Eight pairs of epimeric triterpenoids involving a characteristic spiro-E/F ring from abies faxoniana

Journal of Natural Products

Volumn 78, Issue 1, 2015, Pages 50-60

  Wang, Guo Wei ^a   Lv, Chao ^b,c   Fang, Xin ^b   Tian, Xin Hui ^b   Ye, Ji ^b   Li, Hui Liang ^b   Shan, Lei ^b   Shen, Yun Heng ^b   Zhang, Wei Dong ^a,b  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

^b SECOND MILITARY MEDICAL UNIVERSITY   (China)

^c FUJIAN UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ABIESPIRONE A; ABIESPIRONE B; ABIESPIRONE C; ABIESPIRONE D; ABIESPIRONE E; ABIESPIRONE F; ABIESPIRONE G; ABIESPIRONE H; CARBON; COPPER; CYTOTOXIC AGENT; HYDROGEN; LACTONE; REACTIVE OXYGEN METABOLITE; TRITERPENOID; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CYCLOARTANE; HERBACEOUS AGENT; SPIRO COMPOUND; TRITERPENE;

ABIES; ABIES FAXONIANA; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL CYCLE ARREST; CELL CYCLE PROGRESSION; CELL CYCLE S PHASE; CELL DEATH; CELL VIABILITY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; EPIMER; HEPATOCELLULAR CARCINOMA CELL LINE; HEPATOMA CELL; HEPG2 CELL LINE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC50; INFRARED SPECTROSCOPY; ISOMER; LIVER CELL; MTT ASSAY; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION; CARCINOMA, HEPATOCELLULAR; CELL CYCLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECTS; DRUG SCREENING; ISOLATION AND PURIFICATION; LIVER NEOPLASMS; METABOLISM; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

ABIES FAXONIANA;

ABIES; ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CARCINOMA, HEPATOCELLULAR; CELL CYCLE; DRUG SCREENING ASSAYS, ANTITUMOR; DRUGS, CHINESE HERBAL; HUMANS; LIVER NEOPLASMS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; REACTIVE OXYGEN SPECIES; SPIRO COMPOUNDS; STEREOISOMERISM; TRITERPENES; X-RAY DIFFRACTION;

EID: 84921625424     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np500679s     Document Type: Article

References (31)

1. Zheng, W. J.; Fu, L. G. Flora of China; Science Press: Beijing, 1978; Vol. 7, pp 55-95.
2. Lavoie, S.; Legault, J.; Gauthier, C.; Mshvildadze, V.; Mercier, S.; Pichette, A. Org. Lett. 2012, 14, 1504-1507
3. Tanaka, R.; Usami, Y.; In, Y.; Ishida, T.; Shingu, T.; Matsunaga, S. Chem. Commun. 1992, 18, 1351-1352
4. Matsunaga, S.; Okada, J.; Uyeo, S. Chem. Commun. 1965, 21, 525-527
5. Li, Y. L.; Yang, X. W.; Li, S. M.; Shen, Y. H.; Zeng, H. W.; Liu, X. H.; Tang, J.; Zhang, W. D. J. Nat. Prod. 2009, 72, 1065-1068
6. Li, Y. L.; Gao, Y. X.; Yang, X. W.; Jin, H. Z.; Ye, J.; Simmons, L.; Wang, N.; Steinmetz, A.; Zhang, W. D. Phytochemistry 2012, 81, 159-164
7. Yang, X. W.; Feng, L.; Li, S. M.; Liu, X. H.; Li, Y. L.; Wu, L.; Shen, Y. H.; Tian, J. M.; Zhang, X.; Liu, X. R.; Zhang, W. D. Bioorg. Med. Chem. 2010, 18, 744-754
8. Yang, X. W.; Li, S. M.; Feng, L.; Shen, Y. H.; Tian, J. M.; Liu, X. H.; Zeng, H. W.; Zhang, C.; Zhang, W. D. Tetrahedron 2008, 64, 4354-4362
9. Takayasu, J.; Tanaka, R.; Matsunaga, S.; Ueyama, H.; Tokuda, H.; Hasegawa, T.; Nishino, A.; Nishino, H.; Iwashima, A. Cancer Lett. 1990, 53, 141-144
10. Tanaka, R.; Matsunaga, S. J. Nat. Prod. 1991, 54, 1337-1344
11. Wada, S.; Iida, A.; Tanaka, R. J. Nat. Prod. 2002, 65, 1657-1659
12. O’Neill, J. A.; Gallagher, O. P.; Devine, K. J.; Jones, P. W.; Maguire, A. R. J. Nat. Prod. 2005, 68, 125-128
13. Tanaka, R.; Aoki, H.; Wada, S.; Matsunaga, S. J. Nat. Prod. 1999, 62, 198-200
14. Yang, X. W.; Ding, Y.; Li, X. C.; Ferreira, D.; Shen, Y. H.; Li, S. M.; Wang, N.; Zhang, W. D. Chem. Commun. 2009, 25, 3771-3773
15. Li, Y. L.; Zhang, S. D.; Jin, H. Z.; Tian, J. M.; Shen, Y. H.; Yang, X. W.; Li, H. L.; Zhang, W. D. Tetrahedron 2012, 68, 7763-7767
16. Yang, X. W.; Li, S. M.; Li, Y. L.; Xia, J. H.; Wu, L.; Shen, Y. H.; Tian, J. M.; Wang, N.; Liu, Y.; Zhang, W. D. Eur. J. Org. Chem. 2010, 34, 6531-6534
17. Hasegawa, S.; Kaneko, N.; Hirose, Y. Phytochemistry 1987, 26, 1095-1099
18. Tanaka, R.; Wada, S.; Aoki, H.; Matsunaga, S.; Yamori, T. Helv. Chim. Acta 2004, 87, 240-249
19. Yang, X. W.; Li, S. M.; Wu, L.; Li, Y. L.; Feng, L.; Shen, Y. H.; Tian, J. M.; Tang, J.; Wang, N.; Liu, Y.; Zhang, W. D. Org. Biomol. Chem. 2010, 8, 2609-2616
20. Raldugin, V. A.; Shevtsov, S. A.; Shakirov, M. M.; Roshchin, V. I.; Pentegova, V. A. Khim. Prirod. Soedien. 1989, 2, 207-212
21. Kukina, T. P.; Shakirov, M. M.; Raldugin, V. A. Russ. Chem. Bull. 1998, 47, 2009-2011
22. Jacobson, M. D. Trends Biochem. Sci. 1996, 21, 83-86
23. Pelicano, H.; Carney, D.; Huang, P. Drug Resist. Updat. 2004, 7, 97-110
24. Tsang, W. P.; Chau, S. P.; Kong, S. K.; Fung, K. P.; Kwok, T. T. Life Sci. 2003, 73, 2047-2058
25. Tang, Y.; Chen, R.; Huang, Y.; Li, G.; Huang, Y.; Chen, J.; Duan, L.; Zhu, B. T.; Thrasher, J. B.; Zhang, X.; Li, B. Mol. Cancer Ther. 2014, 13, 1526-1536
26. Gong, K.; Li, W. Free Radical Biol. Med. 2011, 51, 2259-2271
27. Liu, C.; Gong, K.; Mao, X.; Li, W. Int. J. Cancer 2011, 129, 1519-1531
28. Li, M.; Zhang, Z.; Hill, D. L.; Chen, X.; Wang, H.; Zhang, R. Cancer Res. 2005, 65, 8200-8208
29. Wang, W.; Rayburn, E. R.; Velu, S. E.; Nadkarni, D. H.; Murugesan, S.; Zhang, R. Clin. Cancer Res. 2009, 15, 3511-3518
30. Wu, M.; Zhang, H.; Hu, J.; Weng, Z.; Li, C.; Li, H.; Zhao, Y.; Mei, X.; Ren, F.; Li, L. PLoS One 2013, 8, e76000
31. Zhao, D. L.; Zou, L. B.; Lin, S.; Shi, J. G.; Zhu, H. B. Neuropharmacology 2007, 53, 724-732