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Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum
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 condi...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer Berlin Heidelberg
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4131581/ http://dx.doi.org/10.1007/s13659-013-0055-2 |
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author | Yang, Xiao-Long Awakawa, Takayoshi Wakimoto, Toshiyuki Abe, Ikuro |
author_facet | Yang, Xiao-Long Awakawa, Takayoshi Wakimoto, Toshiyuki Abe, Ikuro |
author_sort | Yang, Xiao-Long |
collection | PubMed |
description | 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). [Image: see text] |
format | Online Article Text |
id | pubmed-4131581 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Springer Berlin Heidelberg |
record_format | MEDLINE/PubMed |
spelling | pubmed-41315812014-08-20 Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum Yang, Xiao-Long Awakawa, Takayoshi Wakimoto, Toshiyuki Abe, Ikuro Nat Prod Bioprospect Regular Article 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). [Image: see text] Springer Berlin Heidelberg 2013-08-17 /pmc/articles/PMC4131581/ http://dx.doi.org/10.1007/s13659-013-0055-2 Text en © The Author(s) 2013 https://creativecommons.org/licenses/by/4.0/ This article is published under license to BioMed Central Ltd. Open Access This article is distributed under the terms of the Creative Commons Attribution License which permits any use, distribution and reproduction in any medium, provided the original author(s) and source are credited. |
spellingShingle | Regular Article Yang, Xiao-Long Awakawa, Takayoshi Wakimoto, Toshiyuki Abe, Ikuro Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum |
title | Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum |
title_full | Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum |
title_fullStr | Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum |
title_full_unstemmed | Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum |
title_short | Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum |
title_sort | induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen stagonospora nodorum |
topic | Regular Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4131581/ http://dx.doi.org/10.1007/s13659-013-0055-2 |
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