Regioselective hydroxylation, reduction, and glycosylation of diphenyl compounds by cultured plant cells of Eucalyptus perriniana
Bisphenol A and benzophenone, diphenyl compounds, were regioselectively hydroxylated, reduced, and glycosylated by the cultured plant cells of <i>Eucalyptus perriniana</i>. Three known biotransformation products and two new products, 2-(3-β-<small>D</small>-glucopyranosyloxy-4-hydroxyphenyl)-2-(4-β-<small>D</small>-glucopyranosyloxyphenyl)propane and 2-(3-β-<small>D</small>-glucopyranosyloxy-4-β-<small>D</small>-glucopyranosyloxyphenyl)-2-(4-hydroxyphenyl)propane, were isolated after seven days' incubation of bisphenol A. This shows that the cultured cells of <i>E. perriniana</i> regioselectively hydroxylate at C-6 and C-12 of bisphenol A and that the glycosides can be formed at the hydroxyl group at C-6, 7, 12, and 13. On the other hand, two known products and two new products, 4-<i>O</i>-[6-<i>O</i>-(α-<small>L</small>-rhamnopyranosyl)-β-<small>D</small>-glucopyranosyl]benzophenone and diphenylmethyl 6-<i>O</i>-(β-<small>D</small>-glucopyranosyl)-β-<small>D</small>-glucopyranoside, were obtained from the biotransformation of benzophenone, showing that the cultured cells of <i>E. perriniana</i> regioselectively hydroxylate at C-4 and reduce the carbonyl group of benzophenone and that glycosylation can occur at the hydroxyl group at C-4 and C-7. Thus, both diphenyl compounds were removed from the culture medium and accumulated in cells as glycosides. The biotransformation with <i>E. perriniana</i> would provide a very useful process for the phytoremediation of endocrine disrupting chemicals such as diphenyl compounds. This procedure using enzymatic reactions is simple and environmentally friendly.
- Plant biotechnology
Plant biotechnology 23(3), 291-296, 2006-06-01
Japanese Society for Plant Cell and Molecular Biology