Regioselective hydroxylation, reduction, and glycosylation of diphenyl compounds by cultured cells of Eucalyptus perriniana
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- Kondo Yoko
- Department of Applied Science, Faculty of Science, Okayama University of Science
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- Shimoda Kei
- Department of Pharmacology and Therapeutics, Faculty of Medicine, Oita University
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- Miyahara Keiichi
- Department of Applied Science, Faculty of Science, Okayama University of Science
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- Hamada Hatsuyuki
- National Institute of Fitness and Sports in Kanoya
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- Hamada Hiroki
- Department of Life Science, Faculty of Science, Okayama University of Science
書誌事項
- タイトル別名
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- Regioselective hydroxylation, reduction, and glycosylation of diphenyl compounds by cultured plant cells of Eucalyptus perriniana
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抄録
Bisphenol A and benzophenone, diphenyl compounds, were regioselectively hydroxylated, reduced, and glycosylated by the cultured plant cells of Eucalyptus perriniana. Three known biotransformation products and two new products, 2-(3-β-D-glucopyranosyloxy-4-hydroxyphenyl)-2-(4-β-D-glucopyranosyloxyphenyl)propane and 2-(3-β-D-glucopyranosyloxy-4-β-D-glucopyranosyloxyphenyl)-2-(4-hydroxyphenyl)propane, were isolated after seven days' incubation of bisphenol A. This shows that the cultured cells of E. perriniana 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-O-[6-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]benzophenone and diphenylmethyl 6-O-(β-D-glucopyranosyl)-β-D-glucopyranoside, were obtained from the biotransformation of benzophenone, showing that the cultured cells of E. perriniana 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 E. perriniana 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
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- Plant Biotechnology
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Plant Biotechnology 23 (3), 291-296, 2006
日本植物バイオテクノロジー学会
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詳細情報 詳細情報について
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- CRID
- 1390282679303865856
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- NII論文ID
- 10021908781
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- NII書誌ID
- AA11250821
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- COI
- 1:CAS:528:DC%2BD28XntVWhtLc%3D
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- ISSN
- 13476114
- 13424580
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- NDL書誌ID
- 7943880
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
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- 抄録ライセンスフラグ
- 使用不可