Untargeted Metabolomics Approach for the Discovery of Environment-Related Pyran-2-Ones Chemodiversity in a Marine-Sourced Penicillium restrictum
| Autor: | Fabrice Fleury, Cédric Logé, Samuel Bertrand, Sandra Bourgeade-Delmas, Nathalie Caroff, Emmanuel Gentil, Olivier Grovel, Van-Tuyen Le, Grégory Genta-Jouve, Thibaut Robiou du Pont |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
0301 basic medicine
Aquatic Organisms QH301-705.5 Penicillium restrictum Pharmaceutical Science Mass spectrometry OSMAC 01 natural sciences Article Structure-Activity Relationship 03 medical and health sciences chemistry.chemical_compound Pyran-2-one Drug Discovery Metabolome Animals Metabolomics mussel-derived fungi Food science Biology (General) Pharmacology Toxicology and Pharmaceutics (miscellaneous) Pyrans pyran-2-one biology 010405 organic chemistry Penicillium Mussel biology.organism_classification Mytilus Bivalvia 0104 chemical sciences 030104 developmental biology Untargeted metabolomics chemistry Pyran metabolome France Mussel-derived fungi Blue mussel |
| Zdroj: | Marine Drugs (1660-3397) (MDPI AG), 2021-06-29, Vol. 19, N. 7, P. 378 (26p.) Marine Drugs Volume 19 Issue 7 Marine Drugs, Vol 19, Iss 378, p 378 (2021) |
| Popis: | Very little is known about chemical interactions between fungi and their mollusc host within marine environments. Here, we investigated the metabolome of a Penicillium restrictum MMS417 strain isolated from the blue mussel Mytilus edulis collected on the Loire estuary, France. Following the OSMAC approach with the use of 14 culture media, the effect of salinity and of a mussel-derived medium on the metabolic expression were analysed using HPLC-UV/DAD-HRMS/MS. An untargeted metabolomics study was performed using principal component analysis (PCA), orthogonal projection to latent structure discriminant analysis (O-PLSDA) and molecular networking (MN). It highlighted some compounds belonging to sterols, macrolides and pyran-2-ones, which were specifically induced in marine conditions. In particular, a high chemical diversity of pyran-2-ones was found to be related to the presence of mussel extract in the culture medium. Mass spectrometry (MS)- and UV-guided purification resulted in the isolation of five new natural fungal pyran-2-one derivatives—5,6-dihydro-6S-hydroxymethyl-4-methoxy-2H-pyran-2-one (1), (6S, 1’R, 2’S)-LL-P880β (3), 5,6-dihydro-4-methoxy-6S-(1’S, 2’S-dihydroxy pent-3’(E)-enyl)-2H-pyran-2-one (4), 4-methoxy-6-(1’R, 2’S-dihydroxy pent-3’(E)-enyl)-2H-pyran-2-one (6) and 4-methoxy-2H-pyran-2-one (7)—together with the known (6S, 1’S, 2’S)-LL-P880β (2), (1’R, 2’S)-LL-P880γ (5), 5,6-dihydro-4-methoxy-2H-pyran-2-one (8), (6S, 1’S, 2’R)-LL-P880β (9), (6S, 1’S)-pestalotin (10), 1’R-dehydropestalotin (11) and 6-pentyl-4-methoxy-2H-pyran-2-one (12) from the mussel-derived culture medium extract. The structures of 1-12 were determined by 1D- and 2D-MMR experiments as well as high-resolution tandem MS, ECD and DP4 calculations. Some of these compounds were evaluated for their cytotoxic, antibacterial, antileishmanial and in-silico PTP1B inhibitory activities. These results illustrate the utility in using host-derived media for the discovery of new natural products. |
| Databáze: | OpenAIRE |
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