Dibenzofuran, 4-Chromanone, Acetophenone, and Dithiecine Derivatives: Cytotoxic Constituents from Eupatorium fortunei

被引:8
作者
Chang, Chun-Hao [1 ]
Wu, Semon [2 ]
Hsu, Kai-Cheng [3 ,4 ]
Huang, Wei-Jan [5 ,6 ]
Chen, Jih-Jung [7 ,8 ,9 ]
机构
[1] Natl Yang Ming Chiao Tung Univ, Sch Pharmaceut Sci, Inst Biopharmaceut Sci, Taipei 112, Taiwan
[2] Chinese Culture Univ, Dept Life Sci, Taipei 110, Taiwan
[3] Taipei Med Univ, Coll Med Sci & Technol, Grad Inst Canc Biol & Drug Discovery, Taipei 110, Taiwan
[4] Taipei Med Univ, Coll Med Sci & Technol, PhD Program Canc Mol Biol & Drug Discovery, Taipei 110, Taiwan
[5] Taipei Med Univ, Coll Pharm, PhD Program Biotechnol Res & Dev, Taipei 110, Taiwan
[6] Taipei Med Univ, Coll Pharm, Grad Inst Pharmacognosy, Taipei 110, Taiwan
[7] Natl Yang Ming Chiao Tung Univ, Sch Pharmaceut Sci, Dept Pharm, Taipei 112, Taiwan
[8] Natl Yang Ming Univ, Fac Pharm, Taipei 112, Taiwan
[9] China Med Univ, China Med Univ Hosp, Dept Med Res, Taichung 404, Taiwan
关键词
Eupatorium fortunei; dibenzofuran; cytotoxity; apoptosis; THYMOL DERIVATIVES; PYRROLIZIDINE ALKALOIDS; DISCOVERY; APOPTOSIS;
D O I
10.3390/ijms22147448
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Five new compounds, eupatodibenzofuran A (1), eupatodibenzofuran B (2), 6-acetyl-8-methoxy-2,2-dimethylchroman-4-one (3), eupatofortunone (4), and eupatodithiecine (5), have been isolated from the aerial part of Eupatorium fortunei, together with 11 known compounds (6-16). Compounds 1 and 2 featured a new carbon skeleton with an unprecedented 1-(9-(4-methylphenyl)-6-methyldibe nzo[b,d]furan-2-yl)ethenone. Among the isolates, compound 1 exhibited potent inhibitory activity with IC50 values of 5.95 +/- 0.89 and 5.55 +/- 0.23 mu M, respectively, against A549 and MCF-7 cells. The colony-formation assay demonstrated that compound 1 (5 mu M) obviously decreased A549 and MCF-7 cell proliferation, and Western blot test confirmed that compound 1 markedly induced apoptosis of A549 and MCF-7 cells through mitochondrial- and caspase-3-dependent pathways.
引用
收藏
页数:16
相关论文
共 26 条
[1]   SYNTHESIS OF NATURALLY OCCURRING HYDROXYACETOPHENONE DERIVATIVES [J].
BOHLMANN, F ;
BUHMANN, U .
CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (03) :863-&
[2]   Thymol, Benzofuranoid, and Phenylpropanoid Derivatives: Anti-inflammatory Constituents from Eupatorium cannabinum [J].
Chen, Jih-Jung ;
Tsai, Yun-Chen ;
Hwang, Tsong-Long ;
Wang, Tai-Chi .
JOURNAL OF NATURAL PRODUCTS, 2011, 74 (05) :1021-1027
[3]   One novel nortriterpene and other constituents from Eupatorium fortunei Turcz. [J].
Chen, Yan-Jun ;
Jiang, Hai-Xia ;
Gao, Kun .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 2013, 47 :1-4
[4]   Chemical Constituents from Cimicifuga dahurica and Their Anti-Proliferative Effects on MCF-7 Breast Cancer Cells [J].
Chu Thi Thanh Huyen ;
Bui Thi Thuy Luyen ;
Khan, Ghulam Jilany ;
Ha Van Oanh ;
Ta Manh Hung ;
Li, Hui-Jun ;
Li, Ping .
MOLECULES, 2018, 23 (05)
[5]   Flaxseed extract induces apoptosis in human breast cancer MCF-7 cells [J].
Hu, Tingyan ;
Linghu, Kegang ;
Huang, Siqi ;
Battino, Maurizio ;
Georgiev, Milen I. ;
Zengin, Gokhan ;
Li, Defang ;
Deng, Yun ;
Wang, Y. T. ;
Cao, Hui .
FOOD AND CHEMICAL TOXICOLOGY, 2019, 127 :188-196
[6]   Benzophenone and Benzoylphloroglucinol Derivatives from Hypericum sampsonii with Anti-Inflammatory Mechanism of Otogirinin A [J].
Huang, Chun-Yi ;
Chang, Tzu-Cheng ;
Wu, Yu-Jing ;
Chen, Yun ;
Chen, Jih-Jung .
MOLECULES, 2020, 25 (19)
[7]   Benzofuran derivatives from Eupatorium fortunei [J].
Jiang, Hai Xia ;
Liu, Quan ;
Gao, Kun .
NATURAL PRODUCT RESEARCH, 2008, 22 (11) :937-941
[8]   Relating protein pharmacology by ligand chemistry [J].
Keiser, Michael J. ;
Roth, Bryan L. ;
Armbruster, Blaine N. ;
Ernsberger, Paul ;
Irwin, John J. ;
Shoichet, Brian K. .
NATURE BIOTECHNOLOGY, 2007, 25 (02) :197-206
[9]   Indirubin Inhibits LPS-Induced Inflammation via TLR4 Abrogation Mediated by the NF-kB and MAPK Signaling Pathways [J].
Lai, Jin-lun ;
Liu, Yu-hui ;
Liu, Chang ;
Qi, Ming-pu ;
Liu, Rui-ning ;
Zhu, Xi-fang ;
Zhou, Qiu-ge ;
Chen, Ying-yu ;
Guo, Ai-zhen ;
Hu, Chang-min .
INFLAMMATION, 2017, 40 (01) :1-12
[10]   Taraxacum mongolicum extract induced endoplasmic reticulum stress associated-apoptosis in triple-negative breast cancer cells [J].
Li, Xiao-Hong ;
He, Xi-Ran ;
Zhou, Yan-Yan ;
Zhao, Hai-Yu ;
Zheng, Wen-Xian ;
Jiang, Shan-Tong ;
Zhou, Qun ;
Li, Ping-Ping ;
Han, Shu-Yan .
JOURNAL OF ETHNOPHARMACOLOGY, 2017, 206 :55-64