Cytotoxic prenylated flavones from the stem and root bark of Daphne giraldii

被引：28

作者：

Sun, Qian ^{[1
,2
]}

Wang, Di ^{[1
,2
]}

Li, Fei-Fei ^{[1
,2
,3
]}

Yao, Guo-Dong ^{[4
]}

Li, Xue ^{[5
]}

Li, Ling-Zhi ^{[1
,2
]}

Huang, Xiao-Xiao ^{[1
,2
]}

Song, Shao-Jiang ^{[1
,2
]}

机构：

[1] Shenyang Pharmaceut Univ, Sch Tradit Chinese Mat Med, Shenyang 110016, Peoples R China

[2] Shenyang Pharmaceut Univ, Minist Educ, Key Lab Struct Based Drug Design & Discovery, Shenyang 110016, Peoples R China

[3] Yangtze River Pharmaceut Grp Co Ltd, Taizhou 225300, Peoples R China

[4] Shenyang Pharmaceut Univ, China Japan Res Inst Med Pharmaceut Sci, Shenyang 110016, Peoples R China

[5] Shenyang Pharmaceut Univ, Sch Life Sci & Biopharmaceut, Shenyang 110016, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2016年 / 26卷 / 16期

关键词：

Daphne giraldii; Flavone; Cytotoxicity; Apoptosis; CONSTITUENTS; MECHANISM;

D O I：

10.1016/j.bmcl.2016.07.002

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Three new prenylated flavones (1-3), along with three known analogues (4-6), were isolated from the stem and root bark of Daphne giraldii. Their structures were determined by comprehensive NMR and HRESIMS spectroscopic data analyses. The absolute configurations of compounds 2 and 3 were assigned by optical rotation comparison, CD and [Rh-2(OCOCF3)(4)]-induced CD spectral methods. The in vitro cytotoxicity experiments carried out involving five cancer cell lines (U251, A549, HepG2, MCF-7 and Bcap37) showed that 2 markedly inhibited the proliferation of all tested cells with IC50 values ranging from 4.26 to 20.82 mu M. The preliminary structure-activity relationships of these flavones are discussed. In addition, compound 2 was found to effectively induce apoptosis in HepG2 cells according to a flow cytometry analysis. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：3968 / 3972

页数：5

共 50 条

[11] Cytotoxic prenylated flavones from Artocarpus champeden [J].

Syah, Yana M. ;

Juliawaty, Lia D. ;

Achmad, Sjamsul A. ;

Hakim, Euis H. ;

Ghisalberti, Emilio L. .

JOURNAL OF NATURAL MEDICINES, 2006, 60 (04) :308-312

[12] Antiplasmodial, Antitrypanosomal, and Cytotoxic Activities of Prenylated Flavonoids Isolated from the Stem Bark of Artocarpus styracifolius [J].

Bourjot, Melanie ;

Apel, Cecile ;

Martin, Marie-Therese ;

Grellier, Philippe ;

Nguyen, Van Hung ;

Gueritte, Francoise ;

Litaudon, Marc .

PLANTA MEDICA, 2010, 76 (14) :1600-1604

[13] Flavonoids from Daphne giraldii Nitsche [J].

Su, Juan ;

Wu, Zhijun ;

Shen, Yunheng ;

Liu, Runhui ;

Zhang, Chuan ;

Li, Huiliang ;

Zhang, Weidong .

NATURAL PRODUCT RESEARCH, 2008, 22 (15) :1355-1358

[14] A new coumarin glycoside from Daphne giraldii [J].

Su, Juan ;

Wu, Zhi Jun ;

Liu, Run Hui ;

Shen, Yun Heng ;

Zhang, Chuan ;

Li, Hui Liang ;

Zhang, Wei ;

Zhang, Wei Dong .

CHINESE CHEMICAL LETTERS, 2007, 18 (07) :835-836

[15] A New Compound from Daphne giraldii Nitsche [J].

Wei Xin SUN Qiang ZHANG Jian Qin JIANG Department of Natural Medicine Chemistry China Pharmaceutical University Nanjing .

ChineseChemicalLetters, 2006, (08) :1054-1056

[16] A new coumarin glycoside from Daphne giraldii [J].

Juan Su a Zhi Jun Wu c Run Hui Liu a Yun Heng Shen a Chuan Zhang a Hui Liang Li a Wei Zhang a Wei Dong Zhang ab a Department of Phytochemistry School of Pharmacy Second Military Medical University Shanghai China b School of Pharmacy Shanghai Jiao Tong University Shanghai China c Department of Research Development Shanghai Center of Research Development of New Drugs Shanghai China .

ChineseChemicalLetters, 2007, (07) :835-836

[17] Prenylated xanthones from the root bark of Cudrania tricuspidata [J].

Hwang, Ji Hye ;

Hong, Seong Su ;

Han, Xiang Hua ;

Hwang, Ji Sang ;

Lee, Dongho ;

Lee, Heesoon ;

Yun, Yeo Pyo ;

Kim, Youngsoo ;

Ro, Jai Seup ;

Hwang, Bang Yeon .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (07) :1207-1209

[18] A New Prenylated Flavanone from the Root Bark of Morus [J].

Hong, Seong Su ;

Hong, Sungeun ;

Lee, Hak Ju ;

Mar, Woongchon ;

Lee, Dongho .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (08) :2528-2530

[19] Sophoranone A and B: two new cytotoxic prenylated metabolites and their analogs from the root bark of Sophora flavescens [J].

Long, Guo-Qing ;

Hu, Gao-Sheng ;

Gao, Xiao-Xu ;

Jia, Jing-Ming ;

Wang, An-Hua .

NATURAL PRODUCT RESEARCH, 2022, 36 (06) :1515-1521

[20] Three new flavanols from Daphne giraldii [J].

Su, Juan ;

Wu, Zhi-Jun ;

Shen, Yun-Heng ;

Zhang, Chuan ;

Li, Hui-Liang ;

Liu, Rui-Hui ;

Zhang, Wei-Dong .

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2008, 10 (06) :547-550

← 1 2 3 4 5 →