Hypercohones D-G, New Polycyclic Polyprenylated Acylphloroglucinol Type Natural Products from Hypericum cohaerens

doi:10.1007/s13659-014-0007-5

应用天然产物 ›› 2014, Vol. 4 ›› Issue (2): 73-79.DOI: 10.1007/s13659-014-0007-5

• Original article • 上一篇下一篇

Hypercohones D-G, New Polycyclic Polyprenylated Acylphloroglucinol Type Natural Products from Hypericum cohaerens

Jing-Jing Zhang^1,2, Xing-Wei Yang^1,2, Jun-Zeng Ma¹, Xia Liu¹, Li-Xin Yang¹, Sheng-Chao Yang³, Gang Xu¹

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China

收稿日期:2014-01-13 修回日期:2014-02-24 出版日期:2014-04-24 发布日期:2018-02-11
通讯作者: Sheng-Chao Yang,e-mail:shengchaoyang@163.com;Gang Xu,e-mail:xugang008@mail.kib.ac.cn
基金资助:
The work was financially supported by the foundations from NSFC(20972167), the Young Academic Leader Raising Foundation of Yunnan Province(No. 2009CI073), and the foundation from CAS to Dr G. Xu.

Hypercohones D-G, New Polycyclic Polyprenylated Acylphloroglucinol Type Natural Products from Hypericum cohaerens

Jing-Jing Zhang^1,2, Xing-Wei Yang^1,2, Jun-Zeng Ma¹, Xia Liu¹, Li-Xin Yang¹, Sheng-Chao Yang³, Gang Xu¹

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China

Received:2014-01-13 Revised:2014-02-24 Online:2014-04-24 Published:2018-02-11
Supported by:
The work was financially supported by the foundations from NSFC(20972167), the Young Academic Leader Raising Foundation of Yunnan Province(No. 2009CI073), and the foundation from CAS to Dr G. Xu.

摘要/Abstract

摘要： Four new polycyclic polyprenylated acylphloroglucinol type metabolites, hypercohones D-G(1-4), along with four known analogues(5-8), were isolated from the aerial parts of Hypericum cohaerens. The structures of these isolates were elucidated by extensive spectroscopic methods. The inhibitory activities of these isolates against five human cancer cell lines in vitro were also tested.

关键词: Guttiferae, Hypericum cohaerens, Acylphloroglucinol, Hypercohones D–G

Abstract: Four new polycyclic polyprenylated acylphloroglucinol type metabolites, hypercohones D-G(1-4), along with four known analogues(5-8), were isolated from the aerial parts of Hypericum cohaerens. The structures of these isolates were elucidated by extensive spectroscopic methods. The inhibitory activities of these isolates against five human cancer cell lines in vitro were also tested.

Key words: Guttiferae, Hypericum cohaerens, Acylphloroglucinol, Hypercohones D-G

Jing-Jing Zhang, Xing-Wei Yang, Jun-Zeng Ma, Xia Liu, Li-Xin Yang, Sheng-Chao Yang, Gang Xu. Hypercohones D-G, New Polycyclic Polyprenylated Acylphloroglucinol Type Natural Products from Hypericum cohaerens[J]. 应用天然产物, 2014, 4(2): 73-79.

参考文献

1. R. Ciochina, R.B. Grossman, Chem. Rev. 106, 3963-3986 (2006)
2. I.P. Singh, S.B. Bharate, Nat. Prod. Rep. 23, 558-591 (2006)
3. I.P. Singh, J. Sidana, S.B. Bharate, W.J. Foley, Nat. Prod. Rep. 27, 393-416 (2010)
4. L.J. Zhang, C.T. Chiou, J.J. Cheng, H.C. Huang, L.M. Yang Kuo, C.C. Liao, K.F. Bastow, K.H. Lee, Y.H. Kuo, J. Nat. Prod. 73, 557-562 (2010)
5. R.A. Hussain, A.G. Owegby, P. Parimoo, P.G. Waterman, Planta Med. 44, 78-81 (1982)
6. A.L. Piccinelli, O. Cuesta-Robio, M.B. Chica, N. Mahmood, B. Pagano, M. Pavone, V. Barone, L. Rastrelli, Tetrahedron 61, 8206-8211 (2005)
7. U.M. Acuna, M. Figueroa, A. Kavalier, N. Jancovski, M.J. Basile, E.J. Kennelly, J. Nat. Prod. 73, 1775-1779 (2010)
8. T.N. Griffith, L. Varela-Nallar, M.C. Dinamarca, N.C. Inestrosa, Curr. Med. Chem. 17, 391-406 (2010)
9. Z.Y. Xiao, Q. Mu, W.K.P. Shiu, Y.H. Zeng, S. Gibbons, J. Nat. Prod. 70, 1779-1782 (2007)
10. L. Beerhues, Phytochemistry 67, 2201-2207 (2006)
11. N.S. Bystrov, B.K. Chernov, V.N. Dobrynin, M.N. Kolosov, Tetrahedron Lett. 32, 2791-2794 (1975)
12. P. Avato, in Studies in Natural Products Chemistry, vol. 30, ed. by Atta-ur-Rahman (Elsevier, The Netherlands, 2005), pp. 603-634
13. Y.H. Li, Z.Y. Wu, Flora of China, vol. 50 (Science, Beijing, 1990), p. 12
14. X.W. Yang, X. Deng, X. Liu, C.Y. Wu, X.N. Li, B. Wu, H.R. Luo, Y. Li, H.X. Xu, Q.S. Zhao, G. Xu, Chem. Commun. 48, 5998-6000 (2012)
15. X. Liu, X.W. Yang, C.Q. Chen, C.Y. Wu, J.J. Zhang, J.Z. Ma, H. Wang, Q.S. Zhao, L.X. Yang, G. Xu, Nat. Prod. Bioprospect. 3, 233-237 (2013)
16. X. Liu, X.W. Yang, C.Q. Chen, C.Y. Wu, J.J. Zhang, J.Z. Ma, H. Wang, L.X. Yang, G. Xu, J. Nat. Prod. 76, 1612-1618 (2013)
17. N. Guo, X.Q. Chen, Q.S. Zhao, Acta Bot. Yunnan. 30, 515-518 (2008)
18. X.Q. Chen, Y. Li, X. Cheng, K. Wang, J. He, Z.H. Pan, M.M. Li, L.Y. Peng, G. Xu, Q.S. Zhao, Chem. Biodivers. 7, 196-204 (2010)
19. L. Verotta, G. Appendino, J. Jakupovic, E. Bombardelli, J. Nat. Prod. 63, 412-415 (2000)
20. W. Hashida, N. Tanaka, Y. Kashiwada, M. Sekiya, Y. Ikeshiro, Phytochemistry 69, 2225-2230 (2008)
21. W.B. Xin, X.H. Man, C.J. Zheng, M. Jia, Y.P. Jiang, X.X. Zhao, G.L. Jin, Z.J. Mao, H.Q. Huang, L.P. Qin, Fitoterapia 83, 1540-1547 (2012)
22. M.C. Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker, M.R. Boyd, Cancer Res. 48, 589-601 (1988)

[1]	Ya-Li Hu, Xing-Ren Li, Gang Xu. Carascynol A, a hybrid of caryophyllane-type terpenoid and a C₆ unit degraded by polyprenylated acylphloroglucinols from Hypericum ascyron[J]. 应用天然产物, 2022, 12(6): 38-38.
[2]	Christian Bailly, Gérard Vergoten. Anticancer Properties and Mechanism of Action of Oblongifolin C, Guttiferone K and Related Polyprenylated Acylphloroglucinols[J]. 应用天然产物, 2021, 11(6): 629-641.
[3]	Yan-Song Ye, Man Wu, Na-Na Jiang, Yuan-Zhi Lao, Wen-Wei Fu, Xia Liu, Xing-Wei Yang, Juan Zhang, Hong-Xi Xu, Gang Xu. Dearomatized Isoprenylated Acylphloroglucinol Derivatives with Potential Antitumor Activities from Hypericum henryi[J]. 应用天然产物, 2020, 10(1): 1-11.
[4]	Xin-Wen Zhang, Yan-Song Ye, Fan Xia, Xing-Wei Yang, Gang Xu. Diverse Polyphenols from Hypericum faberi[J]. 应用天然产物, 2019, 9(3): 215-221.
[5]	Xia LIU, Xing-Wei YANG, Chao-Qun CHEN, Chun-Yan WU, Jing-Jing ZHANG, Jun-Zeng MA, Huan WANG, Qin-Shi ZHAO, Li-Xin YANG, Gang XU. Hypercohones A-C, acylphloroglucinol derivatives with homo-adamantane cores from Hypericum cohaerens[J]. 应用天然产物, 2013, 3(5): 233-237.
[6]	Li-Yan PENG, Juan HE, Gang XU, Xing-De WU, Liao-Bin DONG, Xiu GAO, Xiao CHENG, Jia SU, Yan LI, Qin-Shi ZHAO. Euglobal-IIIa, a novel acylphloroglucinol-sesquiterpene derivative from Eucalyptus robusta: absolute structure and cytotoxicity[J]. 应用天然产物, 2011, 1(2): 101-103.

Hypercohones D-G, New Polycyclic Polyprenylated Acylphloroglucinol Type Natural Products from Hypericum cohaerens

Hypercohones D-G, New Polycyclic Polyprenylated Acylphloroglucinol Type Natural Products from Hypericum cohaerens

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 6

编辑推荐

Metrics

本文评价