Diuron herbicide degradation catalyzed by low molecular weight humic acid-like compounds

Salvestrini, Stefano

doi:10.1007/s10311-013-0415-5

Cited by 21 publications

(8 citation statements)

References 15 publications

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“…Comparing the toxicity of diuron to that of its metabolites is highly relevant. As a matter of fact, despite its rather strong persistence in water (Thomas et al, 2002), diuron can be abiotically and biotically degraded (Stasinakis et al 2009;Salvestrini 2013;Zeng & Arnold 2013). Therefore, oysters can be in contact with both diuron and its N-demethylated metabolites in water bodies.…”

Section: Diuron Is More Toxic Than Its Studied Metabolitesmentioning

confidence: 99%

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Comparative embryotoxicity and genotoxicity of the herbicide diuron and its metabolites in early life stages of Crassostrea gigas: Implication of reactive oxygen species production

et al. 2016

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Herbicides are one of the major classes of pollutants contaminating coastal waters over the world. Among them, diuron (3-(3,4-dichlorophenyl)-1,1-dimethylurea) is a phenylurea herbicide frequently detected in oyster-producing area, known to be toxic for this important exploited non-target species. With the aim to investigate the mechanisms by which diuron displays its toxicity in oyster, the implication of both biotransformation and oxygen reactive species (ROS) production was studied considering embryotoxicity and genotoxicity as endpoints. Comparative embryotoxicity and genotoxicity of diuron and its main metabolites (DCPMU, DCPU and 3,4-DCA) were thus studied on oyster larvae by the embryo-larval bioassay on D larvae and the comet assay on trochophore larvae, respectively. Exposures were also performed in presence and absence of known ROS scavenger compounds - ascorbic acid and N-acetylcysteine, to evaluate the involvement of oxyradicals in the toxic responses. In the case of diuron, the production of ROS on exposed oyster larvae was also measured using 2',7'-dichlorodihydrofluorescein diacetate as a probe for flow cytometric analysis. The results we obtained showed the embryotoxicity and genotoxicity of diuron and its metabolites in early life stages of the Pacific oyster. For concentrations ranging from 0.05 to 0.5μgL(-1), diuron appeared significantly more embryotoxic than DCPMU and DCPU (p<0.001). Embryotoxicity decreased with diuron metabolism as follows: diuron≥DCPMU=DCPU, highlighting that biotransformation can constitute a true detoxication pathways in oyster larvae by decreasing the toxicity of the parent compound. In the opposite, no difference was observed between diuron and its metabolites concerning larval development when considering a lower and more environmentally realistic range of concentrations (0.002-0.050μgL(-1)). 3,4-DCA was the only compound that did not show any sign of embryotoxicity, even at concentrations up to 5μgL(-1). Concerning genotoxicity, no significant difference was observed between diuron and all of its metabolites including 3, 4 DCA with damages detected from the concentration of 0.05μgL(-1). As for diuron, the toxicity of the metabolites seems to be mediated in some part by ROS production as clearly demonstrated by the decrease in genotoxicity and developmental abnormalities in the presence of the oxidant scavenger, ascorbic acid.

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Section: Diuron Is More Toxic Than Its Studied Metabolitesmentioning

confidence: 99%

“…DCPU is finally hydrolysed into 3,4-DCA (3,4-Dichloroaniline). Diuron is also slightly photolysed and hydrolysed (Stasinakis et al 2009;Salvestrini 2013;Zeng & Arnold 2013). However, In a laboratory study performed in 15°C filtered seawater, Thomas et al (2002) did not observe any abiotic degradation of diuron over 42 days.…”

Section: Introductionmentioning

confidence: 98%

Comparative embryotoxicity and genotoxicity of the herbicide diuron and its metabolites in early life stages of Crassostrea gigas: Implication of reactive oxygen species production

et al. 2016

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“…The knowledge of molecular properties of HA is essential for understanding their behaviour in natural processes and depuration plants [22]. Here we report a study on the molecular structure of a HA sample from a commercial supplier.…”

Section: Introductionmentioning

confidence: 99%

Macromolecular Structure of a Commercial Humic Acid Sample

et al. 2020

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The molecular structure of a commercial sample of humic acids (HA) was investigated by membrane dialysis experiments (MD) and low-pressure size-exclusion chromatography (LP-SEC). MD showed that HA molecules were retained by dialysis membrane with a cut-off of 6-8 kDa, independently from HA concentration (15 or 150 mg L −1 ), NaHCO 3 concentration (0.005-2.0 mol L −1 ), and from propan 2-ol (0-5 v/v %). SEC experiments at low pressure gave chromatograms with a broad peak, with an elution volume between those of the globular proteins bovine serum albumin (molecular weight = 66.5 kDa) and lysozyme from egg (molecular weight = 14.4 kDa). The pattern of the chromatogram did not vary with HA concentration, and second-run chromatograms of single eluted fractions showed relatively sharp peaks. From these data, we reveal that the commercial HA sample analysed has a macromolecular structure rather than being a supramolecular aggregate of relatively small molecules, as recently proposed for some samples of HA obtained from different sources.

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“…Other researchers have reported the simultaneous presence in the solution of macromolecules and supramolecular assemblies [38]. Recent studies by gel permeation chromatography and long-lasting dialysis experiment using a membrane with selected cut-off have given clear evidence that the HA samples analysed, extracted from leonardite and from compost, have a polymeric structure, and an average molecular weight higher than 8kDa [39].Studies carried out for several decades have intensively studied the interactions of HA with inorganic and organic pollutants [40][41][42]. Among them, studies regarding the fate of pesticides in soil and sediments are of particular importance for environmental implications [43][44][45][46][47].…”

mentioning

confidence: 99%

“…Studies carried out for several decades have intensively studied the interactions of HA with inorganic and organic pollutants [40][41][42]. Among them, studies regarding the fate of pesticides in soil and sediments are of particular importance for environmental implications [43][44][45][46][47].…”

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confidence: 99%

Sorption of Organic Pollutants by Humic Acids: A Review

et al. 2020

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Humic acids (HA) are promising green materials for water and wastewater treatment. They show a strong ability to sorb cationic and hydrophobic organic pollutants. Cationic compounds interact mainly by electrostatic interaction with the deprotonated carboxylic groups of HA. Other functional groups of HA such as quinones, may form covalent bonds with aromatic ammines or similar organic compounds. Computational and experimental works show that the interaction of HA with hydrophobic organics is mainly due to π–π interactions, hydrophobic effect and hydrogen bonding. Several works report that sorbing efficiency is related to the hydrophobicity of the sorbate. Papers about the interaction between organic pollutants and humic acids dissolved in solution, in the solid state and adsorbed onto solid particles, like aluminosilicates and magnetic materials, are reviewed and discussed. A short discussion of the thermodynamics and kinetics of the sorption process, with indication of the main mistakes reported in literature, is also given.

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Diuron herbicide degradation catalyzed by low molecular weight humic acid-like compounds

Cited by 21 publications

References 15 publications

Comparative embryotoxicity and genotoxicity of the herbicide diuron and its metabolites in early life stages of Crassostrea gigas: Implication of reactive oxygen species production

Comparative embryotoxicity and genotoxicity of the herbicide diuron and its metabolites in early life stages of Crassostrea gigas: Implication of reactive oxygen species production

Macromolecular Structure of a Commercial Humic Acid Sample

Sorption of Organic Pollutants by Humic Acids: A Review

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