55(P-25) 八丈島産海綿Penares schulzeiからのα-グルコシダーゼ阻害剤schulzeine A-Cの構造(ポスター発表の部)
書誌事項
- タイトル別名
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- 55(P-25) Schulzeines A-C, New α-Glucosidase Inhibitors from the Marine Sponge Penares schulzei
抄録
α-Glucosidases not only process protein glycosylation, but also control oligosaccharide metabolism. Thus, inhibitors of α-glucosidases are potential therapeutics for the treatment of such diseases as viral diseases, cancer, and diabetes. In the course of our continuing search for potential drug leads from Japanese marine invertebrates, we found a potent α-glucosidase-inhibitory activity in the hydrophilic extract of the marine sponge Penares schulzei, whose bioassay-guided fractionation afforded three new tetrahydroisoquinoline alkaloids named schulzeines A-C. The structure of schulzeine A was elucidated by spectral analysis and chemical degradations to be the isoquinoline alkaloids, encompassing two amino acids and a C_<28> trisulfated fatty acid. The absolute stereochemistry of schulzeine A was determined by application of the advanced Mosher analysis to fragments obtained by chemical degradation. Schulzeine B was a desmethyl derivative of schulzeine A, with a stereogenic center in the tricyclic portion being epimerised. Schulzeine C was an epimer of schulzeine B. NMR data of the tricyclic part in schulzeine C was superimposable on that of schulzeine A, while the fatty acid portion was identical with that of schulzeine B. Schulzeines A-C inhibit α-glucosidase with IC_<50> values of 48-170nM. It should be noted that desulfated schulzeines also inhibited the enzyme albeit with diminished activity, thereby indicating that the activity of schulzeines was not thoroughly due to the presence of the three sulfate groups.
収録刊行物
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- 天然有機化合物討論会講演要旨集
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天然有機化合物討論会講演要旨集 45 (0), 323-328, 2003
天然有機化合物討論会実行委員会
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詳細情報 詳細情報について
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- CRID
- 1390282681056889600
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- NII論文ID
- 110006682314
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- ISSN
- 24331856
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可