Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen <i>Stagonospora nodorum</i>

doi:10.1007/s13659-013-0055-2

Natural Products and Bioprospecting

2013, Vol. 3

Issue (4) : 141-144 DOI: 10.1007/s13659-013-0055-2

Regular Article

Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum

Xiao-Long YANG^a,b, Takayoshi AWAKAWA^a, Toshiyuki WAKIMOTO^a, Ikuro ABE^a

a Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan;
b College of Pharmaceutical Science, Hebei University, Baoding 071002, China

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Abstract Fungal aromatic compounds comprise an important and structurally diverse group of secondary metabolites. Several genome sequencing projects revealed many putative biosynthetic gene clusters of fungal aromatic compounds, but many of these genes seem to be silent under typical laboratory culture conditions. To gain access to this untapped reservoir of natural products, we utilized chemical epigenetic modifiers to induce the expression of dormant biosynthetic genes. As a result, the concomitant supplementation of the histone deacetylase inhibitors suberoylanilide hydroxamic acid (500 μM) and nicotinamide (50 μM) to the culture medium of a fungal pathogen, Stagonospora nodorum, resulted in the isolation of three aromatic compounds (1-3), including a novel natural butyrophenone, (+)-4'-methoxy-(2S)-methylbutyrophenone (1), and two known polyketides, alternariol (2) and (-)-(3R)-mellein methyl ether (3).

Keywords Stagonospora nodorum butyrophenone polyketides epigenetic manipulation

Fund:This work was financially supported by Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and by programs from the National Natural Science Foundation Province of China (21202033), the Natural Science Foundation of Hebei (C2012201047), and the Foundation of Hebei University (179).

Issue Date: 11 February 2018

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Xiao-Long YANG,Takayoshi AWAKAWA,Toshiyuki WAKIMOTO, et al. Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum[J]. Natural Products and Bioprospecting, 2013, 3(4): 141-144.

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http://npb.kib.ac.cn/EN/10.1007/s13659-013-0055-2 OR http://npb.kib.ac.cn/EN/Y2013/V3/I4/141

[1]	Keller, N. P.; Turner, G.; Bennett, J. W. Nat. Rev. Microbiol. 2005, 3, 937-947.
[2]	Hertweck, C.; Luzhetskyy, A.; Rebets, Y.; Bechthold, A. Nat. Prod. Rep. 2007, 24, 162-190.
[3]	Zhou, H.; Li, Y.; Tang, Y. Nat. Prod. Rep. 2010, 27, 839-868.
[4]	Bhathal, J. S.; Loughman, R.; Speijers, J. Eur. J. Plant Pathol. 2003, 109, 435-443.
[5]	Friesen, T. L.; Chu, C. G.; Liu, Z. H.; Xu, S. S.; Halley, S.; Faris, J. D. Theor. Appl. Genet. 2009, 118, 1489-1497.
[6]	Friesen, T. L.; Zhang, Z. C.; Solomon, P. S.; Oliver, R. P.; Faris, J. D. Plant Physiol. 2008, 146, 682.
[7]	Lowe, R. G. T.; Lord, M.; Rybak, K.; Trengove, R. D.; Oliver, R. P.; Solomon, P. S. Fungal Genet. Biol. 2008, 45, 1479-1486.
[8]	Tan, K. C.; Trengove, R. D.; Maker, G. L.; Oliver, R. P.; Solomon, P. S. Metabolomics 2009, 5, 330-335.
[9]	IpCho, S. V. S.; Tan, K. C.; Koh, G.; Gummer, J.; Oliver, R. P.; Trengove, R. D.; Solomon, P. S. Eukaryot. Cell 2010, 9, 1100-1108.
[10]	Hane, J. K.; Lowe, R. G. T.; Solomon, P. S.; Tan, K. C.; Schoch, C. L.; Spatafora, J. W.; Crous, P. W.; Kodira, C.; Birren, B. W.; Galagan, J. E.; Torriani, S. F. F.; McDonald, B. A.; Oliver, R. P. The Plant Cell 2007, 19, 3347-3368.
[11]	Cichewicz, R. H. Nat. Prod. Rep. 2010, 27, 11-22.
[12]	Korver, O. Tetrahedron 1971, 27, 4643-4651.
[13]	Stinson, E. E.; Wise, W. B.; Moreau, R. A.; Jurewicz, A. J.; Pfeffer, P. E. Can. J. Chem. 1986, 64, 1590-1594.
[14]	Klaiklay, S.; Rukachaisirikul, V.; Sukpondma, Y.; Phongpaichit, S.; Buatong, J.; Bussaban, B. Arch. Pharm. Res. 2012, 35, 1127-1131.
[15]	Wicklow, D. T.; Joshi, B. K.; Gamble, W. R.; Gloer, J. B.; Dowd, P. F. Appl. Environ. Microbiol. 1998, 64, 4482-4484.
[16]	Hu, J.; Wang, J.; Miao, C.; Xuan, Q.; Zhai, Y.; Song, F.; Chen, Y.; Wu, S. Zhongguo Zhong Yao Za Zhi 2012, 37, 1602-1606.
[17]	Kennedy, J.; Auclair, K.; Kendrew, S. G.; Park, C.; Vederas, J. C.; Hutchinson, C. R. Science 1999, 284, 1368-1372.
[18]	Miyanaga, A.; Funa, N.; Awakawa, T.; Horinouchi, S. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 871-876.
[19]	Austin, M. B.; Saito, T.; Bowman, M. E.; Haydock, S.; Kato, A.; Moore, B. S.; Kay, R. R.; Noel, J. P. Nat. Chem. Biol. 2006, 2, 494-502.
[20]	Sun, H.; Ho, C. L.; Ding, F.; Soehano, I.; Liu, X. W.; Liang, Z. X. J. Am. Chem. Soc. 2012, 134, 11924-11927.

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