Isolation and chemotaxonomic signifi cance of stenine-and stemoninine-type alkaloids from the roots of <i>Stemona tuberosa</i>

Citation: Rong-Rong Zhang, Hai-Yan Tian, Yi Wu, Xiao-Hui Sun, Jian-Long Zhang, Zhi-Guo Ma, Ren-Wang Jiang. Isolation and chemotaxonomic signifi cance of stenine-and stemoninine-type alkaloids from the roots of Stemona tuberosa[J]. Chinese Chemical Letters, 2014, 25(9): 1252-1255. doi: 10.1016/j.cclet.2014.03.051 shu

Isolation and chemotaxonomic signifi cance of stenine-and stemoninine-type alkaloids from the roots of Stemona tuberosa

通讯作者: Zhi-Guo Ma,
Ren-Wang Jiang,

基金项目:
Thisworkwas supported by the Fundamental Research Funds for the Central Universities (No. 11612603) (No. 11612603)

TechnologyPlanningProjectof ZhongshanCity (No. 2013A3FC0325). (No. 2013A3FC0325)

摘要: One new stenine-type alkaloid, tuberostemonine D (1), together with five known stenine-type alkaloids (2-6) and two known stemoninine-type alkaloids (7 and 8), were isolated from the roots of Stemona tuberosa. Their structureswere elucidated by extensive spectroscopic methods (IR,UV,MS, 1D and 2D NMR), and the structure of 1 was further confirmed by X-ray diffraction analysis. First simultaneous isolation of stenine-and stemoninine-type alkaloids not only added a newchemical type and increased the chemical diversity of Stemona tuberosa, but also provided chemotaxonomic clues for the close relationship between genera Stemona and Stichoneuron, and favored retaining them in the same family.

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English

Isolation and chemotaxonomic signifi cance of stenine-and stemoninine-type alkaloids from the roots of Stemona tuberosa

1.
a Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China;
2.
b Zhongshan Torch Polytechnic, Zhongshan 528436, China;
3.
c Shenzhen Engineering Laboratory of Lingnan Herbal Resource Development and Application, Shenzhen Institute for Drug Control, Shenzhen 518057, China

Corresponding author: Zhi-Guo Ma, Ren-Wang Jiang,

Received Date: 23 January 2014
Fund Project:

Abstract: One new stenine-type alkaloid, tuberostemonine D (1), together with five known stenine-type alkaloids (2-6) and two known stemoninine-type alkaloids (7 and 8), were isolated from the roots of Stemona tuberosa. Their structureswere elucidated by extensive spectroscopic methods (IR,UV,MS, 1D and 2D NMR), and the structure of 1 was further confirmed by X-ray diffraction analysis. First simultaneous isolation of stenine-and stemoninine-type alkaloids not only added a newchemical type and increased the chemical diversity of Stemona tuberosa, but also provided chemotaxonomic clues for the close relationship between genera Stemona and Stichoneuron, and favored retaining them in the same family.

Key words:

1. [1] Pharmacopoeia Commission of People's Republic of China, The Pharmacopoeia of the People's Republic of China, Chemical Industry Publishing House, Beijing, 2005, p. 100.[1] Pharmacopoeia Commission of People's Republic of China, The Pharmacopoeia of the People's Republic of China, Chemical Industry Publishing House, Beijing, 2005, p. 100.
2. [2] Jiangsu New Medical College, Dictionary of Chinese Traditional Medicine, Shanghai People's Publishing House, Shanghai, 1977, pp. 858-861.[2] Jiangsu New Medical College, Dictionary of Chinese Traditional Medicine, Shanghai People's Publishing House, Shanghai, 1977, pp. 858-861.
3. [3] Y.T. Xu, P.C. Shaw, R.W. Jiang, et al., Antitussive and central respiratory depressant effects of Stemona tuberosa, J. Ethnopharmacol. 128 (2010) 679-684.[3] Y.T. Xu, P.C. Shaw, R.W. Jiang, et al., Antitussive and central respiratory depressant effects of Stemona tuberosa, J. Ethnopharmacol. 128 (2010) 679-684.
4. [4] X. Zhou, P.H.H. Leung, N. Li, et al., Oral absorption and antitussive activity of tuberostemonine alkaloids from the roots of Stemona tuberosa, Planta Med. 75 (2009) 575-580.[4] X. Zhou, P.H.H. Leung, N. Li, et al., Oral absorption and antitussive activity of tuberostemonine alkaloids from the roots of Stemona tuberosa, Planta Med. 75 (2009) 575-580.
5. [5] X.Z. Yang, J.Y. Zhu, C.P. Tang, et al., Alkaloids from roots of Stemona sessilifolia and their antitussive activities, Planta Med. 75 (2009) 174-177.[5] X.Z. Yang, J.Y. Zhu, C.P. Tang, et al., Alkaloids from roots of Stemona sessilifolia and their antitussive activities, Planta Med. 75 (2009) 174-177.
6. [6] R.A. Pilli, G.B. Rossoa, M.D.C.F.D. Oliveira, The chemistry of Stemona alkaloids: an update, Nat. Prod. Rep. 27 (2010) 1908-1937.[6] R.A. Pilli, G.B. Rossoa, M.D.C.F.D. Oliveira, The chemistry of Stemona alkaloids: an update, Nat. Prod. Rep. 27 (2010) 1908-1937.
7. [7] R.W. Jiang, P.M. Hon, Y.T. Xu, et al., Isolation and chemotaxonomic significance of tuberostemospironine-type alkaloids from Stemona tuberosa, Phytochemistry 67 (2006) 52-57.[7] R.W. Jiang, P.M. Hon, Y.T. Xu, et al., Isolation and chemotaxonomic significance of tuberostemospironine-type alkaloids from Stemona tuberosa, Phytochemistry 67 (2006) 52-57.
8. [8] R.W. Jiang, P.M. Hon, P.P.H. But, et al., Isolation and stereochemistry of two new alkaloids from Stemona tuberosa, Tetrahedron 58 (2002) 6705-6712.[8] R.W. Jiang, P.M. Hon, P.P.H. But, et al., Isolation and stereochemistry of two new alkaloids from Stemona tuberosa, Tetrahedron 58 (2002) 6705-6712.
9. [9] R.W. Jiang, P.M. Hon, Y. Zhou, et al., Alkaloids and chemical diversity of Stemona tuberosa, J. Nat. Prod. 69 (2006) 749-754.[9] R.W. Jiang, P.M. Hon, Y. Zhou, et al., Alkaloids and chemical diversity of Stemona tuberosa, J. Nat. Prod. 69 (2006) 749-754.
10. [10] H.S. Chung, P.M. Hon, G. Lin, et al., Antitussive activity of Stemona alkaloids from Stemona tuberosa, Planta Med. 69 (2003) 914-920.[10] H.S. Chung, P.M. Hon, G. Lin, et al., Antitussive activity of Stemona alkaloids from Stemona tuberosa, Planta Med. 69 (2003) 914-920.
11. [11] S.W. Liu, H.Z. Fu, W.H. Lin, Alkaloids from roots of Stemona tuberosa, Acta Pharm. Sin. 34 (1999) 372-375.[11] S.W. Liu, H.Z. Fu, W.H. Lin, Alkaloids from roots of Stemona tuberosa, Acta Pharm. Sin. 34 (1999) 372-375.
12. [12] L.G. Lin, H.P.H. Leung, J.Y. Zhu, et al., Croomine-and tuberostemonine-type alkaloids from roots of Stemona tuberosa and their antitussive activity, Tetrahedron 64 (2008) 10155-10161.[12] L.G. Lin, H.P.H. Leung, J.Y. Zhu, et al., Croomine-and tuberostemonine-type alkaloids from roots of Stemona tuberosa and their antitussive activity, Tetrahedron 64 (2008) 10155-10161.
13. [13] L.G. Lin, Q.X. Zhong, T.Y. Cheng, et al., Stemoninines from the roots of Stemona tuberosa, J. Nat. Prod. 69 (2006) 1051-1054.[13] L.G. Lin, Q.X. Zhong, T.Y. Cheng, et al., Stemoninines from the roots of Stemona tuberosa, J. Nat. Prod. 69 (2006) 1051-1054.
14. [14] C. Kuo, T.T. Chu, A study of Stemona alkaloids: I, Acta Chim. Sin. 36 (1978), 291-196.[14] C. Kuo, T.T. Chu, A study of Stemona alkaloids: I, Acta Chim. Sin. 36 (1978), 291-196.
15. [15] H. Greger, Structural relationships, distribution and biological activities of Stemona alkaloids, Planta Med. 72 (2006) 99-113.[15] H. Greger, Structural relationships, distribution and biological activities of Stemona alkaloids, Planta Med. 72 (2006) 99-113.
16. [16] J.P. Hua, D.H. Yang, W.H. Lin, et al., Alkaloids from the roots of Stemona tuberosa, Helv. Chim. Acta 92 (2009) 2125-2133.[16] J.P. Hua, D.H. Yang, W.H. Lin, et al., Alkaloids from the roots of Stemona tuberosa, Helv. Chim. Acta 92 (2009) 2125-2133.
17. [17] K. Sumet, S. Johann, F. Susanne, et al., Structural relationships of Stemona alkaloids: assessment of species-specific accumulation trends for exploiting their biological activities, J. Nat. Prod. 74 (2011) 1931-1938.[17] K. Sumet, S. Johann, F. Susanne, et al., Structural relationships of Stemona alkaloids: assessment of species-specific accumulation trends for exploiting their biological activities, J. Nat. Prod. 74 (2011) 1931-1938.
18. [18] R.A. Ramli, W. Lie, S.G. Pyne, Alkaloids from the roots and leaves of Stichoneuron halabalensis and their acetylcholinesterase inhibitory activities, Nat. Prod. Commun. 8 (2013) 695-698.[18] R.A. Ramli, W. Lie, S.G. Pyne, Alkaloids from the roots and leaves of Stichoneuron halabalensis and their acetylcholinesterase inhibitory activities, Nat. Prod. Commun. 8 (2013) 695-698.

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Isolation and chemotaxonomic signifi cance of stenine-and stemoninine-type alkaloids from the roots of Stemona tuberosa

通讯作者: Zhi-Guo Ma,
Ren-Wang Jiang,

English

Isolation and chemotaxonomic signifi cance of stenine-and stemoninine-type alkaloids from the roots of Stemona tuberosa

Corresponding author: Zhi-Guo Ma, Ren-Wang Jiang,

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Isolation and chemotaxonomic signifi cance of stenine-and stemoninine-type alkaloids from the roots of Stemona tuberosa

通讯作者: Zhi-Guo Ma, Ren-Wang Jiang,

English

Isolation and chemotaxonomic signifi cance of stenine-and stemoninine-type alkaloids from the roots of Stemona tuberosa

Corresponding author: Zhi-Guo Ma, Ren-Wang Jiang,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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