Citation: 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 shu

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

Liu Yanping ^a,b ,
Zhang Xianglin ^a,b ,
Niu Haiyuan ^a,b ,
Guan Chunyan ^a,b ,
Sun Fukang ^a,b ,
Yang Liumeng ^c ,
Fu Yanhui ^a,b,,

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

Corresponding author: Fu Yanhui, fuyanhui80@163.com
Received Date: 15 April 2018
Revised Date: 3 June 2018
Available Online: 29 November 2018
Fund Project: the National Natural Science Foundation of China 21662011the Program for Innovative Research Team in University IRT-16R19the Key Research and Development Project of Haikou City 2017050Project 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)the National Natural Science Foundation of China 31660097the Key Research and Development Project of Hainan Province ZDYF2016221

Figures(2)

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.
- Trigonostemon,
- Trigonostemon heterophyllus,
- stemodane diterpenoid,
- cytotoxicities
1. [1]
2. [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. doi: 10.1021/ja994074q
3. [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. doi: 10.1016/j.tetlet.2009.03.186
4. [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. doi: 10.1021/ol100715x
5. [5]
  Dong, S. H.; Liu, H. B.; Xu, C. H.; Ding, J.; Yue, J. M. J. Nat. Prod. 2011, 74, 2576. doi: 10.1021/np200772n
6. [6]
  Allard, P. M.; Martin, M. T.; Dau, M. E. T. H.; Leyssen, P.; Gueritte, F.; Litaudon, M. Org. Lett. 2012, 14, 342. doi: 10.1021/ol2030907
7. [7]
  Bourjot, M.; Delang, L.; Nguyen, V. H.; Neyts, J.; Gueritte, F.; Leyssen, P.; Litaudon, M. J. Nat. Prod. 2012, 75, 2183. doi: 10.1021/np300637t
8. [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. doi: 10.1016/j.tetlet.2013.09.045
9. [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. doi: 10.1016/j.phytochem.2013.03.003
10. [10]
  Martin, G. D.; Reynolds, W. F.; Reese, P. B. Phytochemistry 2004, 65, 701. doi: 10.1016/j.phytochem.2004.01.011
11. [11]
  Martin, G. D.; Reynolds, W. F.; Reese, P. B. Phytochemistry 2005, 66, 901. doi: 10.1016/j.phytochem.2005.02.019
12. [12]
  Yin, H.; Luo, J. G.; Kong, L. Y. J. Nat. Prod. 2013, 76, 237. doi: 10.1021/np3007217
13. [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. doi: 10.1021/acs.jnatprod.5b00523
14. [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. doi: 10.1021/np200932k
15. [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. doi: 10.1021/acs.jnatprod.7b00163
16. [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. doi: 10.1021/np400110g
17. [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. doi: 10.1021/np300339r
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