Bioactive Diterpenoid Containing a Reversible "Spring-Loaded" (E,Z)-Dieneone Michael Acceptor

被引：22

作者：

Gupta, Prasoon ^{[1
]}

Sharma, Upasana ^{[1
]}

Schulz, Thomas C. ^{[3
]}

Sherrer, Eric S. ^{[3
]}

McLean, Amanda B. ^{[4
]}

Robins, Allan J. ^{[3
]}

West, Lyndon M. ^{[1
,2
]}

机构：

[1] Florida Atlantic Univ, Dept Chem & Biochem, Boca Raton, FL 33431 USA

[2] Univ Georgia, Dept Pharmaceut & Biomed Sci, Athens, GA 30602 USA

[3] Viacyte Inc, Athens, GA 30602 USA

[4] Univ Georgia, Dept Biochem & Mol Biol, Athens, GA 30602 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 15期

基金：

美国国家卫生研究院;

关键词：

STEM-CELL LINES; BRIAREOLATE; METHYL;

D O I：

10.1021/ol201443k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3920 / 3923

页数：4

共 11 条

[1] An NMR Spectroscopic Method to Identify and Classify Thiol-Trapping Agents: Revival of Michael Acceptors for Drug Discovery? [J].

Avonto, Cristina ;

Taglialatela-Scafati, Orazio ;

Pollastro, Federica ;

Minassi, Alberto ;

Di Marzo, Vincenzo ;

De Petrocellis, Luciano ;

Appendino, Giovanni .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :467-471

[2] Diterpenes from gorgonian corals [J].

Berrue, Fabrice ;

Kerr, Russell G. .

NATURAL PRODUCT REPORTS, 2009, 26 (05) :681-710

[3] BRIARANE AND ASBESTINANE DITERPENES FROM BRIAREUM-ASBESTINUM [J].

DOOKRAN, R ;

MAHARAJ, D ;

MOOTOO, BS ;

RAMSEWAK, R ;

MCLEAN, S ;

REYNOLDS, WF ;

TINTO, WF .

TETRAHEDRON, 1994, 50 (07) :1983-1992

[4]

Frisch M. J., 2016, Gaussian 03 Revision B.03

[5] METHYL BRIAREOLATE, THE 1ST BRIAREIN DITERPENE CONTAINING A C-19 METHYL-ESTER [J].

MAHARAJ, D ;

MOOTOO, BS ;

LOUGH, AJ ;

MCLEAN, S ;

REYNOLDS, WF ;

TINTO, WF .

TETRAHEDRON LETTERS, 1992, 33 (50) :7761-7764

[6] Further briareolate esters and briareolides from the Caribbean gorgonian octocoral Briareum asbestinum [J].

Mootoo, BS ;

Ramsewak, R ;

Sharma, R ;

Tinto, WF ;

Lough, AJ ;

McLean, S ;

Reynolds, WF ;

Yang, JP ;

Yu, M .

TETRAHEDRON, 1996, 52 (30) :9953-9962

[7] Effect of Bardoxolone Methyl on Kidney Function in Patients with T2D and Stage 3b-4 CKD [J].

Pergola, Pablo E. ;

Krauth, Melissa ;

Huff, J. Warren ;

Ferguson, Deborah A. ;

Ruiz, Stacey ;

Meyer, Colin J. ;

Warnock, David G. .

AMERICAN JOURNAL OF NEPHROLOGY, 2011, 33 (05) :469-476

[8] Embryonic stem cell lines from human blastocysts: somatic differentiation in vitro [J].

Reubinoff, BE ;

Pera, MF ;

Fong, CY ;

Trounson, A ;

Bongso, A .

NATURE BIOTECHNOLOGY, 2000, 18 (04) :399-404

[9] Application of real-time cell electronic sensing (RT-CES) technology to cell-based assays [J].

Solly, K ;

Wang, XB ;

Xu, X ;

Strulovici, B ;

Zheng, W .

ASSAY AND DRUG DEVELOPMENT TECHNOLOGIES, 2004, 2 (04) :363-372

[10] New Synthetic Triterpenoids: Potent Agents for Prevention and Treatment of Tissue Injury Caused by Inflammatory and Oxidative Stress [J].

Sporn, Michael B. ;

Liby, Karen T. ;

Yore, Mark M. ;

Fu, Liangfeng ;

Lopchuk, Justin M. ;

Gribble, Gordon W. .

JOURNAL OF NATURAL PRODUCTS, 2011, 74 (03) :537-545

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