New Lycopodium alkaloids from Lycopodium obscurum

Xue-Yuan Zhang; Liao-Bin Dong; Fei Liu; Xing-De Wu; Juan He; Li-Yan Peng; Huai-Rong Luo; Qin-Shi Zhao

doi:10.1007/s13659-013-0015-x

. 2013 Apr 1;3(2):52–55. doi: 10.1007/s13659-013-0015-x

New Lycopodium alkaloids from Lycopodium obscurum

Xue-Yuan Zhang ^115,²¹⁵, Liao-Bin Dong ^115,²¹⁵, Fei Liu ^115,²¹⁵, Xing-De Wu ¹¹⁵, Juan He ¹¹⁵, Li-Yan Peng ¹¹⁵, Huai-Rong Luo ¹¹⁵, Qin-Shi Zhao ^115,^✉

PMCID: PMC4131663

Abstract

Three new Lycopodium alkaloids, obscurumines C-E (1–3), along with nine known compounds, were isolated from the club moss Lycopodium obscurum L. Structures of the new compounds were determined on the basis of their spectroscopic analysis and the relative configurations of 1 were established by X-ray crystallographic analysis. All the new isolates were tested for the acetylcholinesterase (AChE) inhibitory activity. graphic file with name 13659_2013_15_Article_Fig1_HTML.jpg

Electronic Supplementary Material

Supplementary material is available for this article at 10.1007/s13659-013-0015-x and is accessible for authorized users.

Keywords: obscurumines, Lydopodium alkaloids, Lycopodium obscurum, acetylcholinesterase (AChE) inhibitory activity

Electronic supplementary material

13659_2013_15_MOESM1_ESM.pdf^{(1.9MB, pdf)}

Supplementary material, approximately 1.94 MB.

13659_2013_15_MOESM2_ESM.cif^{(15.9KB, cif)}

Supplementary material, approximately 15.8 KB.

Footnotes

This article is published with open access at Springerlink.com

References

[1].Hirasawa Y, Kobayashi J, Moritaa H. Heterocycles. 2009;77:679–729. doi: 10.3987/REV-08-SR(F)6. [DOI] [Google Scholar]
[2].Ma X Q, Gang D R. Nat. Prod. Rep. 2004;21:752–772. doi: 10.1039/b409720n. [DOI] [PubMed] [Google Scholar]
[3].Saha M, Carter R G. Org. Lett. 2013;15:736–739. doi: 10.1021/ol303272w. [DOI] [PMC free article] [PubMed] [Google Scholar]
[4].Newton J N, Fischer D F, Sarpong R. Angew. Chem. Int. Ed. 2013;52:1726–1730. doi: 10.1002/anie.201208571. [DOI] [PMC free article] [PubMed] [Google Scholar]
[5].Wang X J, Liu Y B, Li L, Yu S S, Lv H N, Ma S G, Bao X Q, Zhang D, Qu J, Li Y. Org. Lett. 2012;14:5688–5691. doi: 10.1021/ol302701y. [DOI] [PubMed] [Google Scholar]
[6].Zhang H Y. Acta Pharm. Sin. 2012;33:1170–1175. doi: 10.1038/aps.2012.128. [DOI] [PMC free article] [PubMed] [Google Scholar]
[7].Jiangsu New Medical College, Dictionary of Chinese Traditional Medicines (Shang-hai Science and Technology Press, Shanghai, 1977), p. 553.
[8].Morita H, Ishiuchi K, Haganuma A, Hoshino T, Obara Y, Nakahatab N, Kobayashi J. Tetrahedron. 2005;61:1955–1960. doi: 10.1016/j.tet.2005.01.011. [DOI] [Google Scholar]
[9].Hu T, Chandler R F, Hanson A W. Tetrahedron Lett. 1987;28:5993–5996. doi: 10.1016/S0040-4039(00)96845-X. [DOI] [Google Scholar]
[10].Manske R H F, Marion L. Can. J. Res., Sec. B: Chem. Sci. 1944;22:53–55. doi: 10.1139/cjr44b-007. [DOI] [Google Scholar]
[11].He J, Chen X Q, Li M M, Zhao Y, Xu G, Cheng X, Peng L Y, Xie M J, Zheng Y T, Wang Y P, Zhao Q S. Org. Lett. 2009;11:1397–1400. doi: 10.1021/ol900079t. [DOI] [PubMed] [Google Scholar]
[12].Dong L B, Yang J, He J, Luo H R, Wu X D, Deng X, Peng L Y, Cheng X, Zhao Q S. Chem. Commun. 2012;48:9038–9040. doi: 10.1039/c2cc34676a. [DOI] [PubMed] [Google Scholar]
[13].Perrya G S, Meclean D B. Can. J. Res. 1956;34:1189–1199. [Google Scholar]
[14].Morita H, Hirasawa Y, Kobayashi J. J. Nat. Prod. 2005;68:1809–1812. doi: 10.1021/np050389+. [DOI] [PubMed] [Google Scholar]
[15].Takayama H, Katakawa K, Kitajima M, Yamaguchi K, Aimi N. Tetrahedron Lett. 2002;43:8307–8311. doi: 10.1016/S0040-4039(02)02026-9. [DOI] [Google Scholar]
[16].Muñoz O M, Castillo M, Feliciano A S. J. Nat. Prod. 1990;53:200–203. doi: 10.1021/np50067a032. [DOI] [Google Scholar]
[17].Laemmerhold K M, Breit B. Angew. Chem. Int. Ed. 2010;49:2367–2370. doi: 10.1002/anie.200907248. [DOI] [PubMed] [Google Scholar]
[18].Ayer W A, Kasitu G C. Can. J. Res. 1956;34:1077–1086. [Google Scholar]
[19].Katakawa K, Kogure N, Kitajima M, Takayama H. Helv. Chim. Acta. 2009;92:445–452. doi: 10.1002/hlca.200800327. [DOI] [Google Scholar]
[20].Takayama H, Katakawa K, Kitajima M, Kentaro Yamaguchib K, Aimia N. Tetrahedron Lett. 2002;43:8307–8311. doi: 10.1016/S0040-4039(02)02026-9. [DOI] [Google Scholar]
[21].Ellman G L, Courtney K D, Andres V J, Featherstone R M. Biochem. Pharmacol. 1961;7:88–95. doi: 10.1016/0006-2952(61)90145-9. [DOI] [PubMed] [Google Scholar]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

13659_2013_15_MOESM1_ESM.pdf^{(1.9MB, pdf)}

Supplementary material, approximately 1.94 MB.

13659_2013_15_MOESM2_ESM.cif^{(15.9KB, cif)}

Supplementary material, approximately 15.8 KB.

[CR1] [1].Hirasawa Y, Kobayashi J, Moritaa H. Heterocycles. 2009;77:679–729. doi: 10.3987/REV-08-SR(F)6. [DOI] [Google Scholar]

[CR2] [2].Ma X Q, Gang D R. Nat. Prod. Rep. 2004;21:752–772. doi: 10.1039/b409720n. [DOI] [PubMed] [Google Scholar]

[CR3] [3].Saha M, Carter R G. Org. Lett. 2013;15:736–739. doi: 10.1021/ol303272w. [DOI] [PMC free article] [PubMed] [Google Scholar]

[CR4] [4].Newton J N, Fischer D F, Sarpong R. Angew. Chem. Int. Ed. 2013;52:1726–1730. doi: 10.1002/anie.201208571. [DOI] [PMC free article] [PubMed] [Google Scholar]

[CR5] [5].Wang X J, Liu Y B, Li L, Yu S S, Lv H N, Ma S G, Bao X Q, Zhang D, Qu J, Li Y. Org. Lett. 2012;14:5688–5691. doi: 10.1021/ol302701y. [DOI] [PubMed] [Google Scholar]

[CR6] [6].Zhang H Y. Acta Pharm. Sin. 2012;33:1170–1175. doi: 10.1038/aps.2012.128. [DOI] [PMC free article] [PubMed] [Google Scholar]

[CR7] [7].Jiangsu New Medical College, Dictionary of Chinese Traditional Medicines (Shang-hai Science and Technology Press, Shanghai, 1977), p. 553.

[CR8] [8].Morita H, Ishiuchi K, Haganuma A, Hoshino T, Obara Y, Nakahatab N, Kobayashi J. Tetrahedron. 2005;61:1955–1960. doi: 10.1016/j.tet.2005.01.011. [DOI] [Google Scholar]

[CR9] [9].Hu T, Chandler R F, Hanson A W. Tetrahedron Lett. 1987;28:5993–5996. doi: 10.1016/S0040-4039(00)96845-X. [DOI] [Google Scholar]

[CR10] [10].Manske R H F, Marion L. Can. J. Res., Sec. B: Chem. Sci. 1944;22:53–55. doi: 10.1139/cjr44b-007. [DOI] [Google Scholar]

[CR11] [11].He J, Chen X Q, Li M M, Zhao Y, Xu G, Cheng X, Peng L Y, Xie M J, Zheng Y T, Wang Y P, Zhao Q S. Org. Lett. 2009;11:1397–1400. doi: 10.1021/ol900079t. [DOI] [PubMed] [Google Scholar]

[CR12] [12].Dong L B, Yang J, He J, Luo H R, Wu X D, Deng X, Peng L Y, Cheng X, Zhao Q S. Chem. Commun. 2012;48:9038–9040. doi: 10.1039/c2cc34676a. [DOI] [PubMed] [Google Scholar]

[CR13] [13].Perrya G S, Meclean D B. Can. J. Res. 1956;34:1189–1199. [Google Scholar]

[CR14] [14].Morita H, Hirasawa Y, Kobayashi J. J. Nat. Prod. 2005;68:1809–1812. doi: 10.1021/np050389+. [DOI] [PubMed] [Google Scholar]

[CR15] [15].Takayama H, Katakawa K, Kitajima M, Yamaguchi K, Aimi N. Tetrahedron Lett. 2002;43:8307–8311. doi: 10.1016/S0040-4039(02)02026-9. [DOI] [Google Scholar]

[CR16] [16].Muñoz O M, Castillo M, Feliciano A S. J. Nat. Prod. 1990;53:200–203. doi: 10.1021/np50067a032. [DOI] [Google Scholar]

[CR17] [17].Laemmerhold K M, Breit B. Angew. Chem. Int. Ed. 2010;49:2367–2370. doi: 10.1002/anie.200907248. [DOI] [PubMed] [Google Scholar]

[CR18] [18].Ayer W A, Kasitu G C. Can. J. Res. 1956;34:1077–1086. [Google Scholar]

[CR19] [19].Katakawa K, Kogure N, Kitajima M, Takayama H. Helv. Chim. Acta. 2009;92:445–452. doi: 10.1002/hlca.200800327. [DOI] [Google Scholar]

[CR20] [20].Takayama H, Katakawa K, Kitajima M, Kentaro Yamaguchib K, Aimia N. Tetrahedron Lett. 2002;43:8307–8311. doi: 10.1016/S0040-4039(02)02026-9. [DOI] [Google Scholar]

[CR21] [21].Ellman G L, Courtney K D, Andres V J, Featherstone R M. Biochem. Pharmacol. 1961;7:88–95. doi: 10.1016/0006-2952(61)90145-9. [DOI] [PubMed] [Google Scholar]

PERMALINK

New Lycopodium alkaloids from Lycopodium obscurum

Xue-Yuan Zhang

Liao-Bin Dong

Fei Liu

Xing-De Wu

Juan He

Li-Yan Peng

Huai-Rong Luo

Qin-Shi Zhao

Abstract

Electronic Supplementary Material

Electronic supplementary material

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

Cite

Add to Collections

PERMALINK

New Lycopodium alkaloids from Lycopodium obscurum

Xue-Yuan Zhang

Liao-Bin Dong

Fei Liu

Xing-De Wu

Juan He

Li-Yan Peng

Huai-Rong Luo

Qin-Shi Zhao

Abstract

Electronic Supplementary Material

Electronic supplementary material

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

Similar articles

Cited by other articles

Links to NCBI Databases