Monoterpenoid Indole Alkaloids from Inadequately Dried Leaves of Alstonia scholaris

doi:10.1007/s13659-015-0066-2

应用天然产物 ›› 2015, Vol. 5 ›› Issue (4): 185-193.DOI: 10.1007/s13659-015-0066-2

Monoterpenoid Indole Alkaloids from Inadequately Dried Leaves of Alstonia scholaris

Xu-Jie Qin^1,2, Yun-Li Zhao¹, Chang-Wei Song¹, Bei Wang^1,2, Ying-Ying Chen^1,2, Lu Liu^1,2, Qiong Li^1,2, Dan Li^1,2, Ya-Ping Liu¹, Xiao-Dong Luo¹

1. 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;
2. 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

收稿日期:2015-07-17 修回日期:2015-07-23 出版日期:2015-08-24 发布日期:2018-02-11
通讯作者: Ya-Ping Liu,e-mail:liuyaping@mail.kib.ac.cn;Xiao-Dong Luo,e-mail:xdluo@mail.kib.ac.cn
基金资助:
The authors are grateful to the Natural Science Foundation of China(81225024), Collaborative Innovation Center of Southwest EthnicMedicine(Guangxi Normal University), (CICSEM 2013-A), the Ministry of Science and Technology of the People's Republic of China(2014ZX09301307-003), and the Chinese Academy of Sciences(KSZD-EW-Z-004-03) for partial financial support.

Monoterpenoid Indole Alkaloids from Inadequately Dried Leaves of Alstonia scholaris

Xu-Jie Qin^1,2, Yun-Li Zhao¹, Chang-Wei Song¹, Bei Wang^1,2, Ying-Ying Chen^1,2, Lu Liu^1,2, Qiong Li^1,2, Dan Li^1,2, Ya-Ping Liu¹, Xiao-Dong Luo¹

1. 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;
2. 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:2015-07-17 Revised:2015-07-23 Online:2015-08-24 Published:2018-02-11
Supported by:
The authors are grateful to the Natural Science Foundation of China(81225024), Collaborative Innovation Center of Southwest EthnicMedicine(Guangxi Normal University), (CICSEM 2013-A), the Ministry of Science and Technology of the People's Republic of China(2014ZX09301307-003), and the Chinese Academy of Sciences(KSZD-EW-Z-004-03) for partial financial support.

摘要/Abstract

摘要： Six new indole alkaloids, named alstoniascholarines L-Q(1-6), together with nineteen known analogues were isolated from the inadequately dried leaves of Alstonia scholaris. Their structures were elucidated on the basis of extensive analysis of spectroscopic data and by comparison of their physical and spectroscopic data with the literature values. In addition, the new alkaloids were tested for their cytotoxic and neurite outgrowth-promoting activities.

关键词: Alstonia scholaris, Inadequately dried leaves, Indole alkaloids, Alstoniascholarine, Bioactivities

Abstract: Six new indole alkaloids, named alstoniascholarines L-Q(1-6), together with nineteen known analogues were isolated from the inadequately dried leaves of Alstonia scholaris. Their structures were elucidated on the basis of extensive analysis of spectroscopic data and by comparison of their physical and spectroscopic data with the literature values. In addition, the new alkaloids were tested for their cytotoxic and neurite outgrowth-promoting activities.

Key words: Alstonia scholaris, Inadequately dried leaves, Indole alkaloids, Alstoniascholarine, Bioactivities

Xu-Jie Qin, Yun-Li Zhao, Chang-Wei Song, Bei Wang, Ying-Ying Chen, Lu Liu, Qiong Li, Dan Li, Ya-Ping Liu, Xiao-Dong Luo. Monoterpenoid Indole Alkaloids from Inadequately Dried Leaves of Alstonia scholaris[J]. 应用天然产物, 2015, 5(4): 185-193.

参考文献

1. Atta-ur-Rahman, K.A. Alvi, Phytochemistry 26, 2139-2142 (1987)
2. T.S. Kam, K.T. Nyeoh, K.M. Sim, K. Yoganathan, Phytochemistry 45, 1303-1305 (1997)
3. A.P.G. Macabeo, K. Krohn, D. Gehle, R.W. Read, J.J. Brophy, G.A. Cordell, S.G. Franzblau, A.M. Aguinaldo, Phytochemistry 66, 1158-1162 (2005)
4. L. Zhang, C.J. Zhang, D.B. Zhang, J. Wen, X.W. Zhao, Y. Li, K. Gao, Tetrahedron Lett. 55, 1815-1817 (2014)
5. M.S. Khyade, D.M. Kasote, N.P. Vaikos, J. Ethnopharmacol. 153, 1-18 (2014)
6. G.C. Jagetia, M.S. Baliga, J. Ethnopharmacol. 96, 37-42 (2005)
7. M.R. Khan, A.D. Omoloso, M. Kihara, Fitoterapia 74, 736-740 (2003)
8. J.H. Shang, X.H. Cai, T. Feng, Y.L. Zhao, J.K. Wang, L.Y. Zhang, M. Yan, X.D. Luo, J. Ethnopharmacol. 129, 174-181 (2010)
9. S. Channa, A. Dar, S. Ahmed, Atta-ur-Rahman, J. Ethnopharmacol. 97, 469-476 (2005)
10. X.H. Cai, Z.Z. Du, X.D. Luo, Org. Lett. 9, 1817-1820 (2007)
11. X.H. Cai, Q.G. Tan, Y.P. Liu, T. Feng, Z.Z. Du, W.Q. Li, X.D. Luo, Org. Lett. 10, 577-580 (2008)
12. X.H. Cai, Y.P. Liu, T. Feng, X.D. Luo, Chin. J. Nat. Med. 6, 20-22 (2008)
13. T. Feng, X.H. Cai, P.J. Zhao, Z.Z. Du, W.Q. Li, X.D. Luo, Planta Med. 75, 1537-1541 (2009)
14. X.W. Yang, X.J. Qin, Y.L. Zhao, P.K. Lunga, X.N. Li, S.Z. Jiang, G.G. Cheng, Y.P. Liu, X.D. Luo, Tetrahedron Lett. 55, 4593-4596 (2014)
15. X.J. Qin, Y.L. Zhao, P.K. Lunga, X.W. Yang, C.W. Song, G.G. Cheng, L. Liu, Y.Y. Chen, Y.P. Liu, X.D. Luo, Tetrahedron 71, 4372-4378 (2015)
16. T. Yamauchi, F. Abe, R.F. Chen, G.I. Nonaka, T. Santisuk, W.G. Padolina, Phytochemistry 29, 3547-3553 (1990)
17. M.E. Kuehne, F. Xu, C.S. Brook, J. Org. Chem. 59, 7803-7806 (1994)
18. F. Abe, R.F. Chen, T. Yamauchi, N. Marubayashi, I. Ueda, Chem. Pharm. Bull. 37, 887-890 (1989)
19. Habib-ur-Rehman Atta-ur-Rahman, Planta Med. 3, 230-231 (1986)
20. T. Yamauchi, F. Abe, W.G. Padolina, F.M. Dayrit, Phytochemistry 29, 3321-3325 (1990)
21. Y. Morita, M. Hesse, H. Schmid, A. Banerji, J. Banerji, A. Chatterjee, W.E. Oberhansli, Helv. Chim. Acta 60, 1419-1434 (1977)
22. L.D. Antonaccio, N.A. Pereira, B. Gilbert, H. Vorbrueggen, H. Budzikiewicz, J.M. Wilson, L.J. Durham, C. Djerassi, J. Am. Chem. Soc. 84, 2161-2169 (1962)
23. R.H. Burnell, J.D. Medina, Phytochemistry 7, 2045-2051 (1968)
24. D. Keawpradub, H. Takayama, N. Aimi, S.I. Sakai, Phytochemistry 37, 1745-1749 (1994)
25. X.W. Yang, X.D. Luo, P.K. Lunga, Y.L. Zhao, X.J. Qin, Y.Y. Chen, L. Liu, X.N. Li, Y.P. Liu, Tetrahedron 71, 3694-3698 (2015)
26. K.A. Atta-ur-Rahman, S.A. Alvi, W. Abbas, Voeter. Heterocycles 26, 413-419 (1987)
27. Atta-ur-Rahman, M. Asif, M. Ghazala, J. Fatima, K.A. Alvi, Phytochemistry 24, 2771-2773 (1985)
28. W.L. Hu, J.P. Zhu, M. Hesse, Planta Med. 55, 463-466 (1989)
29. M. Pinar, U. Renner, M. Hesse, H. Schmid, Helv. Chim. Acta 55, 2972-2974 (1972)
30. A.A. Salim, M.J. Garson, D.J. Craik, J. Nat. Prod. 67, 1591-1594 (2004)
31. S.Y. Xu, R.L. Bian, X. Chen, Pharmacological Experiment Methodology (People's Medical Publishing House, Beijing, 1991), p. 1167
32. T. Mosmann, J. Immunol. Methods 65, 55-63 (1983)
33. A. Pradines, M. Magazin, P. Schiltz, G. Le Fur, D. Caput, P. Ferrara, J. Neurochem. 64, 1954-1964 (1995)

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Monoterpenoid Indole Alkaloids from Inadequately Dried Leaves of Alstonia scholaris

Monoterpenoid Indole Alkaloids from Inadequately Dried Leaves of Alstonia scholaris

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