Bioactive diterpenoid containing a reversible "spring-loaded" (E,Z)-dieneone Michael acceptor |
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| Authors: | Gupta Prasoon Sharma Upasana Schulz Thomas C Sherrer Eric S McLean Amanda B Robins Allan J West Lyndon M |
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| Institution: | Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, Florida 33431, USA. |
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| Abstract: | Three new briarane diterpenoids, briareolate esters L-N (1-3), have been isolated from a gorgonian Briareum asbestinum. Briareolate esters L (1) and M (2) are the first natural products possessing a 10-membered macrocyclic ring with a (E,Z)-dieneone and exhibit growth inhibition activity against both human embryonic stem cells (BG02) and a pancreatic cancer cell line (BxPC-3). Briareolate ester L (1) was found to contain a "spring-loaded" (E,Z)-dieneone Michael acceptor group that can form a reversible covalent bond to model sulfur-based nucleophiles. |
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