Hypermongones A-J, rare methylated polycyclic polyprenylated acylphloroglucinols from the flowers of hypericum monogynum

Journal of Natural Products

Volumn 78, Issue 5, 2015, Pages 1093-1100

  Xu, Wen Jun ^a   Zhu, Meng Di ^a   Wang, Xiao Bing ^a   Yang, Ming Hua ^a   Luo, Jun ^a   Kong, Ling Yi ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLPHLOROGLUCINOL; HYPERMONGONE; NATURAL PRODUCT; NITRIC OXIDE; UNCLASSIFIED DRUG; HERBACEOUS AGENT; HYPERMONGONE G; LIPOPOLYSACCHARIDE; PHLOROGLUCINOL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG STRUCTURE; FLOWER; HETERONUCLEAR MULTIPLE BOND CORRELATION; HYPERICUM; HYPERICUM MONOGYNUM; IC50; NONHUMAN; X RAY DIFFRACTION; ANALOGS AND DERIVATIVES; ANIMAL; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; HL 60 CELL LINE; HUMAN; ISOLATION AND PURIFICATION; MACROPHAGE; MOUSE; NUCLEAR MAGNETIC RESONANCE;

HYPERICUM;

ANIMALS; DRUGS, CHINESE HERBAL; FLOWERS; HL-60 CELLS; HUMANS; HYPERICUM; INHIBITORY CONCENTRATION 50; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; MOLECULAR STRUCTURE; NITRIC OXIDE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHLOROGLUCINOL; X-RAY DIFFRACTION;

EID: 84930227199     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.5b00066     Document Type: Article

References (33)

1. Ciochina, R.; Grossman, R. B. Chem. Rev. 2006, 106, 3963-3986
2. Chatterjee, S. S.; Bhattacharya, S. K.; Wonnemann, M.; Singer, A.; Müller, W. E. Life Sci. 1998, 63, 499-510
3. Schempp, C. M.; Pelz, K.; Wittmer, A.; Schöpf, E.; Simon, J. C. Lancet 1999, 353, 2129
4. Schempp, C. M.; Winghofer, B.; Ludtke, R.; Simon Haarhaus, B.; Schopf, E.; Simon, J. C. Br. J. Dermatol. 2000, 142, 979-984
5. Albert, D.; Zündorf, I.; Dingermann, T.; Müller, W. E.; Steinhilber, D.; Werz, O. Biochem. Pharmacol. 2002, 64, 1767-1775
6. Feißt, C.; Werz, O. Biochem. Pharmacol. 2004, 67, 1531-1539
7. Schwarz, D.; Kisselev, P.; Roots, I. Cancer Res. 2003, 63, 8062-8068
8. Schempp, C. M.; Kirkin, V.; Simon-Haarhaus, B.; Kersten, A.; Kiss, J.; Termeer, C. C.; Gilb, B.; Kaufmann, T.; Borner, C.; Sleeman, J. P.; Simon, J. C. Oncogene 2002, 21, 1242-1250
9. Dona, M.; Dell'Aica, I.; Pezzato, E.; Sartor, L.; Calabrese, F.; Della Barbera, M.; Donella Deana, A.; Appendino, G.; Borsarini, A.; Caniato, R.; Garbisa, S. Cancer Res. 2004, 64, 6225-6232
10. Martinez Poveda, B.; Quesada, A. R.; Medina, M. A. Int. J. Cancer Suppl. 2005, 117, 775-780
11. 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
12. 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
13. 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
14. Zeng, J. F.; Huo, C. Y. In Flora Reipublicae Popularis Sinicae (Zhongguo Zhiwu Zhi); Science Press: Beijing, 2004; Vol. 50, Chapter 2, pp 12-15.
15. Editorial Committee of the Administration Bureau of Traditional Chinese Medicine. In Chinese Materia Medica (Zhonghua Bencao); Shanghai Science and Technology Press: Shanghai, 1999; Vol. 3, pp 602-603.
16. Beerhues, L. Phytochemistry 2006, 67, 2201-2207
17. Maisenbacher, P.; Kovar, K. A. Planta Med. 1992, 58, 291-293
18. Winkelmann, K.; Heilmann, J.; Zerbe, O.; Rali, T.; Sticher, O. J. Nat. Prod. 2001, 64, 701-706
19. Piccinelli, A. L.; Cuesta-Rubio, O.; Chica, M. B.; Mahmood, N.; Pagano, B.; Pavone, M.; Barone, V.; Rastrelli, L. Tetrahedron 2005, 61, 8206-8211
20. Fukuyama, Y.; Minami, H.; Kuwayama, A. Phytochemistry 1998, 49, 853-857
21. Bolte, M. L.; Bowers, J.; Crow, W. D.; Paton, D. M.; Sakurai, A.; Takahashi, N.; Ujiie, M.; Yoshida, S. Agric. Biol. Chem. 1984, 48, 373-376
22. Wang, W.; Zeng, Y. H.; Osman, K.; Shinde, K.; Rahman, M.; Gibbons, S.; Mu, Q. J. Nat. Prod. 2010, 73, 1815-1820
23. Ramage, G. R.; Stowe, W. J. I. J. Chem. Soc. 1940, 425-426
24. Gorecki, M.; Jablonska, E.; Kruszewska, A.; Suszczynska, A.; Urbanczyk-Lipkowska, Z.; Gerards, M.; Morzycki, J. W.; Szczepek, W. J.; Frelek, J. J. Org. Chem. 2007, 72, 2906-2916
25. Snatzke, G. Angew. Chem., Int. Ed. Engl. 1979, 18, 363-377
26. Di Bari, L.; Pescitelli, G.; Pratelli, C.; Pini, D.; Salvadori, P. J. Org. Chem. 2001, 66, 4819-4825
27. Miller, A. H.; Maletic, V.; Raison, C. L. Biol. Psychiat. 2009, 65, 732-741
28. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339-341
29. Shelxs, G. M.; Sheldrick Acta Crystallogr. 2008, 64, 112-122
30. Yin, H.; Luo, J. G.; Kong, L. Y. J. Nat. Prod. 2013, 76, 237-242
31. Zhang, Y.; Wang, J. S.; Wei, D. D.; Gu, Y. C.; Wang, X. B.; Kong, L. Y. J. Nat. Prod. 2013, 76, 1191-1195
32. Yang, M. H.; Wang, J. S.; Luo, J. G.; Wang, X. B.; Kong, L. Y. Bioorg. Med. Chem. 2011, 19, 1409-1417
33. Li, Q. M.; Luo, J. G.; Wang, X. B.; Yang, M. H.; Kong, L. Y. Fitoterapia 2013, 86, 29-34