Structures of Steroidal Saponins from the Tubers of Brodiaea californica and Their Inhibitory Activity on Tumor Promoter-Induced Phospholipid Metabolism
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概要
- 論文の詳細を見る
Phytochemical examination of the fresh tubers of Brodiaea californica resulted in the isolation of four new steroidal saponins. Their structures were determined, by extensive spectral analysis including two-dimensional (2D) NMR spectroscopy and acid-catalyzed hydrolysis, to be (25S)-spirost-5-ene-1β, 3β-diol [(25S)-ruscogenin] 1-O-{O-β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside} (1), (25S)-ruscogenin 1-O-{O-β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside} (2), the C-20 and C-22 isomer of 2 (3) and the 6'-O-acetyl derivative of 2 (4), respectively. The conformations of the tetrasaccharide moiety of 2 and 4 were inspected through molecular mechanics and molecular dynamics calculation studies, showing that the acetyl group attached to C-6 of the inner glucose was near the C-21 methyl of the aglycon in the calculated preferred conformation of 4,which must cause the downfield shift of 21-Me by 0.07 ppm in comparing the ^1H-NMR of 4 with that of 2. The inhibitory activity of the isolated saponins on 12-O-tetradecanoylphorbor-13-acetate (TPA)-stimulated ^<32>P-incorporation into phospholipids of HeLa cells was evaluated to identify new antitumor-promoter compounds.
- 社団法人日本薬学会の論文
- 1995-06-15
著者
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小池 一男
東邦大学薬学部
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指田 豊
東京薬大・薬・漢方資源応用
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三巻 祥浩
東京薬大・薬・漢方資源応用
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小池 一男
School of Pharmaceutical Sciences, Toho University
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大本 太一
School of Pharmaceutical Sciences, Toho University
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二階堂 保
School of Pharmaceutical Sciences, Toho University
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西野 輔翼
京都府立医科大学 院 分子生化学
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二階堂 保
東邦大学薬学部
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三巻 祥浩
School of Pharmacy, Tokyo University of Pharmacy and Life Science (formerly, Tokyo College of Pharma
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指田 豊
School of Pharmacy, Tokyo University of Pharmacy and Life Science (formerly, Tokyo College of Pharma
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西野 敦子
Department of Biochemistry, Kyoto Prefectural University of Medicine
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里見 佳子
Cancer Prevention Division, National Cancer Center Research Institute
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西野 輔翼
Cancer Prevention Division, National Cancer Center Research Institute
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中村 修
School of Pharmacy, Tokyo University of Pharmacy and Life Science (formerly, Tokyo College of Pharma
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小池 一男
東邦大・薬
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大本 太一
東邦大薬
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中村 修
School Of Pharmacy Tokyo University Of Pharmacy And Life Science (formerly Tokyo College Of Pharmacy
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三巻 祥浩
School Of Pharmacy Tokyo Univ. Of Pharmacy And Life Sciences
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里見 佳子
京都府立医科大学 院 分子生化学
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Mimaki Y
School Of Pharmacy Tokyo University Of Pharmacy And Life Science
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西野 輔翼
Cancer Prevention Division National Cancer Center Research Institute
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西野 敦子
Department Of Biochemistry Kyoto Prefectural University Of Medicine
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Nishino A
Department Of Biochemistry Kyoto Prefectural University Of Medicine
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Satomi Y
National Cancer Center Res. Inst. Tokyo Jpn
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Satomi Yoshiko
National Cancer Center Research Institute
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Sashida Y
School Of Pharmacy Tokyo University Of Pharmacy And Life Science
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小池 一男
School Of Pharmaceutical Sciences Toho University
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