抗霉素A结构改造的研究进展
收稿日期: 2017-02-09
修回日期: 2017-03-03
网络出版日期: 2017-03-08
基金资助
国家自然科学基金(Nos.21472063,21502062)、湖北省教育厅一般项目(No.Q20102606)、襄阳市科技局一般项目(No.2010GG1B33)和低维光电材料与器件湖北省重点实验室(No.HLOM151005)资助项目.
Research Progress in Structural Modification of Antimycin A
Received date: 2017-02-09
Revised date: 2017-03-03
Online published: 2017-03-08
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21472063, 21502062), the Hubei Provincial Department of Education (No. Q20102606), the Xiangyang Science and Technology Bureau (No. 2010GG1B33), and the Hubei Key Laboratory of Low Dimensional Optoelectronic Materials and Devices (No. HLOM151005).
程华 , 聂忍 , 汪万强 , 黄琳 , 刘科 , 陈宬 , 吴琼友 . 抗霉素A结构改造的研究进展[J]. 有机化学, 2017 , 37(6) : 1368 -1381 . DOI: 10.6023/cjoc201702010
Antimycin A is a class of natural products bearing a dilactone-ring moiety as the core skeleton. These compounds have been identified as specific inhibitors of the mitochondrial respiratory chain and bind to the Qi site of the cytochrome bc1 complex. Due to its unique structure and extremly high activity, it has aroused great interest of researchers. The development and biological activities of antimycin A are mainly described, and the recent results of its structural modifications are summarized.
Key words: antimycin A; inhibitor; biological activity; structural modification
[1] Leben, C.; Keitt, G. W. Phytopathology 1948, 38, 898.
[2] Yang, Y. Q.; Wu, Y. K. Chin. J. Org. Chem. 2006, 26, 1370 (in Chinese). (杨永青, 伍贻康, 有机化学, 2006, 26, 1370.)
[3] Dunshee, B. R.; Leben, C.; Keitt, G. W. Strong, F. M. J. Am. Chem. Soc. 1949, 71, 2436.
[4] Lockwood, J. L.; Leben, C.; Keitt, G. W. Phytopathology 1954, 44, 438.
[5] Yonehara, H.; Takeuchi, S. J. Antibiot. 1958, 11, 122.
[6] Liu, W. C.; Strong, F. M. J. Am. Chem. Soc. 1959, 81, 4387.
[7] Schilling, G.; Berti, D.; Kluepfel, D. J. Antibiot. 1970, 23, 81.
[8] Barrow, C. J.; Oleynek, J. J.; Marinelli, V.; Sun, H. H.; Kaplita, P.; Sedlock, D. M.; Gillum, A. M.; Chadwick, C. C.; Cooper, R. J. Antibiot. 1997, 50, 729.
[9] Shiomi, K.; Hatae, K.; Hatano, H.; Matsumoto, A.; Takahashi, Y.; Jiang, C. L.; Tomoda, H.; Kobayashi, S.; Tanaka, H.; ōmura, S. J. Antibiot. 2005, 58, 74.
[10] Hosotani, N.; Kumagai, K.; Nakagawa, H.; Shimatani, T.; Saji, I. J. Antibiot. 2005, 58, 460.
[11] Chen, G.; Lin, B.; Lin, Y.; Xie, F.; Lu, W.; Fong, W. F. J. Antibiot. 2005, 58, 519.
[12] Yan, L. L.; Han, N. N.; Zhang, Y. Q.; Yu, L.Y.; Chen, J.; Wei, Y. Z.; Li, Q. P.; Tao, L.; Zheng, G. H.; Yang, S. E.; Jiang, C. X.; Zhang, X. D.; Huang, Q.; Xugela, H.; Hu, Q. B.; Zhou, L.; Liu, S. W.; Zhang, Z. Z.; He, Q.Y.; Si, S. Y.; Sun, C. H. J. Antibiot. 2010, 63, 259.
[13] Wang, J. Y.; Wen, Y. M.; Chen, X. M.; Lin, Y. H.; Zhou, J. M.; Xie, Y.; Wang, H. W.; Jiang, H.; Zheng, Wei. J. Chromatogr. 2010, 1217, 5687.
[14] Yan, L. L.; Han, N. N.; He, Q. Y.; Chen, J.; Yang, S. E.; Liu, S. W.; Tao, L.; Guo, L.; Jin, J.; Yu, L. Y.; Zhang, Y. Q.; Sun, C. H. Chin. J. Antibiot. 2011, 36, 269 (in Chinese).(闫蕾蕾, 韩宁宁, 何琪杨, 陈杰, 阳素娥, 刘少伟, 陶玲, 郭琳, 靳婧, 余利岩, 张玉琴, 孙承航, 中国抗生素杂志, 2011, 36, 269.)
[15] Leben, C.; Keitt, G. W. Phytopathology 1948, 38, 898.
[16] Tan, H. S.; Che, Q.; Li, D. H.; Gu, Q. Q.; Zhu, T. J. Chin. J. Antibiot. 2015, 40, 892 (in Chinese).(谭洪升, 车茜, 李德海, 顾谦群, 朱天骄, 中国抗生素杂志, 2015, 40, 892.)
[17] Xu, L. Y.; Quan, X. S.; Wang, C.; Sheng, H. F.; Zhou, G. X.; Lin, B. R.; Jiang, R. W.; Yao, X. S. J Antibiot. 2011, 64, 661.
[18] Ishiyama, T.; Endo, T.; Otake, N.; Yonehara, H. J. Antibiot. 1976, 29, 804.
[19] Imamura, N.; Nishijima, M.; Adachi, K.; Sano, H. J. Antibiot. 1993, 46, 241.
[20] Hayashi, K. I.; Nozaki, H. J. Antibiot. 1999, 52, 325.
[21] Yao, C B. F.; Schiebel, M.; Helmke, E.; Anke, H.; Laatsch, H. Z. Naturforsch., B 2006, 61, 320.
[22] Strangman, W. K.; Kwon, H. C.; Broide, D.; Jensen, P. R.; Fenical, W. J. Med. Chem. 2009, 52, 2317.
[23] Schilling, G.; Berti, D.; Kluepfel, D. J. Antibiot. 1970, 23, 81.
[24] Rieske, J. S.; Lipton, S. H.; Baum, H.; Silman, H. I. J. Biol. Chem. 1967, 242, 4888.
[25] Wallace, K. B.; Starkov, A. A. Annu. Rev. Pharmacol. Toxicol. 2000, 40, 353.
[26] Zhang, Z. L.; Luang, L.; Shulmeister, V. M.; Chi, Y. I.; Kim, K. K.; Hung, L. W.; Croftsk, A. R.; Berry, E. A.; Kim, S. H. Nature 1998, 392, 677.
[27] Wang, G. H.; Lin, B. R.; Gao, X. Y.; Xie, S. D. J. Zhongkai Univ. Agric. Technol. 2006, 19, 55 (in Chinese).(王广华, 林壁润, 高向阳, 谢双大, 仲恺农业技术学院学报, 2006, 19, 55.)
[28] Tzung, S. P.; Kim, K. M.; Basañez, G.; Giedt, C. D.; Simon, J.; Zimmerberg, J.; Zhang, K. Y. J.; Hockenbery, D. M. Nat. Cell Biol. 2001, 3, 183.
[29] Sun, J.; Trumpower, B. L. Arch. Biochem. Biophys. 2003, 419, 198.
[30] Barrow, C. J.; Oleynek, J. J.; Marinelli, V.; Sun, H. H.; Kaplita, P.; Sedlock, D. M.; Gillum, A. M.; Chadwick, C. C.; Cooper, R. J. Antibiot, 1997, 50, 729.
[31] Qiu, X. Z.; Ou,Y. J; Yu, L.; Zhang, L. S.; Lu, Y. T.; Chen, Y. A.; Zhou, M.; Zhong, S. Z. Chin. J. Neuroanat. 2004, 20, 167 (in Chinese). (邱小忠, 欧阳钧, 余磊, 张黎声, 陆云涛, 陈瑗, 周玫, 钟世镇, 神经解剖学杂志, 2004, 20, 167.)
[32] Yeh, C. T.; Su, C. L.; F. Huang, C. Y. F.; Lin, J. K. Y.; Lee, W. H.; H. Chang, P. M. H.; Kuo, Y. L.; Liu, Y. W.; Wang, L. S.; Wu, C. H.; Shieh, Y. S.; Jan, Y. H.; Chuang, Y. J.; Hsiao, M.; Wu, A. T. H. J. Evidence-Based Complementary Altern. Med. 2013, 2013, 910451.
[33] Cui, S. N.; Qian, J.; Bo, P. Chin. J. Pharmacol. Toxicol. 2015, 29, 573 (in Chinese).(崔树娜,钱静,卜平,中国药理学与毒理学杂志,2015,29, 573.)
[34] Derse, P. H.; Strong, F. M. Nature 1963, 200, 600.
[35] Huang, L. S.; Cobessi, D.; Tung, E. Y.; Berry, E. A. J. Mol. Biol. 2005, 351, 573.
[36] Dickie, J. P.; Loomans, M. E.; Farley, T. M.; Strong, F. M. J. Med. Chem. 1963, 6, 424.
[37] Okumura, F. S.; Masumura, M.; Horie, T. J. Am. Chem. Soc.1959, 81, 5215.
[38] Selwood, D. L.; Livingstone, D. J.; Comley, J. C. W.; O'Dowd, A. B.; Hudson, A. T.; Jackson, P.; Jandu, K. S.; Rose, V. S. Stables, J. N. J. Med. Chem. 1990, 33, 136.
[39] Hayes, D. J.; O'Dowd, A. B.; Selwood, D. L.; Stables, J. N.; Comley, J. C. W.; Rees, M. J. Mol. Biochem. Parasitol. 1990, 38, 159.
[40] Tokutake, N.; Miyoshi, H.; Nakazato, H.; Iwamura, H. Biochim. Biophys. Acta 1993, 1142, 262.
[41] Miyoshi, H.; Tokutake, N.; Imaeda, Y.; Akagi, T.; Iwamura, H. Biochim. Biophys. Acta 1995, 1229, 149.
[42] Shenin, Y. D.; Belakhov, V. V.; Rozhkova, N. G. Khim. Farm. Zh. 1996, 30, 31.
[43] Fitzpatrick, G. M.; Orth, A. B.; Maurice, C. H.; Richard, B. R.; Werk, T. L.; Davis, G. E. US. 6333432, 2001[Chem. Abstr. 2001, 136, 53582].
[44] Bolgunas, S.; Clark, D. A.; Hanna, W. S.; Mauvais, P. A.; Pember, S. O. J. Med. Chem. 2006, 49, 4762.
[45] Pettit, G. R.; Smith, T. H., Feng, S., Knight, J. C.; Tan, R.; Pettit, R. K. Hinrichs P. A. J. Nat. Prod. 2007, 70, 1073.
[46] Hu, Z. L.; Jiang, X. J.; Han, W. Tetrahedron Lett. 2008, 49, 5192~5195.
[47] Arsianti, A.; Hanafi, M.; Saepudin, E.; Morimoto, T.; Kakiuchi, K. Bioorg. Med. Chem. Lett. 2010, 20, 4018.
[48] Arsianti, A.; Tanimoto, H.; Morimoto, T.; Bahtiar, A.; Takeya, T.; Kakiuchi, K. Tetrahedron 2012, 68, 2884.
[49] Taira, Y.; Okegawa, Y.; Sugimoto, K.; Abe, M.; Miyoshi, H.; Shikanai, T. FEBS Open Biol. 2013, 3, 406.
[50] Yamakoshi, S.; Kawanishi, E. Tetrahedron Lett. 2014, 55, 1175.
[51] Beveridge, R. E.; Batey, R. A. Org. Lett. 2014, 16, 2322.
[52] Ogawa, H.; Iio, H.; Usuki, Y. Chem. Lett. 2015, 44, 1214.
[53] Liu, J.; Zhu, X. J.; Kim, S. J.; Zhang, W. J. Nat. Prod. Rep. 2016, 33, 1146.
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