Journal article
A Molecular Networking Based Discovery of Diketopiperazine Heterodimers and Aspergillicins from Aspergillus caelatus
Department of Biotechnology and Biomedicine, Technical University of Denmark1
Natural Product Discovery, Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark2
Fundación MEDINA3
Center for Microbial Secondary Metabolites, Centers, Technical University of Denmark4
Fungal Chemodiversity, Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark5
The number of species in Aspergillus section Flavi has recently increased to 36 and includes some of the most important and well-known species in the genus Aspergillus. Numerous secondary metabolites, especially mycotoxins, have been reported from species such as A. flavus; however many of the more recently described species are less studied from a chemical point of view.
This paper describes the use of MS/MS-based molecular networking to investigate the metabolome of A. caelatus leading to the discovery of several new diketopiperazine dimers and aspergillicins. An MS-guided isolation procedure yielded six new compounds, including asperazines D-H ( 1-5 ) and aspergillicin H ( 6 ).
Asperazines G and H are artifacts derived from asperazines E and F formed during the separation process by formic acid. Two known compounds, aspergillicins A and C ( 7 and 8 ), were isolated from the same strain. Structures were elucidated by analyzing their HR-MS/MS and NMR spectroscopic data. The absolute configuration of asperazines D-F and aspergillicin H were deduced from the combination of NMR, Marfey's method, and ECD analyses.
Language: | English |
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Publisher: | American Chemical Society and American Society of Pharmacognosy |
Year: | 2022 |
Pages: | 25-33 |
ISSN: | 15206025 and 01633864 |
Types: | Journal article |
DOI: | 10.1021/acs.jnatprod.1c00526 |
ORCIDs: | Larsen, Thomas O. , Wang, Xinhui and Frisvad, Jens C. |