Transformation of 1,1-dichloro-2,2-(4-chlorophenyl)ethane (DDD) by Ralstonia eutropha strain A5

Hay, A

doi:10.1016/s0168-6496(99)00105-1

Cited by 9 publications

(14 citation statements)

References 14 publications

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“…The sequential fragments at m/z = 181 and 152 likely arise from the loss of both chlorines and the further loss of CHO from the base peaks, respectively. These characteristics were previously reported during description of the fragment ions in the mass spectra of monohydroxy-DDT isomers (Nadeau et al 1994) and monohydroxy-DDD isomers (Hay and Focht 2000).…”

Section: Identification Of Monohydroxy-ddt and -Dddsupporting

confidence: 67%

Degradation of chlorinated pesticide DDT by litter-decomposing basidiomycetes

et al. 2011

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One hundred and two basidiomycete strains (93 species in 41 genera) that prefer a soil environment were examined for screening of 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (DDT) biodegradation. Three strains within two litter-decomposing genera, Agrocybe and Marasmiellus, were selected for their DDT biotransformation capacity. Eight metabolites; 1,1-dichloro-2,2-bis(4-chlorophenyl)ethane (DDD), two monohydroxy-DDTs, monohydroxy-DDD, 2,2-dichloro-1,1-bis(4-chlorophenyl)ethanol, putative 2,2-bis(4-chlorophenyl)ethanol and two unidentified compounds were detected from the culture with Marasmiellus sp. TUFC10101. A P450 inhibitor, 1-ABT, inhibited the formation of monohydroxy-DDTs and monohydroxy-DDD from DDT and DDD, respectively. These results indicated that oxidative pathway which was catalyzed by P450 monooxygenase exist beside reductive dechlorination of DDT. Monohydroxylation of the aromatic rings of DDT (and DDD) by fungal P450 is reported here for the first time.

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Section: Identification Of Monohydroxy-ddt and -Dddsupporting

confidence: 67%

Degradation of chlorinated pesticide DDT by litter-decomposing basidiomycetes

et al. 2011

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“…Microorganisms from many different genera are capable of degrading DDT, promoting the loss of HCl via reductive dechlorination and producing DDD as a metabolite, and DDD can undergo reductive dehalogenation (Subba-Rao and Alexander 1985) or hydroxylation of aliphatic moieties (Bumpus and Aust 1987). Hay and Focht (2000) have demonstrated that DDD can be also transformed via dioxygenation and ring fission. Biodegradation using fungi has received relatively little attention compared to the process using bacteria, however, the proposed mechanism of degradation was similar to that in bacteria.…”

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confidence: 99%

Isolation of Brazilian marine fungi capable of growing on DDD pesticide

et al. 2010

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The fungi Aspergillus sydowii Ce15, Aspergillus sydowii Ce19, Aspergillus sydowii Gc12, Bionectria sp. Ce5, Penicillium miczynskii Gc5, Penicillium raistrickii Ce16 and Trichoderma sp. Gc1, isolated from marine sponges Geodia corticostylifera and Chelonaplysylla erecta, were evaluated for their ability to grow in the presence of DDD pesticide. Increasing concentrations of DDD pesticide, i.e., 5.0 mg (1.56 × 10⁻¹² mmol), 10.0 mg (3.12 × 10⁻²) mmol) and 15.0 mg (4.68 × 10⁻² mmol) in solid and liquid culture media were tested. The fungi Trichoderma sp. Gc1 and Penicillium miczynskii Gc5 were able to grow in the presence of up to 15.0 mg of DDD, suggesting their potential for biodegradation. A 100% degradation of DDD was attained in liquid culture medium when Trichoderma sp. Gc1 was previously cultivated for 5 days and supplemented with 5.0 mg of DDD in the presence of hydrogen peroxide. However, the quantitative analysis showed that DDD was accumulated on mycelium and biodegradation level reached a maximum value of 58% after 14 days.

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“…2,3-dihydroxy-DDT would be further metabolized through meta-ring cleavage to form the yellow ring fission product, which would then be catabolized to 4-chlorobenzoic acid (4-CBA). The bacterium Ralstonia eutropha A5 grown on biphenyl was also shown to degrade DDD to form single-ring aromatic compounds via hydroxylation of the aromatic ring and subsequent meta-ring cleavage (Hay and Focht 2000). However, there is Values are means ± SD of triplicate samples limited information on the transformation of DDT and its metabolites via hydroxylation at the aromatic ring and ring cleavage reaction by white rot fungi at present.…”

Section: Discussionmentioning

confidence: 99%

“…This estimation would be supported by the result that mono-and dihydroxylated products were detected in both fungal cultures. Based on these results, we proposed that in Phlebia species, the mechanism for hydroxylation of aromatic ring differ from in bacteria (Nadeau et al 1994;Hay and Focht 2000), and the cytochrome P-450 monooxygenase system plays an important role in the Fig. 3 Proposed pathway for the degradation of DDT by P. lindtneri and P. brevispora.…”

Section: Discussionmentioning

confidence: 99%

“…In bacteria, most reports indicate the reductive dechlorination of DDT to DDD (Langlois 1967;Wedemeyer 1967;Aislabie et al 1997). Interestingly, some bacteria have been reported to degrade DDT and its metabolites by hydroxylation of the aromatic ring via oxidative attack (Nadeau et al 1994;Hay and Focht 2000). Additionally, several fungi have been shown to possess biodegradative capabilities for a broad spectrum of environmentally persistent compounds, including DDT (Subba-Rao and Alexander 1985).…”

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confidence: 99%

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A novel metabolic pathway for biodegradation of DDT by the white rot fungi, Phlebia lindtneri and Phlebia brevispora

et al. 2010

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1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (DDT) was used as the substrate for a degradation experiment with the white rot fungi Phlebia lindtneri GB-1027 and Phlebia brevispora TMIC34596, which are capable of degrading polychlorinated dibenzo-p-dioxin (PCDD) and polychlorinated biphenyls (PCBs). Pure culture of P. lindtneri and P. brevispora with DDT (25 μmol l(-1)) showed that 70 and 30% of DDT, respectively, disappeared in a low-nitrogen medium after a 21-day incubation period. The metabolites were analyzed using gas chromatography/mass spectrometry (GC/MS). Both fungi metabolized DDT to 1,1-dichloro-2,2-bis(4-chlorophenyl)ethane (DDD), 2,2-bis(4-chlorophenyl)acetic acid (DDA) and 4,4-dichlorobenzophenone (DBP). Additionally, DDD was converted to DDA and DBP. DDA was converted to DBP and 4,4-dichlorobenzhydrol (DBH). While DBP was treated as substrate, DBH and three hydroxylated metabolites, including one dihydroxylated DBP and two different isomers of monohydroxylated DBH, were produced from fungal cultures, and these hydroxylated metabolites were efficiently inhibited by the addition of a cytochrome P-450 inhibitor, piperonyl butoxide. These results indicate that the white rot fungi P. lindtneri and P. brevispora can degrade DBP/DBH through hydroxylation of the aromatic ring. Moreover, the single-ring aromatic metabolites, such as 4-chlorobenzaldehyde, 4-chlorobenzyl alcohol and 4-chlorobenzoic acid, were found as metabolic products of all substrate, demonstrating that the cleavage reaction of the aliphatic-aryl carbon bond occurs in the biodegradation process of DDT by white rot fungi.

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Transformation of 1,1-dichloro-2,2-(4-chlorophenyl)ethane (DDD) by Ralstonia eutropha strain A5

Cited by 9 publications

References 14 publications

Degradation of chlorinated pesticide DDT by litter-decomposing basidiomycetes

Degradation of chlorinated pesticide DDT by litter-decomposing basidiomycetes

Isolation of Brazilian marine fungi capable of growing on DDD pesticide

A novel metabolic pathway for biodegradation of DDT by the white rot fungi, Phlebia lindtneri and Phlebia brevispora

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