Stellatolides, a New Cyclodepsipeptide Family from the Sponge Ecionemia acervus: Isolation, Solid-Phase Total Synthesis, and Full Structural Assignment of Stellatolide A

详细信息    查看全文

• 作者：Mar铆a Jes煤s Mart铆n ; Raquel Rodr铆guez-Acebes ; Y茅sica Garc铆a-Ramos ; Valent铆n Mart铆nez ; Carmen Murcia ; Isabel Dig贸n ; Isabel Marco ; Marta Pelay-Gimeno ; Rogelio Fern谩ndez ; Fernando Reyes ; Andr茅s M. Francesch ; Simon Munt ; Judit Tulla-Puche ; Fernando Albericio ; Carmen Cuevas
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：May 7, 2014
• 年：2014
• 卷：136
• 期：18
• 页码：6754-6762
• 全文大小：466K
• 年卷期：v.136,no.18(May 7, 2014)
• ISSN：1520-5126

文摘

The marine environment is a rich source of metabolites with potential therapeutic properties and applications for humans. Here we describe the first isolation, solid-phase total synthesis, and full structural assignment of a new class of cyclodepsipeptides from the Madagascan sponge Ecionemia acervus that shows in vitro cytotoxic activities at submicromolar concentrations. Seven structures belonging to a new family of compounds, given the general name stellatolides, were characterized. The sequence and stereochemistry of all the amino acids in these molecules were established by a combination of spectroscopic analysis, chemical degradation, and derivatization studies. Furthermore, the complete structure of stellatolide A was confirmed by an efficient solid-phase method for the first total synthesis and the full structural assignment of this molecule, including the asymmetric synthesis of the unique 尾-hydroxy acid moiety (Z)-3-hydroxy-6,8-dimethylnon-4-enoic acid.