Monoterpenoid Indole Alkaloids from Inadequately Dried Leaves of Alstonia scholaris

doi:10.1007/s13659-015-0066-2

Natural Products and Bioprospecting ›› 2015, Vol. 5 ›› Issue (4): 185-193.DOI: 10.1007/s13659-015-0066-2

• Original article • Previous Articles Next Articles

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:2018-02-11 Published:2015-08-24
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.

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

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.

Abstract

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

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

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]. Natural Products and Bioprospecting, 2015, 5(4): 185-193.

References

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)

[1]	Ke-Pu Huang, Li-Li Xu, Sheng Li, Yin-Ling Wei, Lian Yang, Xiao-Jiang Hao, Hong-Ping He, Yu Zhang. Uncarialines A-E, new alkaloids from Uncaria rhynchophylla and their anticoagulant activity [J]. Natural Products and Bioprospecting, 2023, 13(2): 13-13.
[2]	Mei-Ling Xiang, Bin-Yuan Hu, Zi-Heng Qi, Xiao-Na Wang, Tian-Zhen Xie, Zhao-Jie Wang, Dan-Yu Ma, Qi Zeng, Xiao-Dong Luo. Chemistry and bioactivities of natural steroidal alkaloids [J]. Natural Products and Bioprospecting, 2022, 12(4): 23-23.
[3]	Zong-Qing Huo, Qian Zhao, Wen-Tao Zhu, Xiao-Jiang Hao, Yu Zhang. Bousmekines A-E, New Alkaloids from Two Bousigonia Species: B.angustifolia and B. mekongensis [J]. Natural Products and Bioprospecting, 2021, 11(2): 207-213.
[4]	Ke Ye, Hong-Lian Ai, Ji-Kai Liu. Identification and Bioactivities of Secondary Metabolites Derived from Endophytic Fungi Isolated from Ethnomedicinal Plants of Tujia in Hubei Province: A Review [J]. Natural Products and Bioprospecting, 2021, 11(2): 185-205.
[5]	Yun-Li Zhao, Zhong-Ping Gou, Jian-Hua Shang, Wan-Yi Li, Yu Kuang, Ming-Yuan Li, Xiao-Dong Luo. Anti-microbial Effects In Vitro and In Vivo of Alstonia scholaris [J]. Natural Products and Bioprospecting, 2021, 11(1): 127-135.
[6]	Lin Wang, Junke Song, Ailin Liu, Bin Xiao, Sha Li, Zhang Wen, Yang Lu, Guanhua Du. Research Progress of the Antiviral Bioactivities of Natural Flavonoids [J]. Natural Products and Bioprospecting, 2020, 10(5): 271-283.
[7]	Meilian Yang, Yudan Wang, Zhifeng Fan, Qingwang Xue, Guy Sedar Singor Njateng, Yaping Liu, Jianxin Cao, Tianrui Zhao, Guiguang Cheng. Acute and Sub-Acute Toxicological Evaluations of Bioactive Alkaloidal Extract from Melodinus henryi and Their Main Chemical Constituents [J]. Natural Products and Bioprospecting, 2020, 10(4): 227-241.
[8]	Yun-Li Zhao, Min Su, Jian-Hua Shang, Xia Wang, Guang-Lei Bao, Jia Ma, Qing-Di Sun, Fang Yuan, Jing-Kun Wang, Xiao-Dong Luo. Acute and Sub-chronic Toxicity of Indole Alkaloids Extract from Leaves of Alstonia scholaris (L.) R. Br. in Beagle Dogs [J]. Natural Products and Bioprospecting, 2020, 10(4): 209-220.
[9]	Yun-Li Zhao, Min Su, Jian-Hua Shang, Xia Wang, Guang-Lei Bao, Jia Ma, Qing-Di Sun, Fang Yuan, Jing-Kun Wang, Xiao-Dong Luo. Genotoxicity and Safety Pharmacology Studies of Indole Alkaloids Extract from Leaves of Alstonia scholaris (L.) R. Br. [J]. Natural Products and Bioprospecting, 2020, 10(3): 119-129.
[10]	Yun-Li Zhao, Min Su, Jian-Hua Shang, Xia Wang, Guy Sedar Singor Njateng, Guang-Lei Bao, Jia Ma, Qing-Di Sun, Fang Yuan, Jing-Kun Wang, Xiao-Dong Luo. Acute and Chronic Toxicity of Indole Alkaloids from Leaves of Alstonia scholaris (L.) R. Br. in Mice and Rats [J]. Natural Products and Bioprospecting, 2020, 10(2): 77-88.
[11]	Hai-Li Yu, Qin Long, Wen-Fang Yi, Bao-Jia Yang, Yu Song, Xiao Ding, Shun-Lin Li, Xiao-Jiang Hao. Two New C21 Steroidal Glycosides from the Roots of Cynanchum paniculatum [J]. Natural Products and Bioprospecting, 2019, 9(3): 209-214.
[12]	Xu-Jie Qin, Wei Ni, Chang-Xiang Chen, Hai-Yang Liu. Untiring Researches for Alternative Resources of Rhizoma Paridis [J]. Natural Products and Bioprospecting, 2018, 8(4): 265-278.
[13]	Yan Deng, Mei-Fen Bao, Bao-Bao Shi, Jing Wu, Xiang-Hai Cai. Three New Indole Alkaloids from Tabernaemontana divaricata [J]. Natural Products and Bioprospecting, 2018, 8(3): 183-188.
[14]	Xin Wei, Li-Ping Jiang, Ying Guo, Afsar Khan, Ya-Ping Liu, Hao-Fei Yu, Bei Wang, Cai-Feng Ding, Pei-Feng Zhu, Ying-Ying Chen, Yun-Li Zhao, Yong-Bing Chen, Yi-Fen Wang, Xiao-Dong Luo. Indole Alkaloids Inhibiting Neural Stem Cell from Uncaria rhynchophylla [J]. Natural Products and Bioprospecting, 2017, 7(5): 413-419.
[15]	Muna Ali Abdalla, Josphat C. Matasyoh. Endophytes as Producers of Peptides: An Overview About the Recently Discovered Peptides from Endophytic Microbes [J]. Natural Products and Bioprospecting, 2014, 4(5): 257-270.

Monoterpenoid Indole Alkaloids from Inadequately Dried Leaves of Alstonia scholaris

Monoterpenoid Indole Alkaloids from Inadequately Dried Leaves of Alstonia scholaris

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments