Regular Article |
|
|
|
|
|
Epigenetic modifier-induced biosynthesis of novel fusaric acid derivatives in endophytic fungi from Datura stramonium L. |
Han-Jing CHEN, Takayoshi AWAKAWA, Jie-Yin SUN, Toshiyuki WAKIMOTO, Ikuro ABE |
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan |
|
|
Abstract The treatment of fungi with DNA methyltransferase (DNMT) and/or histone deacetylase (HDAC) inhibitors is a promising way to activate secondary metabolite biosynthetic pathways that are dormant under normal conditions. In this study, we included an HDAC inhibitor, suberoylanilide hydroxamic acid (SBHA), in the culture medium of endophytic fungi isolated from the medicinal plant Datura stramonium L. The production of two compounds was induced in the culture supplemented with SBHA, and their structures were determined to be the fusaric acid derivatives 5-butyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid and 5-(but-9-enyl)-6-oxo-1,6-dihydropyridine-2-carboxylic acid. The result confirmed that the use of chemical epigenetic modifiers is an effective technique for promoting the expression of silent biosynthetic pathways to produce unique secondary metabolites.
|
Keywords
endophyte
epigenetic modifier
biosynthesis
fusaric acid
|
Issue Date: 11 February 2018
|
|
|
[1] |
Keller, N. P.; Turner, G.; Bennett, J. W. Nat. Rev. Microbiol. 2005, 3, 937-947.
|
[2] |
Williams, R. B.; Henrikson, J. C.; Hoover, A. R.; Lee, A. E.; Cichewicz, R. H. Org. Biomol. Chem. 2008, 7, 1895-1897.
|
[3] |
Henrikson, J. C.; Hoover, A. R.; Joyner, P. M.; Cichewicz, R. H. Org. Biomol. Chem. 2009, 7, 435-438.
|
[4] |
Wang, X.; Sena Filho, J. G.; Hoover, A. R.; King, J. B.; Ellis, T. K.; Powell, D. R.; Cichewicz, R. H. J. Nat. Prod. 2010, 73, 942-948.
|
[5] |
Asai, T.; Yamamoto, T.; Oshima, Y. Tetrahedron Lett. 2011, 52, 7042-7045.
|
[6] |
Kharwar, R. N.; Mishra, A.; Gond, S. K.; Stierle, A.; Stierle, D. Nat. Prod. Rep. 2011, 28, 1208-1228.
|
[7] |
Sun, J.; Awakawa, T.; Noguchi, H.; Abe, I. Bioorg. Med. Chem. Lett. 2012, 22, 6397-6400.
|
[8] |
Burmeister, H. R.; Grove, M. D.; Peterson, R. E.; Weisleder, D.; Plattner, R. D. Appl. Environ. Microbiol. 1985, 50, 311-314.
|
[9] |
Wu, H. S.; Yin, X. M.; Liu, D. Y.; Ling, N.; Bao, W.; Ying, R. R.; Zhu, Y. Y.; Guo, S. W.; Shen, Q. R. Plant. Soil. 2008, 308, 255-266.
|
[10] |
Bacon, C. W.; Porter, J. K.; Norred, W. P.; Leslie, J. F. Appl. Environ. Microbiol. 1996, 62, 4039-4043.
|
[11] |
Xie, Y.; Zhang, W.; Li, Y.; Wang, M.; Cerny, R. L.; Shen, Y.; Du, L. Mycology 2011, 2, 24-29.
|
[12] |
Kühnis, H.; Egil, C.; Eichenbuerger, K.; Hedwall, P. R. U.S. Patent 3,914,239, 1975.
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|