Herbicide metabolism in plants: specificity of peroxidases for aniline substrates.

Lieb, H; Still, Cecil C.

doi:10.1104/pp.44.12.1672

Cited by 18 publications

(8 citation statements)

References 7 publications

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“…Bartha and Bordeleau (1) developed a method to quantify peroxidase activity in soil by using a dimethoxylated aniline (o-dianisidine) as the substrate. Differences in the substrate specificities of peroxidases from different sources were reported by Lieb and Still (19). Peroxidases from barnyard grass (Echinoczhloa crusgalli) and rice plants showed greater substrate specificity on chlorinated anilines than horseradish peroxidase.…”

mentioning

confidence: 76%

Transformation of Halogen-, Alkyl-, and Alkoxy-Substituted Anilines by a Laccase of Trametes versicolor

Hoff

Liu

Bollag

1985

Appl Environ Microbiol

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The laccase of the fungus Trametes versicolor was able to polymerize various halogen-, alkyl-, and alkoxy-substituted anilines, showing substrate specificity similar to that of horseradish peroxidase, whereas the laccase of Rhizoctonia praticola was active only with p-methoxyaniline. The substrate specificities of the enzymes were determined by using gas chromatography to measure the decrease in substrate concentration during incubation. With p-chloroaniline as the substrate, the peroxidase and the Trametes laccase showed maximum activity near pH 4.2. The transformation of this substrate gave rise to a number of oligomers, ranging from dimers to pentamers, as determined by mass spectrometry. The product profiles obtained by high-pressure liquid chromatography were similar for the two enzymes. A chemical reaction was observed between p-chloroaniline and an enzymatically formed dimer, resulting in the formation of a trimer. All three enzymes oxidized p-methoxyaniline to 2-amino-5-p-anisidinobenzoquinone dip -methoxyphenylimine, but only the T. versicolor laccase and the peroxidase caused the formation of a pentamer (2,5-dip -anisidinobenzoquinone dip -methoxyphenylimine). Our results demonstrate that in addition to horseradish peroxidase, a T. versicolor laccase can also polymerize aniline derivatives.

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mentioning

confidence: 76%

Transformation of Halogen-, Alkyl-, and Alkoxy-Substituted Anilines by a Laccase of Trametes versicolor

Hoff

Liu

Bollag

1985

Appl Environ Microbiol

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“…Our analysis did not detect features consistent with the TDZ monomer in African violet tissues and our synthetic biotransformation analysis indicated that the TDZ molecule is cleaved at the amide bridge releasing a thidiazol ring and aniline. Aniline is the product of metabolism of several herbicides and is incorporated into sugar and lignin conjugates [ 49 ]. Previous researchers have determined that derivatives of the 1,2,3-thidiazol-5yl ring are potent anti-senescence compounds [ 7 ].…”

Section: Discussionmentioning

confidence: 99%

“…Using previously described methods synthetic biotransformations were applied to the thidiazuron molecule in Excel: −H 2 , +H 2 , −CH 3 , +CH 3 , +C 6 H 12 O 6 , −C 6 H 12 O 6 , +OH, +OH (×2), +COOH, +NH 2 , +NH 3 , −H, +H [ 37 , 47 , 48 , 49 ]. The monoisotopic mass for each biotransformation (±0.02 Da) was mined within our dataset in order to identify potential anabolic or metabolic products.…”

Section: Methodsmentioning

confidence: 99%

“…Pairwise analysis between control and high TDZ and control and low TDZ were additionally performed in MetaboAnalyst by t-test, volcano analysis, significant analysis of microarray (SAM) analysis and empirical Bayes analysis of microarrays (EBAM) to identify possible important features in specific morphogenetic responses (organogenesis at low TDZ and embryogenesis at high TDZ) [43,44,46,47 [37,[47][48][49]. The monoisotopic mass for each biotransformation (±0.02 Da) was mined within our dataset in order to identify potential anabolic or metabolic products.…”

Section: Detection Of Significant Ions and Linear Trendsmentioning

confidence: 99%

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The Morphoregulatory Role of Thidiazuron: Metabolomics-Guided Hypothesis Generation for Mechanisms of Activity

et al. 2020

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Thidiazuron (TDZ) is a diphenylurea synthetic herbicide and plant growth regulator used to defoliate cotton crops and to induce regeneration of recalcitrant species in plant tissue culture. In vitro cultures of African violet thin petiole sections are an ideal model system for studies of TDZ-induced morphogenesis. TDZ induces de novo shoot organogenesis at low concentrations and somatic embryogenesis at higher concentrations of exposure. We used an untargeted metabolomics approach to identify metabolites in control and TDZ-treated tissues. Statistical analysis including metabolite clustering, pattern and pathway tools, logical algorithms, synthetic biotransformations and hormonomics identified TDZ-induced changes in metabolism. A total of 18,602 putative metabolites with extracted masses and predicted formulae were identified with 1412 features that were found only in TDZ-treated tissues and 312 that increased in response to TDZ. The monomer of TDZ was not detected intact in the tissues but putative oligomers were found in the database and we hypothesize that these may form by a Diels–Alder reaction. Accumulation oligomers in the tissue may act as a reservoir, slowly releasing the active TDZ monomer over time. Cleavage of the amide bridge released TDZ-metabolites into the tissues including organic nitrogen and sulfur containing compounds. Metabolomics data analysis generated six novel hypotheses that can be summarized as an overall increase in uptake of sugars from the culture media, increase in primary metabolism, redirection of terpene metabolism and mediation of stress metabolism via indoleamine and phenylpropanoid metabolism. Further research into the specific mechanisms hypothesized is likely to unravel the mode of action of TDZ and to provide new insights into the control of plant morphogenesis.

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“…for horseradish peroxidase (Sigma type II), EC 1.11.1.7, by the procedure of Lieb and Still (1969). The reaction mixture was incubated for 10 min at 23 °C, and then extracted with 1 vol of chloroform.…”

Section: Methodsmentioning

confidence: 99%

Metabolism of the fungicide 2,6-dichloro-4-nitroaniline in soil

Nk¹,

Kosuge²

1976

J. Agric. Food Chem.

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A 14C-labeled sample of 2,6-dichloro-4-nitroaniline (DCNA, Botran) was incubated in flooded soil that had been amended with D-glucose (1%, w/w). After 3 days the amount of DCNA that could be recovered from the soil decreased to 7% and to 3% after 9 days. Evolution of radioactive carbon dioxide could not be detected even after the 9-day experimental period. Much of the radioactivity (ultimately 65%) could not be removed from the soil sample by extraction with an acetone-water solution. The major metabolite that was extractable from soil was identified as 4-amino-3,5-dichloroacetanilide (ADCAA).The expected metabolic precursor of ADCAA, 2,6-dichloro-p-phenylenediamine (DCPD), was also isolated from the extraction solution. A third compound isolated from soil appeared to be formed by the oxidative dimerization of DCPD. This same compound was also produced by the action of horseradish peroxidase on DCPD in vitro. Six fungi sensitive to DCNA were grown on potato-dextrose agar containing 10 gg/ml of DCNA, DCPD, or ADCAA. DCPD and ADCAA did not significantly affect the growth of any of the fungi tested as compared with controls whereas DCNA completely inhibited or reduced the growth rate in all cases.Because 2,6-dichloro-4-nitroaniline (DCNA) is widely used for control of plant disease, knowledge of its fate in soil is important for its safe use as a fungicide. Experiments on its persistence in soil have revealed that breakdown, apparently as a result of microbial action, is more rapid in soil previously treated with DCNA (Groves and Chough, 1970). In the latter case, [14C]DCNA added to soil was utilized rapidly and 25 to 50% of the radioactivity associated with the chemical was recovered in CO2 evolved from the treated soil. When [14C]DCNA was added to soils not pretreated with DCNA, no 14C02 was evolved. However, it was not determined if DCNA had been altered without evolution of 14C02. Wang and Broadbent (1973) reported that only 2-4% of added DCNA was recovered after 10 days from glucose, alfalfa, and rice straw amended flooded soils as compared with 83.5% recovery from unamended flooded soils. From unamended upland soil, they reported that 99.5% of the DCNA was recovered unchanged after 4 weeks. In all the early studies, metabolic products of DCNA other than CO2 were not identified and potential toxicity of the metabolites was not studied.

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Herbicide metabolism in plants: specificity of peroxidases for aniline substrates.

Cited by 18 publications

References 7 publications

Transformation of Halogen-, Alkyl-, and Alkoxy-Substituted Anilines by a Laccase of Trametes versicolor

Transformation of Halogen-, Alkyl-, and Alkoxy-Substituted Anilines by a Laccase of Trametes versicolor

The Morphoregulatory Role of Thidiazuron: Metabolomics-Guided Hypothesis Generation for Mechanisms of Activity

Metabolism of the fungicide 2,6-dichloro-4-nitroaniline in soil

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