Regioselective hydroxylation, reduction, and glycosylation of diphenyl compounds by cultured plant cells of Eucalyptus perriniana

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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.

収録刊行物

  • Plant biotechnology  

    Plant biotechnology 23(3), 291-296, 2006-06-01 

    Japanese Society for Plant Cell and Molecular Biology

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各種コード

  • NII論文ID(NAID)
    10021908781
  • NII書誌ID(NCID)
    AA11250821
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    13424580
  • NDL 記事登録ID
    7943880
  • NDL 雑誌分類
    ZR3(科学技術--生物学--植物)
  • NDL 請求記号
    Z54-J126
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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