Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum

Ming-Ming Cao; Hong-Ping He; Yu-Cheng Gu; Qiang Zhang; Xiao-Nian Li; Guo-Ying Zuo; Ying-Tong Di; Chun-Mao Yuan; Shun-Lin Li; Yu Zhang; Xiao-Jiang Hao

doi:10.1007/s13659-012-0095-z

. 2013 Feb 26;3(1):29–32. doi: 10.1007/s13659-012-0095-z

Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum

Ming-Ming Cao ^195,²⁹⁵, Hong-Ping He ¹⁹⁵, Yu-Cheng Gu ³⁹⁵, Qiang Zhang ⁴⁹⁵, Xiao-Nian Li ¹⁹⁵, Guo-Ying Zuo ⁵⁹⁵, Ying-Tong Di ¹⁹⁵, Chun-Mao Yuan ¹⁹⁵, Shun-Lin Li ¹⁹⁵, Yu Zhang ^195,^✉, Xiao-Jiang Hao ^195,^✉

PMCID: PMC4131615

Graphical abstract

Two new daphnicyclidin-type Daphniphyllum alkaloids, daphmacrodins A and B (1 and 2) were isolated from the leaves and stems of Daphniphyllum macropodum. Their structures were elucidated by extensive spectroscopic techniques, including 2D NMR spectroscopy and mass spectrometry. The relative configuration of 1 was further confirmed by a single-crystal X-ray diffraction analysis. Their cytotoxic activities against five human cancer cell lines, pesticidal activities against brine shrimp (Artemia salina), and antibacterial activities against five standard bacterial and fungal strains were evaluated. The structure of 1 was successfully transformed to 2 by a chemical method.

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Keywords: Daphniphyllaceae, Daphniphyllum macropodum, cyclopentadienyl anion

Electronic supplementary material

13659_2012_95_MOESM1_ESM.pdf^{(4.9MB, pdf)}

Supplementary material, approximately 4.91 MB.

Footnotes

This article is published with open access at Springerlink.com

Contributor Information

Yu Zhang, Email: zhangyu@mail.kib.ac.cn.

Xiao-Jiang Hao, Email: haoxj@mail.kib.ac.cn.

References

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Associated Data

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

Supplementary Materials

13659_2012_95_MOESM1_ESM.pdf^{(4.9MB, pdf)}

Supplementary material, approximately 4.91 MB.

[CR1] [1] (a).Yamamura S., Irikawa H., Okumura Y., Hirata Y. Bull. Chem. Soc. Jpn. 1975;48:2120–2123. doi: 10.1246/bcsj.48.2120. [DOI] [Google Scholar]

[CR2] [1] (b).Kobayashi J., Morita H. In: The Alkaloids. Cordell G. A., editor. New York: Academic Press; 2003. [Google Scholar]

[CR3] [1] (c).Yamamura S. In: The Alkaloids. Brossi A., editor. New York: Academic Press; 1986. pp. 256–286. [Google Scholar]

[CR4] [1] (d).Kobayashi J., Kubota T. Nat. Prod. Rep. 2009;26:936–962. doi: 10.1039/b813006j. [DOI] [PubMed] [Google Scholar]

[CR5] [2] (a).Heathcock C. H. Angew. Chem. 1992;104:675–691. doi: 10.1002/ange.19921040604. [DOI] [Google Scholar]

[CR6] [2] (b).Heathcock C. H. Proc. Natl. Acad. Sci. USA. 1996;93:14323–14327. doi: 10.1073/pnas.93.25.14323. [DOI] [PMC free article] [PubMed] [Google Scholar]

[CR7] [2] (c).Wallace G. A., Heathcock C. H. J. Org. Chem. 2001;66:450–454. doi: 10.1021/jo001145r. [DOI] [PubMed] [Google Scholar]

[CR8] [2] (c).Xu C., Liu Z., Wang H. F., Zhang B., Xiang Z., Hao X. J., Wang D. Z. G. Org. Lett. 2011;13:1812–1815. doi: 10.1021/ol200312q. [DOI] [PubMed] [Google Scholar]

[CR9] [2] (d).Xu C., Wang L., Hao X. J., Wang D. Z. G. J. Org. Chem. 2012;77:6307–6313. doi: 10.1021/jo300776d. [DOI] [PubMed] [Google Scholar]

[CR10] [3] (a).Niwa H., Hirata Y., Suzuki K. T., Yamamura S. Tetrahedron Lett. 1973;14:2129–2132. doi: 10.1016/S0040-4039(01)86825-8. [DOI] [Google Scholar]

[CR11] [3] (b).Suzuki K. T., Okuda S., Niwa H., Toda M., Hirata Y., Yamamura S. Tetrahedron Lett. 1973;14:799–802. doi: 10.1016/S0040-4039(01)95717-X. [DOI] [Google Scholar]

[CR12] [4] (a).Zhang C. R., Liu H. B., Feng T., Zhu J. Y., Geng M. Y., Yue J. M. J. Nat. Prod. 2009;72:1669–1672. doi: 10.1021/np9003799. [DOI] [PubMed] [Google Scholar]

[CR13] [4] (b).Zhang Q., Di Y. T., Li C. S., Fang X., Tan C. J., Zhang Z., Zhang Y., He H. P., Li S. L., Hao X. J. Org. Lett. 2009;11:2357–2359. doi: 10.1021/ol9007958. [DOI] [PubMed] [Google Scholar]

[CR14] [4] (c).Zhang Y., Di Y. T., He H. P., Li S. F., Lu Y., Gong N. B., Hao X. J. Eur. J. Org. Chem. 2011;2011:4103–4107. doi: 10.1002/ejoc.201100414. [DOI] [Google Scholar]

[CR15] [4] (d).Zhang Y., Di Y. T., Zhang Q., Mu S. Z., Tan C. J., Fang X., He H. P., Li S. L., Hao X. J. Org. Lett. 2009;11:5414–5417. doi: 10.1021/ol902262g. [DOI] [PubMed] [Google Scholar]

[CR16] [5].Kobayashi J., Inaba Y., Shiro M., Yoshida N., Morita H. J. Am. Chem. Soc. 2001;123:11402–11408. doi: 10.1021/ja016955e. [DOI] [PubMed] [Google Scholar]

[CR17] [6] (a).Yang S. P., Yue J. M. Org. Lett. 2004;6:1401–1404. doi: 10.1021/ol049756j. [DOI] [PubMed] [Google Scholar]

[CR18] [6] (b).Gan X. W., Bai H. Y., Chen Q. G., Ma L., Hu L. H. Chem. Biodivers. 2006;3:1255–1259. doi: 10.1002/cbdv.200690127. [DOI] [PubMed] [Google Scholar]

[CR19] [6] (c).Zhang W., Guo Y. W., Krohn K. Chem. Eur. J. 2006;12:5122–5127. doi: 10.1002/chem.200600056. [DOI] [PubMed] [Google Scholar]

[CR20] [6] (d).Tan C. J., Di Y. T., Wang Y. H., Wang Y., Mu S. Z., Gao S., Zhang Y., Kong N. C., He H. P., Zhang J. X., Fang X., Li C. S., Lu Y., Hao X. J. Tetrahedron Lett. 2008;49:3376–3379. doi: 10.1016/j.tetlet.2008.03.126. [DOI] [Google Scholar]

[CR21] [7].Gupton J. T., Telang N., Jia X., Giglio B. C., Eaton J. E., Barelli P. J., Hovaizi M., Hall K. E., Welden R. S., Keough M. J., Worrall E. F., Finzel K. L., Kluball E. J., Kanters R., Smith T. M., Smith S. Q., Nunes S. R., Wright M. T., Birnstihl J. M. Tetrahedron. 2010;66:8485–8493. doi: 10.1016/j.tet.2010.08.075. [DOI] [PMC free article] [PubMed] [Google Scholar]

[CR22] [8] (a).Cao M. M., Zhang Y., He H. P., Huang S. D., Chen D. Z., Tang G. H., Li S. L., Di Y. T., Hao X. J. J. Nat. Prod. 2012;75:1076–1082. doi: 10.1021/np200960z. [DOI] [PubMed] [Google Scholar]

[CR23] [8] (b).Solis P. N., Wright C. W., Anderson M. M., Gupta M. P., Phillipson J. D. Planta Med. 1993;59:250–252. doi: 10.1055/s-2006-959661. [DOI] [PubMed] [Google Scholar]

[CR24] [9].Mosmann T. J. Immunol Methods. 1983;65:55–63. doi: 10.1016/0022-1759(83)90303-4. [DOI] [PubMed] [Google Scholar]

[CR25] [10] (a).Xu S. Y., Bian R. L., Chen X. Pharmacological Experiment Methodology. 3rd ed. Beijing: People’s Medical Publishing House; 2002. pp. 1647–1719. [Google Scholar]

[CR26] [10] (b).Tang G. H., Zhang Y., Gu Y. C., Li S. F., Di Y. T., Wang Y. H., Yang C. X., Zuo G. Y., Li S. L., He H. P., Hao X. J. J. Nat. Prod. 2012;75:996–1000. doi: 10.1021/np3001128. [DOI] [PubMed] [Google Scholar]

[CR27] [11].Sheldrick, G. M. SHELXL97, University of Göttingen: Göttingen, Germany, 1997.

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Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum

Ming-Ming Cao

Hong-Ping He

Yu-Cheng Gu

Qiang Zhang

Xiao-Nian Li

Guo-Ying Zuo

Ying-Tong Di

Chun-Mao Yuan

Shun-Lin Li

Yu Zhang

Xiao-Jiang Hao

Graphical abstract

Electronic Supplementary Material

Electronic supplementary material

Footnotes

Contributor Information

References

Associated Data

Supplementary Materials

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Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum

Ming-Ming Cao

Hong-Ping He

Yu-Cheng Gu

Qiang Zhang

Xiao-Nian Li

Guo-Ying Zuo

Ying-Tong Di

Chun-Mao Yuan

Shun-Lin Li

Yu Zhang

Xiao-Jiang Hao

Graphical abstract

Electronic Supplementary Material

Electronic supplementary material

Footnotes

Contributor Information

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

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