Abietane Diterpernoids from the Roots of Euphorbia ebracteolata

doi:10.1007/s13659-018-0159-9

Natural Products and Bioprospecting ›› 2018, Vol. 8 ›› Issue (2): 131-135.DOI: 10.1007/s13659-018-0159-9

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Abietane Diterpernoids from the Roots of Euphorbia ebracteolata

Yuan-Liang Ma^1,2, Xiao-Han Tang¹, Wen-Juan Yuan^1,3, Xiao Ding¹, Ying-Tong Di¹, Xiao-Jiang Hao¹

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China

Received:2018-02-26 Revised:2018-03-13 Online:2018-04-26 Published:2018-04-24
Contact: Ying-Tong Di, Xiao-Jiang Hao
Supported by:
This research was supported financially by grants from the National Science Foundation of China (21432010, 81573323, and 31770392), Technological Leading Talent Project of Yunnan Province (2015HA020), Central Asian Drug Discovery and Development Center of Chinese Academy of Sciences (CAM201402, CAM201302).

Abietane Diterpernoids from the Roots of Euphorbia ebracteolata

Yuan-Liang Ma^1,2, Xiao-Han Tang¹, Wen-Juan Yuan^1,3, Xiao Ding¹, Ying-Tong Di¹, Xiao-Jiang Hao¹

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China

通讯作者: Ying-Tong Di, Xiao-Jiang Hao
基金资助:
This research was supported financially by grants from the National Science Foundation of China (21432010, 81573323, and 31770392), Technological Leading Talent Project of Yunnan Province (2015HA020), Central Asian Drug Discovery and Development Center of Chinese Academy of Sciences (CAM201402, CAM201302).

Abstract

Abstract: A new ent-abietane diterpernoid, named ebracteolata D (1), along with 11 known analogues, was isolated from the roots of Euphorbia ebracteolata Hayata. The structure of 1 was elucidated on the basis of spectroscopic analysis and molecular modeling. Cytotoxicity of compounds 1-12 was evaluated as well as the effect on the NF-κB pathway. Among them, compound 12, jolkinolide B, displayed broad inhibitory effects against proliferation of tumor cell lines. Mechanistic studies indicated that the compound 12 can inhibit TNF-α induced NF-κB activation, thereby inducing tumor cell apoptosis.

Key words: Euphorbiaceae, Euphorbia ebracteolata, Abietane diterpernoid, Cytotoxic activity

摘要： A new ent-abietane diterpernoid, named ebracteolata D (1), along with 11 known analogues, was isolated from the roots of Euphorbia ebracteolata Hayata. The structure of 1 was elucidated on the basis of spectroscopic analysis and molecular modeling. Cytotoxicity of compounds 1-12 was evaluated as well as the effect on the NF-κB pathway. Among them, compound 12, jolkinolide B, displayed broad inhibitory effects against proliferation of tumor cell lines. Mechanistic studies indicated that the compound 12 can inhibit TNF-α induced NF-κB activation, thereby inducing tumor cell apoptosis.

关键词: Euphorbiaceae, Euphorbia ebracteolata, Abietane diterpernoid, Cytotoxic activity

Yuan-Liang Ma, Xiao-Han Tang, Wen-Juan Yuan, Xiao Ding, Ying-Tong Di, Xiao-Jiang Hao. Abietane Diterpernoids from the Roots of Euphorbia ebracteolata[J]. Natural Products and Bioprospecting, 2018, 8(2): 131-135.

Yuan-Liang Ma, Xiao-Han Tang, Wen-Juan Yuan, Xiao Ding, Ying-Tong Di, Xiao-Jiang Hao. Abietane Diterpernoids from the Roots of Euphorbia ebracteolata[J]. 应用天然产物, 2018, 8(2): 131-135.

References

1. M. Karin, Nature 441, 431-436 (2006)
2. M.B. Alj, V. Barbu, M. Fillet, A. Chariot, B. Relic, N. Jacobs, J. Gielen, M.P. Merville, V. Bours, Oncogene 22, 90-97 (2003)
3. A.S. Baldwin, J. Clin. Invest. 107, 241-246 (2001)
4. H.M. Shen, V. Tergaonkar, Apoptosis 14, 348-363 (2009)
5. J.M. Barret, A. Bouchou, M.L. Marionneau, V. Offrete, N. Cabrol, C. Bailly, Can. Res. 64, 460-460 (2004)
6. A. Vasas, J. Hohmann, Chem. Rev. 114, 8579-8612 (2014)
7. C.S. Huang, S.H. Luo, Y.L. Li, C.H. Li, J. Hua, Y. Liu, S.X. Jing, Y. Wang, M.J. Yang, S.H. Li, Nat. Prod. Bioprospect. 4, 91-92 (2014)
8. Y.F. Yang, J.Q. Peng, L. Shi, Z.R. Li, M.H. Qiu, Nat. Prod. Bioprospect. 3, 99-102 (2013)
9. Chinese Pharmacopoeia Commission, Pharmacopoeia of the People's Republic of China. I (China Medical Science Press, Beijing, 2010)
10. W.J. Yuan, G.P. Yang, J.H. Zhang, Y. Zhang, D.Z. Chen, S.L. Li, Y.T. Di, X.J. Hao, Phytochem. Lett. 18, 176-179 (2016)
11. W.J. Yuan, W.F. Gao, J.H. Zhang, P. Cao, Y. Zhang, D.Z. Chen, S.L. Li, Y.T. Di, X.J. Hao, Nat. Prod. Commun. 12, 63-65 (2017)
12. W.J. Yuan, X. Ding, Z. Wang, B.J. Yang, X.N. Li, Y. Zhang, D.Z. Chen, S.L. Li, Q. Chen, Y.T. Di, H.A. Aisa, X.J. Hao, Sci. Rep. 7, e14507 (2017)
13. Y. Li, M. Xu, X. Ding, C. Yan, Z.Q. Song, L.W. Chen, X.H. Huang, X. Wang, Y.L. Jian, G.H. Tang, C.Y. Tang, Y.T. Di, S.Z. Mu, X.Z. Liu, K. Liu, T. Li, Y.C. Wang, L. Miao, W.X. Guo, X.J. Hao, C.L. Yang, Nat. Cell. Biol. 18, 1065-1077 (2016)
14. A.R. Lal, R.C. Cambie, P.S. Rutledge, P.D. Woodgate, Phytochemistry 29, 2239-2246 (1990)
15. W.X. Wang, X.B. Ding, Acta. Pharm. Sin. 33, 128-131 (1998)
16. H.M. Shi, L.D. Williams, H.H. Sung, H.X. Zhu, Y.I. Nancy, Z.D. Min, Planta Med. 71, 349-354 (2005)
17. Z.G. Liu, Z.L. Li, D.H. Li, N. Li, J. Bai, F. Zhao, D.L. Meng, H.M. Hua, Bioorg. Med. Chem. Lett. 26, 1-5 (2016)
18. D. Uemura, Y. Hirata, Tetrahedron Lett. 15, 1387-1390 (1972)
19. X.Z. Kuang, W. Li, Y. Kanno, N. Yamashita, S. Kikkawa, I. Azumaya, K. Nemoto, Y. Asada, K. Koike, J. Nat. Med. 70, 412-422 (2016)
20. T. Morgenstern, M. Bittner, M. Silva, P. Aqueveque, J. Jakupovica, Phytochemistry 41, 1149-1153 (1996)
21. P.W. Wang, S.M. Henning, D. Herbe, PLoS ONE 5, e10202 (2010)
22. C. Lv, X.H. Yan, Q. Tu, Y.T. Di, C.M. Yuan, X. Fang, Y. BenDavid, L. Xia, J.X. Gong, Y.M. Shen, Z. Yang, X.J. Hao, Angew. Chem. Int. Ed. 55, 7539-7543 (2016)
23. Y. Yan, J.X. Zhang, T. Huang, X.Y. Mao, W. Gu, H.P. He, Y.T. Di, S.L. Li, D.Z. Chen, Y. Zhamg, X.J. Hao, J. Nat. Prod. 78, 811-821 (2015)
24. X.H. Yan, Y.T. Di, X. Fang, S.Y. Yang, H.P. He, S.L. Li, Y. Lu, X.J. Hao, Phytochemistry 72, 508-513 (2011)
25. F.G. Zeng, Q. Su, Y.T. Di, X.J. Hao, Nat. Prod. Res. Dev. 28, 1171-1175 (2016)

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Abietane Diterpernoids from the Roots of Euphorbia ebracteolata

Abietane Diterpernoids from the Roots of Euphorbia ebracteolata

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