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J. Fungi 2018, 4(3), 96; https://doi.org/10.3390/jof4030096

Oryzines A & B, Maleidride Congeners from Aspergillus oryzae and Their Putative Biosynthesis

1
University of Bristol, School of Chemistry, Cantock’s Close, Bristol BS8 1TS, UK
2
Leibniz Universität Hannover, Biomolekulares Wirkstoffzentrum und Institut für Organische Chemie, Schneiderberg 38, 30167 Hannover, Germany
3
University of Bristol, School of Chemistry, Cantock’s Close, Bristol BS8 1TS, UK
4
Leibniz Universität Hannover, Biomolekulares Wirkstoffzentrum und Institut für Organische Chemie, Schneiderberg 38, 30167 Hannover, Germany
*
Author to whom correspondence should be addressed.
Received: 19 July 2018 / Revised: 8 August 2018 / Accepted: 10 August 2018 / Published: 13 August 2018
(This article belongs to the Special Issue Fungal Polyketides and Other Secondary Metabolites)
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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. View Full-Text
Keywords: natural products; citrate synthase; biosynthetic gene cluster; structure elucidation; fatty acid synthase natural products; citrate synthase; biosynthetic gene cluster; structure elucidation; fatty acid synthase
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Wasil, Z.; Kuhnert, E.; Simpson, T.J.; Cox, R.J. Oryzines A & B, Maleidride Congeners from Aspergillus oryzae and Their Putative Biosynthesis. J. Fungi 2018, 4, 96.

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