Biol. Stud. 2018: 12(3–4); 117–140 • DOI:


N. S. Verkholiak, T. B. Peretyatko


In this review, the peripheral pathways for the decomposition of aromatic compounds by bacteria are considered. Aromatic compounds can be degraded with participation of bacteria under aerobic and anaerobic conditions. In the presence of oxygen, aromatic compounds can be metabolized by bacteria of genera Pseudomonas, Rhodococcus, Nocardia, Micrococcus, Bacillus, Pseudomonas, Arthrobacter and others. Under anaerobic conditions, decomposition of compounds with a benzene core is carried out by sulfate-reducing, nitrate-reducing and fermenting bacteria.

Degradation of the aromatic compounds is a complex long-term process, which in natural conditions depends on biotic and abiotic factors. Peripheral pathways for the expansion of aroma compounds differ according to their structure, however, they mainly lead to the formation of central intermediates: catechol – under aerobic conditions and benzoyl-CoA – under anaerobic.

The aromatic compounds that are converted via benzoyl-CoA pathway should contain a carboxyl group (that is, an aromatic acid) or carboxylate to form an aromatic acid in one of the first steps of the metabolism. In this way, a destruction of phenol, o-cresol, catechol and hydroquinone occurs. All intermediate compounds of the reducing benzoyate pathway are СoA-thioesters. Aromatic compounds with two or more hydroxyl groups are less stable and more easily degraded by microorganisms. A decomposition of these compounds is not always associated with carboxylation as an initial stage, and subsequent hydroxylation or rearrangement processes provide a reduction in the stability of the benzene ring.

The review considers a novel pathway for degradation of the aromatic compounds, described by B. Sсhink et al., іn which hydroxyhydroquinone is a central intermediate. Using this pathway, nitrate-reducing bacteria decompose resorcinol, a-resorcylate, 3-hydroxybenzoate, gentisic acid and possibly hydroquinone in hydroxylation and decarboxylation reactions.

Due to high mobility and ability to form contaminants in aquifers, hydrocarbon oils are among the most common pollutants in the groundwater. The initial stages of transformation of the aromatic compounds – of the benzene, toluene, ethylbenzene and xylene (BTEХ) by various microorganisms lead to a formation of benzoyl-CoA, which further decomposes along the benzoyl-CoA pathway. Toluene is most easily exposed to biodestruction in anaerobic conditions among the components of BTEХ.

The activities of agricultural enterprises and various industries contribute to a continuous flow of xenobiotics, in particular of the aromatic nature into the environment. An important issue that should be addressed is a search for a variety of methods for cleaning the contaminated environment. An effective and environmentally safe way is bioremediation, as a technology for the use of living organisms to decompose pollutants into less toxic compounds or transform them into carbon dioxide and water. Therefore, more studies are being conducted on the ability of different types of microorga­nisms to detoxify the environment from pollutants.

Keywords: phenol, aromatic hydrocarbons, hydroquinone, phloroglucinol, рyro­gallol, degradation



1. Anderson R.T., Lovley D.R. Anaerobic bioremediation of benzene under sulfate-reducing conditions in a petroleum-contaminated aquifer. Environ. Sci. Technol, 2000; 34 (11): 2261-6.

2. Annweiler E., Materna A., Safinowski M., Kappler A., Richnow H.H. et al. Anaerobic degradation of 2-methylnaphthalene by a sulfate-reducing enrichment culture. Appl. Environ. Microbiol, 2000; 66: 5329-33.
PMid:11097910 PMCid:PMC92464

3. Antonyuk V.S., Timchik G.S., Bondarenko Yu.Yu., Kovalenko Yu.I., Bondarenko M.O., Gai­dash R.P., Filippova M.V. Coverage in instrument making. Kyiv: NTUU "KPI". Publishing House "Politekhnika", 2016. 360 p. (In Ukrainian)

4. Auburger G., Winter J. Purification and characterisation of benzoyl-CoA synthetase from a syntrophic, benzoate degrading, anaerobic mixed culture. Appl. Microbiol. Biotechnol, 1992; 37: 789-795.

5. Bardova E.A., Bardov P.V., Kolyadenko V.G. New perspective methods in cosmetology. Ukrai­nian Journal of Dermatology, Venerology, Cosmetology, 2004; 4: 56-60. (In Ukrainian)

6. Beller H. R., Spormann A. M. Substrate range of benzylsuccinate synthase from Azoarcus sp. strain T. FEMS. Microbiol. Lett, 1999; 178: 147-53.

7. Beller H. R., Spormann A. M., Sharma P. K. et al. Isolation and Characterization of a Novel Toluene-Degrading Sulfate-Reducing Bacterium. Applied and Environmental Microbiology, 1996; 62: 1188-1196.

8. Bissaillon J.G., Lépine F., Beaudet R., Sylvestre M. Carboxylation of o-cresol by an anaerobic consortium under methanogenic conditions. Appl. Environ. Microbiol, 1991; 57: 2131-2134.

9. Bonting C.F.C, Fuchs G. Anaerobic metabolism of 2-hydroxybenzoic acid (salicylic acid) by a denitrifying bacterium. Arch. Microbiol, 1996; 165: 402-408.

10. Brauman A., Müller J. A., Garcia J-L., Brune A., Schink B. Fermentative degradation of 3-hydroxybenzoate in pure culture by a novel strictly anaerobic bacterium, Sporotomaculum hydroxybenzoicum gen. nov. sp. nov. Int. J. Syst. Bacteriol, 1998; 48: 215-221.

11. Breese K., Fuchs G. 4-Hydroxybenzoyl-CoA reductase (dehydroxylating) from the denitrifying bacterium Thauera aromatica: prosthetic groups, electron donor, and genes of a member of the molybdenum-flavin-iron-sulfur proteins. Eur. J. Biochem, 1998; 251: 916-923.

12. Brune A., Schink B. Phloroglucinol pathway in the strictly anaerobic Pelobacter acidigallici: fermentation of trihydroxybenzenes to acetate via triacetic acid. Arch. Microbiol, 1992; 157: 417-424.

13. Brune A., Schink B. Pyrogallol-to-phloroglucinol conversion and other hydroxyl-transfer reactions catalyzed by cell extracts of Pelobacter acidigallici. J. Bacteriol, 1990; 172: 1070-1076.

14. Coates J.D., Chakraborty R., Lack J.G., O'Connor S.M., Cole K. A. et al. Anaerobic benzene oxidation coupled to nitrate reduction in pure culture by two strains of Dechloromonas. Nature, 2001; 411: 1039-43.

15. Elshahed M.S., Gieg L.M., McInerney M.J., Suflita J.M. Signature metabolites attesting to the in situ attenuation of alkylbenzenes in anaerobic environments. Environ. Sci. Technol, 2001; 35(4): 682-89.

16. Gibson J., Dispensa M., Fogg G. C., Evans D. T., Harwood C. S. 4-Hydroxybenzoate-coenzyme A-ligase from Rhodopseudomonas palustris: purification, gene sequence, and role in anaerobic degradation. J. Bacteriol, 1994; 176: 634-641.

17. Gibson J., Dispensa M., Harwood C. S. 4-Hydroxybenzoyl coenzyme A reductase (dehydroxylating) is required for anaerobic degradation of 4-hydroxybenzoate by Rhodopseudomonas palustris and shares features with molybdenum-containing hydroxylases. J. Bacteriol, 1997; 179: 634-642.

18. Gibson J., Harwood C. Мetabolic diversity in aromatic compound utilization by anaerobic microbes. Annu. Rev. Microbiol, 2002; 56: 345-369.

19. Gorny N., Schink B. Complete anaerobic oxidation of hydroquinone by Desulfococcus sp. strain Hy5: indications of hydroquinone carboxylation to gentisate. Arch. Microbiol, 1994; 162: 131-135.

20. Gorny N., Schink B. Hydroquinone degradation via reductive dehydroxylation of gentisyl-CoA by a strictly anaerobic fermenting bacterium. Arch. Microbiol, 1994; 161: 25-32.

21. Gorny N., Schink B. Anaerobic degradation of catechol by Desulfobacterium sp. strain Cat2 proceeds via carboxylation to protocatechuate. Appl. Environ. Microbiol, 1994; 60: 3396-3340.

22. Harwood C.S., Burchhardt G., Herrmann H., Fuchs G. Anaerobic metabolism of aromatic compounds via the benzoyl-CoA pathway. FEMS Microbiology Reviews, 1999; 22(5): 439-458.

23. He Z., Wiegel J. Purification and characterisation of an oxygen-sensitive, reversible 3,4-dihydroxybenzoate decarboxylase from Clostridium hydroxybenzoicum. J. Bacteriol, 1996; 178: 3539-3543.
PMid:8655551 PMCid:PMC178123

24. Heider J., Spormann A.M., Beller H.R. et al. Anaerobic bacterial metabolism of hydrocarbons. FEMS Microbiology, 1998; 22(5): 459-473.

25. Hirsch W., Schдgger H., Fuchs G. Phenylglyoxylate: NAD+ oxidoreductase (CoA benzoyla­ting), a new enzyme of anaerobic phenylalanine metabolism in the denitrifying bacterium Azoarcus evansii. Eur. J. Biochem, 1998; 251: 907-915.

26. Hopper D. J. Incorporation of [18O]water in the formation of p-hydroxybenzyl alcohol by the p-cresol methylhydroxylase from Pseudomonas putida. Biochem. J, 1978; 175: 345-347.
PMid:736904 PMCid:PMC1186072

27. Kahng H.Y., Kukor J.J., Oh K.H. Characterization of strain HY99, a novel microorganism capable of aerobic and anaerobic degradation of aniline. FEMS Microbiol. Lett, 2000; 190: 215-221.

28. Krieger C.J., Beller H.R., Reinhard M., Spormann A.M. Initial reactions in anaerobic oxidation of m-xylene by the denitrifying bacterium Azoarcus sp. strain T. J. Bacteriol, 1999; 181: 6403-10.

29. Lack A., Fuchs G. Evidence that phenol phosphorylation to phenylphosphate is the first step in anaerobic phenol metabolism in a denitrifying Pseudomonas sp. Arch. Microbiol, 1994; 161: 306-311.

30. Lovley D.R. Bioremediation. Anaerobes to the rescue. Science, 2001; 293: 1444-1446.

31. Lovley D.R. Anaerobic benzene degradation. Biodegradation, 2000; 11: 107-16.

32. Matafonova G.G., Batoev V.B., Sosnin E.A., Christofi N. Combined Method for Degradation of Chlorophenols. Chemistry for Sustainable Development, 2008; 2: 189-195.

33. Meckenstock R.U., Annweiler E., Michaelis W., Richnow H.H., Schink B. Anaerobic naphthalene degradation by a sulfate-reducing enrichment culture. Appl. Environ. Microbiol, 2000; 66: 2743-47.
PMid:10877763 PMCid:PMC92068

34. Mohamed M.E., Seyfried B., Tschech A., Fuchs G. Anaerobic oxidation of phenylacetate and 4-hydroxyphenylacetate to benzoyl-CoA and CO2 in denitrifying Pseudomonas sp. Evidence for an a-oxidation mechanism. Arch. Microbiol, 1993; 159: 563-573.

35. Morasch B., Schink B., Tebbe C., Meckenstock R. U. Degradation of o-xylene and m-xylene by a novel sulfate-reducer belonging to the genus Desulfotomaculum. Arch. Microbiol, 2004; 181 (6): 407-417.

36. Müller J.A., Galushko A.S., Kappler A., Schink B. Anaerobic degradation of m-cresol by Desulfobacterium cetonicum is initiated by formation of 3-hydroxybenzylsuccinate. Arch. Mic­robiol, 1999; 172: 287-294.

37. Müller J.A., Galushko A.S., Kappler A., Schink B. Initiation of anaerobic degradation of p-cresol by formation of 4-hydroxybenzylsuccinate in Desulfobacterium cetonicum. J. Bacteriol, 2001; 183: 752-57.
PMid:11133971 PMCid:PMC94933

38. Рirog T., Antonuk S., Sofilkanich A. Transformation of aromatic compounds in a surfactant by Rhodococcus erythropolis ІMV AL-5017, Acinetobacter calcoaceticus ІMV B-7241 and Nocardia vaccinii ІMV B-7405. Scientific Works of NUFT, 2016; 22(1): 7-13. (In Ukrainian)

39. Pirog T.P., Iutynska G.О., Sofilkanich А.Р., Konon A.D. Microbial surfactants in environmental technologies. Kyiv: Scientific Thought, 2016. 279 р. (In Ukrainian)

40. Rabus R., Wilkes H., Schramm A., Harms G., Behrends A. et al. Anaerobic utilization of alkylbenzenes and n-alkanes from crude oil in an enrichment culture of denitrifying bacteria affiliating with the beta-subclass of Proteobacteria. Environ. Microbiol, 1999; 1: 145-5.

41. Reichenbecher W., Rüdiger A., Kroneck P.M.H., Schink B. One molecule of molybdopterin guanine dinucleotide is associated with each subunit of the heterodimeric Mo-Fe-S protein transhydroxylase of Pelobacter acidigallici as determined by SDS/PAGE and mass spectrometry. Eur. J. Biochem, 1996; 237: 406-413.

42. Reichenbecher W., Schink B. Towards the reaction mechanism of pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici. Biochim. Biophys. Acta, 1999; 1430: 245-253.

43. Reichenbecher W., Philipp B., Suter M. J-F., Schink B. Hydroxyhydroquinone reductase, the initial enzyme involved in the degradation of hydroxyhydroquinone (1,2,4-trihydroxybenzene) by Desulfovibrio inopinatus. Arch. Microbiol, 2000; 173(3): 206-212.

44. Salmanov M., Veliyev М., Babashly A., Bektashi N. Biodegradation of halogen structured aromatic associations with bacteria isolated from Azerbaijan costs of Caspian. Bulletin of the Moscow State Regional University. Series: Natural Sciences, 2010; 2: 45-50. (In Russian)

45. Seyfried B., Tschech A., Fuchs G. Anaerobic degradation of phenylacetate and 4-hydroxyphenylacetate by denitrifying bacteria. Arch. Microbiol, 1991; 155: 249-255.

46. Schink B., Philipp B., Müller J. Anaerobic Degradation of Phenolic Compounds. Naturwissenschaften, 2000; 87(1): 12-23.

47. Schneider S., Fuchs G. Phenylacetyl-CoA: acceptor oxidoreductase, a new alpha-oxidizing enzyme that produces phenylglyoxylate. Assay, membrane localization, and differential production in Thauera aromatica. Arch. Microbiol, 1998; 169: 509-516.

48. Schnell S., Bak F., Pfennig N. Anaerobic degradation of aniline and dihydroxybenzenes by newly isolated sulfate-reducing bacteria and description of Desulfobacterium anilini. Arch. Microbiol, 1989; 152: 556-63.

49. Shcherbina O., Sysa L., Bedzay A. Using gas chromatography methods for the identification of substances of different classes, which determinate fire risk. Bulettin of Lviv State University of Life Safety, 2016; 14: 209-214. (In Ukrainian)

50. Spormann A.M., Widdel F. Metabolism of alkylbenzenes, alkanes, and other hydrocarbons in anaerobic bacteria. Biodegradation, 2000; 11: 85-105.

51. Sullivan E.R., Zhang X., Phelps C., Young L.Y. Anaerobic mineralization of stable-isotope-labeled 2-methylnaphthalene. Appl. Environ. Microbiol, 2001; 67: 4353-57.
PMid:11526046 PMCid:PMC93170

52. Sushko A.R., Dugan A.M., Zhurahivska L.R., Marintsova N.G. Microorganisms as a destructors and indicators of toxicity of heterocyclic compounds. Bulletin of Lviv Polytechnic National University, 2016; 841: 249-257 (In Ukrainian)

53. Timergazina I.F., Perekhodova L.S. To the problem of biological oxidation of oil and petroleum products using hydrocarbon-oxidizing microorganisms. Petroleum Geology - Theoretical and Applied Studies, 2012; 7(1): 1-28. (In Russian)

54. Tyagi M., da Fonseca M.M., de Carvalho C. C. Bioaugmentation and biostimulation strategies to improve the effectiveness of bioremediation processes. Biodegradation, 2011; 22(2): 231-241.

55. Verkholiak N.S., Peretyatko T.B. Utilization of aromatic compounds by bacteria. І. Aerobic and anaerobic destruction. Studia Biologica, 2018; 12(2): 135-156.

56. Vlasovа E.P., Puntus I.F., Petrikov K.V., Filonov A.E., Ponamoreva O.N. Features of the functioning of the enzyme systems for naphthalene biodegradation of the plasmid-containing strain Pseudomonas sp.142nf (pnf142) under various culture conditions. Minsk: Publishing Center of BSU, 2008; 229-231. (In Russian)

57. Winter J., Popoff M. R., Grimont P., Bokkenheuser V.D. Clostridium orbiscindens sp. nov., a human intestinal bacterium capable of cleaving the flavonoid C-ring. Int. J. Syst. Bacteriol, 1991; 41: 355-357.

58. Zhang X., Sullivan E.R., Young L.Y. Evidence for aromatic ring reduction in the biodegradation pathway of carboxylated naphthalene by a sulfate reducing consortium. Biodegradation, 2000; 11: 117-24.

59. Zeyaullah Md., Ahmad R., Naseem A. et аl. Catechol biodegradation by Pseudomonas strain: a critical analysis. Int. J. Chem. Sci, 2009; 7(3): 2211-2221.

60. ZoBell C.E. Action of microorganisms on hydrocarbons. Bacteriol. Rev,1946; 10: 1-49.

61. ZoBell C.E. Assimilation of hydrocarbons by microorganisms. Adv. Enzymol. Relat. Subj. Biochem, 1950; 10: 443-486.



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