Filicinic Acid Based Meroterpenoids with Anti-Epstein-Barr Virus Activities from Hypericum japonicum

Organic Letters

Volumn 18, Issue 9, 2016, Pages 2272-2275

  Hu, Linzhen ^a   Zhang, Yu ^a   Zhu, Hucheng ^a   Liu, Junjun ^a   Li, Hua ^a   Li, Xiao Nian ^b   Sun, Weiguang ^a   Zeng, Junfen ^c   Xue, Yongbo ^a   Zhang, Yonghui ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b KUNMING INSTITUTE OF BOTANY   (China)

^c RENMIN HOSPITAL OF WUHAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; TERPENE;

CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG EFFECT; EPSTEIN BARR VIRUS; HYPERICUM; ISOLATION AND PURIFICATION; MICROBIAL SENSITIVITY TEST; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION;

ANTIVIRAL AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; HERPESVIRUS 4, HUMAN; HYPERICUM; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; MOLECULAR DOCKING SIMULATION; STRUCTURE-ACTIVITY RELATIONSHIP; TERPENES;

EID: 84969705201     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b00906     Document Type: Article

References (32)

1. Grenning, A. J.; Boyce, J. H.; Porco, J. A., Jr. J. Am. Chem. Soc. 2014, 136, 11799-11804 10.1021/ja5060302
2. Singh, I. P.; Sidana, J.; Bharate, S. B.; Foley, W. J. Nat. Prod. Rep. 2010, 27, 393-416 10.1039/b914364p
3. Richard, J. A.; Pouwer, R. H.; Chen, D. Y. K. Angew. Chem., Int. Ed. 2012, 51, 4536-4561 10.1002/anie.201103873
4. Ciochina, R.; Grossman, R. B. Chem. Rev. 2006, 106, 3963-3986 10.1021/cr0500582
5. Gey, C.; Kyrylenko, S.; Hennig, L.; Nguyen, L. H. D; Buettner, A.; Pham, H. D.; Giannis, A. Angew. Chem., Int. Ed. 2007, 46, 5219-5222 10.1002/anie.200605207
6. Richard, J. A. Eur. J. Org. Chem. 2014, 2014, 273-299 10.1002/ejoc.201300815
7. Oya, A.; Tanaka, N.; Kusama, T.; Kim, S. Y.; Hayashi, S.; Kojoma, M.; Hishida, A.; Kawahara, N.; Sakai, K.; Gonoi, T.; Kobayashi, J. J. Nat. Prod. 2015, 78, 258-264 10.1021/np500827h
8. Quiney, C.; Billard, C.; Salanoubat, C.; Fourneron, J. D.; Kolb, J. P. Leukemia 2006, 20, 1519-1525 10.1038/sj.leu.2404301
9. Zhang, S.; Yin, J.; Li, X.; Zhang, J.; Yue, R.; Diao, Y.; Li, H.; Wang, H.; Shan, L.; Zhang, W. BMC Cancer 2014, 14, 689-699 10.1186/1471-2407-14-689
10. Singh, I. P.; Bharate, S. B. Nat. Prod. Rep. 2006, 23, 558-591 10.1039/b600518g
11. Zhu, H.; Chen, C.; Yang, J.; Li, X. N.; Liu, J.; Sun, B.; Huang, S. X.; Li, D.; Yao, G.; Luo, Z.; Li, Y.; Zhang, J.; Xue, Y.; Zhang, Y. Org. Lett. 2014, 16, 6322-6325 10.1021/ol5030579
12. Li, D.; Xue, Y.; Zhu, H.; Li, Y.; Sun, B.; Liu, J.; Yao, G.; Zhang, J.; Du, G.; Zhang, Y. RSC Adv. 2015, 5, 5277-5287 10.1039/C4RA11675E
13. Bharate, S. B.; Khan, S. I.; Tekwani, B. L.; Jacob, M.; Khan, I. A.; Singh, I. P. Bioorg. Med. Chem. 2008, 16, 1328-1336 10.1016/j.bmc.2007.10.055
14. Shao, M.; Wang, Y.; Jian, Y. Q.; Huang, X. J.; Zhang, D. M.; Tang, Q. F.; Jiang, W. X.; Sun, G.; Lv, Z. P.; Zhang, X. Q.; Ye, W. C. Org. Lett. 2012, 14, 5262-5265 10.1021/ol302423b
15. Yang, S. P.; Zhang, X. W.; Ai, J.; Gan, L. S.; Xu, J. B.; Wang, Y.; Su, Z. S.; Wang, L.; Ding, J.; Geng, M. Y.; Yue, J. M. J. Med. Chem. 2012, 55, 8183-8187 10.1021/jm3007454
16. Chenavas, S.; Fiorini Puybaret, C.; Joulia, P.; Larrouquet, C.; Waton, H.; Martinez, A.; Casabianca, H.; Fabre, B. Phytochem. Lett. 2015, 11, 69-73 10.1016/j.phytol.2014.11.002
17. Shou, Q.; Smith, J. E.; Mon, H.; Brkljača, Z.; Smith, A. S.; Smith, D. M.; Griesser, H. J.; Wohlmuth, H. RSC Adv. 2014, 4, 13514-13517 10.1039/c4ra00154k
18. Shao, M.; Wang, Y.; Liu, Z.; Zhang, D. M.; Cao, H. H.; Fan, C. L.; Zhang, X. Q.; Chen, H. R.; Yao, X. S.; Ye, W. C. Org. Lett. 2010, 12, 5040-5043 10.1021/ol102179u
19. Tian, L. W.; Xu, M.; Li, X. C.; Yang, C. R.; Zhu, H. J.; Zhang, Y. J. RSC Adv. 2014, 4, 21373-21378 10.1039/c4ra01078g
20. Wu, L.; Luo, J.; Zhang, Y.; Zhu, M.; Wang, X.; Luo, J.; Yang, M.; Yu, B.; Yao, H.; Dai, Y.; Guo, Q.; Chen, Y.; Sun, H.; Kong, L. Tetrahedron Lett. 2015, 56, 229-232 10.1016/j.tetlet.2014.11.075
21. Wang, J.; Zhai, W. Z.; Zou, Y.; Zhu, J. J.; Xiong, J.; Zhao, Y.; Yang, G. X.; Fan, H.; Hamann, M. T.; Xia, G.; Hu, J. F. Tetrahedron Lett. 2012, 53, 2654-2658 10.1016/j.tetlet.2012.03.073
22. Ishiguro, K.; Yamaki, M.; Takagi, S.; Yamagata, Y.; Tomita, K. J. Chem. Soc., Chem. Commun. 1985, 26-27 10.1039/c39850000026
23. Flack, H. D.; Bernardinelli, G. Chirality 2008, 20, 681-690 10.1002/chir.20473
24. Ma, J. H.; Zhao, F.; Wang, Y.; Liu, Y.; Gao, S. Y.; Ding, L. Q.; Chen, L. X.; Qiu, F. Org. Biomol. Chem. 2015, 13, 8349-8358 10.1039/C5OB00964B
25. Xia, W. J.; Li, D. R.; Shi, L.; Tu, Y. Q. Tetrahedron: Asymmetry 2001, 17, 168-169 10.1016/S0957-4166(01)00255-5
26. Tchuendem, M. H.; Mbah, J. A.; Tsopmo, A.; Ayafor, J. F.; Sterner, O.; Okunjic, C. C.; Iwu, M. M.; Schuster, B. M. Phytochemistry 1999, 52, 1095-1099 10.1016/S0031-9422(99)00344-1
27. Frelek, J.; Szczepek, W. J. Tetrahedron: Asymmetry 1999, 10, 1507-1520 10.1016/S0957-4166(99)00115-9
28. Ballout, M.; Germi, R.; Fafi Kremer, S.; Guimet, J.; Bargues, G.; Seigneurin, J. M.; Morand, P. J. Virol. Methods 2007, 143, 38-44 10.1016/j.jviromet.2007.02.005
29. Billaud, G.; Thouvenot, D.; Morfin, F. Infect. Disord.: Drug Targets 2009, 9, 117-125 10.2174/187152609787847703
30. Lin, J. C. Tzu Chi Med. J. 2005, 17, 1-10
31. Gupta, S. D.; Bommaka, M. K.; Mazaira, G. I.; Galigniana, M. D.; Subrahmanyam, C. V. S; Gowrishankar, N. L.; Raghavendra, N. M. Int. J. Biol. Macromol. 2015, 80, 253-259 10.1016/j.ijbiomac.2015.06.039
32. Lange, O.; Wolf, C.; Dietze, J.; Elsaesser, J.; Morbitzer, R.; Lahaye, T. Nucleic Acids Res. 2014, 42, 7436-7449 10.1093/nar/gku329