Polyketide Production of Pestaloficiols and Macrodiolide Ficiolides Revealed by Manipulations of Epigenetic Regulators in an Endophytic Fungus

Organic Letters

Volumn 18, Issue 8, 2016, Pages 1832-1835

  Wu, Guangwei ^a   Zhou, Haichuan ^a   Zhang, Peng ^a   Wang, Xiuna ^a   Li, Wei ^a   Zhang, Weiwei ^a   Liu, Xingzhong ^a   Liu, Hong Wei ^a   Keller, Nancy P ^b   An, Zhiqiang ^c   Yin, Wen Bing ^a  

^a INSTITUTE OF MICROBIOLOGY   (China)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c UNIVERSITY OF TEXAS MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; FICIOLIDE K; MANNOSE; MONOSACCHARIDE; POLYKETIDE;

ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; EPIGENETICS; FUNGUS; ISOTOPE LABELING; SYNTHESIS; XYLARIALES;

BIOLOGICAL PRODUCTS; EPIGENOMICS; FUNGI; ISOTOPE LABELING; MANNOSE; MOLECULAR STRUCTURE; MONOSACCHARIDES; POLYKETIDES; XYLARIALES;

EID: 84966415413     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b00562     Document Type: Article

References (39)

1. Hoffmeister, D.; Keller, N. P. Nat. Prod. Rep. 2007, 24, 393-416 10.1039/B603084J
2. Bills, G.; Li, Y.; Chen, L.; Yue, Q.; Niu, X. M.; An, Z. Nat. Prod. Rep. 2014, 31, 1348-1375 10.1039/C4NP00046C
3. Rutledge, P. J.; Challis, G. L. Nat. Rev. Microbiol. 2015, 13, 509-523 10.1038/nrmicro3496
4. Cichewicz, R. H. Nat. Prod. Rep. 2010, 27, 11-22 10.1039/B920860G
5. Albright, J. C.; Henke, M. T.; Soukup, A. A.; McClure, R. A.; Thomson, R. J.; Keller, N. P.; Kelleher, N. L. ACS Chem. Biol. 2015, 10, 1535-1541 10.1021/acschembio.5b00025
6. Strauss, J.; Reyes-Dominguez, Y. Fungal Genet. Biol. 2011, 48, 62-69 10.1016/j.fgb.2010.07.009
7. Tang, H. Y.; Zhang, Q.; Gao, Y. Q.; Zhang, A. L.; Gao, J. M. RSC Adv. 2015, 5, 2185-2190 10.1039/C4RA11712C
8. Asai, T.; Morita, S.; Shirata, N.; Taniguchi, T.; Monde, K.; Sakurai, H.; Ozeki, T.; Oshima, Y. Org. Lett. 2012, 14, 5456-5459 10.1021/ol302539s
9. Asai, T.; Morita, S.; Taniguchi, T.; Monde, K.; Oshima, Y. Org. Biomol. Chem. 2016, 14, 646-651 10.1039/C5OB01595B
10. Bok, J. W.; Chiang, Y.-M.; Szewczyk, E.; Reyes-Dominguez, Y.; Davidson, A. D.; Sanchez, J. F.; Lo, H.-C.; Watanabe, K.; Strauss, J.; Oakley, B. R. Nat. Chem. Biol. 2009, 5, 462-464 10.1038/nchembio.177
11. Shinohara, Y.; Kawatani, M.; Futamura, Y.; Osada, H.; Koyama, Y. J. Antibiot. 2016, 69, 4-8 10.1038/ja.2015.73
12. Palmer, J. M.; Bok, J. W.; Lee, S.; Dagenais, T. R.; Andes, D. R.; Kontoyiannis, D. P.; Keller, N. P. PeerJ 2013, 1, e4 10.7717/peerj.4
13. Liu, Y.; Liu, N.; Yin, Y.; Chen, Y.; Jiang, J.; Ma, Z. Environ. Microbiol. 2015, 17, 4615-4630 10.1111/1462-2920.12993
14. Mao, X. M.; Xu, W.; Li, D.; Yin, W. B.; Chooi, Y. H.; Li, Y. Q.; Tang, Y.; Hu, Y. Angew. Chem., Int. Ed. 2015, 54, 7592-7596 10.1002/anie.201502452
15. Yang, X.-L.; Zhang, J.-Z.; Luo, D.-Q. Nat. Prod. Rep. 2012, 29, 622-641 10.1039/c2np00073c
16. Yang, X. L.; Huang, L.; Ruan, X. L. J. Asian Nat. Prod. Res. 2014, 16, 412-417 10.1080/10286020.2014.881356
17. Niu, X.; Hao, X.; Hong, Z.; Chen, L.; Yu, X.; Zhu, X. J. Microbiol. Biotechnol. 2015, 25, 579-588
18. Liu, L. Mycology 2011, 2, 37-45 10.1080/21501203.2011.562248
19. Liu, L.; Li, Y.; Li, L.; Cao, Y.; Guo, L.; Liu, G.; Che, Y. J. Org. Chem. 2013, 78, 2992-3000 10.1021/jo302804h
20. Liu, L.; Li, Y.; Liu, S. C.; Zheng, Z. H.; Chen, X. L.; Zhang, H.; Guo, L. D.; Che, Y. S. Org. Lett. 2009, 11, 2836-2839 10.1021/ol901039m
21. Liu, L.; Liu, S. C.; Jiang, L. H.; Chen, X. L.; Guo, L. D.; Che, Y. S. Org. Lett. 2008, 10, 1397-1400 10.1021/ol800136t
22. Wang, X.; Zhang, X.; Liu, L.; Xiang, M.; Wang, W.; Sun, X.; Che, Y.; Guo, L.; Liu, G.; Guo, L. BMC Genomics 2015, 16, 28 10.1186/s12864-014-1190-9
23. Xu, X.; Liu, L.; Zhang, F.; Wang, W.; Li, J.; Guo, L.; Che, Y.; Liu, G. ChemBioChem 2014, 15, 284-292 10.1002/cbic.201300626
24. Lee, I.; Oh, J.-H.; Shwab, E. K.; Dagenais, T. R.; Andes, D.; Keller, N. P. Fungal Genet. Biol. 2009, 46, 782-790 10.1016/j.fgb.2009.06.007
25. Wang, X.; Wu, F.; Liu, L.; Liu, X.; Che, Y.; Keller, N. P.; Guo, L.; Yin, W.-B. Fungal Genet. Biol. 2015, 81, 221-228 10.1016/j.fgb.2015.03.010
26. Chen, L.; Yue, Q.; Zhang, X.; Xiang, M.; Wang, C.; Li, S.; Che, Y.; Ortiz-Lopez, F. J.; Bills, G. F.; Liu, X.; An, Z. BMC Genomics 2013, 14, 339 10.1186/1471-2164-14-339
27. Yin, W. B.; Amaike, S.; Wohlbach, D. J.; Gasch, A. P.; Chiang, Y. M.; Wang, C. C.; Bok, J. W.; Rohlfs, M.; Keller, N. P. Mol. Microbiol. 2012, 83, 1024-1034 10.1111/j.1365-2958.2012.07986.x
28. Yin, W.-B.; Chooi, Y. H.; Smith, A. R.; Cacho, R. A.; Hu, Y.; White, T. C.; Tang, Y. ACS Synth. Biol. 2013, 2, 629-634 10.1021/sb400048b
29. Liu, S.; Liu, X.; Guo, L.; Che, Y.; Liu, L. Chem. Biodiversity 2013, 10, 2007-2013 10.1002/cbdv.201200361
30. Liu, L.; Liu, S.; Niu, S.; Guo, L.; Chen, X.; Che, Y. J. Nat. Prod. 2009, 72, 1482-1486 10.1021/np900308s
31. Peng, J.; Gao, H.; Li, J.; Ai, J.; Geng, M.; Zhang, G.; Zhu, T.; Gu, Q.; Li, D. J. Org. Chem. 2014, 79, 7895-7904 10.1021/jo5010179
32. Mühlenfeld, A.; Achenbacht, H. Phytochemistry 1988, 27, 3853-3855 10.1016/0031-9422(88)83031-0
33. Krohn, K.; Farooq, U.; Flörke, U.; Schulz, B.; Draeger, S.; Pescitelli, G.; Salvadori, P.; Antus, S.; Kurtán, T. Eur. J. Org. Chem. 2007, 2007, 3206-3211 10.1002/ejoc.200601128
34. Kind, R.; Zeeck, A.; Grabley, S.; Thiericke, R.; Zerlin, M. J. Nat. Prod. 1996, 59, 539-540 10.1021/np960083q
35. Dommerholt, F.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1991, 32, 1499-1502 10.1016/0040-4039(91)80368-G
36. Marco-Contelles, J.; Molina, M. T.; Anjum, S. Chem. Rev. 2004, 104, 2857-2900 10.1021/cr980013j
37. Kastanias, M. A.; Chrysayi-Tokousbalides, M. J. Agric. Food Chem. 2005, 53, 5943-5947 10.1021/jf050792m
38. Zhou, Y.; Murphy, A. C.; Samborskyy, M.; Prediger, P.; Dias, L. C.; Leadlay, P. F. Chem. Biol. 2015, 22, 745-754 10.1016/j.chembiol.2015.05.010
39. Zhou, Y.; Prediger, P.; Dias, L. C.; Murphy, A. C.; Leadlay, P. F. Angew. Chem., Int. Ed. 2015, 54, 5232-5235 10.1002/anie.201500401