Uptake and metabolism of nonylphenol in plants: Isomer selectivity involved with direct conjugation.
Nonylphenol (NP), an environmental estrogen, is actually a complicated mixture of isomers, although it is commonly considered to be a single compound. There are many routes for crops to come into contact with NP; however, little is known about the plant uptake and metabolism of NP, especially at the isomer level. This study comparatively evaluated the uptake and in-planta metabolism of 4-n-NP and its 10 isomers using both carrot cells and intact plants. The rapid metabolism of 4-n-NP was observed in the callus tissues and intact plants with half-lives of 2 h and 4.72 d, respectively. Six conjugates of 4-n-NP were identified in the cell extracts using high resolution mass spectrometry. The primary transformation pathway was found to be the direct conjugation (Phase II metabolism) with the parent compound at the hydroxyl. Furthermore, 4-NP isomers with short side chains and/or bulky α-substituents were more resistant to plant metabolism and showed a greater tendency for accumulation. The influence of the side chains to the isomer selectivity was verified by the molecular docking between glycosyltransferase and 4-NP isomers. This study highlighted the necessity to consider isomer-specificity in the plant accumulation of NP and the environmental and human health implications of NP conjugates.