New spirocyclic sesquiterpenes from the marine sponge Geodia exigua

Tetrahedron
2003.0

Abstract

Three new spirocyclic sesquiterpenes designated exiguamide (1), exicarbamate (2) and exigurin (3), together with (2)-10-epiaxisonitrile-3 (4), have been isolated from the marine sponge Geodia exigua. All four compounds possess the spiro[4.5]decene skeleton and their structures were determined on the basis of spectroscopic data. The structure of 1 was confirmed by X-ray crystallographic analysis and the absolute configuration was determined by applying the modified Mosher's method on its amine derivative. Exiguamide (1) inhibited cell fate specification during sea urchin embryogenesis at a minimum inhibitory concentration of 0.4 mM. q 2003 Elsevier Science Ltd. All rights reserved.

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