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Biotransformation of nitro-polycyclic aromatic compounds by vegetable and fruit cell extracts

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Abstract

Extracts from various vegetables and fruits were investigated for their abilities to reduce nitro-polycyclic aromatic hydrocarbons (NPAHs). The extracts from grape and onion exhibited an interesting selectivity, yielding corresponding hydroxylamines or amines as major products under mild conditions of 30 °C and pH 7.0. Grape extracts reduced the 4-nitro-1,8-naphthalic anhydride with the highest conversion rate (>99%) and the highest ratio of hydroxylamine to amine (95:5). In contrast, the onion extracts reduced 4-nitro-1,8-naphthalic anhydride with a conversion rate of 94% and a ratio of hydroxylamine to amine of 8:92. The thiol-reducing agent, β-mercaptoethanol, and metal cations, Ca2+ and Mg2+, greatly increased the reductive efficiency. This work provides an alternative strategy for biotransformation of nitro-polycyclic compounds.

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References

  • Abhilash, P.C., Jamil, S., Singh, N., 2009. Transgenic plants for enhanced biodegradation and phytoremediation of organic xenobiotics. Biotechnol. Adv., 27(4):474–488. [doi:10.1016/j.biotechadv.2009.04.002]

    Article  PubMed  CAS  Google Scholar 

  • Castelli, F., Micieli, D., Ottimo, S., Minniti, Z., Sarpietro, M.G., Librando, V., 2008. Absorption of nitro-polycyclic aromatic hydrocarbons by biomembrane models: effect of the medium lipophilicity. Chemosphere, 73(7):1108–1114. [doi:10.1016/j.chemosphere.2008.07.023]

    Article  PubMed  CAS  Google Scholar 

  • Dai, R., Chen, J., Lin, J., Xiao, S., Chen, S., Deng, Y., 2009. Reduction of nitro phenols using nitroreductase from E. coli in the presence of NADH. J. Hazard. Mater., 170(1):141–143. [doi:10.1016/j.jhazmat.2009.04.122]

    Article  PubMed  CAS  Google Scholar 

  • Doran, P.M., 2009. Application of plant tissue cultures in phytoremediation research: incentives and limitations. Biotechnol. Bioeng., 103(1):60–76. [doi:10.1002/bit.22280]

    Article  PubMed  CAS  Google Scholar 

  • Dua, M., Singh, A., Sethunathan, N., Johri, A.K., 2002. Biotechnology and bioremediation: successes and limitations. Appl. Microbiol. Biotechnol., 59(2-3):143–152. [doi:10.1007/s00253-002-1024-6]

    Article  PubMed  CAS  Google Scholar 

  • Hallas, L.E., Alexander, M., 1983. Microbial transformation of nitroaromatic compounds in sewage effluent. Appl. Environ. Microbiol., 45(4):1234–1241.

    PubMed  CAS  Google Scholar 

  • Haritash, A.K., Kaushik, C.P., 2009. Biodegradation aspects of polycyclic aromatic hydrocarbons (PAHs): a review. J. Hazard. Mater., 169(1-3):1–15. [doi:10.1016/j.jhazmat.2009.03.137]

    Article  PubMed  CAS  Google Scholar 

  • Laine, D.F., Cheng, I.F., 2007. The destruction of organic pollutants under mild reaction conditions: a review. Microchem. J., 85(2):183–193. [doi:10.1016/j.microc.2006.07.002]

    Article  CAS  Google Scholar 

  • Lewis, N.A., Ray, A.M., 1984. The effect of anions on redox reactions. Inorg. Chem., 23(22):3649–3653. [doi:10.1021/ic00190a044]

    Article  Google Scholar 

  • Macek, T., Mackova, M., Kas, J., 2000. Exploitation of plants for the removal of organics in environmental remediation. Biotechnol. Adv., 18(1):23–34. [doi:10.1016/S0734-9750(99)00034-8]

    Article  PubMed  CAS  Google Scholar 

  • Marvin-Sikkema, F.D., de Bont, J.A., 1994. Degradation of nitroaromatic compounds by microorganisms. Appl. Microbiol. Biotechnol., 42(4):499–507. [doi:10.1007/BF00173912]

    Article  PubMed  CAS  Google Scholar 

  • Matsuda, T., Yamanaka, R., Nakamura, K., 2009. Recent progress in biocatalysis for asymmetric oxidation and reduction. Tetrahedron: Asymmetry, 20(5):513–557. [doi:10.1016/j.tetasy.2008.12.035]

    Article  CAS  Google Scholar 

  • Medina, V.F., Larson, S.L., Agwaramgbo, L., Perez, W., Escalon, L., 2004. Treatment of trinitrotoluene by crude plant extracts. Chemosphere, 55(5):725–732. [doi:10.1016/j.chemosphere.2003.12.014]

    Article  PubMed  CAS  Google Scholar 

  • Muck, A., Kubát, P., Oliveira, A., Ferreira, L.F.V., Cvacka, J., Civis, S., Zelinger, Z., Barek, J., Zima, J., 2002. Photodegradation of 1-nitropyrene in solution and in the adsorbed state. J. Hazard. Mater., 95(1–2):175–184. [doi:10.1016/S0304-3894(02)00120-6]

    Article  PubMed  CAS  Google Scholar 

  • Parrish, Z.D., Banks, M.K., Schwab, A.P., 2004. Effectiveness of phytoremediation as a secondary treatment for polycyclic aromatic hydrocarbons (PAHs) in composted soil. Int. J. Phytorem., 6(2):119–137. [doi:10.1080/16226510490454803]

    Article  CAS  Google Scholar 

  • Ramos, J.L., González-Pérez, M.M., Caballero, A., van Dillewijn, P., 2005. Bioremediation of polynitrated aromatic compounds: plants and microbes put up a fight. Curr. Opin. Biotechnol., 16(3):275–281. [doi:10.1016/j.copbio.2005.03.010]

    Article  PubMed  CAS  Google Scholar 

  • Roldán, M.D., Pérez-Reinado, E., Castillo, F., Moreno-Vivián, C., 2008. Reduction of polynitroaromatic compounds: the bacterial nitroreductases. FEMS Microbiol. Rev., 32(3): 474–500. [doi:10.1111/j.1574-6976.2008.00107.x]

    Article  PubMed  Google Scholar 

  • Schackmann, A., Muller, R., 1991. Reduction of nitroaromatic compounds by different Pseudomonas species under aerobic conditions. Appl. Microbiol. Biotechnol., 34(6): 809–813. [doi:10.1007/BF00169355]

    Article  CAS  Google Scholar 

  • Shen, J., Zhang, J., Zuo, Y., Wang, L., Sun, X., Li, J., Han, W., He, R., 2009. Biodegradation of 2,4,6-trinitrophenol by Rhodococcus sp. isolated from a picric acid-contaminated soil. J. Hazard. Mater., 163(2–3):1199–1206. [doi:10.1016/j.jhazmat.2008.07.086]

    Article  PubMed  CAS  Google Scholar 

  • Spain, J.C., 1995. Biodegradation of nitroaromatic compounds. Annu. Rev. Microbiol., 49(1):523–555. [doi:10.1146/annurev.mi.49.100195.002515]

    Article  PubMed  CAS  Google Scholar 

  • Teramoto, H., Tanaka, H., Wariishi, H., 2004. Degradation of 4-nitrophenol by the lignin-degrading basidiomycete Phanerochaete chrysosporium. Appl. Microbiol. Biotechnol., 66(3):312–317. [doi:10.1007/s00253-004-1637-z]

    Article  PubMed  CAS  Google Scholar 

  • Tocher, J.H., 1997. Reductive activation of nitroheterocyclic compounds. Gen. Pharmacol., 28(4):485–487. [doi:10.1016/S0306-3623(96)00283-2]

    Article  PubMed  CAS  Google Scholar 

  • van Aken, B., 2009. Transgenic plants for enhanced phytoremediation of toxic explosives. Curr. Opin. Biotechnol., 20(2):231–236. [doi:10.1016/j.copbio.2009.01.011]

    Article  PubMed  Google Scholar 

  • Wu, Y., Luo, Y., Zou, D., Ni, J., Liu, W., Teng, Y., Li, Z., 2008. Bioremediation of polycyclic aromatic hydrocarbons contaminated soil with Monilinia sp.: degradation and microbial community analysis. Biodegradation, 19(2):247–257. [doi:10.1007/s10532-007-9131-9]

    Article  PubMed  CAS  Google Scholar 

  • Yoon, J.M., Aken, B.V., Schnoor, J.L., 2006. Leaching of contaminated leaves following uptake and phytoremediation of RDX, HMX, and TNT by poplar. Int. J. Phytorem., 8(1):81–94. [doi:10.1080/15226510500507128]

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. School of Life Science and Biotechnology, Dalian University of Technology, Dalian, 116024, China

    Bo Xie, Jun Yang & Qing Yang

  2. National Key Laboratory of Biochemical Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing, 100190, China

    Bo Xie

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  1. Bo Xie
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  2. Jun Yang
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  3. Qing Yang
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Correspondence to Jun Yang or Qing Yang.

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Project supported by the National Basic Research Program (973) of China (No. 2010CB126102), the National Natural Science Foundation of China (No. 31070715), the National High-Tech R&D Program (863) of China (No. 2011AA10A204), the National Key Technology R&D Program of China (No. 2011BAE06B05), and the Fundamental Research Funds for the Central Universities (No. DUT10LK33), China

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Xie, B., Yang, J. & Yang, Q. Biotransformation of nitro-polycyclic aromatic compounds by vegetable and fruit cell extracts. J. Zhejiang Univ. Sci. B 13, 248–253 (2012). https://doi.org/10.1631/jzus.B1100254

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  • DOI: https://doi.org/10.1631/jzus.B1100254

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