Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Evidence for the involvement of multiple pathways in the biodegradation of 1- and 2-methylnaphthalene by Pseudomonas putida CSV86

  • 248 Accesses

  • 68 Citations

Abstract

Pseudomonas putida CSV86, a soil bacterium, grows on 1- and 2-methylnaphthalene as the sole source of carbon and energy. In order to deduce the pathways for the biodegradation of 1- and 2-methylnaphthalene, metabolites were isolated from the spent medium and purified by thin layer chromatography. Emphasis has been placed on the structural characterisation of isolated intermediates by GC-MS, demonstration of enzyme activities in the cell free extracts and measurement of oxygen uptake by whole cells in the presence of various probable metabolic intermediates. The data obtained from such a study suggest the possibility of occurrence of multiple pathways in the degradation of 1- and 2-methylnaphthalene. We propose that, in one of the pathways, the aromatic ring adjacent to the one bearing the methyl moiety is oxidized leading to the formation of methylsalicylates and methylcatechols. In another pathway the methyl side chain is hydroxylated to-CH2OH which is further converted to-CHO and-COOH resulting in the formation of naphthoic acid as the end product. In addition to this, 2-hydroxymethylnaphthalene formed by the hydroxylation of the methyl group of 2-methylnaphthalene undergoes aromatic ring hydroxylation. The resultant dihydrodiol is further oxidised by a series of enzyme catalysed reactions to form 4-hydroxymethyl catechol as the end product of the pathway.

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

References

  1. Altenschmidt U, Fuchs G (1991) Anaerobic degradation of toluene in denitrifying Pseudomonas sp.: indication for toluene methylhydroxylation and benzoyl-CoA as central aromatic intermediate. Arch Microbiol 156: 152–158

  2. Barnsley EA (1975) The induction of the enzymes of naphthalene metabolism in pseudomonads by salicylate and 2-aminobenzoate. J Gen Microbiol 88: 193–196

  3. Barnsley EA (1976) Naphthalene metabolism of pseudomonads: the oxidation of 1,2-dihydroxynaphthalene to 2-hydroxychromene-2-carboxylic acid and the formation of 2′-hydroxybenzalpyruvate. Biochem Biophys Res Commun 72: 1116–1121

  4. Barnsley EA (1988) Metabolism of 2,6-dimethylnaphthalene by Flavoacteria. Appl Environ Microbiol 54: 428–433

  5. Bayly RC, Dagley S, Gibson DT (1966) The metabolism of cresols by species of Pseudomonas. Biochem J 101: 293–301

  6. Boylan DB, Tripp BW (1971) Determination of hydrocarbons in seawater extracts of crude oil and crude oil fractions. Nature 230: 44–47

  7. Breger RK, Franklin RB, Lech JJ (1981) Metabolism of 2-methylnaphthalene to isomeric dihydrodiols by hepatic microsomes of rat and rainbow trout. Drug Metab Dispos 9: 88–93

  8. Cane PA, Williams PA (1982) The plasmid coded metabolism of naphthalene and 2-methylnaphthalene in Pseudomonas strains: Phenotypic changes correlated with structural modification of the plasmid PWW 60–1. J Gen Microbiol 128: 2281–2290

  9. Cerniglia CE, Freeman JP, Althaus JR, Van Baalen C (1983) Metabolism and toxicity of 1- and 2-methylnaphthalene and their derivatives in cyanobacteria. Arch Microbiol 136: 177–183

  10. Cerniglia CE, Lambert KJ, Miller DW, Freeman JP (1984) Transformation of 1- and 2-methylnaphthalene by Cunninghamella elegans. Appl Environ Microbiol 47: 111–118

  11. Darville RG, Wilhm JL (1984) The effect of naphthalene on oxygen consumption and hemoglobin concentration in Chironomus attenuatus and an oxygen consumption and life cycle of Tanytarus dissimilis. Environ Toxicol Chem 3: 135–141

  12. Davey JF, Gibson DT (1974) Bacterial metabolism of para- & meta-xylene: oxidation of a methyl substituent. J Bacteriol 119: 923–929

  13. Dean-Raymond D, Bartha R (1975) Biodegradation of some polynuclear aromatic petroleum components by marine bacteria. Dey Ind Microbiol 16: 97–110

  14. Dolfing J, Jeyer J, Binder-Eicher P, Schwarzenbach RP (1990) Isolation and characterization of a bacterium that mineralizes toluene in the absence of molecular oxygen. Arch Microbiol 154: 336–341

  15. Ensley BD, Gibson DT, LaBorde AL (1982) Oxidation of naphthalene by a multicomponent enzyme system from Pseudomonas sp. strain NCIB 9816. J Bacteriol 149: 948–954

  16. Gibson DT, Subramanyam V (1984) Microbial Degradation of aromatic hydrocarbons. In: Gibson DT (ed) Microbial degradation of organic compounds. Marcel Dekker, New York, pp 180–252

  17. Gibson DT, Hensley M, Yoshioka H, Mabry TJ (1970) Formation of (+)-cis-2,3-dihydroxy-1-methyl cyclohexa-4,6-diene from toluene by Pseudomonas putida. Biochemistry 9: 1626–1630

  18. Griffin KA, Johnson CB, Breger RK, Franklin RB (1983) Pulmonary toxicity of 2-methylnaphthalene: lack of a relationship between toxicity, dihydrodiol formation and irreversible binding of cellular macromolecules in DBA/2J mice. Toxicology 26: 213–230

  19. Honda T, Kiyozumi M, Kojma S (1990) Alkylnaphthalene. XI. Pulmonary toxicity of naphthalene, 2-methylnaphthalene and isopropylnaphthalenes in mice. Chem Pharm Bull 38: 3130–3135

  20. Kaubisch N, Daly JW, Jerina DM (1972) Arene oxides as intermediates in the oxidative metabolism of aromatic compounds. Isomerization of methyl-substituted arene oxides. Biochemistry 11: 3080–3088

  21. Lee CC, Craig WK, Smith PJ (1974) Water-soluble hydrocarbons from crude oil. Bull Environ Contam Toxicol 12: 212–216

  22. Lowry OH, Rosebrough MJ, Farr AL, Randall RJ (1951) Protein measurement with Folin phenol reagent. J Biol Chem 193: 265–275

  23. Patel TR, Gibson DT (1974) Purification and properties of (+) cis-Naphthalene dihydrodiol dehydrogenase of Pseudomonas putida. J Bacteriol 119: 879–888

  24. Sparling J, Chittim B, Clegg BS, Safe S, Crocker JFS (1978) The tissue distribution and clearance of Aerotex 3470, an aromatic hydrocarbon solvent. Chemosphere 7: 607–614

  25. Struble VG, Hermon HJ (1983) Molecular basis for inhibition of mitochondrial respiration by naphthalene. Bull Environ Contam Toxicol 31: 644–648

  26. Williams PA, Catterall FA, Murray K (1975) Metabolism of naphthalene, 2-methylnaphthalene, salicylate and benzoate by Pseudomonas PG: regulation of tangential pathways. J Bacteriol 124: 679–685

  27. Winters K, O'Donnel R, Batterton JC, Van Baalen C (1976) Water soluble components of four fuel oils: chemical characterization and effects on growth of microalgae. Mar Biol (NY) 36: 269–276

  28. Wirtz RA, Turrentine Jr JD, Fox RC (1981) Area repellents for mosquitoes (Diptera: Culcidae): identification of the active ingredients in a petroleum oil fraction. J Med Entomol 18: 126–128

Download references

Author information

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Mahajan, M.C., Phale, P.S. & Vaidyanathan, C.S. Evidence for the involvement of multiple pathways in the biodegradation of 1- and 2-methylnaphthalene by Pseudomonas putida CSV86. Arch. Microbiol. 161, 425–433 (1994). https://doi.org/10.1007/BF00288954

Download citation

Key words

  • Pseudomonas
  • Methylnaphthalenes
  • Metabolism
  • Hydroxylation
  • Oxygenases
  • Aromatic ring cleavage