Journal Article

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

Nobuyoshi Nakajima, Yukiko Ohshima, Shigeko Serizawa, Tomoko Kouda, John S. Edmonds, Fujio Shiraishi, Mitsuko Aono, Akihiro Kubo, Masanori Tamaoki, Hikaru Saji and Masatoshi Morita

in Plant and Cell Physiology

Published on behalf of Japanese Society of Plant Physiologists

Volume 43, issue 9, pages 1036-1042
Published in print September 2002 | ISSN: 0032-0781
Published online September 2002 | e-ISSN: 1471-9053 | DOI: http://dx.doi.org/10.1093/pcp/pcf130
Processing of Bisphenol A by Plant Tissues: Glucosylation by Cultured BY-2 Cells and Glucosylation/Translocation by Plants of Nicotiana tabacum

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  • Biochemistry
  • Molecular and Cell Biology
  • Plant Sciences and Forestry

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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-β-d-glucopyranoside (BPAG) by mass spectrometry, nuclear magnetic resonance spectroscopy and by hydrolysis with β-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 β-glucoside and translocated the metabolites to their leaves.

Keywords: Keywords: Bisphenol A — BY-2 cells — Glucoside — Nicotiana tabacum — Phytoremediation.; Abbreviations: BPA, bisphenol A (4,4′-isopropylidenediphenol); BPAG, 4,4′-isopropylidenediphenol-O-β-d-glucopyranoside; NMR, nuclear magnetic resonance; FAB-MS, fast atom bombardment mass spectrometry; MSD, Murashige-Skoog medium containing 16 µM of 2,4-D

Journal Article.  3947 words.  Illustrated.

Subjects: Biochemistry ; Molecular and Cell Biology ; Plant Sciences and Forestry

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