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

doi:10.5246/jcps.2011.05.054

Abstract

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

CLC Number:

R916.41

Supporting:

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.

References

[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.