied Aspects”), Moscow: PRESS-BOOK.RU, 2018, pp. 258–262.

  24. Keyser, P., Pujar, B.G., Eaton, R.W., and Ribbons, D.W., Environ. Health Perspect., 1976, vol. 18, pp. 159–166.

    Article  CAS  Google Scholar 

  25. Kiyohara, H. and Nagao, K., J. Gen. Microbiol., 1978, vol. 105, no. 1, pp. 69–75.

    Article  CAS  Google Scholar 

  26. Puntus, I.F., Filonov, A.E., Akhmetov, L.I., Karpov, A.V., and Boronin, A.M., Microbiology (Moscow), 2008, vol. 77, no. 1, pp. 7–15.

    Article  CAS  Google Scholar 

  27. Seo, J.S., Keum, Y.-S., and Li, Q.X., Int. J. Environ. Res. Public Health, 2009, vol. 6, no. pp. 279–309.

  28. Eaton, R.W. and Ribbons, D.W., J. Bacteriol., 1982, vol. 151, no. 1, pp. 48–57.

    Article  CAS  Google Scholar 

  29. Chang, H.K. and Zylstra, G.J., J. Bacteriol., 1998, vol. 180, no. 24, pp. 6529–6537.

    Article  CAS  Google Scholar 

  30. Liang, D.-W., Zhang, T., Fang, H.H.P., and He, J., Appl. Microbiol. Biotechnol., 2008, vol. 80, no. 2, pp. 183–198.

    Article  CAS  Google Scholar 

  31. Al-Bari, M.A., Sayeed, M.A., Rahman, M.S., and Mossadik, M.A., Res. J. Med. Sci., 2006, vol. 1, no. 2, pp. 77–81.

    Google Scholar 

  32. Babu, B. and Wu, J.-T., Sci. Total Environ., 2010, vol. 408, no. 21, pp. 4969–4975.

    Article  CAS  Google Scholar 

  33. Parke, D. and Ornston, L.N., J. Bacteriol., 1986, vol. 165, no. 1, pp. 288–292.

    Article  CAS  Google Scholar 

  34. Husein, A.I., Ali-Shtayeh, M.S., Jamous, R.M., Jondi, W.J., and Zatar, N., A-a, Int. J. Curr. Res. Acad. Rev., 2014, vol. 2, no. 9, pp. 195–203.

    CAS  Google Scholar 

  35. Semenov, A.A., Enikeev, A.G., Snetkova, L.V., Permyakov, A.V., Sokolova, N.A., and Dudareva, L.V., Dokl. Biochem. Biophys., 2016, vol. 471, no. 3, pp. 421–422.

    Article  CAS  Google Scholar 

  36. Kim, S.-J., Kim, S.-I., and Han, Y.-S., Kor. J. Gerontol., 1997, vol. 7, no. 3, pp. 70–76.

    Google Scholar 

  37. Shafikova, T.N., Omelichkina, Yu.V., Enikeev, A.G., Boyarkina, S.V., Gvil’dis, D.E., and Semenov, A.A., Dokl. Biol. Sci., 2018, vol. 480, no. 3, pp. 107–109.

    Article  CAS  Google Scholar 

  38. Krishnan, S., Prabhu, Y., and Phale, P.S., Indian J. Biochem. Biophys., 2004, vol. 41, no. 5, pp. 227–232.

    CAS  PubMed  Google Scholar 

  39. Pastukhova, E.S., Egorova, D.O., Yastrebova, O.V., and Plotnikova, E.G., Vestn. Perm. Univ., Ser. Biol., 2010, no. 3, pp. 24–28.

  40. Makarova, L.E., Morits, A.S., Sokolova, N.A., and Nesterkina, I.S., Mekhanizmy ustoichivosti rastenii i mikroorganizmov k neblagopriyatnym usloviyam sredy. Sbornik materialov Godichnogo sobraniya OFR, Vseross. nauchn. konf. (Mechanisms of Resistance of Plants and Microorganisms to Adverse Environmental Conditions: Proceedings of the Annual Conference of the Society of Plant Physiologists, All-Russia Scientific Conference), Irkutsk: Inst. Geogr. im. V.B. Sochavy, Sib. Otd., Ross. Akad. Nauk, 2018, pp. 488–492. https://doi.org/10.31255/978-5-94797-319-8-488-491

  41. Berestetskii, V.A., Metodicheskie rekomendatsii po polucheniyu novykh shtammov Rhizobium leguminosarum i otsenki ikh effektivnosti (Guidelines for Obtaining New Strains of Rhizobium leguminosarum and Assessment of Their Efficiency), Leningrad: VNIISKhM, 1976.

  42. Hartwig, U.A., Josef, C.M., and Phillips, D.A., Plant Physiol., 1991, vol. 95, no. 3, pp. 797–803.

    Article  CAS  Google Scholar 

  43. Santi, V. and Kannagi, A., J. Chem. Pharm. Res., 2016, vol. 8, no. 3, pp. 700–707.

    Google Scholar 

  44. Kim, S.M., Yoo, J.A., Baek, J.M., and Cho, K.H., Toxicol. in Vitro, 2015, vol. 30, no. 1, pp. 383–393.

    Article  CAS  Google Scholar 

  45. Akimova, G.P., Sokolova, M.G., and Nechaeva, L.V., Russ. J. Plant Physiol., 1999, vol. 46, no. 5, pp. 806–810.

    Google Scholar 

Download references

ACKNOWLEDGMENTS

The work was conducted on the equipment available in the Bioanalitica Center for Collective Use of the Siberian Institute of Plant Physiology and Biochemistry of the Siberian Branch of the Russian Academy of Sciences (Irkutsk, Russia).

Author information

Authors and Affiliations

  1. Siberian Institute of Plant Physiology and Biochemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    L. E. Makarova, A. S. Morits, N. A. Sokolova, I. G. Petrova, A. A. Semenov, L. V. Dudareva, M. S. Tretyakova & A. V. Sidorov

  2. Irkutsk State Medical University, Ministry of Healthcare of the Russian Federation, 664003, Irkutsk, Russia

    A. V. Sidorov

Authors
  1. L. E. Makarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Morits
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. A. Sokolova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. G. Petrova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Semenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. L. V. Dudareva
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. M. S. Tretyakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. A. V. Sidorov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. E. Makarova.

Ethics declarations

The authors declare that they have no conflict of interest. This article does not contain any studies involving animals or human participants performed by any of the authors.

Additional information

Translated by E. Martynova

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Makarova, L.E., Morits, A.S., Sokolova, N.A. et al. Degradation of N-phenyl-2-naphthylamine by Rhizobium leguminosarum bv. viciae, Pseudomonas syringae pv. pisi, and Clavibacter michiganensis sps. sepedonicus Bacteria. Appl Biochem Microbiol 56, 202–210 (2020). https://doi.org/10.1134/S0003683820010123

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0003683820010123

Keywords:

Search

Navigation