Hypercohin K, a polycyclic polyprenylated acylphloroglucinol with an unusual spiro-fused cyclopropane ring from Hypericum cohaerens

Tetrahedron Letters

Volumn 56, Issue 41, 2015, Pages 5537-5540

  Yang, Xing Wei ^a   Yang, Jing ^a   Liao, Yang ^a,b   Ye, Ye ^a,b   Li, Yan Ping ^a   Yang, Shu Ya ^a,b   Xia, Fan ^a   Xu, Gang ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Absolute configuration; Acetylcholinesterase; Hypercohin K; Hypericum cohaerens; Polycyclic polyprenylated acylphloroglucinol

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOPROPANE; HYPERCOHIN K; PHLOROGLUCINOL DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CIRCULAR DICHROISM; COMPARATIVE STUDY; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DRUG STRUCTURE; HUMAN; HUMAN CELL; HYPERICUM; HYPERICUM COHAERENS; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84941261815     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.08.033     Document Type: Article

References (41)

1. C.J. Thibodeaux, W. Chang, and H. Liu Chem. Rev. 112 2012 1681 1709
2. D.Y.-K. Chen, R.H. Pouwer, and J.-A. Richard Chem. Soc. Rev. 41 2012 4631 4642
3. R. Faust Angew. Chem., Int. Ed. 40 2001 2251 2253
4. J. Salaün Top. Curr. Chem. 207 2000 1 67
5. D.L. Boger, T. Ishizaki, and H. Zarrinmayeh J. Am. Chem. Soc. 113 1991 6645 6649
6. T.F. Schneider, J. Kaschel, and D.B. Werz Angew. Chem., Int. Ed. 53 2014 5504 5523
7. H.-U. Reissig, and R. Zimmer Chem. Rev. 103 2003 1151 1196
8. R. Ciochina, and R.B. Grossman Chem. Rev. 106 2006 3963 3986
9. I.P. Singh, J. Sidana, S.B. Bharate, and W.J. Foley Nat. Prod. Rep. 27 2010 393 416
10. Q. Zhang, B. Mitasev, J. Qi, and J.A. Porco Jr. J. Am. Chem. Soc. 132 2010 14212 14215
11. J. Qi, A.B. Beeler, Q. Zhang, and J.A. Porco Jr. J. Am. Chem. Soc. 132 2010 13642 13644
12. Y. Shimizu, S.-L. Shi, H. Usuda, M. Kanai, and M. Shibasaki Angew. Chem., Int. Ed. 49 2010 1103 1106
13. N. Biber, K. Mows, and B. Plietker Nat. Chem. 3 2011 938 942
14. J.-A. Richard, R.H. Pouwer, and D.Y.-K. Chen Angew. Chem., Int. Ed. 51 2012 4536 4561
15. B.A. Sparling, D.C. Moebius, and M.D. Shair J. Am. Chem. Soc. 135 2013 644 647
16. W.J. Tian, Y. Yu, X.J. Yao, H.F. Chen, Y. Dai, X.K. Zhang, and X.S. Yao Org. Lett. 16 2014 3448 3451
17. A.J. Grenning, J.H. Boyce, and J.A. Porco Jr. J. Am. Chem. Soc. 136 2014 11799 11804
18. 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, and G. Xu Chem. Commun. 48 2012 5998 6000
19. X.W. Yang, Y. Ding, J.J. Zhang, X. Liu, L.X. Yang, X.N. Li, D. Ferreira, L.A. Walker, and G. Xu Org. Lett. 16 2014 2434 2437
20. J.J. Zhang, J. Yang, Y. Liao, X.W. Yang, J.Z. Ma, Q.L. Xiao, L.X. Yang, and G. Xu Org. Lett. 16 2014 4912 4915
21. Y. Liao, X. Liu, J. Yang, Y.Z. Lao, X.W. Yang, X.N. Li, J.J. Zhang, Z.J. Ding, H.X. Xu, and G. Xu Org. Lett. 16 2014 6346 6349
22. X.W. Yang, M.M. Li, X. Liu, D. Ferreira, Y. Ding, J.J. Zhang, Y. Liao, H.B. Qin, and G. Xu J. Nat. Prod. 78 2015 885 895
23. Y.H. Li Z.Y. Wu, Ed. Flora of China Vol. 50 1990 Science Press Beijing 12
24. X. Liu, X.W. Yang, C.Q. Chen, C.Y. Wu, J.J. Zhang, J.Z. Ma, H. Wang, L.X. Yang, and G. Xu J. Nat. Prod. 76 2013 1612 1618
25. 4Na, 523.2824).
26. L.A. Decosterd, H. Stoeckli-Evans, J.-C. Chapuis, B. Sordat, and K. Hostettmann Helv. Chim. Acta 72 1989 1833 1845
27. W. Hashida, N. Tanaka, Y. Kashiwada, M. Sekiya, Y. Ikeshiro, and Y. Takaishi Phytochemistry 69 2008 2225 2230
28. R.M. Silverstein, and F.X. Webster Spectrometric Identification of Organic Compounds 6th ed. 1998 John Wiley & Sons New York
29. C. Diedrich, and S. Grimme J. Phys. Chem. A 107 2003 2524 2539
30. N. Berova, L. Di Beri, and G. Pescitelli Chem. Soc. Rev. 36 2007 914 931
31. P. Adam, D. Arigoni, A. Bacher, and W. Eisenreich J. Med. Chem. 45 2002 4786 4793
32. K. Karppinen, J. Hokkanen, A. Tolonen, S. Mattila, and A. Hohtola Phytochemistry 68 2007 1038 1045
33. N. Nualkaew, H. Morita, Y. Shimokawa, K. Kinjo, T. Kushiro, W. De-Eknamkul, Y. Ebizuka, and I. Abe Phytochemistry 77 2012 60 69
34. R.A. Hussain, A.G. Owegby, P. Parimoo, and P.G. Waterman Planta Med. 44 1982 78 81
35. G.E. Henry, H. Jacobs, C.M.S. Carrington, S. McLean, and W.F. Reynolds Tetrahedron Lett. 37 1996 8663 8666
36. H.P. Pepper, H.C. Lam, W.M. Bloch, and J.H. George Org. Lett. 14 2012 5162 5164
37. Y.M. Fan, P. Yi, Y. Li, C. Yan, T. Huang, W. Gu, Y. Ma, L.J. Huang, J.X. Zhang, C.L. Yang, Y. Li, C.M. Yuan, and X.J. Hao Org. Lett. 17 2015 2066 2069
38. T.N. Griffith, L. Varela-Nallar, M.C. Dinamarca, and N.C. Inestrosa Curr. Med. Chem. 17 2010 391 406
39. G. Stojanovic, A. Dordevic, and A. Smelcerovic Curr. Med. Chem. 20 2013 2273 2295
40. 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, and M.R. Boyd Cancer Res. 48 1988 589 601
41. G.L. Ellman, K.D. Courtney, V. Andres Jr. , and R.M. Featherstone Biochem. Pharmacol. 7 1961 88 95