Spiculoic acids A and B, new polyketides isolated from the Caribbean marine sponge Plakortis angulospiculatus.

Abstract

[structure: see text] Two novel polyketides, spiculoic acids A (1) and B (2), have been isolated from extracts of the Caribbean marine sponge Plakortisangulospiculatus. The structures of 1 and 2 were elucidated by detailed analysis of spectroscopic data. Spiculoic acid A (1) showed in vitro cytotoxicity against human breast cancer MCF-7 cells. It has a putative polyketide biogenetic origin that involves incorporation of four butyrate units and a Diels Alderase catalyzed intramolecular [4 + 2] cycloaddition reaction.

• Authors: Xin-Hui Huang, Rob van Soest, Michel Roberge, Raymond J Andersen
• Journal: Organic letters (Org Lett) Vol. 6 Issue 1 Pg. 75-8 (Jan 08 2004) ISSN: 1523-7060 [Print] United States
• PMID: 14703354 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Carboxylic Acids
• Indans
• Macrolides
• spiculoic acid A
• spiculoic acid B

Topics

• Animals
• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Apoptosis
• Carboxylic Acids (chemistry, isolation & purification, pharmacology)
• Cell Line, Tumor
• Drug Screening Assays, Antitumor
• Humans
• Indans (chemistry, isolation & purification, pharmacology)
• Macrolides (chemistry, isolation & purification, pharmacology)
• Magnetic Resonance Spectroscopy
• Molecular Structure
• Porifera (chemistry)
• Stereoisomerism