Benzoyl ester formation in Aspergillus ustus by hijacking the polyketide acyl intermediates with alcohols
Accumulation of two benzoyl esters in Aspergillus ustus after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis for these esters has not been elucidated prior to this study. Here, we demonstrate that these compounds are artifical products of the phenethy...
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| Published in | Archives of microbiology Vol. 203; no. 4; pp. 1795 - 1800 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Berlin/Heidelberg
Springer Berlin Heidelberg
01.05.2021
Springer Nature B.V |
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| Online Access | Get full text |
| ISSN | 0302-8933 1432-072X 1432-072X |
| DOI | 10.1007/s00203-021-02182-0 |
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| Abstract | Accumulation of two benzoyl esters in
Aspergillus ustus
after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis for these esters has not been elucidated prior to this study. Here, we demonstrate that these compounds are artifical products of the phenethyl polyketide ustethylin A biosynthestic pathway. In addition, four aditional benzoyl esters with different methylation levels were also isolated and identified as shunt products. Feeding experiments provided evidence that the enzyme-bound polyketide acyl intermediates are hijacked by externally fed MeOH or EtOH, leading to the formation of the benzoyl esters.
Graphic abstract |
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| AbstractList | Accumulation of two benzoyl esters in
Aspergillus ustus
after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis for these esters has not been elucidated prior to this study. Here, we demonstrate that these compounds are artifical products of the phenethyl polyketide ustethylin A biosynthestic pathway. In addition, four aditional benzoyl esters with different methylation levels were also isolated and identified as shunt products. Feeding experiments provided evidence that the enzyme-bound polyketide acyl intermediates are hijacked by externally fed MeOH or EtOH, leading to the formation of the benzoyl esters.
Graphic abstract Accumulation of two benzoyl esters in Aspergillus ustus after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis for these esters has not been elucidated prior to this study. Here, we demonstrate that these compounds are artifical products of the phenethyl polyketide ustethylin A biosynthestic pathway. In addition, four aditional benzoyl esters with different methylation levels were also isolated and identified as shunt products. Feeding experiments provided evidence that the enzyme-bound polyketide acyl intermediates are hijacked by externally fed MeOH or EtOH, leading to the formation of the benzoyl esters.Graphic abstract Accumulation of two benzoyl esters in Aspergillus ustus after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis for these esters has not been elucidated prior to this study. Here, we demonstrate that these compounds are artifical products of the phenethyl polyketide ustethylin A biosynthestic pathway. In addition, four aditional benzoyl esters with different methylation levels were also isolated and identified as shunt products. Feeding experiments provided evidence that the enzyme-bound polyketide acyl intermediates are hijacked by externally fed MeOH or EtOH, leading to the formation of the benzoyl esters. Accumulation of two benzoyl esters in Aspergillus ustus after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis for these esters has not been elucidated prior to this study. Here, we demonstrate that these compounds are artifical products of the phenethyl polyketide ustethylin A biosynthestic pathway. In addition, four aditional benzoyl esters with different methylation levels were also isolated and identified as shunt products. Feeding experiments provided evidence that the enzyme-bound polyketide acyl intermediates are hijacked by externally fed MeOH or EtOH, leading to the formation of the benzoyl esters. Accumulation of two benzoyl esters in Aspergillus ustus after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis for these esters has not been elucidated prior to this study. Here, we demonstrate that these compounds are artifical products of the phenethyl polyketide ustethylin A biosynthestic pathway. In addition, four aditional benzoyl esters with different methylation levels were also isolated and identified as shunt products. Feeding experiments provided evidence that the enzyme-bound polyketide acyl intermediates are hijacked by externally fed MeOH or EtOH, leading to the formation of the benzoyl esters. Accumulation of two benzoyl esters in Aspergillus ustus after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis for these esters has not been elucidated prior to this study. Here, we demonstrate that these compounds are artifical products of the phenethyl polyketide ustethylin A biosynthestic pathway. In addition, four aditional benzoyl esters with different methylation levels were also isolated and identified as shunt products. Feeding experiments provided evidence that the enzyme-bound polyketide acyl intermediates are hijacked by externally fed MeOH or EtOH, leading to the formation of the benzoyl esters.Accumulation of two benzoyl esters in Aspergillus ustus after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis for these esters has not been elucidated prior to this study. Here, we demonstrate that these compounds are artifical products of the phenethyl polyketide ustethylin A biosynthestic pathway. In addition, four aditional benzoyl esters with different methylation levels were also isolated and identified as shunt products. Feeding experiments provided evidence that the enzyme-bound polyketide acyl intermediates are hijacked by externally fed MeOH or EtOH, leading to the formation of the benzoyl esters. |
| Author | Zheng, Liujuan Li, Shu-Ming |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33483795$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1016_j_fm_2023_104336 crossref_primary_10_1021_acs_orglett_1c04189 crossref_primary_10_1039_D1OB02006D |
| Cites_doi | 10.1039/b704420h 10.1038/s41579-018-0121-1 10.1021/acs.orglett.0c02719 10.1038/nrmicro1286 10.1371/journal.pone.0116089 10.1055/s-2006-941472 10.1021/acs.orglett.9b04002 10.1039/C4NP00106K 10.1021/bi9009049 10.1039/D0NP00026D 10.1038/nrmicro2465 |
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| Keywords | Benzoyl esters Polyketides Biosynthesis Alcohols feeding Aspergillus ustus |
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| Snippet | Accumulation of two benzoyl esters in
Aspergillus ustus
after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis... Accumulation of two benzoyl esters in Aspergillus ustus after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis... Accumulation of two benzoyl esters in Aspergillus ustus after feeding with alcohols was reported 30 years ago. To the best of our knowledge, the biosynthesis... |
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| SubjectTerms | Alcohol Alcohols Archives & records Aspergillus Aspergillus ustus Biochemistry Biomedical and Life Sciences Biosynthesis Biotechnology Cell Biology Ecology Enzymes Esters Ethanol Experiments Fermentation Intermediates Life Sciences Metabolites Methylation Microbial Ecology Microbiology Microorganisms Natural products Original Paper polyketides |
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| Title | Benzoyl ester formation in Aspergillus ustus by hijacking the polyketide acyl intermediates with alcohols |
| URI | https://link.springer.com/article/10.1007/s00203-021-02182-0 https://www.ncbi.nlm.nih.gov/pubmed/33483795 https://www.proquest.com/docview/2514870627 https://www.proquest.com/docview/2480473766 https://www.proquest.com/docview/2551949470 https://pubmed.ncbi.nlm.nih.gov/PMC8055633 |
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