Biotransformation of Benzaldehyde-Type and Acetophenone-Type Derivatives by Pharbitis nil Hairy Roots
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- Kanho Hideki
- School of Bioresources, Hiroshima Prefectural University, Japan
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- Yaoya Sayaka
- School of Bioresources, Hiroshima Prefectural University, Japan
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- Kawahara Nobuo
- National Institute of Health Sciences, Japan
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- Nakane Takahisa
- Showa Pharmaceutical University
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- Takase Yoichi
- Showa Pharmaceutical University
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- Masuda Kazuo
- Showa Pharmaceutical University
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- Kuroyanagi Masanori
- School of Bioresources, Hiroshima Prefectural University, Japan
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The glucosylation of some coumarin and flavone derivatives on incubation with the hairy roots of morning glory (Pharbitis nil) was previously reported. We further studied the biotransformation of benzaldehyde- and acetophenone-type derivatives. Vanillin and isovanillin were reduced to alcoholic derivatives and glucosylated at the phenolic and the alcoholic hydroxyl groups. In the case of 3,4-dihydroxybenzaldehyde, the formyl group was reduced and the 3-hydroxyl or 4-hydroxyl groups were glucosylated to give monoglucosides. The 3-hydroxyl group was predominantly glucosylated to the 4-hydroxyl group. 4-β-D-Glucopyranosyloxy-3-methoxybenzylalcohol was obtained in low yield. In time-course experiments with vanillin, it was found that the high-level reduction of the formyl group and glucosylation of the phenolic hydroxyl group occurred, and finally 4-O-β-D-glucopyranosylvanillylalcohol was obtained as the main product. In the case of 3,4-dimethoxybenzaldehyde, 3,4,5-trimethoxybenzaldehyde, and salicylaldehyde, the formyl groups were reduced, and then the hydroxyl groups at the benyl position were glucosylated to give alcoholic glucosides in relatively high yields. In 4-hydroxy-3-methoxyacetophenone, the 4-hydroxyl group was glucosylated and two dimerized glucosides, biphenyl and biphenylether types, were obtained in low yields. In acetophenone, 1-β-D-glucopyranosyloxy-1-phenylethane and 2-β-D-glucopyranosyloxyacetophenone were obtained. As mentioned above P. nil hairy roots showed various biotransformative activities including glucosylation of phenolic and benzylic hydroxyl groups, reduction of the formyl group near the benzene ring, and phenol oxidation dimerization. The glucosylation reaction was especially interesting for the production of valuable glucosides.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 53 (4), 361-365, 2005
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390001204169720832
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- NII論文ID
- 10016652873
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- NII書誌ID
- AA00602100
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- COI
- 1:CAS:528:DC%2BD2MXksVKnu74%3D
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 7292008
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- PubMed
- 15802832
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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
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可