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Fallaxosides B1 and D3, triterpene glycosides with novel skeleton types of aglycones from the sea cucumber Cucumaria fallax
Tetrahedron ( IF 2.1 ) Pub Date : 2017-03-29 16:18:34
Alexandra S. Silchenko, Anatoly I. Kalinovsky, Sergey A. Avilov, Pavel S. Dmitrenok, Vladimir I. Kalinin, Dmitrii V. Berdyshev, Ekaterina A. Chingizova, Pelageya V. Andryjaschenko, Kirill V. Minin, Valentin A. Stonik

Two unprecedented triterpene glycosides, fallaxosides B1 and D3 with aglycones of new skeletal types were isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The first of these aglycones is formed as result of intramolecular aldol condensation of a precursor having 1,6-diketone functionality, while the second one by pinacol-pinacolone-like rearrangement of another precursor, probably containing 7,8,9-trihydroxy fragment (or its 8,9-epoxy-7-hydroxy analog). The structures of these compounds were established by analysis of 1D, 2D NMR, ESI MS and CD data with using the quantum-chemical calculations.

中文翻译:

Fallaxosides B1和D3,三萜糖苷与海参黄瓜角豆苷的新型骨架类型的糖苷配基

从海参Cucumaria fallax(Cucumariidae,Dendrochirotida)中分离出两种前所未有的三萜糖苷,即具有新骨架类型糖苷的fallaxosides B 1和D 3。这些糖苷配基中的第一个是分子内醛醇缩合形成的,该分子具有1,6-二酮官能团,而第二个糖苷配基是通过另一种可能含有7,8,9-三羟基片段的前体的频哪醇-品那龙的重排而形成的(或其8,9-环氧-7-羟基类似物)。通过使用量子化学计算对1D,2D NMR,ESI MS和CD数据进行分析,可以确定这些化合物的结构。
更新日期:2017-03-30
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