13-Methyl-3,4-seco-ent-podocarpanes, rare C18-diterpenoids from the roots of Flueggea virosa

被引:9
作者
Chao, Chih-Hua [1 ,2 ]
Cheng, Ju-Chien [3 ]
Shen, De-Yang [4 ]
Huang, Hui-Chi [5 ]
Wu, Yang-Chang [1 ,2 ,6 ,7 ]
Wu, Tian-Shung [4 ,8 ,9 ]
机构
[1] China Med Univ, Sch Pharm, Taichung 40402, Taiwan
[2] China Med Univ Hosp, Chinese Med Res & Dev Ctr, Taichung 40402, Taiwan
[3] China Med Univ, Dept Med Lab Sci & Biotechnol, Taichung 40402, Taiwan
[4] Natl Cheng Kung Univ, Dept Pharm, Tainan 70101, Taiwan
[5] China Med Univ, Dept Chinese Pharmaceut Sci & Chinese Med Resourc, Taichung 40402, Taiwan
[6] China Med Univ Hosp, Ctr Mol Med, Taichung 40447, Taiwan
[7] Kaohsiung Med Univ, Grad Inst Nat Prod, Kaohsiung 80708, Taiwan
[8] Tajen Univ, Dept Pharm, Pingtung 90741, Taiwan
[9] Tajen Univ, Grad Inst Pharmaceut Technol, Pingtung 90741, Taiwan
关键词
HEPATITIS-C VIRUS;
D O I
10.1039/c6ra00843g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
As a part of our continuing search for anti-HCV agents from a medicinal plant, Flueggea virosa, we identified fourteen new ingredients, including 13-methyl-3,4-seco-ent-podocarpanes (1-13) and a new naphthalene derivative (14). Their structures were determined by analysis of 2D NMR spectroscopic data, while their absolute configurations were determined by comparison of specific optical rotations with related analogues in the literature. The therapeutic potential against hepatitis C virus (HCV) infection was evaluated for the isolates. Compound 8 showed the most potent anti-HCV activity with a therapeutic index (TI = IC50/EC50) of 100.5.
引用
收藏
页码:34708 / 34714
页数:7
相关论文
共 15 条
[1]   seco-Hinokiol, a new abietane diterpenoid from Rosmarinus officinalis [J].
Cantrell, CL ;
Richheimer, SL ;
Nicholas, GM ;
Schmidt, BK ;
Bailey, DT .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (01) :98-100
[2]   Anti-Hepatitis C Virus Dinorditerpenes from the Roots of Flueggea virosa [J].
Chao, Chih-Hua ;
Cheng, Ju-Chien ;
Shen, De-Yang ;
Wu, Tian-Shung .
JOURNAL OF NATURAL PRODUCTS, 2014, 77 (01) :22-28
[3]   Trinorditerpenes from the roots of Flueggea virosa [J].
Chao, Chih-Hua ;
Cheng, Ju-Chien ;
Hwang, Tsong-Long ;
Shen, De-Yang ;
Wu, Tian-Shung .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (02) :447-449
[4]   Bioactive norditerpenoids from Flickingeria fimbriata [J].
Chen, Jin-Long ;
Zhao, Zhi-Min ;
Xue, Xue ;
Tang, Gui-Hua ;
Zhu, Long-Ping ;
Yang, De-Po ;
Jiang, Lin .
RSC ADVANCES, 2014, 4 (28) :14447-14456
[5]   New diterpenes from Jatropha divaricata [J].
Denton, RW ;
Harding, WW ;
Anderson, CI ;
Jacobs, H ;
McLean, S ;
Reynolds, WF .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (06) :829-831
[6]  
Gelfand M., 1985, TRADITIONAL MED PRAC
[7]   Hepatitis C Virus Replication Is Modulated by the Interaction of Nonstructural Protein NS5B and Fatty Acid Synthase [J].
Huang, Jing-Tang ;
Tseng, Ching-Ping ;
Liao, Mei-Huei ;
Lu, Shao-Chun ;
Yeh, Wei-Zhou ;
Sakamoto, Naoya ;
Chen, Chuan-Mu ;
Cheng, Ju-Chien .
JOURNAL OF VIROLOGY, 2013, 87 (09) :4994-5004
[8]   Synthesis and Anti-HCV Activity of 4-Hydroxyamino α-Pyranone Carboxamide Analogues [J].
Konreddy, Ananda Kumar ;
Toyama, Massaki ;
Ito, Wataru ;
Bal, Chandralata ;
Baba, Masanori ;
Sharon, Ashoke .
ACS MEDICINAL CHEMISTRY LETTERS, 2014, 5 (03) :259-263
[9]   Multiple effects of honokiol on the life cycle of hepatitis C virus [J].
Lan, Keng-Hsin ;
Wang, Ying-Wen ;
Lee, Wei-Ping ;
Lan, Keng-Li ;
Tseng, Szu-Han ;
Hung, Li-Rong ;
Yen, Sang-Hue ;
Lin, Han-Chieh ;
Lee, Shou-Dong .
LIVER INTERNATIONAL, 2012, 32 (06) :989-997
[10]   Three novel 3,4-seco-podocarpane trinorditerpenoids from Aleurites moluccana [J].
Liu, Haiyang ;
Di, Yingtong ;
Yang, Junyun ;
Teng, Fei ;
Lu, Yi ;
Ni, Wei ;
Chen, Changxiang ;
Hao, Xiaojiang .
TETRAHEDRON LETTERS, 2008, 49 (35) :5150-5151