Degradation of a Nonylphenol Single Isomer by Sphingomonas Sp. Strain TTNP3 Leads to a Hydroxylation-induced Migration Product

Overview

Journal Appl Environ Microbiol

Specialties Environmental Health
Microbiology

Date 2004 Nov 6

PMID 15528560

Citations 6

Authors

P F X Corvini

R J W Meesters

A Schaffer

H F Schroder

R Vinken

J Hollender

Affiliations

Soon will be listed here.

Abstract

Sphingomonas sp. strain TTNP3 degrades 4(3',5'-dimethyl-3'-heptyl)-phenol and unidentified metabolites that were described previously. The chromatographic analyses of the synthesized reference compound and the metabolites led to their identification as 2(3',5'-dimethyl-3'-heptyl)-1,4-benzenediol. This finding indicates that the nonylphenol metabolism of this bacterium involves unconventional degradation pathways where an NIH shift mechanism occurs.

Citing Articles

Comparative Analysis of the Genetic Basis of Branched Nonylphenol Degradation by Sphingobium amiense DSM 16289 and Sphingobium cloacae JCM 10874.

Ootsuka M, Nishizawa T, Hasegawa M, Kurusu Y, Ohta H Microbes Environ. 2018; 33(4):450-454.

PMID: 30518740 PMC: 6308004. DOI: 10.1264/jsme2.ME18077.

Biodegradation of 7-Hydroxycoumarin in 7HK4 via -Hydroxylation of 3-(2,4-Dihydroxyphenyl)-propionic Acid.

Krikstaponis A, Meskys R Molecules. 2018; 23(10).

PMID: 30321993 PMC: 6222606. DOI: 10.3390/molecules23102613.

Occurrence and biodegradation of nonylphenol in the environment.

Mao Z, Zheng X, Zhang Y, Tao X, Li Y, Wang W Int J Mol Sci. 2012; 13(1):491-505.

PMID: 22312266 PMC: 3269700. DOI: 10.3390/ijms13010491.

Purification and characterization of hydroquinone dioxygenase from Sphingomonas sp. strain TTNP3.

Kolvenbach B, Lenz M, Benndorf D, Rapp E, Fousek J, Vlcek C AMB Express. 2011; 1(1):8.

PMID: 21906340 PMC: 3222310. DOI: 10.1186/2191-0855-1-8.

Role of P450 monooxygenases in the degradation of the endocrine-disrupting chemical nonylphenol by the white rot fungus Phanerochaete chrysosporium.

Subramanian V, Yadav J Appl Environ Microbiol. 2009; 75(17):5570-80.

PMID: 19542331 PMC: 2737932. DOI: 10.1128/AEM.02942-08.

References

Corvini P, Vinken R, Hommes G, Schmidt B, Dohmann M . Degradation of the radioactive and non-labelled branched 4(3',5'-dimethyl 3'-heptyl)-phenol nonylphenol isomer by sphingomonas TTNP3. Biodegradation. 2004; 15(1):9-18. DOI: 10.1023/b:biod.0000009937.20251.d2. View

Koerts J, Soffers A, Vervoort J, de Jager A, Rietjens I . Occurrence of the NIH shift upon the cytochrome P450-catalyzed in vivo and in vitro aromatic ring hydroxylation of fluorobenzenes. Chem Res Toxicol. 1998; 11(5):503-12. DOI: 10.1021/tx980053i. View

McCarthy D, Claude A, Copley S . In vivo levels of chlorinated hydroquinones in a pentachlorophenol-degrading bacterium. Appl Environ Microbiol. 1997; 63(5):1883-8. PMC: 168479. DOI: 10.1128/aem.63.5.1883-1888.1997. View

Ushiba Y, Takahara Y, Ohta H . Sphingobium amiense sp. nov., a novel nonylphenol-degrading bacterium isolated from a river sediment. Int J Syst Evol Microbiol. 2003; 53(Pt 6):2045-8. DOI: 10.1099/ijs.0.02581-0. View

Tanghe T, Dhooge W, Verstraete W . Isolation of a bacterial strain able to degrade branched nonylphenol. Appl Environ Microbiol. 1999; 65(2):746-51. PMC: 91090. DOI: 10.1128/AEM.65.2.746-751.1999. View

Lobos J, Leib T, Su T . Biodegradation of bisphenol A and other bisphenols by a gram-negative aerobic bacterium. Appl Environ Microbiol. 1992; 58(6):1823-31. PMC: 195690. DOI: 10.1128/aem.58.6.1823-1831.1992. View

Soares A, Guieysse B, Delgado O, Mattiasson B . Aerobic biodegradation of nonylphenol by cold-adapted bacteria. Biotechnol Lett. 2003; 25(9):731-8. DOI: 10.1023/a:1023466916678. View

Vallini G, Frassinetti S, Scorzetti G . Candida aquaetextoris sp. nov., a new species of yeast occurring in sludge from a textile industry wastewater treatment plant in Tuscany, Italy. Int J Syst Bacteriol. 1997; 47(2):336-40. DOI: 10.1099/00207713-47-2-336. View

van Ginkel C . Complete degradation of xenobiotic surfactants by consortia of aerobic microorganisms. Biodegradation. 1996; 7(2):151-64. DOI: 10.1007/BF00114627. View

10.

Corti A, Frassinetti S, Vallini G, DAntone S, Fichi C, Solaro R . Biodegradation of nonionic surfactants. I. Biotransformation of 4-(1-nonyl)phenol by a Candida maltosa isolate. Environ Pollut. 1995; 90(1):83-7. DOI: 10.1016/0269-7491(94)00080-w. View

11.

Fujii K, Yamamoto R, Tanaka T, Hirakawa T, Kikuchi S . Potential of a new biotreatment: Sphingomonas cloacae S-3T degrades nonylphenol in industrial wastewater. J Ind Microbiol Biotechnol. 2003; 30(9):531-5. DOI: 10.1007/s10295-003-0072-y. View

12.

Jerina D, Daly J . Arene oxides: a new aspect of drug metabolism. Science. 1974; 185(4151):573-82. DOI: 10.1126/science.185.4151.573. View

13.

Jonkers N, Laane R, de Voogt P . Fate of nonylphenol ethoxylates and their metabolites in two Dutch estuaries: evidence of biodegradation in the field. Environ Sci Technol. 2003; 37(2):321-7. DOI: 10.1021/es020121u. View

14.

Martin G, Dijols S, Artaud I . Hydroxylation reaction catalyzed by the Burkholderia cepacia AC1100 bacterial strain. Involvement of the chlorophenol-4-monooxygenase. Eur J Biochem. 1999; 261(2):533-9. DOI: 10.1046/j.1432-1327.1999.00309.x. View

15.

Soto A, Justicia H, Wray J, Sonnenschein C . p-Nonyl-phenol: an estrogenic xenobiotic released from "modified" polystyrene. Environ Health Perspect. 1991; 92:167-73. PMC: 1519400. DOI: 10.1289/ehp.9192167. View

16.

Apajalahti J, Salkinoja-Salonen M . Dechlorination and para-hydroxylation of polychlorinated phenols by Rhodococcus chlorophenolicus. J Bacteriol. 1987; 169(2):675-81. PMC: 211832. DOI: 10.1128/jb.169.2.675-681.1987. View

17.

Meesters R, Schroder H . Simultaneous determination of 4-nonylphenol and bisphenol A in sewage sludge. Anal Chem. 2002; 74(14):3566-74. DOI: 10.1021/ac011258q. View

18.

Corvini P, Vinken R, Hommes G, Mundt M, Hollender J, Meesters R . Microbial degradation of a single branched isomer of nonylphenol by Sphingomonas TTNP3. Water Sci Technol. 2004; 50(5):189-94. View

19.

Guroff G, Daly J, Jerina D, Renson J, WITKOP B, UDENFRIEND S . Hydroxylation-induced migration: the NIH shift. Recent experiments reveal an unexpected and general result of enzymatic hydroxylation of aromatic compounds. Science. 1967; 157(3796):1524-30. DOI: 10.1126/science.157.3796.1524. View

20.

Soares A, Guieysse B, Mattiasson B . Biodegradation of nonylphenol in a continuous packed-bed bioreactor. Biotechnol Lett. 2003; 25(12):927-33. DOI: 10.1023/a:1024032218981. View