Unknown

Dataset Information

0

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

Json Xml
altmetric image

Publications

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]

Similar Datasets

Unknown A mechanochromic donor-acceptor torsional spring.
| S-EPMC8270966 | biostudies-literature
Unknown Nucleophilicity of Glutathione: A Link to Michael Acceptor Reactivities.
| S-EPMC6899611 | biostudies-literature
Unknown Multifunctional Injectable Hydrogel Loaded with Cerium-Containing Bioactive Glass Nanoparticles for Diabetic Wound Healing.
| S-EPMC8151889 | biostudies-literature
Unknown Helioscopianoids A-Q, bioactive jatrophane diterpenoid esters from Euphorbia helioscopia.
| S-EPMC6147808 | biostudies-other
Unknown Michael-type cyclizations in lantibiotic biosynthesis are reversible.
| S-EPMC4433588 | biostudies-literature
Unknown Determining Michael Acceptor Reactivity from Kinetic, Mechanistic, and Computational Analysis for the Base-catalyzed Thiol-Michael Reaction.
| S-EPMC8409055 | biostudies-literature
Unknown The Emerging Therapeutic Potential of Nitro Fatty Acids and Other Michael Acceptor-Containing Drugs for the Treatment of Inflammation and Cancer.
| S-EPMC7495092 | biostudies-literature
Unknown Spring-loaded Syringe for Multiple Rapid Injections.
| S-EPMC5418984 | biostudies-literature
Unknown Bioactive Abietane-Type Diterpenoid Glycosides from Leaves of Clerodendrum infortunatum (Lamiaceae).
| S-EPMC8306933 | biostudies-literature
Unknown Allocolchicinoids bearing a Michael acceptor fragment for possible irreversible binding of tubulin.
| S-EPMC7578708 | biostudies-literature