Polycyclic Polyprenylated Acylphloroglucinol Congeners Possessing Diverse Structures from Hypericum henryi

Journal of Natural Products

Volumn 78, Issue 4, 2015, Pages 885-895

  Yang, Xing Wei ^a,d   Li, Ming Ming ^a   Liu, Xia ^a,c   Ferreira, Daneel ^b   Ding, Yuanqing ^c   Zhang, Jing Jing ^a,c   Liao, Yang ^a,c   Qin, Hong Bo ^a   Xu, Gang ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

^d UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CHOLINESTERASE INHIBITOR; HYPERICUM HENRYI EXTRACT; HYPHENRONE A; HYPHENRONE G; HYPHENRONE H; HYPHENRONE I; HYPHENRONE J; HYPHENRONE K; HYPHENRONE L; HYPHENRONE M; HYPHENRONE N; HYPHENRONE O; HYPHENRONE P; HYPHENRONE Q; PACLITAXEL; PLANT EXTRACT; PLANT MEDICINAL PRODUCT; POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOL; UNCLASSIFIED DRUG; ACETYLCHOLINESTERASE; KETONE; PERFORATUMONE; PHLOROGLUCINOL; TERPENE;

ALDOL REACTION; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOMIMETICS; BIOSYNTHESIS; CANCER CELL LINE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYCLIZATION; CYCLOADDITION; DECARBOXYLATION; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HUMAN; HUMAN CELL; HYPERICUM; HYPERICUM HENRYI; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE;

HYPERICUM HENRYI;

ACETYLCHOLINESTERASE; HUMANS; HYPERICUM; KETONES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHLOROGLUCINOL; TERPENES;

EID: 84928802688     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.5b00057     Document Type: Article

References (57)

1. Ciochina, R.; Grossman, R. B. Chem. Rev. 2006, 106, 3963 - 3986
2. Singh, I. P.; Bharate, S. B. Nat. Prod. Rep. 2006, 23, 558 - 591
3. Zhang, Q.; Mitasev, B.; Qi, J.; Porco, J. A., Jr. J. Am. Chem. Soc. 2010, 132, 14212 - 14215
4. Qi, J.; Beeler, A. B.; Zhang, Q.; Porco, J. A., Jr. J. Am. Chem. Soc. 2010, 132, 13642 - 13644
5. Shimizu, Y.; Shi, S.-L.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2010, 49, 1103 - 1106
6. Biber, N.; Mows, K.; Plietker, B. Nat. Chem. 2011, 3, 938 - 942
7. Richard, J.-A.; Pouwer, R. H.; Chen, D. Y.-K. Angew. Chem., Int. Ed. 2012, 51, 4536 - 4561
8. Sparling, B. A.; Moebius, D. C.; Shair, M. D. J. Am. Chem. Soc. 2013, 135, 644 - 647
9. Tian, W. J.; Yu, Y.; Yao, X. J.; Chen, H. F.; Dai, Y.; Zhang, X. K.; Yao, X. S. Org. Lett. 2014, 16, 3448 - 3451
10. Grenning, A. J.; Boyce, J. H.; Porco, J. A., Jr. J. Am. Chem. Soc. 2014, 136, 11799 - 11804
11. Adam, P.; Arigoni, D.; Bacher, A.; Eisenreich, W. J. Med. Chem. 2002, 45, 4786 - 4793
12. Boubakir, Z.; Beuerle, T.; Liu, B.; Beerhues, L. Phytochemistry 2005, 66, 51 - 57
13. Karppinen, K.; Hokkanen, J.; Tolonen, A.; Mattila, S.; Hohtola, A. Phytochemistry 2007, 68, 1038 - 1045
14. Nualkaew, N.; Morita, H.; Shimokawa, Y.; Kinjo, K.; Kushiro, T.; De-Eknamkul, W.; Ebizuka, Y.; Abe, I. Phytochemistry 2012, 77, 60 - 69
15. Maisenbacher, P.; Kovar, K. A. Planta Med. 1992, 58, 291 - 293
16. Henry, G. E.; Jacobs, H.; Carrington, C. M. S.; McLean, S.; Reynolds, W. F. Tetrahedron Lett. 1996, 37, 8663 - 8666
17. Avato, P. In Studies in Natural Products Chemistry; Atta-ur Rahman, Ed.; Elsevier: Amsterdanm, 2005; Vol. 30, pp 603 - 634.
18. Griffith, T. N.; Varela-Nallar, L.; Dinamarca, M. C.; Inestrosa, N. C. Curr. Med. Chem. 2010, 17, 391 - 406
19. Yang, X. W.; Deng, X.; Liu, X.; Wu, C. Y.; Li, X. N.; Wu, B.; Luo, H. R.; Li, Y.; Xu, H. X.; Zhao, Q. S.; Xu, G. Chem. Commun. 2012, 48, 5998 - 6000
20. Liu, X.; Yang, X. W.; Chen, C. Q.; Wu, C. Y.; Zhang, J. J.; Ma, J. Z.; Wang, H.; Yang, L. X.; Xu, G. J. Nat. Prod. 2013, 76, 1612 - 1618
21. Yang, X. W.; Ding, Y.; Zhang, J. J.; Liu, X.; Yang, L. X.; Li, X. N.; Ferreira, D.; Walker, L. A.; Xu, G. Org. Lett. 2014, 16, 2434 - 2437
22. Zhang, J. J.; Yang, J.; Liao, Y.; Yang, X. W.; Ma, J. Z.; Xiao, Q. L.; Yang, L. X.; Xu, G. Org. Lett. 2014, 16, 4912 - 4915
23. Lan, M. In South Yunnan Materia Medica; Wu, Z. Y.; Gao, L., Ed.; Science Press: Kunming, 2008; Vol. 1, pp 236 - 240.
24. Wu, Q. L.; Wang, S. P.; Du, L. J.; Yang, J. S.; Xiao, P. G. Phytochemistry 1998, 49, 1395 - 1402
25. Chen, X. Q.; Li, Y.; Cheng, X.; Wang, K.; He, J.; Pan, Z. H.; Li, M. M.; Peng, L. Y.; Xu, G.; Zhao, Q. S. Chem. Biodiversity 2010, 7, 196 - 204
26. Guo, N.; Chen, X. Q.; Zhao, Q. S. Acta Bot. Yunnan. 2008, 30, 515 - 518
27. Wu, J.; Cheng, X. F.; Harrison, L. J.; Goh, S.-H.; Sim, K.-Y. Tetrahedron Lett. 2004, 45, 9657 - 9659
28. Nicolaou, K. C.; Carenzi, G. E. A.; Jeso, V. Angew. Chem., Int. Ed. 2005, 44, 3895 - 3899
29. Verotta, L.; Appendino, G.; Jakupovic, J.; Bombardelli, E. J. Nat. Prod. 2000, 63, 412 - 415
30. Verotta, L.; Appendino, G.; Belloro, E.; Jakupovic, J.; Bombardelli, E. J. Nat. Prod. 1999, 62, 770 - 772
31. Vugdelija, S.; Vajs, V.; Trifunovic, S.; Djokovic, D.; Milosavljevic, S. Molecules 2000, 5, M158
32. Schwerfeger, H.; Fokin, A. A.; Schreiner, P. R. Angew. Chem., Int. Ed. 2008, 47, 1022 - 1036
33. Van der Schyf, C. J.; Geldenhuys, W. J. Neurotherapeutics 2009, 6, 175 - 186
34. Wanka, L.; Iqbal, K.; Schreiner, P. R. Chem. Rev. 2013, 113, 3516 - 3604
35. Liu, J.; Obando, D.; Liao, V.; Lifa, T.; Codd, R. Eur. J. Med. Chem. 2011, 46, 1949 - 1963
36. Hu, L. H.; Sim, K. Y. Tetrahedron Lett. 1998, 39, 7999 - 8002
37. Hu, L. H.; Sim, K. Y. Org. Lett. 1999, 1, 879 - 882
38. Hu, L. H.; Sim, K. Y. Tetrahedron Lett. 1999, 40, 759 - 762
39. Ishida, Y.; Shirota, O.; Sekita, S.; Someya, K.; Tokita, F.; Nakane, T.; Kuroyanagi, M. Chem. Pharm. Bull. 2010, 58, 336 - 343
40. Zeng, Y. H.; Osman, K.; Xiao, Z. Y.; Gibbons, S.; Mu, Q. Phytochem. Lett. 2012, 5, 200 - 205
41. Liu, X.; Yang, X. W.; Chen, C. Q.; Wu, C. Y.; Zhang, J. J.; Ma, J. Z.; Wang, H.; Zhao, Q. S.; Yang, L. X.; Xu, G. Nat. Prod. Bioprospect. 2013, 3, 233 - 237
42. Tian, W. J.; Qiu, Y. Q.; Jin, X. J.; Chen, H. F.; Yao, X. J.; Dai, Y.; Yao, X. S. Tetrahedron 2014, 70, 7912 - 7916
43. 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
44. Lin, Y. L.; Wu, Y. S. Helv. Chim. Acta 2003, 86, 2156 - 2163
45. Flack, H. D. Acta Crystallogr. 1983, A39, 876 - 881
46. Hooft, R. W. W.; Straver, L. H.; Spek, A. L. J. Appl. Crystallogr. 2008, 4, 96 - 103
47. Decosterd, L. A.; Stoeckli-Evans, H.; Chapuis, J.-C.; Sordat, B.; Hostettmann, K. Helv. Chim. Acta 1989, 72, 1833 - 1845
48. Hashida, W.; Tanaka, N.; Kashiwada, Y.; Sekiya, M.; Ikeshiro, Y.; Takaishi, Y. Phytochemistry 2008, 69, 2225 - 2230
49. Thoison, O.; Cuong, D. D.; Gramain, A.; Chiaroni, A.; Hung, N. V.; Sevenet, T. Tetrahedron 2005, 61, 8529 - 8535
50. Pepper, H. P.; Lam, H. C.; Bloch, W. M.; George, J. H. Org. Lett. 2012, 14, 5162 - 5164
51. Cholpisut, T.; Wong, P.; Thunwadee, R.; Sarot, C.; Uma, P.; Suwanna, D.; Surat, L. J. Nat. Prod. 2012, 75, 1660 - 1664
52. Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Cancer Res. 1988, 48, 589 - 601
53. Ellman, G. L.; Courtney, K. D.; Andres, V., Jr.; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88 - 95
54. Yazaki, K.; Sasaki, K.; Tsurumaru, Y. Phytochemistry 2009, 70, 1739 - 1745
55. Botta, B.; Menedez, P.; Zappia, G.; Alves de Lima, R.; Torge, R.; Delle Monache, G. Curr. Med. Chem. 2009, 16, 3414 - 3468
56. Marin, M.; Manez, S. Curr. Med. Chem. 2013, 20, 272 - 279
57. Bartmanska, A.; Tronina, T.; Poplonski, J.; Huszcza, E. Curr. Drug Metab. 2013, 14, 1083 - 1097