Contribution to the Detection and Identification of Oxidation Metabolites of Nonylphenol in Sphingomonas sp. strain TTNP3
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Sphingomonas sp. strain TTNP3 has been previously described as a bacterium that is capable of degrading the technical mixture of nonylphenol (NP) isomers and also the 4(3′,5′-dimethyl-3′-heptyl)-phenol single isomer of NP. Until recently, 3,5-dimethyl-3-heptanol was the only reported metabolite of 4(3′,5′-dimethyl-3′-heptyl)-phenol. A short time ago, the detection of an intracellular metabolite resulting from the oxidation of 4(3′,5′-dimethyl-3′-heptyl)-phenol which was identified as 2(3,5-dimethyl-3-heptyl)-benzenediol has been reported. A decisive element for this identification was the occurrence of some slight differences with the two most probable metabolites i.e. 4(3′,5′-dimethyl-3′-heptyl)-resorcinol and 4(3′,5′-dimethyl-3′-heptyl)-catechol. These facts led us to hypothesise some NIH shift mechanisms explaining the formation of 2(3′,5′-dimethyl-3′-heptyl)-benzenediol. In the present work, we describe the steps that led to the detection of these metabolites in the intracellular fraction of Sphingomonas sp. strain TTNP3. The formation of analogous intracellular metabolites resulting from the degradation of the technical mixture of NP is reported. To further elucidate these degradation products, studies were carried out with cells grown with 4(3′,5′-dimethyl-3′-heptyl)-phenol as sole carbon source. The description of the syntheses of reference compounds, i.e. 4(3′,5′-dimethyl-3′-heptyl)-resorcinol and 4(3′,5′-dimethyl-3′-heptyl)-catechol and their comparative analyses with the intermediates of the degradation of 4(3′,5′-dimethyl-3′-heptyl)-phenol are presented.
Keywords4(3′,5′-Dimethyl-3′-heptyl)-phenol Branched isomer Metabolites Nonylphenol Oxidation Sphingomonas
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The authors wish to thank Dr J. Runsink and Mrs A. Müller for measurement of the NMR spectra at the Institute for Organic Chemistry and Maike Meindorf for her technical support. The work of LabMET was made possible by a grant from the FWO (Flemish Fund Scientific Research) n° G.0102.00N.
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