Recent Research Progress in Anticancer Alkaloid Lamellarin N and Lamellarin L

doi:10.6023/cjoc201209034

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 483-491.DOI: 10.6023/cjoc201209034 Previous Articles Next Articles

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抗肿瘤生物碱Lamellarin N和Lamellarin L的研究进展

王爱玲^a,d, 赵壮志^a,b, 郑学仿^b,c, 曹洪玉^b,c

a 大连大学环境与化学工程学院大连 116622;
b 大连大学辽宁省生物有机化学重点实验室大连 116622;
c 大连大学生物工程学院大连 116622;
d 东北农业大学农学院哈尔滨 150030

收稿日期:2012-09-24 修回日期:2012-10-16 发布日期:2012-10-26
通讯作者: 郑学仿 E-mail:dlxfzheng@126.com
基金资助:
国家自然科学基金(No. 20871024)、辽宁省优秀人才培养计划(No. RC-04-10)、大连市优秀青年科技人才基金(No. 2009J22DW038)资助项目.

Recent Research Progress in Anticancer Alkaloid Lamellarin N and Lamellarin L

Wang Ailing^a,d, Zhao Zhuangzhi^a,b, Zheng Xuefang^b,c, Cao Hongyu^b,c

a College of Environment and Chemical Engineering, Dalian University, Dalian 116622;
b Liaoning Key Laboratory of Bio-organic Chemistry, Dalian University, Dalian 116622;
c College of Bioengineering, Dalian University, Dalian 116622;
d College of Agronomy, Northeast Agricultural University, Harbin 150030

Received:2012-09-24 Revised:2012-10-16 Published:2012-10-26
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20871024), the Talents Training Plan of Liaoning Province (No. RC-04-10) and the Outstanding Young Talent Fund from the Dalian Science and Technology Bureau (No. 2009J22DW038).

Lamellarins, a family of hexacyclic pyrrole alkaloids, originally isolated from marine invertebrates, display promising activities. The lamellarin N (LMN) is a member of the lamenllarin compounds. LMN exhibits a significant cytotoxicity against a large panel of cancer cell lines and potent inhibitors of various protein kinases which is better than lamellarin D (LMD). LMN and lamellarin L (LML) are similar in structure and activity. Therefore, the isolation, synthesis, biological activity and anti-cancer activity mechanism of LMN and LML are summarized.

Key words: lamellarin N, lamellarin L, protein kinases inhibitor, cytotoxic activity, chemical synthesis

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Wang Ailing, Zhao Zhuangzhi, Zheng Xuefang, Cao Hongyu. Recent Research Progress in Anticancer Alkaloid Lamellarin N and Lamellarin L[J]. Chin. J. Org. Chem., 2013, 33(03): 483-491.

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References

[1] Banwell, M. G.; Flynn, B. L. CN 1307580, 2001 [Chem. Abstr. 1999, 132, 50151].

[2] Yang, G.; Wang, A. L.; Chen, H. L.; You, Y. C. Chin. J. Org. Chem. 2005, 25, 641 (in Chinese).
(杨光, 王爱玲, 陈惠麟, 由业诚, 有机化学, 2005, 25, 641.)

[3] Baily, C.; Francesch, S.; Mateourbano, M. C.; Jimenez, G. J.; Pastordel Castillo, A.; Cuevas Marchante, C. CN 1688585, 2005 [Chem. Abstr. 2004, 140, 199492].

[4] Davidson, B, S. Chem. Rev. 1993, 93, 1771.

[5] Fan, H.; Peng, J.; Hamann, M. T.; Hu, L. F. Chem. Rev. 2008, 108, 264.

[6] Bailly, C. Curr. Med. Chem: Anti-Cancer Agents 2004, 4, 363.

[7] Andersen, R. J.; Faulkner, D. J.; Cun-heng, H.; Van Duyne, G. G.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492.

[8] You, Y. C.; Wang, A. L.; Li, D. P.; Yang, G. Biomed. Mater. 2006, 1, L7.

[9] You, Y. C.; Yang, G.; Wang, A. L.; Li, D. P. Curr. Appl. Phys. 2005, 5, 535.

[10] Gong, B. H.; Li, D. P.; Chen, H. B.; You, Y. C. Chem. Res. Appl. 2006, 18, 1209 (in Chinese).
(宫本海, 李德鹏, 陈宏博, 由业诚, 化学研究与应用, 2006, 18, 1209.)

[11] He, Y. R.; You, Y. C.; Hu, J. H.; Wang, A. L.; Yu, X. S.; Hu, D. H. Biomed. Mater. 2007, 2, 102.

[12] He, Y. R.; Li, D. P.; Yang, G.; Wang, A. L.; You, Y. C.; Hu, D. H.; Yu, X. S. Chin. J. Nat. Med. 2007, 5, 150 (in Chinese).
(何宇荣, 李德鹏, 杨光, 王爱玲, 由业诚, 胡代花, 于小松, 中国天然药物, 2007, 5, 150.)

[13] Wang, A. L.; Han, R.; Zhang, X. H.; Hu, J. H.; You, Y. C. Chem. Res. Appl. 2009, 21, 1335 (in Chinese).
(王爱玲, 韩闰, 张晓辉, 胡皆汗, 由业诚, 化学研究与应用, 2009, 21, 1335.)

[14] Liao, S. H.; Li, D. P.; Liu, R.; Wang, A. L. Chem. Res. Appl. 2011, 23, 961 (in Chinese).
(廖少寒, 李德鹏, 刘冉, 王爱玲, 化学研究与应用, 2011, 23, 961.)

[15] Kluza, J.; Gallego, M.-A.; Loyens, A.; Beauvillain, J.-C.; Sousa-Faro, J.-F.; Cuebas, C.; Marchetti, P.; Bailly, C. Cancer Res. 2006, 66, 3177.

[16] Facompré, M.; Tardy, C.; Bal-Mahieu, C.; Colson, P.; Perez, C.; Manzanares, I.; Cuevas, C.; Bailly, C. Cancer Res. 2003, 63, 7392.

[17] Dias, N.; Vezin, H.; Lansiaux, A.; Bailly, C. Top. Curr. Chem. 2005, 253, 89.

[18] You, Y. C.; Hu, D. H.; Li, D. P.; Wang, A. L.; Yu, X. S. Chin. J. Org. Chem. 2008, 28, 797(in Chinese).
(由业诚, 胡代花, 李德鹏, 王爱玲, 于小松, 有机化学, 2008, 28, 797.)

[19] Chittchang, M.; Batsomboon, P.; Ruchirawat, S.; Ploypradith, P. Chem. Med. Chem. 2009, 4, 457.

[20] Shen, L.; Hu, Y. Chin. J. Org. Chem. 2009, 29, 867.

[21] Fukuda, T.; Ishibashi, F.; Iwao, M. Heterocycles 2011, 83, 491.

[22] Pla, D.; Albericio, M.; Alvarez, M. Med. Chem. Commun. 2011, 2, 689.

[23] Carroll, A. R.; Bowden, B. F.; Coll, J. C. Aust. J. Chem. 1993, 46, 489.

[24] Venkata, M.; Reddy, M. V. R.; Faulkner, D. J.; Venkateswarlu, Y.; Rao, M. R. Tetrahedron 1997, 53, 3456.

[25] Urban, S.; Hobbs, L.; Hooper, J. N. A.; Capon, R. J. Aust. J. Chem. 1995, 48, 1491.

[26] Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147.

[27] Cironi, P.; Manzanares, I.; Albericio, F.; Alvarez, M. Org. Lett. 2003, 5, 2959.

[28] Ploypradith, P.; Mahidol, C.; Sahakitpichan, P.; Wongbundit, S.; Ruchirawat, S. Angew. Chem., Int. Ed. 2004, 43, 866.

[29] Fujikawa, N.; Ohta, T.; Yamaguchi, T.; Fukuda, T.; Ishibashi, F.; Iwao, M. Tetrahedron 2006, 62, 594.

[30] Chen, L.; Xu, M. H. Adv. Synth. Catal. 2009, 351, 2005.

[31] Shen, L.; Yang, X.; Yang, B.; He, Q.; Hu, Y. Eur. J. Med. Chem. 2010, 45, 11.

[32] Li, Q.; Jiang, J.; Fan, A.; Cui, Y.; Jia, Y. Org. Lett. 2011, 13, 312.

[33] Korotaev, V. Y.; Sosnovskikh, V. Y.; Barkov, A. Y.; Slepukhin, P. A.; Ezhikova, M. A.; Kodess, M. I.; Shklyaev, Y. V. Tetrahedron 2011, 67, 8685.

[34] Flynn, B.L.; Banwell, M. G. ChemInform 2012, 43, 22.

[35] Quesada, A. R.; Gravalos, M. D. G.; Puentes, J. L. F. Br. J. Cancer 1996, 74, 677.

[36] Reddy, M. V. R.; Faulkner, D. J.; Venkateswarlu, Y. Tetrahedron 1997, 53, 3457.

[37] Cantrell, C. L.; Groweiss, A.; Gustafson, K. R.; Boyd, M. R. Nat. Prod. Lett. 1999, 14, 39.

[38] Reddy, M. V. R.; Rao, M. R.; Hansen, M. S. T.; Rubins, K.; Bushman, F. D.; Venkateswarlu, Y.; Faulkner, D. J. J. Med. Chem. 1999, 42, 1901.

[39] Ham, J.; Kang, H. Bull. Korean Chem. Soc. 2002, 23, 163.

[40] Ridley, C. P.; Reddy, M. V. R.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285.

[41] Tardy, C.; Facompre, M.; Laine, W.; Baldeyrou, B.; Garcia-Gravalos, D.; Francesch, A.; Mateo, C.; Pastor, A.; Jimenez, J. A.; Manzanares, I.; Bailly, C. Bioorg. Med. Chem. 2004, 12, 1697.

[42] Reddy, S. M.; Srinivasulu, M.; Satyanaranyana, N.; Kondapi, A. K.; Venkateswarlu, Y. Tetrahedron 2005, 61, 9242.

[43] Ozols, R. F.; Cunnion, R. E.; Kleker, R. W. J. Clin. Oncol. 1987, 5, 641.

[44] Mirski, S. E. L.; Gerlach, J. H.; Cole, S. P. C. Cancer Res. 1987, 47, 2594.

[45] Cole, S. P. C.; Chanda, E. R.; Dicke, F. P.; Gerlach, J. H.; Mirski, S. E. L. Cancer Res. 1991, 51, 3345.

[46] Evans, C. D.; Mirski, S. E. L.; Danks, M. K.; Cole, S. P. C. Cancer Chemother. Pharmacol. 1994, 34, 242.

[47] Cole, S. P. C.; Bhardwaj, G.; Gerlach, J. H.; Mackie, J. E.; Grant, C. E.; Almquist, K. C.; Stewart, A. J.; Kurz, E. U.; Duncan, M. V.; Deelet, R. G. Science 1992, 258, 1650.

[48] Hipfne, D. R.; Gauldie, S. D.; Deeley, R. G.; Cole, S. P. C. Cancer Res. 1994, 54, 5788.

[49] Baunbæk, D.; Trinkler, N.; Ferandin, Y.; Lozach, O.; Ploypradith, P.; Rucirawat, S.; Ishibashi, F.; Iwao, M.; Meijer, L. Mar. Drugs 2008, 6, 514.

[50] Bach, S.; Knockaert, M.; Lozach, O.; Reinhardt, J.; Baratte, B.; Schmitt, S.; Coburn, S. P.; Tang, L.; Jiang, T.; Liang, D. C.; Gallons, H.; Dierick, J. F.; Totzke, F.; Meijer, L. J. Biol. Chem. 2005, 280, 31208.

[51] Beetayeb, K.; Oumata, N.; Echalier, A.; Ferandin, Y.; Endicott, J.; Galons, H.; Meijer, L. Oncogene 2008, 27, 5759.

[52] Nguyen, M.; Marcellus, R. C.; Roulston, A.; Watson, M.; Serfass, L.; Murthy Madiraju, S. R.; Goulet, D.; Viallet, J.; Billot, X.; Acoca, E.; Purisima, E.; Johnstone, R. W.; Beauparlant, P.; Shore, G. C. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 19512.

[53] Yadav, J. S.; Gayathri, K. U.; Reddy, B. V.; Subba, P. Synlett 2009, 43.

[54] Liermann, J. C.; Opatz, T. J. Org. Chem. 2008, 73, 4526.

[55] 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.
[56] Hasse, K.; Willis, A. C.; Banwell, M. G. Eur. J. Org. Chem. 2011, 76, 88.

抗肿瘤生物碱Lamellarin N和Lamellarin L的研究进展

Recent Research Progress in Anticancer Alkaloid Lamellarin N and Lamellarin L

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