Literature DB >> 21749084

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

Prasoon Gupta1, Upasana Sharma, Thomas C Schulz, Eric S Sherrer, Amanda B McLean, Allan J Robins, Lyndon M West.   

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.
© 2011 American Chemical Society

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21749084      PMCID： PMC3410444          DOI： 10.1021/ol201443k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Application of real-time cell electronic sensing (RT-CES) technology to cell-based assays.

Authors:  Kelli Solly; Xiaobo Wang; Xiao Xu; Berta Strulovici; Wei Zheng
Journal:  Assay Drug Dev Technol       Date:  2004-08       Impact factor: 1.738

2.  An NMR spectroscopic method to identify and classify thiol-trapping agents: revival of Michael acceptors for drug discovery?

Authors:  Cristina Avonto; Orazio Taglialatela-Scafati; Federica Pollastro; Alberto Minassi; Vincenzo Di Marzo; Luciano De Petrocellis; Giovanni Appendino
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-10       Impact factor: 15.336

3.  Embryonic stem cell lines from human blastocysts: somatic differentiation in vitro.

Authors:  B E Reubinoff; M F Pera; C Y Fong; A Trounson; A Bongso
Journal:  Nat Biotechnol       Date:  2000-04       Impact factor: 54.908

Review 4.  Diterpenes from gorgonian corals.

Authors:  Fabrice Berrue; Russell G Kerr
Journal:  Nat Prod Rep       Date:  2009-03-25       Impact factor: 13.423

5.  Embryonic stem cell lines derived from human blastocysts.

Authors:  J A Thomson; J Itskovitz-Eldor; S S Shapiro; M A Waknitz; J J Swiergiel; V S Marshall; J M Jones
Journal:  Science       Date:  1998-11-06       Impact factor: 47.728

Review 6.  New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress.

Authors:  Michael B Sporn; Karen T Liby; Mark M Yore; Liangfeng Fu; Justin M Lopchuk; Gordon W Gribble
Journal:  J Nat Prod       Date:  2011-02-10       Impact factor: 4.050
  6 in total
  5 in total

1.  A concise synthetic route to the stereotetrad core of the briarane diterpenoids.

Authors:  Nicholas G Moon; Andrew M Harned
Journal:  Org Lett       Date:  2015-04-14       Impact factor: 6.005

2.  Torsional steering as friend and foe: development of a synthetic route to the briarane diterpenoid stereotetrad.

Authors:  Nicholas G Moon; Andrew M Harned
Journal:  Org Biomol Chem       Date:  2017-02-22       Impact factor: 3.876

3.  Briareolate esters from the gorgonian Briareum asbestinum.

Authors:  Rian J Meginley; Prasoon Gupta; Thomas C Schulz; Amanda B McLean; Allan J Robins; Lyndon M West
Journal:  Mar Drugs       Date:  2012-08-10       Impact factor: 6.085

4.  Absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum.

Authors:  Dawrin Pech-Puch; Pedro Joseph-Nathan; Eleuterio Burgueño-Tapia; Carlos González-Salas; Diana Martínez-Matamoros; David M Pereira; Renato B Pereira; Carlos Jiménez; Jaime Rodríguez
Journal:  Sci Rep       Date:  2021-01-12       Impact factor: 4.379

Review 5.  Briarane diterpenoids isolated from gorgonian corals between 2011 and 2013.

Authors:  Jyh-Horng Sheu; Yung-Husan Chen; Yu-Hsin Chen; Yin-Di Su; Yu-Chia Chang; Jui-Hsin Su; Ching-Feng Weng; Chia-Hung Lee; Lee-Shing Fang; Wei-Hsien Wang; Zhi-Hong Wen; Yang-Chang Wu; Ping-Jyun Sung
Journal:  Mar Drugs       Date:  2014-04-10       Impact factor: 5.118
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.