Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum

doi:10.1007/s13659-012-0095-z

Natural Products and Bioprospecting ›› 2013, Vol. 3 ›› Issue (1): 29-32.DOI: 10.1007/s13659-012-0095-z

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Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum

Ming-Ming CAO^a,b, Hong-Ping HE^a, Yu-Cheng GU^c, Qiang ZHANG^d, Xiao-Nian LI^a, Guo-Ying ZUO^e, Ying-Tong DI^a, Chun-Mao YUAN^a, Shun-Lin LI^a, Yu ZHANG^a, Xiao-Jiang HAO^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China;
c Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire, RG426 EY, UK;
d Northwest A & F University, Yangling 712100, China;
e Research Center of Natural Medicine, Clinical School of Kunming General Hospital of Chengdu Military Command, Kunming 650032, China

Received:2012-11-30 Revised:2013-02-16 Online:2018-02-11 Published:2013-02-24

Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum

Ming-Ming CAO^a,b, Hong-Ping HE^a, Yu-Cheng GU^c, Qiang ZHANG^d, Xiao-Nian LI^a, Guo-Ying ZUO^e, Ying-Tong DI^a, Chun-Mao YUAN^a, Shun-Lin LI^a, Yu ZHANG^a, Xiao-Jiang HAO^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China;
c Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire, RG426 EY, UK;
d Northwest A & F University, Yangling 712100, China;
e Research Center of Natural Medicine, Clinical School of Kunming General Hospital of Chengdu Military Command, Kunming 650032, China

通讯作者: Xiao-Jiang HAO,E-mail:haoxj@mail.kib.ac.cn;Yu ZHANG,E-mail:zhangyu@mail.kib.ac.cn

Abstract

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.

Key words: Daphniphyllaceae, Daphniphyllum macropodum, cyclopentadienyl anion

摘要： 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.

关键词: Daphniphyllaceae, Daphniphyllum macropodum, cyclopentadienyl anion

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. Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum[J]. Natural Products and Bioprospecting, 2013, 3(1): 29-32.

References

[1] (a) Yamamura, S.; Irikawa, H.; Okumura, Y.; Hirata, Y. Bull. Chem. Soc. Jpn. 1975, 48, 2120-2123. (b) Kobayashi, J.; Morita, H. In The Alkaloids; Cordell G. A., Ed.; Academic Press:New York, 2003, vol. 60, pp. 165-205. (c) Yamamura, S. In The Alkaloids; Brossi, A., Ed.; Academic Press:New York, 1986, vol. 29, pp. 256-286. (d) Kobayashi, J.; Kubota, T. Nat. Prod. Rep. 2009, 26, 936-962.
[2] (a) Heathcock, C. H. Angew. Chem. 1992, 104, 675-691. (b) Heathcock, C. H. Proc. Natl. Acad. Sci. USA. 1996, 93, 14323-14327. (c) Wallace, G. A.; Heathcock, C. H. J. Org. Chem. 2001, 66, 450-454. (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. (d) Xu, C.; Wang, L.; Hao, X. J.; Wang, D. Z. G. J. Org. Chem. 2012, 77, 6307-6313.
[3] (a) Niwa, H.; Hirata, Y.; Suzuki, K. T.; Yamamura, S. Tetrahedron Lett. 1973, 14, 2129-2132. (b) Suzuki, K. T.; Okuda, S.; Niwa, H.; Toda, M.; Hirata, Y.; Yamamura, S. Tetrahedron Lett. 1973, 14, 799-802.
[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. (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. (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. (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.
[5] Kobayashi, J.; Inaba, Y.; Shiro, M.; Yoshida, N.; Morita, H. J. Am. Chem. Soc. 2001, 123, 11402-11408.
[6] (a)Yang, S. P.; Yue, J. M. Org. Lett. 2004, 6, 1401-1404; (b) Gan, X. W.; Bai, H. Y.; Chen, Q. G.; Ma, L.; Hu, L. H. Chem. Biodivers. 2006, 3, 1255-1259; (c) Zhang, W.; Guo, Y. W.; Krohn, K. Chem. Eur. J. 2006, 12, 5122-5127. (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.
[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.
[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. (b) Solis, P. N.; Wright, C. W.; Anderson, M. M.; Gupta, M. P.; Phillipson, J. D. Planta Med. 1993, 59, 250-252.
[9] Mosmann, T. J. Immunol Methods 1983, 65, 55-63.
[10] (a) Xu, S. Y.; Bian, R. L.; Chen, X. Pharmacological Experiment Methodology, 3rd ed; People's Medical Publishing House:Beijing, 2002, pp. 1647-1719. (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.
[11] Sheldrick, G. M. SHELXL97, University of Gottingen:Gottingen, Germany, 1997.

Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum

Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum

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