Abstract
Nitroaromatics chemicals (NACs) are the major pollutants released during the post-industrialization phase of the environment and most of the nitroaromatic compounds are toxic andmutagenic for living organisms. Substituents on nitro on the NAC consist of an electron-withdrawing character, which causes resistance toward biodegradation. Therefore, the oxidativeattack by bacterial oxygen becomes difficult. Nevertheless, many powerful bacteria have adapted to use NAC using oxygen. An increase in the number of nitro groups and the substitutionof electron-withdrawing on the aromatic ring causes an increase in the recalcitrant character to force the nitromatics used by the partial reduction mechanism. Nitroaromatic compounds are partially or completely degraded by a wide range of microorganisms, using the oxidative and reductive downgrading pathways to convert NACs completely into CO2 and H2O or partially to organic compounds. It is the genetic machinery present in microbes that directs the conversion of NAC to simple products. While aerobic bacteria use the aerobic and partial reductive catabolic pathways systems, anaerobic bacteria were able to use only the reductive mechanism to use NAC.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Begum, S. S., & Arundhati, A. (2016). A study of bioremediation of methyl parathion in vitro using potential Pseudomonas sp. isolated from agricultural soil, Visakhapatnam. India. International Journal of Current Microbiology and Applied Sciences, 5, 464–474. https://doi.org/10.20546/ijcmas.2016.502.052
Blanchard-Fillion, B., Prou, D., Polydoro, M., Spielberg, D., Tsika, E., Wang, Z., Hazen, S. L., Koval, M., Przedborski, S., & Ischiropoulos, H. (2006). Metabolism of 3-nitrotyrosine induces apoptotic death in dopaminergic cells. The Journal of Neuroscience, 26, 6124–6130. https://doi.org/10.1523/JNEUROSCI.1038-06.2006
Chatterjee, S., Deb, U., Datta, S., Walther, C., & Gupta, D. K. (2017). Common explosives (TNT, RDX, HMX) and their fate in the environment: Emphasizing bioremediation. Chemosphere, 184, 438–451. https://doi.org/10.1016/j.chemosphere.2017.06.008
Chirino, B., Strahsburger, E., Agulló, L., González, M., & Seeger, M. (2013). Genomic and functional analyses of the 2-aminophenol catabolic pathway and partial conversion of its substrate into picolinic acid in Burkholderia xenovorans LB400. PLoS One, 8, e75746. https://doi.org/10.1371/journal.pone.0075746
Donlon, B. A., Razo-Flores, E., Lettinga, G., & Field, J. A. (1996). Continuous detoxification, transformation and degradation of nitrophenols in upflow anaerobic sludge blanket (USAB) reactors. Biotechnology and Bioengineering, 51, 439–449. https://doi.org/10.1002/(SICI)1097-0290(19960820)51:4<439::AID-BIT7>3.0.CO;2-J
French, C. E., Nicklin, S., & Bruce, N. C. (1998). Aerobic degradation of 2,4,6-trinitrotoluene by Enterobacter cloacae PB2 and by pentaerythritol tetranitrate reductase. Applied and Environmental Microbiology, 64(8), 2864–2868. https://doi.org/10.1128/AEM.64.8.2864-2868
Ghosh, S., Sanval, P., & Kumar, R. (2017). Evolution of C4 plants and controlling factors: Insight from n-alkane isotopic values of NW Indian Siwalik paleosols. Organic Geochemistry, 110, 110–121. https://doi.org/10.1016/j.orggeochem.2017.04.009
Groenewegen, P. E., Breeuwer, P., van Helvoort, J. M., Langenhoff, A. A., de Vries, F. P., & deBont, J. A. (1992). Novel degradative pathway of 4-nitrobenzoate in Comamonas acidovorans NBA-10. Journal of General Microbiology, 138, 1599–1605. https://doi.org/10.1128/AEM.00739-16
Haigler, B. E., & Spain, J. C. (1993). Biodegradation of 4-nitrotoluene by Pseudomonas sp. strain 4NT. Applied and Environmental Microbiology, 59(7), 2239–2243. https://doi.org/10.1128/AEM.59.7.2239-2243.1993
Haigler, B. E., Wallace, W. H., & Spain, J. C. (1994). Biodegradation of 2-nitrotoluene by Pseudomonas sp. strain JS42. Applied and Environmental Microbiology, 60, 3466–3469. https://doi.org/10.1128/AEM.60.9.3466-3469.1994
Huang, S., Lindahl, P. A., Wang, C., Bennett, G. N., Rudolph, F. B., & Hughes, J. B. (2000). 2,4,6-Trinitrotoluene reduction by carbon monoxide dehydrogenase from Clostridium thermoaceticum. Applied and Environmental Microbiology, 66, 1474. https://doi.org/10.1128/aem.66.4.1474-1478.2000
James, K. D., Hughes, M. A., & Williams, P. A. (2000). Cloning and expression of ntnD, encoding a novel NAD (P)+-independent 4-nitrobenzyl alcohol dehydrogenase from Pseudomonas sp. strain TW3. Journal of Bacteriology, 182, 3136–3141. https://doi.org/10.1128/jb.182.11.3136-3141.2000
Ju, K. S., & Parales, R. E. (2006). Control of substrate specificity by active site residues in nitrobenzene 1,2-dioxygenase. Applied and Environmental Microbiology, 72, 1817–1824. https://doi.org/10.1128/AEM.72.3.1817-1824.2006
Ju, K. S., & Parales, R. E. (2009). Application of nitroarene dioxygenases in the design of novel strains that degrade chloronitrobenzenes. Microbial Biotechnology, 2, 241–252. https://doi.org/10.1111/j.1751-7915.2008.00083.x
Juhas, M., Van der Meer, J. R., Gaillard, M., Harding, R. M., Hood, D., & Crook, D. W. (2009). Genomic islands: Tools of bacterial horizontal gene transfer and evolution. FEMS Microbiology Reviews, 33, 376–393. https://doi.org/10.1111/j.1574-6976.2008.00136.x
Kapley, A., & Purohit, H. (2009). Genomic tools in bioremediation. Indian Journal of Microbiology, 49, 108–113. https://doi.org/10.1007/s12088-009-0012-2
Katsivela, E., Wray, V., Pieper, D. H., & Wittich, R. M. (1999). Initial reactions in the biodegradation of 1-chloro-4-nitrobenzene by a newly isolated bacterium, strain LW1. Applied and Environmental Microbiology, 65, 1405–1412. https://doi.org/10.1128/AEM.65.4.1405-1412.1999
Kulkarni, M., & Chaudhari, A. (2007). Microbial remediation of nitro-aromatic compounds: An overview. Journal of Environmental Management, 85, 496–512. https://doi.org/10.1016/j.jenvman.2007.06.009
Kumari, S., Regar, R. K., Bajaj, A., Ratnasekhar, C., Satyanarayana, G. N. V., Mudiam, M. K. R., & Manickam, N. (2017). Simultaneous biodegradation of polyaromatic hydrocarbons by a Stenotrophomonas sp: Characterization of nid genes and effect of surfactants on degradation. Indian Journal of Microbiology, 57, 60–67. https://doi.org/10.1007/s12088-016-0612-6
Lenke, H., Achtnich, C., & Knackmuss, H. J. (2000). Perspeptives of bioelimination of polynitroaromatic compounds. In J. C. Spain, J. B. Highes, & H. J. Knackmuss (Eds.), Biodegradation of nitroaromatic compounds and explosives (pp. 91–126). Lewis Publishers. https://doi.org/10.1023/B:WIBI.0000021720.03712.12
Liu, H., Wang, S. J., & Zhou, N. Y. (2005). Anew isolate of Pseudomonas stutzeri that degrades 2-chloronitrobenzene. Biotechnology Letters, 27, 275–278. https://doi.org/10.1007/s10529-004-8293-3
Liu, D. F., Min, D., Cheng, L., Zhang, F., Li, D. B., Xiao, X., Sheng, G. P., & Yu, H. Q. (2017). Anaerobic reduction of 2,6-Dinitrotoluene by Shewanella oneidensis MR-1: Roles of Mtr respiratory pathway and nfnB. Biotechnology and Bioengineering, 114, 761–768. https://doi.org/10.1002/bit.26212
McCormick, N., Feeherry, F. E., & Levinson, H. S. (1976). Microbial transformation of 2, 4, 6-trinitrotoluene and other nitroaromatic compounds. Applied and Environmental Microbiology, 31, 949–958. https://doi.org/10.1128/AEM.31.6.949-958.1976
Min, J., Zhang, J. J., & Zhou, N. Y. (2016). A two-component para-nitrophenol monooxygenase initiates a novel 2-chloro-4-nitrophenol catabolic pathway in Rhodococcus imtechensis RKJ300. Applied and Environmental Microbiology, 82, 714–723. https://doi.org/10.1128/AEM.03042-15
Min, J., Chen, W., Wang, J., & Hu, X. (2017). Genetic and biochemical characterization of 2-chloro-5-nitrophenol degradation in a newly isolated bacterium, Cupriavidus sp. Strain CNP-8. Frontiers in Microbiology, 8, 1778. https://doi.org/10.3389/fmicb.2017.01778
Nishino, S. F., & Spain, J. C. (1993). Degradation of nitrobenzene by a Pseudomonas pseudoalcaligenes. Applied and Environmental Microbiology, 59(8), 2520–2525. https://doi.org/10.1128/aem.59.8.2520-2525.1993
Nishino, S. F., & Spain, J. C. (1995). Oxidative pathway for the biodegradation of nitrobenzene by Comamonas sp. strain JS765. Applied and Environmental Microbiology, 61(6), 2308–2313. https://doi.org/10.1128/AEM.61.6.2308-2313.1995
Nishino, S. F., & Spain, J. C. (2001). Technology status review: Bioremediation of dinitrotoluene (DNT).
Nishino, S., & Spain, J. C. (2006). Biodegradation of 3-nitrotyrosine by Burkholderia sp. strain JS165 and Variovorax paradoxus JS171. Applied and Environmental Microbiology, 72, 1040–1044. https://doi.org/10.1128/AEM.72.2.1040-1044.2006
Nishino, S. F., Spain, J. C., & He, Z. (2000). Strategies for aerobic degradation of nitroaromatic compounds by bacteria: Process discovery to field application. In J. C. Spain, J. B. Hughes, & H. J. Knackmuss (Eds.), Biodegradation of nitroaromatic compounds and explosives (pp. 7–61). Lewis Publishers. https://doi.org/10.1023/B:WIBI.0000021720.03712.12
Nishino, S. F., Spain, J. C., & He, Z. (2002). Biodegradation, transformation and bioremediation of nitroaromatic compounds. In C. J. Hurst, R. L. Crawford, G. R. Knudsen, M. J. McInerey, & L. D. Stetzenbach (Eds.), Manual of environmental microbiology (2nd ed., pp. 987–996). ASM Press. ISBN-10: 953-51-2179-0, ISBN-13: 978-953-51-2179-4.
Park, H. S., & Kim, H. S. (2000). Identification and characterization of the nitrobenzene catabolic plasmids pNB1 and pNB2 in Pseudomonas putida HS12. Journal of Bacteriology, 182(3), 573–580. https://doi.org/10.1128/jb.182.3.573-580.2000
Park, H. S., Lim, S. J., Chang, Y. K., Livingston, A. G., & Kim, H. S. (1999). Degradation of chloronitrobenzenes by a coculture of Pseudomonas putida and a Rhodococcus sp. Applied and Environmental Microbiology, 65(3), 1083–1091.
Payne, R. B., Qu, Y., Nishino, S. F., & Spain, J. C. (2007). Abstract. In General Meeting of the American Society for Microbiology, Toronto, Canada, 21 to 25 May 2007. abstr. Q-013. https://doi.org/10.1128/MMBR.00006-10
Peres, C. M., Van Aken, B., Naveau, H., & Agathos, S. N. (1999). Continuous degradation of mixtures of 4-nitrobenzoate and 4-aminobenzoate by immobilized cells of Burkholderia cepacia strain PB4. Applied Microbiology and Biotechnology, 52, 440–445. https://doi.org/10.1007/s002530051544
Purohit, H. J., Kapley, A., Khardenavis, A., Qureshi, A., & Dafale, N. A. (2016). Chapter three-insights in waste management bioprocesses using genomic tools. Advances in Applied Microbiology, 97, 121–170. https://doi.org/10.1016/bs.aambs.2016.09.002
Qu, Y., & Spain, J. C. (2010). Biodegradation of 5-nitroanthranilic acid by Bradyrhizobium sp. strain JS329. Applied and Environmental Microbiology, 76, 1417–1422. https://doi.org/10.1128/AEM.02816-09
Qureshi, A., & Purohit, H. J. (2002). Isolation of bacterial consortia for degradation of p-nitrophenol from agricultural soil. The Annals of Applied Biology, 140, 159–162. https://doi.org/10.1111/j.1744-7348.2002.tb00168.x
Qureshi, A., Verma, V., Kapley, A., & Purohit, H. J. (2007). Degradation of 4-nitroaniline by Stenotrophomonas strain HPC 135. International Biodeterioration and Biodegradation, 60, 215–218. https://doi.org/10.1016/j.ibiod.2007.03.004
Qureshi, A., Mohan, M., Kanade, G. S., Kapley, A., & Purohit, H. J. (2009). In situ bioremediation of organochlorine-pesticide-contaminated microcosm soil and evaluation by gene probe. Pest Management Science, 65(7), 798–804. https://doi.org/10.1002/ps.1757
Rankin, L. D., Bodenmiller, D. M., Partridge, J. D., Nishino, S. F., Spain, J. C., & Spiro, S. (2008). Escherichia coli NsrR regulates a pathway for the oxidation of 3-nitrotyramine to 4-hydroxy-3-nitrophenylacetate. Journal of Bacteriology, 190, 6170–6177. https://doi.org/10.1128/JB.00508-08
Razo-Flores, E., Donlon, B., Lettinga, G., & Field, J. A. (1997). Biotransformation and biodegradation of N-substituted aromatics in methanogenic granular sludge. FEMS Microbiology Reviews, 20, 525–538. https://doi.org/10.1111/j.1574-6976.1997.tb00335.x
Rhys-Williams, W., Taylor, S. C., & Williams, P. A. (1993). A novel pathway for the catabolism of 4-nitrotoluene by Pseudomonas. Journal of General Microbiology, 139, 1967–1972. https://doi.org/10.1099/00221287-139-9-1967
Rieger, P. G., & Knackmuss, H. J. (1995). Basic knowledge and perspectives on biodegradation of 2,4,6 trinitrotoluene and related nitroaromatic compounds in contaminated soil. In J. C. Spain (Ed.), Biodegradation of nitroaromatic compounds (pp. 1–18). Plenum Press. https://doi.org/10.1007/978-3-662-05794-0_4
Saha, S. P., Banik, S. P., Majumder, A., Noor, A., Biswas, K., Hasan, N., Banerjee, N., Saha, P., Das, R., Halder, S., & Parveen, S. (2014). Bioremediation of methyl parathion by bacterial strains isolated from fresh vegetables. Journal of Environment and Sociobiology, 11, 43–56.
Saha, S., Badh, N., Pal, S., Biswas, R., & Nandy, T. (2017). Carbon and nutrient-limiting conditions stimulate biodegradation of low concentration of phenol. Biochemical Engineering Journal, 126, 40–49. dx.doi.org. https://doi.org/10.1590/0104-6632.20170341s20150388
Samanta, S. K., Bhushan, B., Chauhan, A., & Jain, R. K. (2000). Chemotaxis of a Ralstonia sp. SJ98 toward different nitroaromatic compounds and their degradation. Biochemical and Biophysical Research Communications, 269, 117–123. https://doi.org/10.1006/bbrc.2000.2204
Selvaratnam, C., Thevarajoo, S., Ee, R., Chan, K. G., Bennett, J. P., Goh, K. M., & Chong, C. S. (2016). Genome sequence of Roseivirga sp. Strain D-25 and its potential applications from the genomic aspect. Marine Genomics, 28, 29–31. https://doi.org/10.1016/j.margen.2016.04.004
Sengupta, K., Maiti, T. K., & Saha, P. (2015). Degradation of 4-nitrophenol in presence of heavy metals by a halotolerant Bacillus sp. Strain BUPNP2, having plant growth promoting traits. Symbiosis, 65(3), 157–163. https://doi.org/10.1007/s13199-015-0327-1
Singh, D., Mishra, K., & Ramanthan, G. (2015). Bioremediation of nitroaromatic compounds. In Wastewater treatment engineering. Intech Open. https://doi.org/10.5772/61253
Thangaraj, K., Kapley, A., & Purohit, H. J. (2008). Characterization of diverse Acinetobacter isolates for utilization of multiple aromatic compounds. Bioresource Technology, 99(7), 2488–2494. https://doi.org/10.1016/j.biortech.2007.04.053
Thijs, S., Van Hamme, J., Gkorezis, P., Rineau, F., Weyens, N., & Vangronsveld, J. (2014). Draft genome sequence of Raoultella ornithinolytica TNT, a trinitrotoluene-denitrating and plant growth-promoting strain isolated from explosive-contaminated soil. Genome Announcements, 2(3), e00491–e00414. https://doi.org/10.1128/genomeA.00491-14
Tikariha, H., Pal, R. R., Qureshi, A., Kapley, A., & Purohit, H. J. (2016). In silico analysis for prediction of degradative capacity of Pseudomonas putida SF1. Gene, 591(2), 382–392. https://doi.org/10.1016/j.gene.2016.06.028
Tiwari, J., Naoghare, P., Sivanesan, S., & Bafana, A. (2017). Biodegradation and detoxification of chloronitroaromatic pollutant by Cupriavidus. Bioresource Technology, 223, 184–191. https://doi.org/10.1016/j.biortech.2016.10.043
Torres, R. M., Grosset, C., Steiman, R., & Alary, J. (1996). Liquid chromatography study of degradation and metabolism of pentachloronitrobenzene by four soil micromycetes. Chemosphere, 33(4), 683–692. https://doi.org/10.1016/S1002-0160(10)60076-8
Van Aken, B., Hofrichter, M., Scheibner, K., Hatakka, A., Naveau, H., & Agathos, S. N. (1999). Transformation and mineralization of 2,4,6-trinitrotoluene (TNT) by manganese peroxidase from the white-rot basidiomycete Phlebia radiata. Biodegradation, 10, 83–91. https://doi.org/10.1023/A:1008371209913
Wu, J. F., Jiang, C. Y., Wang, B. J., Ma, Y. F., Liu, Z. P., & Liu, S. J. (2006). Novel partial reductive pathway for 4-chloronitrobenzene and nitrobenzene degradation in Comamonas sp. strain CNB-1. Applied and Environmental Microbiology, 72, 1759–1765. https://doi.org/10.1128/AEM.72.3.1759-1765.2006
Xu, Y., Yu, M., & Shen, A. (2016). Complete genome sequence of the polychlorinated biphenyl degrader Rhodococcus sp. WB1. Genome Announcements, 4(5), e00996–e00916. https://doi.org/10.1128/genomeA.00996-16
Yabannavar, A. V., & Zylstra, G. J. (1995). Cloning and characterization of the genes for p-nitrobenzoate degradation from Pseudomonas pickettii YH105. Applied and Environmental Microbiology, 61, 4284–4290. https://doi.org/10.1128/AEM.61.12.4284-4290.1995
Yadav, T. C., Pal, R. R., Shastri, S., Jadeja, N. B., & Kapley, A. (2015). Comparative metagenomics demonstrating different degradative capacity of activated biomass treating hydrocarbon contaminated wastewater. Bioresource Technology, 188, 24–32. https://doi.org/10.1016/j.biortech.2015.01.141
Yanzhen, M., Yang, L., Xiangting, X., & Wei, H. (2016). Complete genome sequence of a bacterium Pseudomonas fragi P121, a strain with degradation of toxic compounds. Journal of Biotechnology, 224, 68–69. https://doi.org/10.1016/j.jbiotec.2016.03.019
Zhang, C., & Bennett, G. N. (2005). Biodegradation of xenobiotics by anaerobic bacteria. Applied and Environmental Microbiology, 67, 600–618. https://doi.org/10.1007/s00253-004-1864-3
Zhen, D., Liu, H., Wang, S. J., Zhang, J. J., Zhao, F., & Zhou, N. Y. (2006). Plasmid-mediated degradation of 4-chloronitrobenzene by newly isolated Pseudomonas putida strain ZWL73. Applied Microbiology and Biotechnology, 72, 797–803. https://doi.org/10.1007/s00253-006-0345-2
Zheng, C. L., Zhou, J. T., Zhao, L. H., Lu, H., Qu, B. C., & Wang, J. (2007). Isolation and characterization of a nitrobenzene degrading Streptomyces strain from activated sludge. Bulletin of Environmental Contamination and Toxicology, 78(2), 163–167. https://doi.org/10.1007/s00128-007-9031-z
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2021 The Author(s), under exclusive license to Springer Nature Switzerland AG
About this chapter
Cite this chapter
Ramesh, B., Kameswaran, S., Venkatrayulu, C., Chandra, M.S., Reddy, G.V.S., Ramakrishna, M. (2021). Microbial Capacities for Utilization of Nitroaromatics. In: Maddela, N.R., GarcÃa, L.C. (eds) Innovations in Biotechnology for a Sustainable Future. Springer, Cham. https://doi.org/10.1007/978-3-030-80108-3_12
Download citation
DOI: https://doi.org/10.1007/978-3-030-80108-3_12
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-80107-6
Online ISBN: 978-3-030-80108-3
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)