Biosynthetic Pathway for the Epipolythiodioxopiperazine Acetylaranotin in Aspergillus terreus Revealed by Genome-Based Deletion Analysis
Epipolythiodioxopiperazines (ETPs) are a class of fungal secondary metabolites derived from diketopiperazines. Acetylaranotin belongs to one structural subgroup of ETPs characterized by the presence of a seven-membered 4,5-dihydrooxepine ring. Defining the genes involved in acetylaranotin biosynthes...
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| Published in | Journal of the American Chemical Society Vol. 135; no. 19; pp. 7205 - 7213 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
15.05.2013
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| Abstract | Epipolythiodioxopiperazines (ETPs) are a class of fungal secondary metabolites derived from diketopiperazines. Acetylaranotin belongs to one structural subgroup of ETPs characterized by the presence of a seven-membered 4,5-dihydrooxepine ring. Defining the genes involved in acetylaranotin biosynthesis should provide a means to increase the production of these compounds and facilitate the engineering of second-generation molecules. The filamentous fungus Aspergillus terreus produces acetylaranotin and related natural products. Using targeted gene deletions, we have identified a cluster of nine genes (including one nonribosomal peptide synthetase gene, ataP) that is required for acetylaranotin biosynthesis. Chemical analysis of the wild-type and mutant strains enabled us to isolate 17 natural products from the acetylaranotin biosynthesis pathway. Nine of the compounds identified in this study are natural products that have not been reported previously. Our data have allowed us to propose a biosynthetic pathway for acetylaranotin and related natural products. |
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| AbstractList | Epipolythiodioxopiperazines (ETPs) are a class of fungal secondary metabolites derived from diketopiperazines. Acetylaranotin belongs to one structural subgroup of ETPs characterized by the presence of a seven-membered 4,5-dihydrooxepine ring. Defining the genes involved in acetylaranotin biosynthesis should provide a means to increase the production of these compounds and facilitate the engineering of second-generation molecules. The filamentous fungus Aspergillus terreus produces acetylaranotin and related natural products. Using targeted gene deletions, we have identified a cluster of nine genes (including one nonribosomal peptide synthetase gene, ataP) that is required for acetylaranotin biosynthesis. Chemical analysis of the wild-type and mutant strains enabled us to isolate 17 natural products from the acetylaranotin biosynthesis pathway. Nine of the compounds identified in this study are natural products that have not been reported previously. Our data have allowed us to propose a biosynthetic pathway for acetylaranotin and related natural products. Epipolythiodioxopiperazines (ETPs) are a class of fungal secondary metabolites derived from diketopiperazines. Acetylaranotin belongs to one structural subgroup of ETPs characterized by the presence of a seven-membered 4,5-dihydrooxepine ring. Defining the genes involved in acetylaranotin biosynthesis should provide a means to increase production of these compounds and facilitate the engineering of second-generation molecules. The filamentous fungus Aspergillus terreus produces acetylaranotin and related natural products. Using targeted gene deletions, we have identified a cluster of nine genes including one nonribosomal peptide synthetase gene, ataP , which is required for acetylaranotin biosynthesis. Chemical analysis of the wild type and mutant strains enabled us to isolate seventeen natural products from the acetylaranotin biosynthesis pathway. Nine of the compounds identified in this study are previously not reported natural products. Our data allow us to propose a biosynthetic pathway for acetylaranotin and related natural products. Epipolythiodioxopiperazines (ETPs) are a class of fungal secondary metabolites derived from diketopiperazines. Acetylaranotin belongs to one structural subgroup of ETPs characterized by the presence of a seven-membered 4,5-dihydrooxepine ring. Defining the genes involved in acetylaranotin biosynthesis should provide a means to increase the production of these compounds and facilitate the engineering of second-generation molecules. The filamentous fungus Aspergillus terreus produces acetylaranotin and related natural products. Using targeted gene deletions, we have identified a cluster of nine genes (including one nonribosomal peptide synthetase gene, ataP) that is required for acetylaranotin biosynthesis. Chemical analysis of the wild-type and mutant strains enabled us to isolate 17 natural products from the acetylaranotin biosynthesis pathway. Nine of the compounds identified in this study are natural products that have not been reported previously. Our data have allowed us to propose a biosynthetic pathway for acetylaranotin and related natural products.Epipolythiodioxopiperazines (ETPs) are a class of fungal secondary metabolites derived from diketopiperazines. Acetylaranotin belongs to one structural subgroup of ETPs characterized by the presence of a seven-membered 4,5-dihydrooxepine ring. Defining the genes involved in acetylaranotin biosynthesis should provide a means to increase the production of these compounds and facilitate the engineering of second-generation molecules. The filamentous fungus Aspergillus terreus produces acetylaranotin and related natural products. Using targeted gene deletions, we have identified a cluster of nine genes (including one nonribosomal peptide synthetase gene, ataP) that is required for acetylaranotin biosynthesis. Chemical analysis of the wild-type and mutant strains enabled us to isolate 17 natural products from the acetylaranotin biosynthesis pathway. Nine of the compounds identified in this study are natural products that have not been reported previously. Our data have allowed us to propose a biosynthetic pathway for acetylaranotin and related natural products. |
| Author | Bruno, Kenneth S Guo, Chun-Jun Wang, Clay C. C Sanchez, James F Chiang, Yi-Ming Chang, Shu-Ling Yeh, Hsu-Hua |
| AuthorAffiliation | Pacific Northwest National Laboratory Chia Nan University of Pharmacy and Science University of Southern California |
| AuthorAffiliation_xml | – name: Chia Nan University of Pharmacy and Science – name: Pacific Northwest National Laboratory – name: University of Southern California – name: 4 Department of Biotechnology, Chia Nan University of Pharmacy and Science, Tainan 71710, Taiwan – name: 5 Department of Chemistry, College of Letters, Arts, and Sciences, University of Southern California, Los Angeles, CA 90089, USA – name: 2 Chemical and Biological Process Development Group, Energy and Environment Directorate, Pacific Northwest National Laboratory, Richland, WA 99352, USA – name: 1 Department of Pharmacology and Pharmaceutical Sciences, School of Pharmacy, University of Southern California, Los Angeles, CA 90089, USA – name: 3 Graduate Institute of Pharmaceutical Science, Chia Nan University of Pharmacy and Science, Tainan 71710, Taiwan |
| Author_xml | – sequence: 1 givenname: Chun-Jun surname: Guo fullname: Guo, Chun-Jun – sequence: 2 givenname: Hsu-Hua surname: Yeh fullname: Yeh, Hsu-Hua – sequence: 3 givenname: Yi-Ming surname: Chiang fullname: Chiang, Yi-Ming – sequence: 4 givenname: James F surname: Sanchez fullname: Sanchez, James F – sequence: 5 givenname: Shu-Ling surname: Chang fullname: Chang, Shu-Ling – sequence: 6 givenname: Kenneth S surname: Bruno fullname: Bruno, Kenneth S – sequence: 7 givenname: Clay C. C surname: Wang fullname: Wang, Clay C. C email: clayw@usc.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23586797$$D View this record in MEDLINE/PubMed |
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| Snippet | Epipolythiodioxopiperazines (ETPs) are a class of fungal secondary metabolites derived from diketopiperazines. Acetylaranotin belongs to one structural... |
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| SubjectTerms | Aspergillus - chemistry Aspergillus - enzymology Aspergillus - genetics Aspergillus - metabolism Aspergillus terreus biochemical pathways biosynthesis Biosynthetic Pathways chemical analysis diketopiperazines engineering fungi Gene Deletion genes Genome, Fungal Multigene Family mutants Oxepins - chemistry Oxepins - metabolism Piperazines - chemistry Piperazines - metabolism secondary metabolites |
| Title | Biosynthetic Pathway for the Epipolythiodioxopiperazine Acetylaranotin in Aspergillus terreus Revealed by Genome-Based Deletion Analysis |
| URI | http://dx.doi.org/10.1021/ja3123653 https://www.ncbi.nlm.nih.gov/pubmed/23586797 https://www.proquest.com/docview/1352279556 https://www.proquest.com/docview/2431954244 https://pubmed.ncbi.nlm.nih.gov/PMC3695726 |
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