The uptake, accumulation, and long-distance transport of organophosphate esters (OPEs) in four kinds of plants were investigated by hydroponic experiments. The uptake kinetics (k 1,root) of OPEs in plant roots were determined by the binding of OPEs with the proteins in plant roots and apoplastic sap for the hydrophobic compounds, which correlated well with the transpiration capacity of the plants for the hydrophilic compounds. However, the accumulation capacity of OPEs in plant root was controlled by the partition of OPEs to plant lipids. As a consequence, OPEs were taken up the fastest in wheat root as a result of its highest protein content but least accumulated as a result of its lowest lipid content. The translocation factor of the OPEs decreased quickly with the hydrophobicity (log K ow) increasing, suggesting that the hydrophobic OPEs were hard to translocate from roots to shoots. The hydrophilic OPEs, such as tris­(2-chloroisopropyl) phosphate and tris­(2-butoxyethyl) phosphate, were ambimobile in the plant xylem and phloem, suggesting that they could move to the edible parts of plants and enhanced risk to human health.

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As a frequently detected organophosphorus flame retardant in the environment, 2-ethylhexyl diphenyl phosphate (EHDPHP) is vulnerable to biotransformation, while the transformation mechanisms and potential toxicities of its transformation products remain unclear. In the present study, in vivo transformation products of EHDPHP in exposed zebrafish for 21d were analyzed by suspect screening and identified by mass spectrometry. Fifteen metabolites were identified, including 10 phase I and 5 phase II products with monohydroxylated products being primary, among which 5-OH-EHDPHP was the most predominant. Two sulfation products and one terminal desaturation metabolite of EHDPHP were reported for the first time. A density functional calculation coupled with molecular docking disclosed that the specific conformation of EHDPHP docked in the protein pockets favored the primary formation of 5-OH-EHDPHP, which was fortified to be a more suitable biomarker of EHDPHP exposure. The in vitro tests suggested that EHDPHP transformation took place not only in liver but also in intestine, where gut microbes played an important role. Due to lack of standards, in silico toxicity prediction combined with molecular docking indicated that several metabolites potentially cause higher toxicities than EHDPHP. The results provide deep insight into the potential health risks due to specific in vivo transformation of EHDPHP.

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