Aplysiols A and B, squalene-derived polyethers from the mantle of the sea hare Aplysia dactylomela

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• 作者：Emiliano Manzo ; Margherita Gavagnin ; Giuseppe Bifulco ; Paola Cimino ; Simone Di Micco ; M. Letizia Ciavatta ; Yue Wei Guo ; Guido Cimino
• 关键词：Marine natural products ; Molluscs ; Aplysiol ; Absolute stereochemistry
• 刊名：Tetrahedron
• 出版年：2007
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：1 October 2007
• 卷：63
• 期：40
• 页码：9970-9978
• 文件大小：328 K

摘要

Two novel triterpenoids, aplysiols A (5) and B (6), have been isolated, together with structurally related known metabolites, from a South China Sea collection of the anaspidean mollusc Aplysia dactylomela. The structures of 5 and 6 were determined mainly by spectroscopic NMR techniques. The absolute stereochemistry of compound 5 was deduced by Mosher's method as well as by biogenetical consideration, whereas the absolute stereochemistry of compound 6 was established also using an integrated NMR-QM (Quantum Mechanical) approach, based on the combination of ¹³C NMR chemical shifts and ^2,3J_C–H coupling constant DFT (density functional theory) calculations.