Metabolism of the environmental estrogen bisphenol A by plant cell suspension cultures.
The metabolism of the environmental estrogen bisphenol A (BPA) was studied in heterotrophic plant cell suspension cultures of soybean (Glycine max), wheat (Triticum aestivum), foxglove (Digitalis purpurea), and thorn apple (Datura stramonium), which were regarded as metabolic model systems for intact plants. Three main metabolic routes of BPA were observed in the tissues. Most of the radioactivity found in the cell extracts consisted of carbohydrate conjugates of BPA amounting to about 85% (foxglove), 80% (wheat), 7% (soybean) and 15% (thorn apple) of applied 14C. The second main route was formation of non-extractable residues. Portions detected were low in foxglove (3.9% of applied 14C), moderate in wheat (13.5%), high in thorn apple (27.4%) and soybean (49.4%). With thorn apple, BPA derived bound residues were preponderantly resistant towards acid treatment; only traces of BPA were released. The third route was the formation of a highly polar, presumably polymeric material detected in media of soybean and thorn apple (29.3% and 36.0% of applied 14C, respectively). The mechanism of its formation remained unknown. In thorn apple, this highly polar material was formed extremely rapidly, and was considerably stable. Only traces of BPA were liberated by hydrolytic treatment with cellulase or acid. During hydrolysis experiments with glycoside fractions, non-extractable residues and highly polar materials, low amounts of presumably primary metabolites of BPA (up to 6% of applied 14C) were detected besides the parent compound; their chemical structures remained unclear.
Schmidt
B
B
Department of Biology V, Technical University Aachen, Germany. burkhard.schmidt@post.rwth-aachen.de
Schuphan
I
I
D001559:Benzhydryl Compounds; D002250:Carbon Radioisotopes / Q000378:metabolism; D018929:Cell Culture Techniques / Q000379:methods; D002478:Cells, Cultured; D002480:Cellulase / Q000378:metabolism; D003470:Culture Media; D013286:Datura stramonium / Q000378:metabolism; D004070:Digitalis / Q000378:metabolism; D004785:Environmental Pollutants / Q000378:metabolism*; D004968:Estrogens, Non-Steroidal / Q000378:metabolism*; D006027:Glycosides / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D006868:Hydrolysis; D010636:Phenols / Q000378:metabolism*; D059828:Plant Cells; D010944:Plants / Q000378:metabolism*; D013025:Glycine max / Q000378:metabolism; D014908:Triticum / Q000378:metabolism; D000098826:Bisphenol A Compounds
D001559:Benzhydryl Compounds; D002250:Carbon Radioisotopes; D002480:Cellulase; D003470:Culture Media; D004785:Environmental Pollutants; D004968:Estrogens, Non-Steroidal; D006027:Glycosides; D010636:Phenols; C006780:bisphenol A; D000098826:Bisphenol A Compounds