Hydroxylated polychlorobornanes – Synthesis and characterization of new potential toxaphene metabolites

Kapp, Thomas; Vetter, Walter

doi:10.1016/j.chemosphere.2010.10.034

Cited by 4 publications

(18 citation statements)

References 24 publications

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“…To get further insight about CTT that suffered aerobic transformation, two replicates of toxaphene extract from the biosolid culture, which were supplemented with camphor, as well as one control sample of the original weathered toxaphene were diluted 1 : 10 with isooctane and analysed by GC/ECNI‐MS on a 7890/5975C system equipped with a 30 m × 0·25 mm ID × 0·25 µ m film thickness Optima 5 MS capillary column (Macherey‐Nagel, Düren, Germany). In addition, aliquots of the sample solutions were fractionated by adsorption chromatography on activated silica gel (8 g) according to Kapp and Vetter (2011). Specifically, fraction F1 was obtained with 48 ml n ‐hexane (target compounds: removal of PCBs, which are isobaric with hydroxylated CTTs (OH‐CTTs)), followed by 50 ml of n ‐hexane/ethyl acetate (9 : 1, v/v, F2, target compounds: CTTs) and 50 ml of ethyl acetate (F3, target compounds: OH‐CTTs) for elution.…”

Section: Methodsmentioning

confidence: 99%

“…Knowledge about the occurrence of oxidized metabolites of toxaphene in the environment was hampered by the lack of analytical standards and because they can be erroneously identified as PCBs. However, advances in these two aspects were recently achieved (Kapp and Vetter 2011) allowing to identify for the first time hydroxylated metabolite of toxaphene in the liver samples of polar bears (Reger et al . 2017).…”

Section: Introductionmentioning

confidence: 99%

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Evidence for cometabolic transformation of weathered toxaphene under aerobic conditions using camphor as a co‐substrate

Prieto

Klimm

Roldán

et al. 2020

J. Appl. Microbiol.

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Aims Toxaphene is a persistent organic pollutant, composed of approximately 1000 highly chlorinated bicyclic terpenes. The purpose of this study was to evaluate if camphor, a structural analogue of toxaphene, could stimulate aerobic biotransformation of weathered toxaphene. Methods and Results Two enrichment cultures that degrade camphor as the sole carbon source were established from contaminated soil and biosolids. These cultures were used to evaluate aerobic transformation of weathered toxaphene. Only the biosolids culture could transform compounds of technical toxaphene (CTTs) in the presence of camphor, while no transformation was observed in the presence of glucose or with toxaphene as a sole carbon source. The transformed toxaphene had lower concentration of CTTs with longer retention times, and higher concentration of compounds with lower retention times. Gas chromatography with electron capture negative ion mass spectrometry (GC/ECNI‐MS) showed that aerobic biotransformation mainly occurred with Cl8‐ and Cl9‐CTTs compounds. The patterns of Cl6‐ and Cl7‐CTTs were also simplified albeit to a much lesser extent. Seven camphor‐degrading bacteria were isolated from the enrichment culture but none of them could degrade toxaphene. Conclusion Camphor degrading culture can aerobically transform CCTs via reductive pathway probably by co‐metabolism using camphor as a co‐substrate. Significance and Impact of the Study Since camphor is naturally produced by different plants, this study suggests that stimulation of aerobic transformation of toxaphene may occur in nature. Moreover plants, which produce camphor or similar compounds, might be used in bioremediation of contaminated soils.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Evidence for cometabolic transformation of weathered toxaphene under aerobic conditions using camphor as a co‐substrate

Prieto

Klimm

Roldán

et al. 2020

J. Appl. Microbiol.

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“…25 However, hydroxylated CTTs (OH-CTTs) have not been detected so far in authentic environmental samples. 27 This may be due to the lack of suitable analytical standards because synthesis of OH-CTTs results in a complex mixture of hundreds of compounds which has to be simplified by means of a timeconsuming process. 27 Furthermore, OH-CTTs can be easily misinterpreted as polychlorinated biphenyls (PCBs) in gas chromatography with mass spectrometry (GC/MS) chromatograms due to their isobaric character (same nominal mass, same retention time).…”

Section: ■ Introductionmentioning

confidence: 99%

“…27 Furthermore, OH-CTTs can be easily misinterpreted as polychlorinated biphenyls (PCBs) in gas chromatography with mass spectrometry (GC/MS) chromatograms due to their isobaric character (same nominal mass, same retention time). 27 Due to their highly developed metabolism system, which is known to generate hydroxylated PCBs (OH-PCBs) as well as hydroxylated polybrominated biphenyls (OH-PBBs) and polybrominated diphenyl ethers (OH-PBDEs), polar bears (Ursus maritimus) were selected for analytical purposes within the present study. 28−31 The aim of this study was to develop a method for the verification of the occurrence of OH-CTTs in environmental samples.…”

Section: ■ Introductionmentioning

confidence: 99%

“…28−31 The aim of this study was to develop a method for the verification of the occurrence of OH-CTTs in environmental samples. For this purpose, an OH-CTT mixture consisting of >200 compounds was synthesized according to Kapp and Vetter, 27 followed by fractionation with countercurrent chromatography (CCC). CCC is an all-liquid-based (semi-) preparative instrumental chromatography method typically used for the isolation of natural products 32,33 which was previously also successfully used in the field of polyhalogenated compounds.…”

Section: ■ Introductionmentioning

confidence: 99%

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Analysis and Characterization of Polychlorinated Hydroxybornanes as Metabolites of Toxaphene Using a Polar Bear Model

Reger

Gallistl

Skírnisson

et al. 2017

Environ. Sci. Technol.

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Abiotic and biotic transformation of toxaphene (camphechlor) results in the selective enrichment of recalcitrant congeners while other, less persistent compounds of technical toxaphene (CTTs) are degraded. Until now, there has been little knowledge on oxidation transformation of toxaphene. For instance, the existence of hydroxylated CTTs (OH-CTTs) in authentic environmental and food samples has not been proven. For this reason, we synthesized a mixture consisting of tetra- to heptachlorinated OH-CTTs and simplified it by countercurrent chromatography (CCC). Thus, 227 OH-CTTs were detected in the CCC fractions (12 tetra-, 117 penta-, 81 hexa-, and 17 heptachlorinated OH-CTTs), which was >50% more than detected before the fractionation. One CCC fraction consisting of only 18 OH-CTTs was used to develop a sample cleanup method which aimed to remove CTTs, isobaric PCBs, and sample matrix. The final cleanup procedure consisted of (i) gel permeation chromatography (GPC) and adsorption chromatography using (ii) deactivated and (iii) activated silica gel. Hence, up to 320 and 4350 μg/kg lipid weight of octa- and nonachlorinated CTTs were detected in four liver samples and adipose tissue of polar bears, respectively. Furthermore, the presence of one hexachlorinated OH-CTT isomer could be verified in the samples, which was about 1% of the octachlorinated CTTs determined in the liver samples.

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Estudio de la degradación aeróbica de toxafeno en suelos contaminados de el Copey, César

Ortegón¹

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El toxafeno es una mezcla de cientos de compuestos policlorados y pertenece al grupo de contaminantes orgánicos persistentes (COPs). En Colombia este insecticida se aplicó en cultivos de algodón ubicados en El Copey, Cesar, al prohibirse su uso en los 90 fue almacenado inadecuadamente generando contaminación de suelos y agua subterránea. Por su alto grado de cloración, los estudios sobre la biodegradación se han centrado en condiciones anaerobias, y no se conoce el alcance de la degradación e aerobia.

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Hydroxylated polychlorobornanes – Synthesis and characterization of new potential toxaphene metabolites

Cited by 4 publications

References 24 publications

Evidence for cometabolic transformation of weathered toxaphene under aerobic conditions using camphor as a co‐substrate

Evidence for cometabolic transformation of weathered toxaphene under aerobic conditions using camphor as a co‐substrate

Analysis and Characterization of Polychlorinated Hydroxybornanes as Metabolites of Toxaphene Using a Polar Bear Model

Estudio de la degradación aeróbica de toxafeno en suelos contaminados de el Copey, César

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