Chinese Journal of Organic Chemistry >
Discovery of a New Pyrazinone Natural Product by Genome Mining
Received date: 2016-02-18
Revised date: 2016-03-01
Online published: 2016-03-18
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 81373307 & 81473124).
The genomic sequences of Streptomyces sp. TP-A0365 were scanned using a secondary metabolite genome mining approach. A new nonribosomal peptide synthetase (NRPS) gene responsible for the biosynthesis of an unknown pyrazinone compound was found. The biosynthetic pathway of related compound was disrupted by inactivating the NRPS gene. Comparing the fermentation products of the mutant strain and the original strain (TG1301 derived from Streptomyces sp. TP-A0365), we caught compound 1 which disappeared in the mutant strain. Compound 1 was isolated from 20 L fermentation cultures of the original strain and its structure was established as 3-isopropyl-7,8-dihydropyrrolo[1,2-a]pyrazin-4(6H)-one, a new pyrazinone compound designated as provalin
Key words: pyrazinone; Streptomyces; genome mining; biosynthesis
Kang Wen-Jia , Wu Sheng , Hua Huiming , Pan Hai-Xue , Tang Gong-Li . Discovery of a New Pyrazinone Natural Product by Genome Mining[J]. Chinese Journal of Organic Chemistry, 2016 , 36(7) : 1696 -1699 . DOI: 10.6023/cjoc201602016
[1] Wyatt, M. A.; Wang, W.; Roux, C. M.; Beasley, F. C.; Heinrichs, D. E.; Dunman, P. M.; Magarvey, N. A. Science 2010, 329, 294.
[2] Zimmermann, M.; Fischbach, M. A. Chem. Biol. 2010, 17, 925.
[3] Alvarez, M. E.; White, C. B.; Gregory, J.; Kydd, G. C.; Harris, A.; Sun, H. H.; Gillum, A. M.; Cooper, R. J. Antibiot. 1995, 48, 1165.
[4] Tatsuta, K.; Fujimoto, K.; Yamashita, M.; Tsuchiya, T.; Umezawa, S. J. Antibiot. 1973, 26, 606.
[5] Tang, Y.-Q.; Sattler, I.; Thiericke, R.; Grabley, S.; Feng, X.-Z. Eur. J. Org. Chem. 2000, 2, 261.
[6] Motohashi, K.; Inaba, K.; Fuse, S.; Doi, T.; Izumikawa, M.; Khan, S. T.; Takagi, M.; Takahashi, T.; Shinya, K. J. Nat. Prod. 2011, 74, 1630.
[7] Jansen, R.; Sood, S.; Mohr, K. I.; Kunze, B.; Irschik, H.; Stadler, M.; Müller, R. J. Nat. Prod. 2014, 77, 2545.
[8] Kyeremeh, K.; Acquah, K. S.; Camas, M.; Tabudravu, J.; Houssen, W.; Deng, H.; Jaspars, M. Mar. Drugs 2014, 12, 5197.
[9] Bian, X.; Shao, M.; Pan, H.; Wang, K.; Huang, S.; Wu, X.; Xue, C.; Hua, H.; Pei, Y.; Bai, J. Nat. Prod. Res. 2016, 30, 125.
[10] Secor, P. R.; Jennings, L. K.; James, G. A.; Kirker, K. R.; Pulcini, E. D.; McInnerney, K.; Gerlach, R.; Livinghouse, T.; Hilmer, J. K.; Bothner, B.; Fleckman, P.; Olerud, J. E.; Stewart, P. S. PLoS One 2012, 7, e40973.
[11] Taggi, A. E.; Stevenson, T. M.; Bereznak, J. F.; Sharpe, P. L.; Gutteridge, S.; Forman, R.; Bisaha, J. J.; Cordova, D.; Crompton, M.; Geist, L.; Kovacs, P.; Marshall, E.; Sheth, R.; Stavis, C.; Tseng, C. P. Bioorg. Med. Chem. 2016, 24, 435.
[12] Gising, J.; Belfrage, A. K.; Alogheli, H.; Ehrenberg, A.; Åkerblom, E.; Svensson, R.; Artursson, P.; Karlén, A.; Danielson, U. H.; Larhed, M.; Sandström, A. J. Med. Chem. 2014, 57, 1790.
[13] Zhang, X.; Glunz, P. W.; Jiang, W.; Schmitt, A.; Newman, M.; Barbera, F. A.; Bozarth, J. M.; Rendina, A. R.; Wei, A.; Wen, X.; Rossi, K. A.; Luettgen, J. M.; Wong, P. C.; Knabb, R. M.; Wexler, R. R.; Scott Priestley, E. Bioorg. Med. Chem. Lett. 2013, 23, 1604.
[14] Wyatt, M. A.; Mok, M. C.; Junop, M.; Magarvey, N. A. Chembiochem 2012, 13, 2408.
[15] Huang, W.; Xu, H.; Li, Y.; Zhang, F.; Chen, X.-Y.; He, Q.-L.; Igarashi, Y.; Tang, G.-L. J. Am. Chem. Soc. 2012, 134, 8831.
/
〈 |
|
〉 |