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Plant and Cell Physiology, 2002, Vol. 43, No. 9 1036-1042
© 2002 Oxford University Press

Processing of Bisphenol A by Plant Tissues: Glucosylation by Cultured BY-2 Cells and Glucosylation/Translocation by Plants of Nicotiana tabacum

Nobuyoshi Nakajima1,4, Yukiko Ohshima2, Shigeko Serizawa2, Tomoko Kouda2, John S. Edmonds2, Fujio Shiraishi2, Mitsuko Aono3, Akihiro Kubo3, Masanori Tamaoki1, Hikaru Saji3 and Masatoshi Morita2

1 Biodiversity Research Project, National Institute for Environmental Studies, Onogawa, Tsukuba, Ibaraki, 305-8506 Japan
2 Endocrine Disrupters Research Project, National Institute for Environmental Studies, Onogawa, Tsukuba, Ibaraki, 305-8506 Japan
3 Environmental Biology Division, National Institute for Environmental Studies, Onogawa, Tsukuba, Ibaraki, 305-8506 Japan

Bisphenol A (BPA, 4,4'-isopropylidenediphenol), an endocrine disrupter with estrogenic properties, was supplied to tobacco BY-2 cells in suspension culture and the chemical nature of its metabolites was investigated. The concentration of BPA in the culture medium decreased rapidly and became undetectable at 2.5 h after the application. Four metabolites of BPA were observed in a methanol extract of the cells when the culture was supplemented with [14C]BPA. The most abundant metabolite was determined to be 4,4'-isopropylidenediphenol-O-ß-D-glucopyranoside (BPAG) by mass spectrometry, nuclear magnetic resonance spectroscopy and by hydrolysis with ß-glucosidase. This identification was confirmed by synthesis. When [14C]BPA was administrated to tobacco seedlings from their roots, radioactivity was incorporated in BPAG and three unidentified metabolites. These metabolites were accumulated in the leaves after 4 h exposure, indicating that tobacco seedlings absorbed BPA through their root systems, metabolized to its ß-glucoside and translocated the metabolites to their leaves.

4 Corresponding author: E-mail: naka-320@nies.go.jp; Fax +81-298-2490


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