uzakuescУченые записки Казанского университета. Серия Естественные наукиUchenye Zapiski Kazanskogo Universiteta Seriya Estestvennye Nauki2542-064X2500-218XKazan (Volga Region) Federal University10.26907/2542-064X.2024.3.459-475uzakuesc-164Research ArticleСтатьиОсобенности разложения моногидроксибифенилов аэробными штаммами, изолированными из бактериальных ассоциаций–деструкторов ароматических поллютантовDegradation of Mono-Hydroxybiphenyls by Aerobic Strains Isolated from the Bacterial Associations Breaking Down Aromatic PollutantsКирьяноваТ. Д.Kir’yanovaT. D.

Кирьянова Татьяна Денисовна, аспирант,

ул. Голева, д. 13, г. Пермь, 614081.

Perm, 614081.

kitadi2101@gmail.comЕгороваД. О.EgorovaD. O.

Егорова Дарья Олеговна, доктор биологических наук, доцент, старший научный сотрудник,

ул. Голева, д. 13, г. Пермь, 614081.

Perm, 614081.

daryao@rambler.ruИнститут экологии и генетики микроорганизмов УрО РАН – филиал Пермского федерального исследовательского центра УрО РАНРоссияInstitute of Ecology and Genetics of Microorganisms, Ural Branch, Russian Academy of SciencesRussian Federation2024220920241663459475Copyright © Кирьянова Т.Д., Егорова Д.О., 20242024Кирьянова Т.Д., Егорова Д.О.Kir’yanova T.D., Egorova D.O.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://uzakuesc.elpub.ru/jour/article/view/164

Штаммы Micrococcus sp. PNS1, Ochrobactrum sp. PNS5, Stenotrophomonas sp. PNS6, Pseudomonas sp. PNB3, Brevibacterium sp. PNB5, Achromobacter sp. PNB6 и Bosea sp. PNB7, выделенные из ассоциаций PN2 и PN2-B, осуществляют разложение моно-гидроксилированных бифенилов, содержащих в качестве заместителя гидрокси-группу у 3 или 4 атома в молекуле бифенила. Максимальная эффективность деструкции 3-гидроксибифенила составляла 98 %, а 4-гидроксибифенила – 100 % у разных штаммов. У всех исследуемых штаммов был амплифицирован фрагмент гена bphA, кодирующего биосинтез бифенил-2,3-диоксигеназы. Показано, что последовательности гена bphA, полученные в настоящем исследовании, формируют самостоятельную ветвь на графической модели, отображающей их уровень сходства с известными последовательностями данного гена. У штамма Pseudomonas sp. PNB3 выявлено наличие гена benA, кодирующего биосинтез бензоат-1,2-диоксигеназы, и располагающегося в одной ветви эволюционного дерева с геном benA известного штамма-деструктора Pseudomonas putida KT2440. Анализ полученных результатов показал, что трансформация 3-гидрокси- и 4-гидроксибифенилов исследуемыми штаммами происходит в результате диоксигенирования незамещенного кольца молекулы бифенила с последующим расщеплением на 3- и 4-гидроксибензойные кислоты соответственно. Таким образом, исследованные штаммы являются перспективными для применения в технологиях разложения не только хлорбифенилов, но и гидроксилированных бифенилов.

Micrococcus sp. PNS1, Ochrobactrum sp. PNS5, Stenotrophomonas sp. PNS6, Pseudomonas sp. PNB3, Brevibacterium sp. PNB5, Achromobacter sp. PNB6, and Bosea sp. PNB7 were isolated from the PN2 and PN2-B associations and screened for their ability to degrade mono-hydroxylated biphenyls with hydroxyl groups at the C3 or C4 atoms in the biphenyl molecule. The maximum degradation efficiency was 98 % for 3-hydroxybiphenyl and up to 100 % for 4-hydroxybiphenyl with various strains. All strains showed amplification of a fragment of the bphA gene encoding biphenyl-2,3-dioxygenase biosynthesis. Sequence analysis of the bphA gene revealed a distinct branch on the tree topology, indicating its similarity level with known sequences of this gene. Pseudomonas sp. PNB3 was found to possess the benA gene encoding benzoate-1,2-dioxygenase biosynthesis and positioned on the same evolutionary branch as the benA gene from the well-known biphenyl degrader Pseudomonas putida KT2440. The results obtained demonstrate that the transformation of 3-hydroxy- and 4-hydroxybiphenyls by the isolated strains occurs through dioxygenation of the unsubstituted ring of the biphenyl molecule, with subsequent cleavage into 3- and 4-hydroxybenzoic acids, respectively. Therefore, the strains that were examined are promising for potential application in technologies aimed at degrading both chlorobiphenyls and hydroxylated biphenyls.

гидроксибифенилполихлорбифенилыаэробные бактерииштаммыhydroxybiphenylpolychlorinated biphenylsaerobic bacteriastrainsИсследование по изучению генетических детерминант (bph- и ben-генов) выполнено при поддержке гранта Российского научного фонда (проект № 24-24-00498). В исследовании использовано оборудование ЦКП «Исследование материалов и вещества».The investigation of genetic determinants (bph and ben genes) was supported by the Russian Science Foundation (project no. 24-24-00498). The study was carried out with the equipment of the Research Center for Materials and Substances.ReferencesТрегер Ю. СОЗ – стойкие и очень опасные // Chem. J. 2013. № 1–2. P. 30–34.Treger Yu. POPs are persistent and very dangerous. Chem. J., 2013, nos. 1–2, pp. 30–34. (In Russian)Erickson M.D., Kaley R.G., II Application of polychlorinated biphenyls // Environ. Sci. Pollut. Res. 2011. V. 18, No 2. P. 135–151. https://doi.org/10.1007/s11356-010-0392-1.Erickson M.D., Kaley R.G., II Application of polychlorinated biphenyls. Environ. Sci. Pollut. Res., 2011, vol. 18, no. 2, pp. 135–151. https://doi.org/10.1007/s11356-010-0392-1.Zhang P., Ge L., Gao H., Yao T., Fang X., Zhou C., Na G. Distribution and transfer pattern of Polychlorinated Biphenyls (PCBs) among the selected environmental media of Ny-Ålesund, the Arctic: As a case study // Mar. Pollut. Bull. 2014. V. 89, No 1–2. P. 267–275. https://doi.org/10.1016/j.marpolbul.2014.09.050.Zhang P., Ge L., Gao H., Yao T., Fang X., Zhou C., Na G. Distribution and transfer pattern of Polychlorinated Biphenyls (PCBs) among the selected environmental media of NyÅlesund, the Arctic: As a case study. Mar. Pollut. Bull., 2014, vol. 89, nos. 1–2, pp. 267–275. https://doi.org/10.1016/j.marpolbul.2014.09.050.Xu Y., Yu M., Shen A. Complete genome sequence of the polychlorinated biphenyl degrader Rhodococcus sp. WB1 // Genome Announce. 2016. V. 4, No 5. Art. e00996-16. https://doi.org/10.1128/genomea.00996-16.Xu Y., Yu M., Shen A. Complete genome sequence of the polychlorinated biphenyl degrader Rhodococcus sp. WB1. Genome Announce, 2016, vol. 4, no. 5, art. e00996-16. https://doi.org/10.1128/genomea.00996-16.Zhao Q., Bai J., Lu Q., Gao Z., Jia J., Cui B., Liu X. Polychlorinated biphenyls (PCBs) in sediments/soils of different wetlands along 100-year coastal reclamation chronosequence in the Pearl River Estuary, China // Environ. Pollut. 2016. V. 213. P. 860–869. https://doi.org/10.1016/j.envpol.2016.03.039.Zhao Q., Bai J., Lu Q., Gao Z., Jia J., Cui B., Liu X. Polychlorinated biphenyls (PCBs) in sediments/soils of different wetlands along 100-year coastal reclamation chronosequence in the Pearl River Estuary, China. Environ. Pollut., 2016, vol. 213, pp. 860–869. https://doi.org/10.1016/j.envpol.2016.03.039.Nam I.-H., Chon C.-M., Jung K.-Y., Kim J.-G. Biodegradation of biphenyl and 2-chlorobiphenyl by a Pseudomonas sp. KM-04 isolated from PCBs-contaminated coal mine soil // Bull. Environ. Contam. Toxicol. 2014. V. 93, No 1. P. 89–94. https://doi.org/10.1007/s00128-014-1286-6.Nam I.-H., Chon C.-M., Jung K.-Y., Kim J.-G. Biodegradation of biphenyl and 2-chlorobiphenyl by a Pseudomonas sp. KM-04 isolated from PCBs-contaminated coal mine soil. Bull. Environ. Contam. Toxicol., 2014, vol. 93, no. 1, pp. 89–94. https://doi.org/10.1007/s00128-014-1286-6.Serdar B., LeBlanc W.G., Norris J.M., Dickinson L.M. Potential effects of polychlorinated biphenyls (PCBs) and selected organochlorine pesticides (OCPs) on immune cells and blood biochemistry measures: A cross-sectional assessment of the NHANES 2003-2004 data // Environ. Health. 2014. V. 13, No 1. Art. 114. https://doi.org/10.1186/1476-069x-13-114.Serdar B., LeBlanc W.G., Norris J.M., Dickinson L.M. Potential effects of polychlorinated biphenyls (PCBs) and selected organochlorine pesticides (OCPs) on immune cells and blood biochemistry measures: A cross-sectional assessment of the NHANES 2003-2004 data. Environ. Health, 2014, vol. 13, no. 1, art. 114. https://doi.org/10.1186/1476-069x-13-114.Hu J., Qian M., Zhang Q., Cui J., Yu C., Su X., Shen C., Hashmi M.Z., Shi J. Sphingobium fuliginis HC3: A novel and robust isolated biphenyl-and polychlorinated biphenylsdegrading bacterium without dead-end intermediates accumulation // PloS One. 2015. V. 10, No 4. Art. e0122740. https://doi.org/10.1371/journal.pone.0122740.Hu J., Qian M., Zhang Q., Cui J., Yu C., Su X., Shen C., Hashmi M.Z., Shi J. Sphingobium fuliginis HC3: A novel and robust isolated biphenyl-and polychlorinated biphenyls-degrading bacterium without dead-end intermediates accumulation. PloS One, 2015, vol. 10, no. 4, art. e0122740. https://doi.org/10.1371/journal.pone.0122740.Shuai J., Yu X., Zhang J., Xiong A.-S., Xiong F. Regional analysis of potential polychlorinated biphenyl degrading bacterial strains from China // Braz. J. Microbiol. 2016. V. 47, No 3. P. 536–541. https://doi.org/10.1016/j.bjm.2014.12.001.Shuai J., Yu X., Zhang J., Xiong A.-S., Xiong F. Regional analysis of potential polychlorinated biphenyl degrading bacterial strains from China. Braz. J. Microbiol., 2016, vol. 47, no. 3, pp. 536–541. https://doi.org/10.1016/j.bjm.2014.12.001.Murugan K., Vasudevan N. Intracellular toxicity exerted by PCBs and role of VBNC bacterial strains in biodegradation // Ecotoxicol. Environ. Saf. 2018. V. 157. P. 40–60. https://doi.org/10.1016/j.ecoenv.2018.03.014.Murugan K., Vasudevan N. Intracellular toxicity exerted by PCBs and role of VBNC bacterial strains in biodegradation. Ecotoxicol. Environ. Saf., 2018, vol. 157, pp. 40–60. https://doi.org/10.1016/j.ecoenv.2018.03.014.Devi N.L. Persistent organic pollutants (POPs): Environmental risks, toxicological effects, and bioremediation for environmental safety and challenges for future research // Saxena G., Bharagava R. (Eds.) Bioremediation of Industrial Waste for Environmental Safety. V. I: Industrial waste and its management. Singapore: Springer, 2023. Р. 53–76. https://doi.org/10.1007/978-981-13-1891-7_4.Devi N.L. Persistent organic pollutants (POPs): Environmental risks, toxicological effects, and bioremediation for environmental safety and challenges for future research. In: Saxena G., Bharagava R. (Eds.) Bioremediation of Industrial Waste for Environmental Safety. Vol. I: Industrial waste and its management. Singapore, Springer, 2023, pp. 53–76. https://doi.org/10.1007/978-981-13-1891-7_4.Final Act of the Conference of Plenipotentiaries on the Stockholm Convention on Persistent Organic Pollutants (Stockholm, 22–23 May 2001) // United Nations Environment Programme. Geneva, 2001. 44 p.Final Act of the Conference of Plenipotentiaries on the Stockholm Convention on Persistent Organic Pollutants (Stockholm, 22–23 May 2001). United Nations Environment Programme. Geneva, 2001. 44 p.Zhu L., Zhou J., Zhang R., Tang X., Wang J., Li Y., Zhang Q., Wang W. Degradation mechanism of biphenyl and 4,4′-dichlorobiphenyl cis-dihydroxylation by non-heme 2,3 dioxygenases BphA: A QM/MM approach // Chemosphere. 2020. V. 247. Art. 125844. https://doi.org/10.1016/j.chemosphere.2020.125844.Zhu L., Zhou J., Zhang R., Tang X., Wang J., Li Y., Zhang Q., Wang W. Degradation mechanism of biphenyl and 4,4′-dichlorobiphenyl cis-dihydroxylation by non-heme 2,3 dioxygenases BphA: A QM/MM approach. Chemosphere, 2020, vol. 247, art. 125844. https://doi.org/10.1016/j.chemosphere.2020.125844.Negret-Bolagay D., Zamora-Ledezma C., Chuya-Sumba C., De Sousa F.B., Whitehead D., Alexis F., Guerrero V.H. Persistent organic pollutants: The trade-off between potential risks and sustainable remediation methods // J. Environ. Manage. 2021. V. 300. Art. 113737. https://doi.org/10.1016/j.jenvman.2021.113737.Negret-Bolagay D., Zamora-Ledezma C., Chuya-Sumba C., De Sousa F.B., Whitehead D., Alexis F., Guerrero V.H. Persistent organic pollutants: The trade-off between potential risks and sustainable remediation methods. J. Environ. Manage., 2021, vol. 300, art. 113737. https://doi.org/10.1016/j.jenvman.2021.113737.Cámara B., Herrera C., González M., Couve E., Hofer B., Seeger M. From PCBs to highly toxic metabolites by the biphenyl pathway // Environ. Microbiol. 2004. V. 6, No 8. P. 842–850. https://doi.org/10.1111/j.1462-2920.2004.00630.x.Cámara B., Herrera C., González M., Couve E., Hofer B., Seeger M. From PCBs to highly toxic metabolites by the biphenyl pathway. Environ. Microbiol., 2004, vol. 6, no. 8, pp. 842–850. https://doi.org/10.1111/j.1462-2920.2004.00630.x.Passatore L., Rossetti S., Juwarkar A.A., Massacci A. Phytoremediation and bioremediation of polychlorinated biphenyls (PCBs): State of knowledge and research perspectives // J. Hazard. Mater. 2014. V. 278. P. 189–202. https://doi.org/10.1016/j.jhazmat.2014.05.051.Passatore L., Rossetti S., Juwarkar A.A., Massacci A. Phytoremediation and bioremediation of polychlorinated biphenyls (PCBs): State of knowledge and research perspectives. J. Hazard. Mater., 2014, vol. 278, pp. 189–202. https://doi.org/10.1016/j.jhazmat.2014.05.051.Tehrani R., Lyv M.M., Kaveh R., Schnoor J.L., Van Aken B. Biodegradation of monohydroxylated PCBs by Burkholderia xenovorans // Biotechnol. Lett. 2012. V. 34, No 12. P. 2247–2252. https://doi.org/10.1007/s10529-012-1037-x.Tehrani R., Lyv M.M., Kaveh R., Schnoor J.L., Van Aken B. Biodegradation of mono-hydroxylated PCBs by Burkholderia xenovorans. Biotechnol. Lett., 2012, vol. 34, no. 12, pp. 2247–2252. https://doi.org/10.1007/s10529-012-1037-x.Sun J., Pan L., Zhu L. Formation of hydroxylated and methoxylated polychlorinated biphenyls by Bacillus subtilis: New insights into microbial metabolism // Sci. Total Environ. 2018. V. 613–614. P. 54–61. https://doi.org/10.1016/j.scitotenv.2017.09.063.Sun J., Pan L., Zhu L. Formation of hydroxylated and methoxylated polychlorinated biphenyls by Bacillus subtilis: New insights into microbial metabolism. Sci. Total Environ., 2018, vols. 613–614, pp. 54–61. https://doi.org/10.1016/j.scitotenv.2017.09.063.Li C., Liu J., Wu N., Pan X., Feng J., Al-Basher G., Allam A.A., Qu R., Wang Z. Photochemical formation of hydroxylated polychlorinated biphenyls (OH-PCBs) from decachlorobiphenyl (PCB-209) on solids/air interface // J. Hazard. Mater. 2019. V. 378. Art. 120758. https://doi.org/10.1016/j.jhazmat.2019.120758.Li C., Liu J., Wu N., Pan X., Feng J., Al-Basher G., Allam A.A., Qu R., Wang Z. Photochemical formation of hydroxylated polychlorinated biphenyls (OH-PCBs) from decachlorobiphenyl (PCB-209) on solids/air interface. J. Hazard. Mater., 2019, vol. 378, art. 120758. https://doi.org/10.1016/j.jhazmat.2019.120758.Macková M., Vrchotová B., Francová K., Sylvestre M., Tomaniová M., Lovecká P., Demnerová K., Macek T. Biotransformation of PCBs by plant and bacteria – consequences of plant-microbe interactions // Eur. J. Soil Biol. 2007. V. 43, No 4. P. 233–241. https://doi.org/10.1016/j.ejsobi.2007.02.006.Macková M., Vrchotová B., Francová K., Sylvestre M., Tomaniová M., Lovecká P., Demnerová K., Macek T. Biotransformation of PCBs by plant and bacteria – consequences of plant-microbe interactions. Eur. J. Soil Biol., 2007, vol. 43, no. 4, pp. 233–241. https://doi.org/10.1016/j.ejsobi.2007.02.006.Moody J., Doerge D., Freeman J., Cerniglia C. Degradation of biphenyl by Mycobacte- rium sp. strain PYP-1 // Appl. Microbiol. Biotechnol. 2002. V. 58, No 3. P. 364–369. https://doi.org/10.1007/s00253-001-0878-3.Moody J., Doerge D., Freeman J., Cerniglia C. Degradation of biphenyl by Mycobacterium sp. strain PYP-1. Appl. Microbiol. Biotechnol., 2002, vol. 58, no. 3, pp. 364–369. https://doi.org/10.1007/s00253-001-0878-3.Yoo M., Kim D., Zylstra G.J., Kang B.S., Kim E. Biphenyl hydroxylation enhanced by an engineered o-xylene dioxygenase from Rhodococcus sp. strain DK17 // Res. Microbiol. 2011. V. 162, No 7. P. 724–728. https://doi.org/10.1016/j.resmic.2011.04.013.Yoo M., Kim D., Zylstra G.J., Kang B.S., Kim E. Biphenyl hydroxylation enhanced by an engineered o-xylene dioxygenase from Rhodococcus sp. strain DK17. Res. Microbiol., 2011, vol. 162, no. 7, pp. 724–728. https://doi.org/10.1016/j.resmic.2011.04.013.Kanteev M., Bregman-Cohen A., Deri B., Shahar A., Adir N., Fishman A. A crystal structure of 2-hydroxybiphenyl 3-monooxygenase with bound substrate provides insights into the enzymatic mechanism // Biochim. Biophys. Acta, Proteins Proteomics. 2015. V. 1854, No 12. P. 1906–1913. https://doi.org/10.1016/j.bbapap.2015.08.002.Kanteev M., Bregman-Cohen A., Deri B., Shahar A., Adir N., Fishman A. A crystal structure of 2-hydroxybiphenyl 3-monooxygenase with bound substrate provides insights into the enzymatic mechanism. Biochim. Biophys. Acta, Proteins Proteomics, 2015, vol. 1854, no. 12, pp. 1906–1913. https://doi.org/10.1016/j.bbapap.2015.08.002.Suman J., Sredlova K., Fraraccio S., Jerabkova M., Strejcek M., Kabickova H., Cajthaml T., Uhlik O. Transformation of hydroxylated polychlorinated biphenyls by bacterial 2-hydroxybiphenyl 3-monooxygenase // Chemosphere. 2024. V. 349. Art. 140909. https://doi.org/10.1016/j.chemosphere.2023.140909.Suman J., Sredlova K., Fraraccio S., Jerabkova M., Strejcek M., Kabickova H., Cajthaml T., Uhlik O. Transformation of hydroxylated polychlorinated biphenyls by bacterial 2-hydroxybiphenyl 3-monooxygenase. Chemosphere, 2024, vol. 349, art. 140909. https://doi.org/10.1016/j.chemosphere.2023.140909.Bordoloi N.K., Rai S.K., Chaudhuri M.K., Mukherjee A.K. Deep-desulfurization of dibenzothiophene and its derivatives present in diesel oil by a newly isolated bacterium Achromobacter sp. to reduce the environmental pollution from fossil fuel combustion // Fuel Process. Technol. 2014. V. 119. P. 236–244. https://doi.org/10.1016/j.fuproc.2013.10.014.Bordoloi N.K., Rai S.K., Chaudhuri M.K., Mukherjee A.K. Deep-desulfurization of dibenzothiophene and its derivatives present in diesel oil by a newly isolated bacterium Achromobacter sp. to reduce the environmental pollution from fossil fuel combustion. Fuel Process. Technol., 2014, vol. 119, pp. 236–244. https://doi.org/10.1016/j.fuproc.2013.10.014.Sun J., Zhu L., Pan L., Wei Z., Song Y., Zhang Y., Qu L., Zhan Y. Detection of methoxylated and hydroxylated polychlorinated biphenyls in sewage sludge in China with evidence for their microbial transformation // Sci. Rep. 2016. V. 6, No 1. Art. 29782. https://doi.org/10.1038/srep29782.Sun J., Zhu L., Pan L., Wei Z., Song Y., Zhang Y., Qu L., Zhan Y. Detection of methoxylated and hydroxylated polychlorinated biphenyls in sewage sludge in China with evidence for their microbial transformation. Sci. Rep., 2016, vol. 6, no. 1, art. 29782. https://doi.org/10.1038/srep29782.Sondossi M., Sylvestre M., Ahmad D., Massé R. Metabolism of hydroxybiphenyl and chloro-hydroxybiphenyl by biphenyl/chlorobiphenyl degrading Pseudomonas testosteroni, strain B-356 // J. Ind. Microbiol. 1991. V. 7, No 2. P. 77–88. https://doi.org/10.1007/BF01576069.Sondossi M., Sylvestre M., Ahmad D., Massé R. Metabolism of hydroxybiphenyl and chloro-hydroxybiphenyl by biphenyl/chlorobiphenyl degrading Pseudomonas testosteroni, strain B-356. J. Ind. Microbiol., 1991, vol. 7, no. 2, pp. 77–88. https://doi.org/10.1007/BF01576069.Yamada T., Shimomura Y., Hiraoka Y., Kimbara K. Oxidative stress by biphenyl metabolites induces inhibition of bacterial cell separation // Appl. Microbiol. Biotechnol. 2006. V. 73, No 2. P. 452–457. https://doi.org/10.1007/s00253-006-0472-9.Yamada T., Shimomura Y., Hiraoka Y., Kimbara K. Oxidative stress by biphenyl metabolites induces inhibition of bacterial cell separation. Appl. Microbiol. Biotechnol., 2006, vol. 73, no. 2, pp. 452–457. https://doi.org/10.1007/s00253-006-0472-9.Bhalla R., Tehrani R., Van Aken B. Toxicity of hydroxylated polychlorinated biphenyls (HO-PCBs) using the bioluminescent assay Microtox® // Ecotoxicology. 2016. V. 25, No 7. P. 1438–1444. https://doi.org/10.1007/s10646-016-1693-z.Bhalla R., Tehrani R., Van Aken B. Toxicity of hydroxylated polychlorinated biphenyls (HO-PCBs) using the bioluminescent assay Microtox®. Ecotoxicology, 2016, vol. 25, no. 7, pp. 1438–1444. https://doi.org/10.1007/s10646-016-1693-z.Egorova D., Kyr’yanova T., Pyankova A., Anan’ina L., Plotnikova E. Selective pressure of biphenyl/polychlorinated biphenyls on the formation of aerobic bacterial associations and their biodegradative potential // Folia Microbiol. 2021. V. 66, No 4. P. 659–676. https://doi.org/10.1007/s12223-021-00873-1.Egorova D., Kyr’yanova T., Pyankova A., Anan’ina L., Plotnikova E. Selective pressure of biphenyl/polychlorinated biphenyls on the formation of aerobic bacterial associations and their biodegradative potential. Folia Microbiol., 2021, vol. 66, no. 4, pp. 659–676. https://doi.org/10.1007/s12223-021-00873-1.Hernandez B.S., Koh S.-C., Chial M., Focht D.D. Terpene-utilizing isolates and their relevance to enhanced biotransformation of polychlorinated biphenyls in soil // Biodegradation. 1997. V. 8, No 3. P. 153–158. https://doi.org/10.1023/A:1008255218432.Hernandez B.S., Koh S.-C., Chial M., Focht D.D. Terpene-utilizing isolates and their relevance to enhanced biotransformation of polychlorinated biphenyls in soil. Biodegradation, 1997, vol. 8, no. 3, pp. 153–158. https://doi.org/10.1023/A:1008255218432.Baggi G., Bernasconi S., Zangrossi M., Cavalca L., Andreoni V. Co-metabolism of di- and trichlorobenzoates in a 2-chlorobenzoate-degrading bacterial culture: Effect of the position and number of halo-substituents // Int. Biodeterior. Biodegrad. 2008. V. 62, No 1. P. 57–64. https://doi.org/10.1016/j.ibiod.2007.12.002.Baggi G., Bernasconi S., Zangrossi M., Cavalca L., Andreoni V. Co-metabolism of di- and trichlorobenzoates in a 2-chlorobenzoate-degrading bacterial culture: Effect of the position and number of halo-substituents. Int. Biodeterior. Biodegrad., 2008, vol. 62, no. 1, pp. 57–64. https://doi.org/10.1016/j.ibiod.2007.12.002.Baldwin B.R., Nakatsu C.H., Nies L. Detection and enumeration of aromatic oxygenase genes by multiplex and real-time PCR // Appl. Environ. Microbiol. 2003. V. 69, No 6. P. 3350–3358. https://doi.org/10.1128/AEM.69.6.3350-3358.2003.Baldwin B.R., Nakatsu C.H., Nies L. Detection and enumeration of aromatic oxygenase genes by multiplex and real-time PCR. Appl. Environ. Microbiol., 2003, vol. 69, no. 6, pp. 3350–3358. https://doi.org/10.1128/AEM.69.6.3350-3358.2003.Егорова Д.О., Пьянкова А.А. Скрининг гена альфа-субъединицы бензоат диоксигеназы в бактериальных ассоциациях, полученных в результате селекции на (хлор)ароматических соединениях // Вестник Пермского Университета. Сер. Биология. 2019. Вып. 4. С. 464–470. https://doi.org/10.17072/1994-9952-2019-4-464-470.Egorova D.O., Pjankova A.A. Alpha-subunit benzoate dioxygenase gene screening in bacterial associations obtained by selection on (chlorine) aromatic compounds. Vestn. Permsk. Univ. Ser. Biol., 2019, no. 4, pp. 464–470. https://doi.org/10.17072/1994-9952-2019-4-464-470. (In Russian)Francova K., Macková M., Macek T., Sylvestre M. Ability of bacterial biphenyl dioxygenases from Burkholderia sp. LB400 and Comamonas testosterone B-356 to catalyze oxygenation of ortho-hydroxychlorobiphenyls formed from PCBs by plants // Environ. Pollut. 2004. V. 127, No 1. P. 41–48. https://doi.org/10.1016/S0269-7491(03)00257-4.Francova K., Macková M., Macek T., Sylvestre M. Ability of bacterial biphenyl dioxygenases from Burkholderia sp. LB400 and Comamonas testosterone B-356 to catalyze oxygenation of ortho-hydroxychlorobiphenyls formed from PCBs by plants. Environ. Pollut., 2004, vol. 127, no. 1, pp. 41–48. https://doi.org/10.1016/S0269-7491(03)00257-4.van Duuren J.B.J.H., Wijte D., Leprince A., Karge B., Puchałka J., Wery J., Martins dos Santos V.A.P., Eggink G., Mars A.E. Generation of a catR deficient mutant of P. putida KT2440 that produces cis,cis-muconate from benzoate at high rate and yield // J. Biotechnol. 2011. V. 156, No 3. P. 163–172. https://doi.org/10.1016/j.jbiotec.2011.08.030.van Duuren J.B.J.H., Wijte D., Leprince A., Karge B., Puchałka J., Wery J., Martins dos Santos V.A.P., Eggink G., Mars A.E. Generation of a catR deficient mutant of P. putida KT2440 that pro- duces cis,cis-muconate from benzoate at high rate and yield. J. Biotechnol., 2011, vol. 156, no. 3, pp. 163–172. https://doi.org/10.1016/j.jbiotec.2011.08.030.Kahlon R.S. (Ed.) Pseudomonas: Molecular and Applied Biology. Springer Int. Publ., 2016. 519 p. http://dx.doi.org/10.1007/978-3-319-31198-2.Kahlon R.S. (Ed.) Pseudomonas: Molecular and Applied Biology. Springer Int. Publ., 2016. 519 p. http://dx.doi.org/10.1007/978-3-319-31198-2.

The authors declare that there are no conflicts of interest present.