Processing of bisphenol A by plant tissues: glucosylation by cultured BY-2 cells and glucosylation/translocation by plants of Nicotiana tabacum.
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 [(14)C]BPA. The most abundant metabolite was determined to be 4,4'-isopropylidenediphenol-O-beta-D-glucopyranoside (BPAG) by mass spectrometry, nuclear magnetic resonance spectroscopy and by hydrolysis with beta-glucosidase. This identification was confirmed by synthesis. When [(14)C]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 beta-glucoside and translocated the metabolites to their leaves.
D001559:Benzhydryl Compounds; D001673:Biodegradation, Environmental; D001692:Biological Transport / Q000502:physiology; D002250:Carbon Radioisotopes / Q000378:metabolism; D002478:Cells, Cultured; D005960:Glucosides / Q000737:chemistry / Q000378:metabolism*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010636:Phenols / Q000378:metabolism*; D014026:Nicotiana / Q000166:cytology / Q000378:metabolism*; D001617:beta-Glucosidase / Q000378:metabolism; D000098826:Bisphenol A Compounds
D001559:Benzhydryl Compounds; D002250:Carbon Radioisotopes; D005960:Glucosides; D010636:Phenols; D001617:beta-Glucosidase; C470376:bisphenol A-O-beta-D-glucopyranoside; D000098826:Bisphenol A Compounds; C006780:bisphenol A