Notes

A New Stemodane Diterpenoid from the Stems and Leaves of Trigonostemon heterophyllus

  • Liu Yanping ,
  • Zhang Xianglin ,
  • Niu Haiyuan ,
  • Guan Chunyan ,
  • Sun Fukang ,
  • Yang Liumeng ,
  • Fu Yanhui
Expand
  • a Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158;
    b Key Laboratory of Southern Medicinal Plants Resources of Haikou City, Hainan Normal University, Haikou 571158;
    c Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming 650223

Received date: 2018-04-15

  Revised date: 2018-06-03

  Online published: 2018-06-29

Supported by

Project supported by the Key Research and Development Project of Hainan Province (No. ZDYF2016221), the Key Research and Development Project of Haikou City (No. 2017050), the National Natural Science Foundation of China (Nos. 21662011, 31660097) and the Program for Innovative Research Team in University (No. IRT-16R19).

Abstract

A new stemodane diterpenoid, trigoheterone A (1), together with seven known diterpenoids, was isolated from the stems and leaves of Trigonostemon heterophyllus. Their structures were established on the basis of extensive spectral analyses. All known compounds were isolated from the genus Trigonostemon for the first time. The cytotoxicities of all isolated compounds were evaluated against five cancer cell lines (HL-60, A549, SMMC-7721, MCF-7 and SW480). As a result, eight compounds exhibited significant inhibitory effects with IC50 values comparable to those of cisplatin.

Cite this article

Liu Yanping , Zhang Xianglin , Niu Haiyuan , Guan Chunyan , Sun Fukang , Yang Liumeng , Fu Yanhui . A New Stemodane Diterpenoid from the Stems and Leaves of Trigonostemon heterophyllus[J]. Chinese Journal of Organic Chemistry, 2018 , 38(11) : 3137 -3140 . DOI: 10.6023/cjoc201804028

References

[1] Flora Reipublicae Popularis Sinicae Editorial Board, Flora Reipublicae Popularis Sinicae, Vol. 44(2), Science Press, Beijing, 1996, p. 162(in Chinese). (中国植物志编辑委员会, 中国植物志, Vol. 44(2), 科学出版社, 北京, 1996, p. 162.)
[2] Jayasuriya, H.; Zink, D. L.; Singh, S. B.; Borris, R. P.; Nanakorn, W.; Beck, H. T.; Balick, M. J.; Goetz, M. A.; Slayton, L.; Gregory, L.; Zakson-Aiken, M. J. Am. Chem. Soc. 2000, 122, 4998.
[3] Hu, X. J.; Wang, Y. H.; Kong, L. Y.; He, H. P.; Gao, S.; Liu, H. Y.; Ding, J.; Xie, H.; Di, Y. T.; Hao, X. J. Tetrahedron Lett. 2009, 50, 2917.
[4] Tan, C. J.; Di, Y. T.; Wang, Y. H.; Zhang, Y.; Si, Y. K.; Zhang, Q.; Gao, S.; Hu, X. J.; Fang, X.; Li, S. F.; Hao, X. J. Org. Lett. 2010, 12, 2370.
[5] Dong, S. H.; Liu, H. B.; Xu, C. H.; Ding, J.; Yue, J. M. J. Nat. Prod. 2011, 74, 2576.
[6] Allard, P. M.; Martin, M. T.; Dau, M. E. T. H.; Leyssen, P.; Gueritte, F.; Litaudon, M. Org. Lett. 2012, 14, 342.
[7] Bourjot, M.; Delang, L.; Nguyen, V. H.; Neyts, J.; Gueritte, F.; Leyssen, P.; Litaudon, M. J. Nat. Prod. 2012, 75, 2183.
[8] Yang, B.; Chen, G. Y.; Song, X. P.; Yang, L. Q.; Han, C. R.; Wu, X. Y.; Zheng, C. J.; Ran, X.; Tang, R. F. Tetrahedron Lett. 2013, 54, 6434.
[9] Li, S. F.; Zhang, Y.; Huang, N.; Zheng, Y. T.; Di, Y. T.; Li, S. L.; Cheng, Y. Y.; He, H. P.; Hao, X. J. Phytochemistry 2013, 93, 216.
[10] Martin, G. D.; Reynolds, W. F.; Reese, P. B. Phytochemistry 2004, 65, 701.
[11] Martin, G. D.; Reynolds, W. F.; Reese, P. B. Phytochemistry 2005, 66, 901.
[12] Yin, H.; Luo, J. G.; Kong, L. Y. J. Nat. Prod. 2013, 76, 237.
[13] Win, N. N.; Ito, T.; Aimaiti, S.; Kodama, T.; Tanaka, M.; Ngwe, H.; Asakawa, Y.; Abe, I.; Morita, H. J. Nat. Prod. 2015, 78, 2306.
[14] Liu, Y. W.; Cheng, Y. B.; Liaw, C. C.; Chen, C. H.; Guh, J. H.; Hwang, T. L.; Tsai, J. S.; Wang W. B.; Shen, Y. C. J. Nat. Prod. 2012, 75, 689.
[15] Jiang, H. Y.; Wang, W. G.; Tang, J. W.; Liu, M.; Li, X. R.; Hu, K., Du, X.; Li, X. N.; Zhang, H. B.; Pu, J. X.; Sun, H. D. J. Nat. Prod. 2017, 80, 2026.
[16] Inaba, Y.; Hasuda, T.; Hitotsuyanagi, Y.; Aoyagi, Y.; Fujikawa, N.; Onozaki, A.; Watanabe, A.; Kinoshita, T.; Takeya, K. J. Nat. Prod. 2013, 76, 1085.
[17] Fu, Y. H.; Zhang, Y.; He, H. P.; Hou, L.; Di, Y. T.; Li, S. L.; Luo, X. D.; Hao, X. J. J. Nat. Prod. 2012, 75, 1987.

Outlines

/