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Bioactive diterpenoid containing a reversible "spring-loaded" (E,Z)-dieneone Michael acceptor.


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.

SUBMITTER: Gupta P 

PROVIDER: S-EPMC3410444 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Bioactive diterpenoid containing a reversible "spring-loaded" (E,Z)-dieneone Michael acceptor.

Gupta Prasoon P   Sharma Upasana U   Schulz Thomas C TC   Sherrer Eric S ES   McLean Amanda B AB   Robins Allan J AJ   West Lyndon M LM  

Organic letters 20110712 15


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 rev  ...[more]

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