Koanolide A, antiproliferative germacrane-type sesquiterpene lactone from Koanophyllon gibbosum

被引：4

作者：

Castillo, Quirico A. ^{[1
,2
]}

Padron, Jose M. ^{[3
]}

Wojtas, Lukasz ^{[4
]}

Keramane, Mehdi ^{[5
]}

Germosen, Evelyn A. ^{[2
]}

机构：

[1] UASD, Fac Ciencias, Escuela Quim, Ciudad Univ, Santo Domingo, DN, Dominican Rep

[2] UASD, Fac Ciencias, Inst Quim, Ciudad Univ, Santo Domingo, DN, Dominican Rep

[3] Univ La Laguna, Ctr Invest Biomed Canarias CIBICAN, Inst Univ Bioorgan Antonio Gonzalez IUBO AG, BioLab, San Cristobal la Laguna 38206, Spain

[4] Univ S Florida, Dept Chem, 4202 East Fowler Ave, Tampa, FL 33612 USA

[5] McMaster Univ, Biointerfaces Inst, Engn Technol Bldg,Room 413,1280 Main St West, Hamilton, ON L8S 0A3, Canada

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 25期

关键词：

Koanophyllon gibbosum; Koanolide A; Germacranolides; Sesquiterpene lactones;

D O I：

10.1016/j.tetlet.2019.05.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new germacrane-type sesquiterpene lactone, koanolide A (1), was isolated from the aerial parts of Koanophyllon gibbosum. The new structure was elucidated using spectroscopic and spectrometric data analyses, including 1D and 2D NMR. The absolute configuration of compound 1 was established by X-ray crystallography. The antiproliferative activity of 1 was studied in a panel of six representative human solid tumor cell lines and showed GI(50) values ranging from 0.34 to 20 mu M. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：1640 / 1642

页数：3

共 10 条

[1] ON ENANTIOMORPH-POLARITY ESTIMATION [J].

FLACK, HD .

ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881

[2] What made sesquiterpene lactones reach cancer clinical trials? [J].

Ghantous, Akram ;

Gali-Muhtasib, Hala ;

Vuorela, Heikki ;

Saliba, Najat A. ;

Darwiche, Nadine .

DRUG DISCOVERY TODAY, 2010, 15 (15-16) :668-678

[3] Determination of absolute structure using Bayesian statistics on Bijvoet differences [J].

Hooft, Rob W. W. ;

Straver, Leo H. ;

Spek, Anthony L. .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2008, 41 :96-103

[4]

Liogier A. H., 1996, FLORA ESPANOLA, P142

[5] Perspectives on Sesquiterpene Lactones in Inflammation and Cancer [J].

Merfort, Irmgard .

CURRENT DRUG TARGETS, 2011, 12 (11) :1560-1573

[6]

Modzelewska Aneta, 2005, Current Medicinal Chemistry - Anti-Cancer Agents, V5, P477, DOI 10.2174/1568011054866973

[7] Development of Anticancer Agents from Plant-Derived Sesquiterpene Lactones [J].

Ren, Yulin ;

Yu, Jianhua ;

Kinghorn, A. Douglas .

CURRENT MEDICINAL CHEMISTRY, 2016, 23 (23) :2397-2420

[8] Synthesis and identification of unprecedented selective inhibitors of CK1ε [J].

Silveira-Dorta, Gaston ;

Sousa, Ines J. ;

Fernandes, Miguel X. ;

Martin, Victor S. ;

Padron, Jose M. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 96 :308-317

[9] Structure validation in chemical crystallography [J].

Spek, Anthony L. .

ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY, 2009, 65 :148-155

[10]

Zhang Siyuan, 2005, Current Medicinal Chemistry - Anti-Cancer Agents, V5, P239, DOI 10.2174/1568011053765976

← 1 →