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
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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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Keywords:
- Stemona tuberosa,
- Alkaloid,
- Tuberostemonine-type
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[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.
-
[2]
[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.
-
[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.
-
[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.
-
[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.
-
[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.
-
[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.
-
[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.
-
[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.
-
[11]
[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.
-
[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.
-
[14]
[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.
-
[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.
-
[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.
-
[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.
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