Chinese Journal of Organic Chemistry >
Progresses in the Total Synthesis and Structure Modification Studies of Lycorine
Received date: 2014-09-24
Revised date: 2014-10-29
Online published: 2014-12-10
Supported by
Project supported by the Harbin University of Commerce Doctoral Research Project (No.14LG12) and the Natural Science Fund for Young Teachers of Harbin University of Commerce (No.HCUL2013019).
Lycorine is a very important class of isoquinoline alkaloids of the amaryllidaceae alkaloids. In recent years, pharmaceutical and organic chemists discovered that lycorine and their derivatives have anti-tumor, anti-inflammatory, inhibiting acetylcholinesterase, anti-malarial, cardiovascular protection and other effects. Because of its complex and unique molecular structure and extensive pharmaceutical activities, lycorine has attracted considerable research effort. The recent progresses in the synthesis and structural modification of lycorine are summarized in this review.
Key words: lycorine; total synthesis; derivatives; structure modification
Liu Yingjie , Ding Zeyang , Tan Chong , Yuan Hongliang , Ji Yubin . Progresses in the Total Synthesis and Structure Modification Studies of Lycorine[J]. Chinese Journal of Organic Chemistry, 2015 , 35(5) : 1009 -1021 . DOI: 10.6023/cjoc201409038
[1] Huang, B. X.; Fu, S. G.; Zhu, P. L. Jiangxi Forestry Sci. Technol. 2012, 40(1), 22 (in Chinese).
(黄宝祥, 符树根, 朱培林, 江西林业科技, 2012, 40(1), 22.)
[2] Cook, J. W.; Loudon, J. D. In The Alkaloids, Eds.: Manske, R. H. F.; Holmes, H. L., Academic Press, New York, 1952, Vol. II, pp. 331~352.
[3] Kondo, H.; Uyeo, S. Chem. Ber. 1935, 68, 1756.
[4] Nakagawa, Y.; Uyeo, S. J. Chem. Soc. 1959, 3736.
[5] Lamoral-Theys, D.; Decaestecker, C.; Mathieu, V.; Dubois, J.; Kornienko, A.; Kiss, R.; Evidente, A.; Potter, L. Mini-Rev. Med. Chem. 2010, 10, 41.
[6] Cedron, J. C.; Gutierrez, D.; Flores. N.; Ravelo, A. G.; Estevez- Braun, A. Bioorg. Med. Chem. 2010, 18, 4694.
[7] Toriizuka, Y.; Kinoshita, E.; Kogure, N.; Kitajima, M.; Ishiyama, A.; Otoguro, K.; Yamada, H.; Omura, S.; Takayama, H. Bioorg. Med. Chem. 2008, 16, 10182.
[8] Citoglu, G.; Tanker, M.; Gumusel, B. Phytother. Res. 1998, 12, 205.
[9] Tanker, M.; Citoglu, G.; Gumuhel, B.; Hener, B. Int. J. Pharmacogn. 1996, 34, 194.
[10] Kretzing, S.; Abrahama, G.; Seiwert, B.; Ungemach, F. R.; Krugel, U.; Regenthal, R. Toxicon 2011, 57, 117.
[11] Hwang, Y. C.; Chu, P. L.; Yang, W.; Chen, W.; Yates, M. V. Antiviral Res. 2008, 77, 232.
[12] Li, S. Y.; Chen, C.; Zhang, H.; Guo, H.; Wang, H.; Wang, L.; Zhang, X.; Hua, S.; Yu, J.; Xiao, P.; Li, R.; Tan, X. Antiviral Res. 2005, 67, 18.
[13] Renard-Nozaki, J.; Kim, T.; Imakura, Y.; Kihara, M.; Kobayashi, S. Res. Virol. 1989, 140, 115.
[14] Zhou, M.; Deng, L.; Kashanchi, F.; Brady, J. N.; Shatkin, A. J.; Kumar, A. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 12666.
[15] Gabrielsen, B.; Monath, T. P.; Huggins, J. W.; Kefauver, D. F. J. Nat. Prod. 1992, 55, 1569.
[16] Liu, J.; Li, Y.; Tang, L. J; Zhang, G. P.; Hu, W. X. Biomed. Pharmacother. 2007, 61, 229.
[17] Min, B. S.; Gao, J. J.; Nakamura, N.; Kim, Y. H.; Hattori, M. Chem. Pharm. Bull. 2001, 49, 1217.
[18] Cao, Z.; Yu, D.; Fu, S.; Zhang, G.; Pan, Y.; Bao, M,; Tu, J.; Shang, B.; Guo, P.; Yang, P.; Zhou, Q. Toxicol. Lett. 2013, 218, 174.
[19] Chapsal, B. D.; Ojima, I. Org. Lett. 2006, 8, 1395.
[20] Fujioka, H.; Murai, K.; Ohba, Y.; Hirose, H.; Kita, Y. Chem. Commun. 2006, 832;
[21] Dong, L.; Xu, Y. J.; Cun, L. F.; Cui, X.; Jiang, Y. Z.; Gong, L. Z. Org. Lett. 2005, 7, 4285;
[22] Banwell, M. G.; Harvey, J. E.; Hockless, D. C. R. J. Org. Chem. 2000, 65, 4241.
[23] Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933.
[24] Trossell, K. Tetrahedron Lett. 1974, 623.
[25] Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K.; Hamada, Y.; Kotera, K.; Iitaka, Y. Tetrahedron 1984, 40, 1783.
[26] Møller, O.; Steinberg, E. M.; Torssell, K. Acta Chem. Scand. Sect. B 1978, 32, 98.
[27] Yamada, K.; Yamashita, M.; Sumiyoshi, T.; Ni-Shimura, K.; Tomioka, K. Org. Lett. 2009, 11, 1631.
[28] Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341.
[29] Sun, Z. W.; Zhou, M. T.; Li, X.; Meng, X. L.; Peng, F. Z.; Zhang, H. B.; Shao, Z. H. Chem. Eur. J. 2014, 20, 6112.
[30] Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210.
[31] Pozsgay, V.; Ohgi, T.; Hecht, S. M. J. Org. Chem. 1981, 46, 3763.
[32] Boeckman, R. J.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250.
[33] Elgorash, E. E.; Stafford, G. I.; Van Staden, J. Planta Med. 2004, 70(3), 260.
[34] Wang, P.; Li, L. F.; Wang, Q. Y.; Shang, L. Q.; Shi, P. Y.; Yin, Z. ChemMedChem 2014, 9, 1522.
[35] Tan, C. X.; Schrader, K. K.; Mizuno, C. S.; Rimando, A. M. J. Agric. Food Chem. 2011, 59, 5977.
[36] Evdokimov, N. M.; Theys, D. L.; Mathieu, V.; Andolfi, A.; Frolova, L. V.; Pelly, S. C.; Otterlo, W.; Magedov, I. V.; Kiss, R.; Evidente, A.; Kornienko, A. Bioorg. Med. Chem. 2011, 19, 7252.
[37] Dasari, R.; Banuls, L. M.; Masi, M.; Pelly, S. C.; Mathieu, V.; Green, I. R.; Otterlo, W. A. L.; Evidente, A.; Kiss, R.; Kornienko, A. Bioorg. Med. Chem. Lett. 2014, 24, 923.
[38] Giordani, R. B.; Junior, C. O. R.; Andrade, J. P.; Bastida, J.; Zuanazzi, J. A.; Tasca, T.; Almeida, M. V.; Chem. Biol. Drug Des. 2012, 80, 129.
[39] Lamora-Theys, D.; Andolfi, A.; Goietsenoven, G. V.; Cimmino, A.; Calve, B. L.; Wauthoz, N.; Megalizzi, V.; Gras, T.; Bruyere, C.; Dubois, J.; Mathieu, V.; Kornienko, A.; Kiss, R.; Evidente, A. J. Med. Chem. 2009, 52, 6244.
[40] Munulty, J.; Nair, J.; Little, J.; Brennan, J.; Bastida, J. Bioorg. Med. Chem. Lett. 2010, 20, 5290.
[41] Toriizuka, Y.; Kinoshita, E.; Kogure, N.; Kitajima, M.; Ishiyama, A.; Otoguro, K.; Yamada, H.; Omura, S.; Takayama, H. Bioorg. Med. Chem. 2008, 16, 10182.
[42] Evidente, A.; Cicala, M. R.; Randazzo, G.; Riccio, R.; Calabrese, G.; Liso, R.; Arrigoni, O. Phytochemisry 1983, 22, 2193.
[43] Huang, W. J.; Singh, O. V.; Chen, C. H.; Chiou, S. Y.; Lee, S. S. Helv. Chim. Acta 2002, 85, 1069.
[44] Cedron, J. C.; Gutierrez, D.; Plores, N.; Ravelo, A. C.; Estevez, B. A. Bioorg. Med. Chem. 2010, 18, 4694.
[45] Lee, S. S.; Venkatesham, U.; Rao, C. P. R.; Lam, S. H.; Lin, J. H. Bioorg. Med. Chem. 2007, 15 1034.
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