Details
| Original language | English |
|---|---|
| Article number | 96 |
| Journal | Journal of Fungi |
| Volume | 4 |
| Issue number | 3 |
| Early online date | 13 Aug 2018 |
| Publication status | Published - Sept 2018 |
Abstract
Aspergillus oryzae is traditionally used in East Asia for the production of food and brewing. In addition, it has been developed into a suitable host for the heterologous expression of natural product biosynthetic genes and gene clusters, enabling the functional analysis of the encoded enzymes. A. oryzae shares a 99.5% genome homology with Aspergillus flavus, but their secondary metabolomes differ significantly and various compounds unique to A. oryzae have been reported. While using A. oryzae as a host for heterologous expression experiments we discovered two new metabolites in extracts of A. oryzae M-2-3 with an unusual maleidride backbone, which were named oryzine A and B. Their structures were elucidated by high resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) analysis. Their structural relationships with known maleidrides implied involvement of a citrate synthase (CS) and a polyketide (PKS) or fatty acid synthase (FAS) in their biosynthesis. Analysis of the A. oryzae genome revealed a single putative biosynthetic gene cluster (BGC) consistent with the hypothetical biosynthesis of the oryzines. These findings increase knowledge of the chemical potential of A. oryzae and are the first attempt to link a novel product of this fungus with genomic data.
Keywords
- Biosynthetic gene cluster, Citrate synthase, Fatty acid synthase, Natural products, Structure elucidation
ASJC Scopus subject areas
- Agricultural and Biological Sciences(all)
- Ecology, Evolution, Behavior and Systematics
- Agricultural and Biological Sciences(all)
- Plant Science
- Medicine(all)
- Microbiology (medical)
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In: Journal of Fungi, Vol. 4, No. 3, 96, 09.2018.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Oryzines A & B, Maleidride Congeners from Aspergillus oryzae and Their Putative Biosynthesis
AU - Wasil, Zahida
AU - Kuhnert, Eric
AU - Simpson, Thomas J.
AU - Cox, Russell J.
N1 - Funding information: This research was funded by EPSRC (Engineering and Physical Sciences research council) grant number EP/F066104/1 and DFG (Deutsche Forschungsgemeinschaft) grant number CO 1328/4-1. The authors thank Jenny Rose and Walid Bakeer for technical assistance. Zahida Wasil Thanks the Government of Pakistan (Higher Education Commission) for funding. We are grateful to Daniel Wibberg for the re-annotation of the A. oryzae genomic data.
PY - 2018/9
Y1 - 2018/9
N2 - Aspergillus oryzae is traditionally used in East Asia for the production of food and brewing. In addition, it has been developed into a suitable host for the heterologous expression of natural product biosynthetic genes and gene clusters, enabling the functional analysis of the encoded enzymes. A. oryzae shares a 99.5% genome homology with Aspergillus flavus, but their secondary metabolomes differ significantly and various compounds unique to A. oryzae have been reported. While using A. oryzae as a host for heterologous expression experiments we discovered two new metabolites in extracts of A. oryzae M-2-3 with an unusual maleidride backbone, which were named oryzine A and B. Their structures were elucidated by high resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) analysis. Their structural relationships with known maleidrides implied involvement of a citrate synthase (CS) and a polyketide (PKS) or fatty acid synthase (FAS) in their biosynthesis. Analysis of the A. oryzae genome revealed a single putative biosynthetic gene cluster (BGC) consistent with the hypothetical biosynthesis of the oryzines. These findings increase knowledge of the chemical potential of A. oryzae and are the first attempt to link a novel product of this fungus with genomic data.
AB - Aspergillus oryzae is traditionally used in East Asia for the production of food and brewing. In addition, it has been developed into a suitable host for the heterologous expression of natural product biosynthetic genes and gene clusters, enabling the functional analysis of the encoded enzymes. A. oryzae shares a 99.5% genome homology with Aspergillus flavus, but their secondary metabolomes differ significantly and various compounds unique to A. oryzae have been reported. While using A. oryzae as a host for heterologous expression experiments we discovered two new metabolites in extracts of A. oryzae M-2-3 with an unusual maleidride backbone, which were named oryzine A and B. Their structures were elucidated by high resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) analysis. Their structural relationships with known maleidrides implied involvement of a citrate synthase (CS) and a polyketide (PKS) or fatty acid synthase (FAS) in their biosynthesis. Analysis of the A. oryzae genome revealed a single putative biosynthetic gene cluster (BGC) consistent with the hypothetical biosynthesis of the oryzines. These findings increase knowledge of the chemical potential of A. oryzae and are the first attempt to link a novel product of this fungus with genomic data.
KW - Biosynthetic gene cluster
KW - Citrate synthase
KW - Fatty acid synthase
KW - Natural products
KW - Structure elucidation
UR - http://www.scopus.com/inward/record.url?scp=85054697972&partnerID=8YFLogxK
U2 - 10.3390/jof4030096
DO - 10.3390/jof4030096
M3 - Article
AN - SCOPUS:85054697972
VL - 4
JO - Journal of Fungi
JF - Journal of Fungi
IS - 3
M1 - 96
ER -