title: Metabolism of [14C]-2,4-dichlorophenol in edible plants.
abstract: Several 2,4-dichlorophenoxyacetic acid (2,4-D)-sensitive plants have been modified by genetic engineering with tfdA gene to acquire 2,4-D tolerance. The expression product of this gene degrades 2,4-D to 2,4-dichlorophenol (DCP), which is less phytotoxic but could cause a problem of food safety. After a comparison of 2,4-D and DCP metabolism in transgenic 2,4-D-tolerant and wild cotton (Gossypium hirsutum L.), a direct study of DCP metabolism in edible plants was performed. After petiolar uptake of a [U-phenyl-(14)C]-DCP solution followed by a 48 h water chase, aqueous extracts were analysed by high-performance liquid chromatography. Metabolites were thereafter isolated and their structural identities were determined by enzymatic and chemical hydrolyses and mass spectrometry analyses. The metabolic fate of DCP was equivalent to 2,4-D metabolism in transgenic 2,4-D-tolerant cotton. In addition, DCP metabolism was similar in transgenic and wild cotton. The major terminal metabolites were DCP-saccharide conjugates in all species, essentially DCP-(6-O-malonyl)-glucoside or its precursor DCP-glucose. The significance of this metabolic pathway with regard to food safety is discussed.
authors.affiliation: INRA, UMR Xénobiotiques, 180 Ch. de Tournefeuille, BP3, F-31931 Toulouse Cedex 9, France. flaurent@toulouse.inra.fr
authors.forename: François
authors.initials: F
authors.lastname: Laurent
authors.forename: Laurent
authors.initials: L
authors.lastname: Debrauwer
authors.forename: Sophie
authors.initials: S
authors.lastname: Pascal-Lorber
mesh_terms: D015084:2,4-Dichlorophenoxyacetic Acid / Q000378:metabolism*; D000421:Alcaligenes / Q000235:genetics; D027461:Beta vulgaris / Q000378:metabolism*; D029688:Brassica napus / Q000378:metabolism*; D002250:Carbon Radioisotopes; D002851:Chromatography, High Pressure Liquid; D003368:Gossypium / Q000235:genetics / Q000378:metabolism; D006540:Herbicides / Q000378:metabolism*; D018551:Solanum lycopersicum / Q000378:metabolism*; D013058:Mass Spectrometry; D006899:Mixed Function Oxygenases; D030821:Plants, Genetically Modified / Q000378:metabolism; D011198:Solanum tuberosum / Q000378:metabolism*
chemical_list: D002250:Carbon Radioisotopes; D006540:Herbicides; D015084:2,4-Dichlorophenoxyacetic Acid; D006899:Mixed Function Oxygenases; C084087:2,4-dichlorophenoxyacetate-alpha-ketoglutarate dioxygenase