海洋天然产物片螺素及其相关吡咯生物碱近期研究进展

doi:10.5246/jcps.2011.05.054

海洋天然产物片螺素及其相关吡咯生物碱近期研究进展

范爱丽, 林文翰, 贾彦兴^*

北京大学医学部天然药物及仿生药物国家重点实验室, 北京 100191

收稿日期:2011-04-12 修回日期:2011-07-10 出版日期:2011-09-20 发布日期:2011-09-20
通讯作者: 贾彦兴*

Recent progress in the research on lamellarins and related pyrrole-derived alkaloids from marine organisms

Ai-Li Fan, Wen-Han Lin, Yan-Xing Jia^*

State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Science Center, Beijing 100191, China

Received:2011-04-12 Revised:2011-07-10 Online:2011-09-20 Published:2011-09-20
Contact: Yan-Xing Jia*

摘要/Abstract

摘要： 片螺素(lamellarin)及其相关的吡咯生物碱是一类从海洋生物中分离得到的具有新颖结构和显著生物活性的海洋生物碱。其结构特征是都具有3,4-二芳基-2-酸酯或酰胺母核。本综述概述了近期关于lamellarin及其相关吡咯生物碱的提取分离、全合成、生物活性及其构效关系等方面的研究。

关键词: 片螺素, 海洋生物碱, 合成, 生物活性

Abstract: Lamellarins and related pyrrole-derived alkaloids are a large family of marine alkaloids with novel structures and promising bioactivities. They have been isolated from diverse marine organisms and all of them feature a 3,4-diarylpyrrole 2-carboxylic acid ester or amide moiety. This article provides an overview of recent literatures on lamellarins and related pyrrole-derived alkaloids, including their isolation, total synthesis, biological and structure activity relationship (SAR) studies.

Key words: Lamellarin, Marine alkaloids, Synthesis, Bioactivities

中图分类号:

R916.41

Supporting:

Foundation items: National Natural Science Foundation of China (Grant No. 30930109, 20972007, 20802005), the National Basic Research Program of China (973 Program, Grant No. 2010CB833200), and NCET (Program for New Century Excellent Talents in University).
^*Corresponding author. Tel.: 86-10-82805166

范爱丽, 林文翰, 贾彦兴^*. 海洋天然产物片螺素及其相关吡咯生物碱近期研究进展[J]. , DOI: 10.5246/jcps.2011.05.054.

Ai-Li Fan, Wen-Han Lin, Yan-Xing Jia^*. Recent progress in the research on lamellarins and related pyrrole-derived alkaloids from marine organisms[J]. , DOI: 10.5246/jcps.2011.05.054.

参考文献

[1] Andersen, R.J.; Faulkner, D.J.; He, C.; Van Duyne, G.D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492-5495.
[2] Urban, S.; Hickford, S.J.H.; Blunt, J.W.; Munro, M.H.G. Curr. Org. Chem. 2000, 4, 765-807.
[3] Bowden, B.F. Stud. Nat. Prod. Chem. 2000, 23, 233-283.
[4] Bailly, C. Anti-Cancer Agents. Med. Chem. 2004, 4, 363-378.
[5] Cironi, P.; Albericio, F.; Álvarez, M. Prog. Heterocycl. Chem. 2004, 16, 1-26.
[6] Yang, G.; Wang, A.L.; Chen, H.L.; You, Y.C. Chin. J. Org. Chem. 2005, 25, 641-653.
[7] Handy, S.T.; Zhang, Y.A. Org. Prep. Proced. Int. 2005, 37, 411-445.
[8] Fan, H.; Peng, J.; Hamann, M.T.; Hu, J.F. Chem. Rev. 2008, 108, 264-287.
[9] Pla, D.; Albericio, F.; Álvarez, M. Anti-Cancer Agents Med. Chem. 2008, 8, 746-760.
[10] Fan, G.; Li, Z.; Shen, S.; Zeng, Y.; Yang, Y.; Xu, M.; Bruhn, T.; Bruhn, H.; Morschhäuser, J.; Bringmann, G.; Lin, W. Bioorg. Med. Chem. 2010, 18, 5466-5474.
[11] Lu, Y.; Arndtsen, B.A. Org. Lett. 2009, 11, 1369-1372.
[12] Li, Q.; Fan, A.; Lu, Z.; Cui, Y.; Lin, W.; Jia, Y. Org. Lett. 2010, 12, 4066-4069.
[13] Li, Q.; Jiang, J.; Fan, A.; Cui, Y.; Jia, Y. Org. Lett. 2011, 13, 312-315.
[14] Liermann, J.C.; Opatz, T. J. Org. Chem. 2008, 73, 4526-4531.
[15] Yasui, E.; Wada, M.; Takamura, N. Tetrahedron Lett. 2009, 50, 4762-4765.
[16] Gupton, J.T.; Banner, E.J.; Sartin, M.D.; Coppock, M.B.; Hempel, J.E.; Kharlamova, A.; Fisher, D.C.; Giglio, B.C.; Smith, K.L.; Keough, M.J.; Smith, T.M.; Kanters, R.P.F.; Dominey, R.N.; Sikorski, J.A. Tetrahedron. 2008, 64, 5246-5253.
[17] Gupton, J.T.; Giglio, B.C.; Eaton, J.E.; Rieck, E.A.; Smith, K.L.; Keough, M.J.; Barelli, P.J.; Firich, L.T.; Hempel, J.E.; Smith, T.M.; Kanters, R.P.F. Tetrahedron. 2009, 65, 4283-4292.
[18] Yadav, J.S.; Gayathri, K.U.; Reddy, B.V.S.; Prasad, A.R. Synlett. 2009, 43-46.
[19] Chen, L.; Xu, M.H. Adv. Synth. Catal. 2009, 351, 2005-2012.
[20] Zhang, P.Y.; Wong, I.L.K.; Yan, C.S.W.; Zhang, X.Y.; Jiang, T.; Chow, L.M.C.; Wan, S.B. J. Med. Chem. 2010, 53, 5108-5120.
[21] Shen, L.; Yang, X.; Yang, B.; He, Q.; Hu, Y. Eur. J. Med. Chem. 2010, 45, 11-18.
[22] Hasse, K.; Willis, A.C.; Banwell, M.G. Eur. J. Org. Chem. 2011, 88-99.
[23] Fukuda, T.; Sudo, E.I.; Shimokawa, K.; Iwao, M. Tetrahedron. 2008, 64, 328-338.
[24] Zhang, Y.; Handy, S.T. Open Org. Chem. J. 2008, 2, 58-64.
[25] Ohta, T.; Fukuda, T.; Ishibashi, F.; Iwao, M. J. Org. Chem. 2009, 74, 8143-8153.
[26] Baunbæk, D.; Trinkler, N.; Ferandin, Y.; Lozach, O.; Ploypradith, P.; Rucirawat, S.; Ishibashi, F.; Iwao, M.; Meijer, L. Mar. Drugs. 2008, 6, 514-527.
[27] Thipnate, P.; Liu, J.; Hannongbua, S.; Hopfinger, A.J. J. Chem. Inf. Mod. 2009, 49, 2312-2322.
[28] Pla, D.; Francesch, A.; Calvo, P.; Cuevas, C.; Aligué, R.; Albericio, F.; Álvarez, M. Bioconjug. Chem. 2009, 20, 1100-1111.
[29] Pla, D.; Martí, M.; Farrera-Sinfreu, J.; Pulido, D.; Francesch, A.; Calvo, P.; Cuevas, C.; Royo, M.; Aligué, R.; Albericio, F.; Álvarez, M. Bioconjug. Chem. 2009, 20, 1112-1121.
[30] Kluza, J.; Gallego, M.A.; Loyens, A.; Beauvillian, J.C.; Sousa-Faro, J.M.; Cuevas, C.; Marchetti, P.; Bailly, C. Cancer Res. 2006, 66, 3177-3187.
[31] Ballot, C.; Kluza, J.; Martoriati, A.; Nyman, U.; Formstecher, P.; Joseph, B.; Bailly, C.; Marchetti, P. Mol. Cancer Ther. 2009, 8, 3307-3317.
[32] Ballot, C.; Kluza, J.; Lancel, S.; Martoriati, A.; Hassoun, S.M.; Mortier, L.; Vienne, J.C.; Briand, G.; Formstecher, P.; Bailly, C.; Nevière, R.; Marchetti, P. Apoptosis. 2010, 15, 769-781.
[33] Barthomeuf, C.; Bourguet-Kondracki, M.L.; Kornprobst, J.M. Anti-Cancer Agents Med. Chem. 2008, 8, 886-903.