Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 19, Pages 7190-7198Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo071003y
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[GRAPHICS] Novel nitrogenous diterpenoids, spongolactams A-C (1-3), were isolated as trace components of an Okinawan marine sponge, Spongia sp., by an LC/MS-guided assay for farnesyl transferase (FTase) inhibitors. Their structures were elucidated by spectroscopic analyses. To evaluate their structures and biological activity, the metabolites were semisynthesized from the known furanoditerpene 5, obtained from the same sponge. Three related compounds 4, 13, and 16 were also semisynthesized. The IC50 values against FTase for 1-3 were 23, 130, and >260 mu M, respectively, while the IC50 values against a human tumor cell line were 2.0, 3.5, and 20 mu M, respectively. The structure-activity relationships within the six compounds suggest some positive correlation between FTase inhibitory and cytotoxic activities.
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