The metabolism of cypermethrin in plants: The conjugation of the cyclopropyl moiety

Wright, A. N.; Roberts, Terry R.; Dutton, Alan J.; Doig, Mira

doi:10.1016/0048-3575(80)90084-x

Cited by 25 publications

(8 citation statements)

References 6 publications

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“…5), unambiguously identified here by NMR analyses as a DCP‐Glc‐Pent conjugate, had the glycosidic linkage α(1→6). Several xenobiotic glycoside conjugates are capable of undergoing glycosyl extension to form further polysaccharide derivatives, but the presence of pentose residues seldom has been described [33–36]. Furthermore, deoxypentose conjugates have been suspected in the metabolism of 4‐ n ‐non‐ylphenol in Lemna minor , although a possible endogenous origin of these compounds cannot be totally excluded [37].…”

Section: Discussionmentioning

confidence: 99%

Metabolic fate of [¹⁴C]‐2,4‐dichlorophenol in tobacco cell suspension cultures

Laurent¹,

Canlet²,

Debrauwer³

et al. 2007

Enviro Toxic and Chemistry

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In plant tissues, xenobiotics often are conjugated with natural constituents such as sugars, amino acids, glutathione, and malonic acid. Usually, conjugation processes result in a decrease in the reactivity and toxicity of xenobiotics by increasing the water solubility and polarity of conjugates, and reducing their mobility. Due to their lack of an efficient excretory system, xenobiotic conjugates finally are sequestered in plant storage compartments or cell vacuoles, or are integrated as bound residues in cell walls. Chlorophenols are potentially harmful pollutants that are found in numerous natural and agricultural systems. We studied the metabolic fate of 2,4-dichlorophenol (DCP) in cell-suspension cultures of tobacco (Nicotiana tabacum L.). After a standard metabolism experiment, 48 h of incubation with a [U-phenyl-(14)C]-DCP solution, aqueous extracts of cell suspension cultures were analyzed by high-performance liquid chromatography (HPLC). Metabolites then were isolated and their chemical structures determined by enzymatic and chemical hydrolyses, electrospray ionization-mass spectrometry in negative mode (ESI-NI), and (1)H nuclear magnetic resonance analyses. The main terminal metabolites identified were DCP-glycoside conjugates, DCP-(6-O-malonyl)-glucoside, DCP-(6-O-acetyl)-glucoside, and their precursor, DCP-glucoside. More unusual and complex DCP conjugates such as an alpha(1-->6)-glucosyl-pentose and a triglycoside containing a glucuronic acid were further characterized. All the metabolites identified were complex glycoside conjugates. However, these conjugates still may be a source of DCP in hydrolysis reactions caused by microorganisms in the environment or in the digestive tract of animals and humans. Removal of xenobiotics by glycoside conjugation thus may result in underestimation of the risk associated with toxic compounds like DCP in the environment or in the food chain.

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Section: Discussionmentioning

confidence: 99%

Metabolic fate of [¹⁴C]‐2,4‐dichlorophenol in tobacco cell suspension cultures

Laurent¹,

Canlet²,

Debrauwer³

et al. 2007

Enviro Toxic and Chemistry

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show abstract

“…5), unambiguously identified here by NMR analyses as a DCP-Glc-Pent conjugate, had the glycosidic linkage ␣(1→6). Several xenobiotic glycoside conjugates are capable of undergoing glycosyl extension to form further polysaccharide derivatives, but the presence of pentose residues seldom has been described [33][34][35][36]. Furthermore, deoxypentose conjugates have been suspected in the metabolism of 4-n-nonylphenol in Lemna minor, although a possible endogenous origin of these compounds cannot be totally excluded [37].…”

Section: Discussionmentioning

confidence: 99%

Metabolic Fate of [14c]-2,4-Dichlorophenol in Tobacco Cell Suspension Cultures

LAURENT¹,

CANLET²,

DEBRAUWER³

et al. 2007

Environ Toxicol Chem

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In plant tissues, xenobiotics often are conjugated with natural constituents such as sugars, amino acids, glutathione, and malonic acid. Usually, conjugation processes result in a decrease in the reactivity and toxicity of xenobiotics by increasing the water solubility and polarity of conjugates, and reducing their mobility. Due to their lack of an efficient excretory system, xenobiotic conjugates finally are sequestered in plant storage compartments or cell vacuoles, or are integrated as bound residues in cell walls. Chlorophenols are potentially harmful pollutants that are found in numerous natural and agricultural systems. We studied the metabolic fate of 2,4-dichlorophenol (DCP) in cell-suspension cultures of tobacco (Nicotiana tabacum L.). After a standard metabolism experiment, 48 h of incubation with a [U-phenyl-14 C]-DCP solution, aqueous extracts of cell suspension cultures were analyzed by high-performance liquid chromatography (HPLC). Metabolites then were isolated and their chemical structures determined by enzymatic and chemical hydrolyses, electrospray ionization-mass spectrometry in negative mode (ESI-NI), and 1 H nuclear magnetic resonance analyses. The main terminal metabolites identified were DCP-glycoside conjugates, DCP-(6-O-malonyl)-glucoside, DCP-(6-O-acetyl)-glucoside, and their precursor, DCP-glucoside. More unusual and complex DCP conjugates such as an ␣(1→6)-glucosyl-pentose and a triglycoside containing a glucuronic acid were further characterized. All the metabolites identified were complex glycoside conjugates. However, these conjugates still may be a source of DCP in hydrolysis reactions caused by microorganisms in the environment or in the digestive tract of animals and humans. Removal of xenobiotics by glycoside conjugation thus may result in underestimation of the risk associated with toxic compounds like DCP in the environment or in the food chain.

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“…8,10,11) Cypermethrin Table 1. The solvent systems for two-dimensional development were illustrated, for example, as follows: (A, B) indicated development in the first direction with solvent system A and in the second direction with solvent system B.…”

Section: Reference Compoundsmentioning

confidence: 99%

Metabolism of the Pyrethroid Insecticide Cypermethrin in Cabbages

et al. 1986

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Metabolism in cabbage plants of (1R)-cis-and (1R)-traps-isomers of Cypermethrin [(RS)-a-cyano-3-phenoxybenzyl(1RS)-cis, trans-3-(2, 2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate] was investigated with 14C preparations labeled separately in the benzylphenyl ring and cyclopropyl ring. The half-life of disappearance was about 4-5 days and 7-8 days for traps-and cis-cypermethrin, respectively. Both isomers of cypermethrin underwent epimerization to (1 S)-isomers, cis/trans isomerization, ester bond cleavage, hydroxylation of the phenoxy group in the alcohol moiety or the geminal methyl group in the acid moiety, hydration of the CN group to the CONH2 group with subsequent hydrolysis to the COOH group, and conjugation of the resultant carboxylic acids and alcohols with sugars. The major metabolites from the alcohol moiety were glycoside conjugates of 3-(4-hydroxyphenoxy)benzoic acid and 3-phenoxybenzoic acid, and glycoside conjugates of 3-(2, 2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid from the acid moiety. Cypermethrin and its metabolites hardly translocated from the treated leaves to other parts of the plants.

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The metabolism of cypermethrin in plants: The conjugation of the cyclopropyl moiety

Cited by 25 publications

References 6 publications

Metabolic fate of [¹⁴C]‐2,4‐dichlorophenol in tobacco cell suspension cultures

Metabolic fate of [¹⁴C]‐2,4‐dichlorophenol in tobacco cell suspension cultures

Metabolic Fate of [14c]-2,4-Dichlorophenol in Tobacco Cell Suspension Cultures

Metabolism of the Pyrethroid Insecticide Cypermethrin in Cabbages

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The metabolism of cypermethrin in plants: The conjugation of the cyclopropyl moiety

Cited by 25 publications

References 6 publications

Metabolic fate of [14C]‐2,4‐dichlorophenol in tobacco cell suspension cultures

Metabolic fate of [14C]‐2,4‐dichlorophenol in tobacco cell suspension cultures

Metabolic Fate of [14c]-2,4-Dichlorophenol in Tobacco Cell Suspension Cultures

Metabolism of the Pyrethroid Insecticide Cypermethrin in Cabbages

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Metabolic fate of [¹⁴C]‐2,4‐dichlorophenol in tobacco cell suspension cultures

Metabolic fate of [¹⁴C]‐2,4‐dichlorophenol in tobacco cell suspension cultures