吩嗪-1-羧酸及其类似物研究进展
收稿日期: 2019-04-09
修回日期: 2019-05-16
网络出版日期: 2019-06-03
基金资助
国家重点研发计划(2018YFD0200500);国家自然科学基金(31672069);长江大学优秀博士学位论文培育计划资助项目
Research Progress of Phenazine-1-carboxylic Acid and Its Analogue
Received date: 2019-04-09
Revised date: 2019-05-16
Online published: 2019-06-03
Supported by
Project supported by the National Key R&D Program of China(2018YFD0200500);The National Natural Science Foundation of China(31672069);The Funds for Excellent Doctoral Dissertation Cultivation Program in Yangtze University
朱祥 , 吴清来 , 李俊凯 . 吩嗪-1-羧酸及其类似物研究进展[J]. 有机化学, 2019 , 39(10) : 2744 -2758 . DOI: 10.6023/cjoc201904023
Phenazine-1-carboxylic acid (PCA) as a natural product widely exists in microbial metabolites of Pseudomonads and Streptomycetes, which displays potent inhibitory activities against plant pathogens, and has medical antibacterial and antitumor effects, and so on. In this review, the biosynthesis and chemosynthesis of phenazine-1-carboxylic acid are summarized. At the same time, the diverse biological evaluations of its biosynthetic and chemosynthetic analogues are summarized, which could provide reference for the study of structural modifications and biological activities of these analogues.
Key words： phenazine-1-carboxylic acid; analogues; research progress
| [1] | Abdelfattah, M. S.; Toume, K.; Ishibashi, M. J. Antibiot. 2011, 64, 271. |
| [2] | Jasim, B.; Anisha, C.; Rohini, S.; Kurian, J. M.; Jyothis, M Radhakrishnan, E. K .; World J. Microb. Biot. 2014, 30, 1649. |
| [3] | K?gl, F Postowsky, J. J .; Justus Liebig's Ann. Chem. 1930, 480, 280. |
| [4] | Ou, J. G.; Lu, Y. H . Chem. Reag. 1982, 4, 41 (in Chinese). |
| [4] | ( 欧进国, 陆蕴华, 化学试剂, 1982, 4, 41.) |
| [5] | Isono, K.; Suzuki, S.; Sawazaki, T.; Nakamura, G.; Kawasaki, M.; Yamashita, T.; Anzai, K.; Serizawa, Y.; Sekiyama, Y. J. Antibiot. 1955, 8, 19. |
| [6] | Nelson, C. D.; Toohey, J. I . US 3367765, 1968. |
| [7] | Abdelfattah, M. S.; Ishikawa, N.; Karmakar, U. K.; Yamaku, K.; Ishibashi, M . J. Antibiot. 2016, 69, 446. |
| [8] | Thanabalasingam, D.; Kumar, N. S.; Jayasinghe, L.; Fujimoto, Y. Nat. Prod. Commun. 2015, 10, 1659. |
| [9] | Wu, Q. L.; Xu, Z. H.; Li, J. K. Chin. J. Pestic. Sci. 2016, 18, 669 (in Chinese). |
| [9] | ( 吴清来, 徐志红, 李俊凯 , 农药学学报, 2016, 18, 669.) |
| [10] | Hu, H. B.; Xu, Y. Q.; Feng, C.; Xue, H. Z.; Hur, B. K. J Microbiol. Biotechnol. 2005, 15, 86. |
| [11] | Wang, C. H.; Zhu, X. D.; Xu, Y. Q.; Feng, Z. T. J. Shanghai Jiaotong Univ. 2000, 34, 1574 (in Chinese). |
| [11] | ( 王灿华, 祝新德, 许煜泉, 冯镇泰 , 上海交通大学学报, 2000, 34, 1574.) |
| [12] | Xu, Y. Q.; Tang, W. N.; Zheng, Y. L.; Zhong, Z. X.; Xu, T. W. J. Shanghai Jiaotong Univ. 1999, 33, 210 (in Chinese). |
| [12] | ( 许煜泉, 唐玮宁, 郑有丽, 钟仲贤, 徐悌惟 , 上海交通大学学报, 1999, 33, 210.) |
| [13] | Zheng, W. J.; Xu, S.; Zhou, M. G . Chin. J. Pestic. Sci. 2011, 13, 28(in Chinese). |
| [13] | ( 郑文君, 徐曙, 周明国 , 农药学学报, 2011, 13, 28.) |
| [14] | Jin, Y.; Hu, H. B.; Zhang, X. H.; Xu, Y. Q. Acta Agric. Shanghai 2005, 21, 106 (in Chinese). |
| [14] | ( 金颖, 胡洪波, 张雪洪, 许煜泉 , 上海农业学报, 2005, 21, 106.) |
| [15] | Xu, Y. Q. Fine Spec. Chem. 2004, 12, 8 (in Chinese). |
| [15] | ( 许煜泉 , 精细与专用化学品, 2004, 12, 8.) |
| [16] | Guttenberger, N.; Blankenfeldt, W.; Breinbauer, R. Bioorg. Med. Chem. 2017, 25, 6149. |
| [17] | Mavrodi, D. V.; Blankenfeldt, W.; Thomashow, L.S. Annu. Rev. Phytopathol. 2006, 44, 417. |
| [18] | Price-Whelan, A.; Dietrich, L. E.; Newman, D. K. Nat. Chem. Biol. 2006, 2, 71. |
| [19] | Zhang, F. H.; Xu, Y. Q.; Zhang, X. H . Agrochem. Res. Appl. 2006, 10, 4 (in Chinese). |
| [19] | ( 张锋华, 许煜泉, 张雪洪 , 农药研究与应用, 2006, 10, 4.) |
| [20] | Chin-A-Woeng, T. F.; Bloemberg, G. V Lugtenberg, B. J. .; New Phytol. 2003, 157, 503. |
| [21] | Laursen, J. B.; Nielsen, J. Chem. Rev. 2004, 104, 1663. |
| [22] | Ingledew, W. M.; Campbell, J. J. R. Can. J. Microbiol. 1969, 15, 535. |
| [23] | Calhoun, D. H.; Carson, M.; Jensen, R. A. Microbiology 1972, 72, 581. |
| [24] | Turner, J. M Messenger, A. J .; Adv. Microb. Physiol. 1986, 27, 211. |
| [25] | Pierson, L. S.; Pierson, E. A. Appl. Microbiol. Biotechnol. 2010, 86, 1659. |
| [26] | Blankenfeldt, W.; Parsons, J. F. Curr. Opin. Struct. Biol. 2014, 29, 26. |
| [27] | Ahuja, E. G.; Janning, P.; Mentel, M.; Graebsch, A.; Breinbauer, R.; Hiller, W.; Costisella, B.; Thomashow, L. S.; Mavrodi, D. V.; Blankenfeldt, W. J. Am. Chem. Soc. 2008, 130, 17053. |
| [28] | Chen, M.; Cao, H.; Peng, H.; Hu, H.; Wang, W.; Zhang, X. PloS One 2014, 9, e98537. |
| [29] | Mavrodi, D. V.; Bonsall, R. F.; Delaney, S. M.; Soule, M. J.; Phillips, G.; Thomashow, L. S. J. Bacteriol. 2001, 183, 6454. |
| [30] | Girard, G.; van Rij, E. T.; Lugtenberg, B. J.; Bloemberg, G. V. Microbiology 2006, 152, 43. |
| [31] | Clemo, G. R.; Mcilwain, H . J. Chem. Soc. 1934,1991. |
| [32] | Spicer, J. A.; Gamage, S. A.; Rewcastle, G. W.; Finlay, G. J.; Bridewell, D. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 2000, 43, 1350. |
| [33] | Zhu, H. J.; Zhu, X. L.; He, G. K.; Song, G. L.; Huang, R. J.; Shi, L . CN 103304496, 2013. |
| [34] | Zhu, H. J.; Zhan, Q. Y.; Zhu, X. L.; He, G. K.; Song, G. L.; Liu, R.; Liu, Q . CN 104045601, 2014 (in Chinese). |
| [35] | Vivian, D. L.; Hartwell, J. L.; Watermans, H. C. J. Org. Chem. 1954, 19, 1641. |
| [36] | Rewcastle, G. W.; Denny, W. A Baguley, B. C .; J. Med. Chem. 1987, 30, 843. |
| [37] | Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264. |
| [38] | Raju, B. C.; Prasad, K. V.; Saidachary, G.; Sridhar, B. Org. Lett. 2014, 16, 420. |
| [39] | Laha, J. K.; Tummalapalli, K. S.; Gupta, A. Org. Lett. 2014, 16, 4392. |
| [40] | Leisinger, T.; Margraff, R. Microbiol. Rev. 1979, 43, 422. |
| [41] | Budzikiewicz, H. FEMS Microbiol. Lett. 1993, 104, 209. |
| [42] | Brisbane, P. G.; Janik, L. J.; Tate, M. E.; Warren, R. F . Antimicrob. Agents Chemother. 1987, 31, 1967. |
| [43] | Jayatilake, G. S.; Thornton, M. P.; Leonard, A. C.; Grimwade, J. E.; Baker, B. J. J. Nat. Prod. 1996, 59, 293. |
| [44] | Zhou, L.; Jiang, H. X.; Jin, K. M.; Sun, S.; Zhang, W.; Zhang, X. H.; He, Y. W. Acta Microbiol. Sin. 2015, 55, 401 (in Chinese). |
| [44] | ( 周莲, 蒋海霞, 金凯明, 孙爽, 张薇, 张雪洪, 何亚文 , 微生物学报, 2015, 55, 401.) |
| [45] | Gong, X. J.; Feng, Z. T.; Zhang, H. Y.; Shen, L. J.; Wang, X. X.; Zhang, J. W . CN 103343150, 2013. |
| [46] | Sakamoto, S.; Watanabe, T.; Kohda, Y.; Iijima, M.; Sawa, R.; Okada, M.; Kawada, M . J. Antibiot. 2017, 70, 1146. |
| [47] | Dasgupta, D.; Kumar, A.; Mukhopadhyay, B.; Sengupta, T. K. Appl. Microbiol. Biotechnol. 2015, 99, 8653. |
| [48] | Parsons, J. F.; Calabrese, K.; Eisenstein, E.; Ladner, J. E . Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2110. |
| [49] | Messenger, A. J.; Turner, J. M . FEMS Microbiol. Lett. 1983, 18, 65. |
| [50] | Umezawa, H.; Hayano, S.; Maeda, K.; Ogata, Y.; Okami, Y . Jpn. Med. J. 1950, 3, 111. |
| [51] | Kidani, Y. Chem. Pharm. Bull. 1959, 7, 74. |
| [52] | Chatterjee, S.; Vijayakumar, E. K. S.; Franco, C. M. M.; Maurya, R.; Blumbach, J.; Ganguli, B. N. J. Antibiot. 1995, 48, 1353. |
| [53] | Krastel, P.; Zeeck, A.; Gebhardt, K.; Fiedler, H. P.; Rheinheimer, J. ChemInform 2003, 34, 794. |
| [54] | Pusecker, K.; Laatsch, H.; Helmke, E.; Weyland, H . J. Antibiot. 1997, 50, 479. |
| [55] | Gilpin, M. L.; Fulston, M.; Payne, D.; Cramp, R.; Hood, I . J. Antibiot. 1995, 48, 1081. |
| [56] | Gao, X.; Lu, Y.; Xing, Y.; Ma, Y.; Lu, J.; Bao, W.; Wang, Y.; Xi, T. Microbiol. Res. 2012, 167, 616. |
| [57] | Choi, E. J.; Kwon, H. C.; Ham, J.; Yang, H. O. J. Antibiot. 2009, 62, 621. |
| [58] | Smitka, T. A.; Bunge, R. H.; Wilton, J. H.; Hokanson, G. C.; French, J. C.; Cun-Heng, H. E.; Clardy, J. J. Antibiot. 1986, 39, 800. |
| [59] | Hosoya, Y.; Adachi, H.; Nakamura, H.; Nishimura, Y.; Naganawa, H.; Okami, Y.; Takeuchi, T. Tetrahedron Lett. 1996, 37, 9227. |
| [60] | Sakthivel, N.; Kumar, R . US 7365194, 2005. |
| [61] | Tamaoki, T.; Kasai, M.; Shirahata, K Tomita, F. J. Antibiot. 1982, 35, 979. |
| [62] | Abdel-Mageed, W. M.; Milne, B. F.; Wagner, M.; Schumacher, M.; Sandor, P.; Pathom-aree, W.; Goodfellow, M.; Bull, A. T.; Horikoshi, K.; Ebel, R.; Diederich, M.; Fiedler, H.; Jaspars, M. Org. Biomol. Chem. 2010, 8, 2352. |
| [63] | Wagner, M.; Abdel-Mageed, W. M.; Ebel, R.; Bull, A. T.; Goodfellow, M.; Fiedler, H. P.; Jaspars, M. J. Nat. Prod. 2014, 77, 416. |
| [64] | Abdelfattah, M. S.; Kazufumi, T.; Ishibashi, M . J. Nat. Prod. 2010, 73, 1999. |
| [65] | Abdelfattah, M. S.; Toume, K.; Ishibashi, M. Chem. Pharm. Bull. 2011, 59, 508. |
| [66] | Liang, Y.; Chen, L.; Ye, X.; Anjum, K.; Lian, X. Y.; Zhang, Z. Nat. Prod. Res. 2017, 31, 411. |
| [67] | Gamage, S. A.; Rewcastle, G. W.; Baguley, B. C.; Charlton, P. A.; Denny, W. A . Bioorg. Med. Chem. 2006, 14, 1160. |
| [68] | Wang, S.; Miller, W.; Milton, J.; Vicker, N.; Stewart, A.; Charlton, P.; Mistry, P.; Hardick, D.; Denny, W. A. Bioorg. Med. Chem. Lett. 2002, 12, 415. |
| [69] | De Logu, A.; Palchykovska, L. H.; Kostina, V. H.; Sanna, A.; Meleddu, R.; Chisu, L.; Alexeeva, I. V.; Shved, A. D. Int. J. Antimicrob. Agents 2009, 33, 223. |
| [70] | Hovorun, D. M.; Deriabin, O. M.; Rybalko, S. L.; Samijlenko, S. P.; Starosyla, D. B.; Platonov, M. O.; Palchykovska, L. G. Biopolym. Cell 2012, 28, 477. |
| [71] | Gupta, A.; Jaiswal, A.; Prachnad, S . Int. J. Pharm. Life Sci. 2014, 5, 3230. |
| [72] | Udumula, V.; Endres, J. L.; Harper, C. N.; Jaramillo, L.; Zhong, H. A.; Bayles, K. W.; Conda-Sheridan, M. Eur. J. Med. Chem. 2017, 125, 710. |
| [73] | Krishnaiah, M.; de Almeida, N. R.; Udumula, V.; Song, Z.; Chhonker, Y. S.; Abdelmoaty, M. M.; do Nascimento, V. A.; Murry, D. J.; Conda-Sheridan, M. Eur. J. Med. Chem. 2018, 143, 936. |
| [74] | Wang, M. Z.; Xu, H.; Yu, S. J.; Feng, Q.; Wang, S. H.; Li, Z. M . J. Agric. Food Chem. 2010, 58, 3651. |
| [75] | Ye, L.; Zhang, H.; Xu, H.; Zou, Q.; Cheng, C.; Dong, D.; Xu, Y.; Li, R. Bioorg. Med. Chem. Lett. 2010, 20, 7369. |
| [76] | Puopolo, G.; Masi, M.; Raio, A.; Andolfi, A.; Zoina, A.; Cimmino, A.; Evidente, A. Nat. Prod. Res. 2013, 27, 956. |
| [77] | Li, B.; Lv, L.; Sun, Q.; Zhu, D. Q.; Li, Z. N.; Wang, G . CN 105418518, 2016. |
| [78] | Zhang, S.; Chen, H. X.; Du, X. B.; Zhang, Q.; Xu, Y. Q. Acta Agric. Shanghai 2015, 31 1 (in Chinese). |
| [78] | ( 张穗, 陈海霞, 杜兴彬, 张强, 许煜泉 , 上海农业学报, 2015, 31, 1.) |
| [79] | Niu, J.; Chen, J.; Xu, Z.; Zhu, X.; Wu, Q Li, J. .; Bioorg. Med. Chem. Lett. 2016, 26, 5384. |
| [80] | Xiong, Z.; Niu, J.; Liu, H.; Xu, Z.; Li, J.; Wu, Q . Bioorg. Med. Chem. Lett. 2017, 27, 2010. |
| [81] | Liu, H.; Yu, L. H.; Xiong, Z. P.; Zhang, M.; Li, J. K.; Xu, Z. H.; Wu, Q. L. Chin. J. Pest. Sci. 2017, 19, 290 (in Chinese). |
| [81] | ( 柳豪, 余林花, 熊志鹏, 张敏, 李俊凯, 徐志红, 吴清来 , 农药学学报, 2017, 19, 290.) |
| [82] | Qin, C.; Yu, D. Y.; Zhou, X. D.; Zhang, M.; Wu, Q. L.; Li, J. K . J. Asian Nat. Prod. Res. 2018. |
| [83] | Zhu, X.; Zhang, M.; Yu, L.; Xu, Z.; Yang, D.; Du, X.; Wu, Q.; Li, J . Nat. Prod. Res. 2018,1. |
| [84] | Lu, X.; Zhu, X.; Zhang, M.; Wu, Q.; Zhou, X.; Li, J . Nat. Prod. Res. 2018,1. |
| [85] | Zhu, X.; Yu, L.; Zhang, M.; Xu, Z.; Yao, Z.; Wu, Q.; Du, X.; Li, J. Chem. Cent. J. 2018, 12, 111. |
| [86] | Han, F.; Yan, R.; Zhang, M.; Xiang, Z.; Wu, Q.; Li, J . Nat. Prod. Res. 2019,1. |
| [87] | Niu, J.; Nie, D.; Yu, D.; Wu, Q.; Yu, L.; Yao, Z.; Du, X.; Li, J. Pestic. Biochem. Physiol. 2017, 143, 8. |
| [88] | Yu, L.; Huang, D.; Zhu, X.; Zhang, M.; Yao, Z.; Wu, Q.; Xu, Z.; Li, J. Molecules 2018, 23, 2139. |
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