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New Triterpenoids from the Fruits of Schisandra wilsoniana and Their Biological Activities

  • Gao, Xue-Mei (Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities) ;
  • Li, Yun-Qi (Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities) ;
  • Shu, Li-Dan (Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities) ;
  • Shen, Yan-Qiong (Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities) ;
  • Yang, Li-Ying (Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities) ;
  • Yang, Liu-Meng (Key Laboratory of Animal Models and Human Disease Mechanisms and Laboratory of Molecular Immunopharmacology, Kunming Institute of Zoology, Chinese Academy of Sciences) ;
  • Zheng, Yong-Tang (Key Laboratory of Animal Models and Human Disease Mechanisms and Laboratory of Molecular Immunopharmacology, Kunming Institute of Zoology, Chinese Academy of Sciences) ;
  • Sun, Han-Dong (State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences) ;
  • Xiao, Wei-Lie (State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences) ;
  • Hu, Qiu-Fen (Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities)
  • Received : 2012.09.07
  • Accepted : 2012.12.13
  • Published : 2013.03.20

Abstract

Investigation of an organic extract of the fruits Schisandra wilsoniana led to the isolation of two new highly oxygenated nortriterpenoids, named schilancidilactones V-W (1-2). Their structures were elucidated by spectroscopic evidence. Compounds 1-2 feature a double bond between C-7 and C-8 compared with related known nortriterpenoids isolated from the genus Schisandra. Compounds 1 and 2 were tested for their anti-HIV-1 activities and cytotoxicity. The results revealed that compounds 1 and 2 showed moderate anti-HIV-1 activities with $EC_{50}$ 3.05 and 2.87 ${\mu}g/mL$, respectively, and compound 1 showed high cytotoxicity against KB and MDA-MB-231 cell with $IC_{50}$ values of 3.18 and 5.22 ${\mu}M$, respectively.

Keywords

References

  1. Huang, S. X.; Li, R. T.; Liu, J. P.; Lu, Y.; Chang, Y.; Lei, C.; Xiao, W. L.; Yang, L. B.; Zheng, Q. T.; Sun, H. D. Org. Lett. 2007, 9, 2079. https://doi.org/10.1021/ol070510z
  2. He, F.; Li, X. Y.; Yang, G. Y.; Li, X. N.; Luo, X.; Zou, J.; Li, Y.; Xiao, W. L.; Sun, H. D. Tetrahedron 2012, 68, 440. https://doi.org/10.1016/j.tet.2011.11.026
  3. Huang, S. X.; Yang, L. B.; Xiao, W. L.; Lei, C.; Liu, J. P.; Lu, Y.; Weng, Z. Y.; Li, L. M.; Li, R. T.; Yu, J. L.; Zheng, Q. T.; Sun, H. D. Chem. Eur. J. 2007, 13, 4816. https://doi.org/10.1002/chem.200700346
  4. Xiao, W. L.; Huang, H. X.; Zhang, L.; Tian, R. R.; Wu, L.; Li, X. L.; Pu, J. X.; Zheng, Y. T.; Lu, Y.; Li, R. T.; Zheng, Q. T.; Sun, H. D. J. Nat. Prod. 2006, 69, 650. https://doi.org/10.1021/np060047j
  5. Li, R. T.; Xiao, W. L.; Shen, Y. H.; Zhao, Q. S.; Sun, H. D. Chem. Eur. J. 2005, 11, 2989. https://doi.org/10.1002/chem.200500063
  6. Yang, G. Y.; Wang, R. R.; Mu, H. X.; Li, Y. K.; Xiao, W. L.; Yang, L. M.; Pu, J. X.; Zheng, Y. T.; Sun, H. D. Chem. Pharm. Bull. 2011, 59, 1344. https://doi.org/10.1248/cpb.59.1344
  7. Yang, G. Y.; Xiao, W. L.; Chang, Y.; Wang, R. R.; Pu, J. X.; Gao, X. M.; Lei, C.; Sun, H. D. Helv. Chim. Acta 2008, 91, 1871. https://doi.org/10.1002/hlca.200890200
  8. Yang, G. Y.; Li, Y. K.; Wang, R. R.; Xiao, W. L.; Yang, L. M.; Pu, J. X.; Zheng, Y. T.; Sun, H. D. J. Asian Nat. Prod. Res. 2010, 12, 470. https://doi.org/10.1080/10286020.2010.489823
  9. Yang, G. Y.; Li, Y. K.; Wang, R. R.; Li, X. N.; Xiao, W. L.; Yang, L. M.; Pu, J. X.; Zheng, Y. T.; Sun, H. D. J. Nat. Prod. 2010, 73, 915. https://doi.org/10.1021/np100067w
  10. Zhang, X. J.; Yang, G. Y.; Wang, R. R.; Pu, J. X.; Sun, H. D.; Xiao, W. L.; Zheng, Y. T. Chem. Biodivers. 2010, 7, 2692. https://doi.org/10.1002/cbdv.200900367
  11. Ma, W. H.; Huang, H.; Zhou, P.; Chen, D. F. J. Nat. Prod. 2009, 72, 676. https://doi.org/10.1021/np8007864
  12. Ma, W. H.; Lu, Y.; Huang, H.; Zhou, P.; Chen, D. F. Bioorg. Med. Chem. Lett. 2009, 19, 4958. https://doi.org/10.1016/j.bmcl.2009.07.078
  13. Fan, Y. P.; Duan, L. P.; Dong, X. H.; Dai, Y.; Li, G. P. Asian J. Chem. 2009, 21, 5488.
  14. Yang, G. Y.; Li, Y. K.; Zhang, X. J.; Li, X. N.; Yang, L. M.; Shi, Y. M.; Xiao, W. L.; Zheng, Y. T.; Sun, H. D. Nat. Prod. Bioprosp. 2011, 1, 33. https://doi.org/10.1007/s13659-011-0008-6
  15. Xiao, W. L.; Li, R. T.; Huang, S. X.; Pu, J. X.; Sun, H. D. Nat. Prod. Rep. 2008, 25, 871. https://doi.org/10.1039/b719905h
  16. Editoria Committee of Flora Yunnanica, Flora Yunnanica; Science Press: Beijing, 2000; Vol. 11, p 16.
  17. Wang, J. H.; Tam, S. C.; Huang, H.; Ouyang, D. Y.; Wang, Y. Y.; Zheng, Y. T. Biochem. Biophys. Res. Commun. 2004, 317, 965. https://doi.org/10.1016/j.bbrc.2004.03.139
  18. Mosmann, T. J. Immunol. Methods 1983, 65, 55. https://doi.org/10.1016/0022-1759(83)90303-4

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