Citation: 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 shu

Discovery of a New Pyrazinone Natural Product by Genome Mining

Kang Wen-Jia ^a ,
Wu Sheng ^b ,
Hua Huiming ^a,*,, ,
Pan Hai-Xue ^b ,
Tang Gong-Li ^b,*,,

a.
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016
b.
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Hua Huiming, Tang Gong-Li,
Received Date: 18 February 2016
Revised Date: 1 March 2016

Fund Project: the National Natural Science Foundation of China Nos. 81373307 & 81473124

Figures(3)

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
- pyrazinone,
- Streptomyces,
- genome mining,
- biosynthesis
1. [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. [2]
  Zimmermann, M.; Fischbach, M. A. Chem. Biol. 2010, 17, 925.
3. [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. [4]
  Tatsuta, K.; Fujimoto, K.; Yamashita, M.; Tsuchiya, T.; Umezawa, S. J. Antibiot. 1973, 26, 606.
5. [5]
  Tang, Y.-Q.; Sattler, I.; Thiericke, R.; Grabley, S.; Feng, X.-Z. Eur. J. Org. Chem. 2000, 2, 261.
6. [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. [7]
  Jansen, R.; Sood, S.; Mohr, K. I.; Kunze, B.; Irschik, H.; Stadler, M.; Müller, R. J. Nat. Prod. 2014, 77, 2545.
8. [8]
  Kyeremeh, K.; Acquah, K. S.; Camas, M.; Tabudravu, J.; Houssen, W.; Deng, H.; Jaspars, M. Mar. Drugs 2014, 12, 5197.
9. [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. [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. [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. [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. [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. [14]
  Wyatt, M. A.; Mok, M. C.; Junop, M.; Magarvey, N. A. Chembiochem 2012, 13, 2408.
15. [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.
1. [1]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
2. [2]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
3. [3]
  Ying Zhang , Fang Ge , Zhimin Luo . AI-Driven Biochemical Teaching Research: Predicting the Functional Effects of Gene Mutations. University Chemistry, 2025, 40(3): 277-284. doi: 10.12461/PKU.DXHX202412104
4. [4]
  Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
5. [5]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
6. [6]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
7. [7]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
8. [8]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
9. [9]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
10. [10]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
11. [11]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
12. [12]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
13. [13]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
14. [14]
  . . Chinese Journal of Inorganic Chemistry, 2024, 40(12): 0-0.
15. [15]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
16. [16]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
17. [17]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
18. [18]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
19. [19]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
20. [20]
  Zhibei Qu , Changxin Wang , Lei Li , Jiaze Li , Jun Zhang . Organoid-on-a-Chip for Drug Screening and the Inherent Biochemistry Principles. University Chemistry, 2024, 39(7): 278-286. doi: 10.3866/PKU.DXHX202311039

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2367)
HTML views(439)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142