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Article

Untargeted Metabolomics Approach for the Discovery of Environment-Related Pyran-2-Ones Chemodiversity in a Marine-Sourced Penicillium restrictum

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Faculty of Pharmacy, University of Nantes, EA 2160-Mer Molécules Santé, 9 rue Bias BP 53508, CEDEX 1, 44035 Nantes, France
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Group of Mechanism and Regulation of DNA Repair and IMPACT Platform, UFIP UMR CNRS 6286, University of Nantes, 44322 Nantes, France
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Laboratoire EA3826, University of Nantes, IRS2 Nantes Biotech, CEDEX 1, 44100 Nantes, France
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UMR 125 PharmaDev, University of Toulouse, IRD, 31400 Toulouse, France
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EA1155-IICIMED, University of Nantes, IRS2 Nantes Biotech, CEDEX 1, 44100 Nantes, France
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Laboratory Ecology, Evolution, Interactions of Amazonian Systems (LEEISA), USR 3456, University of French Guiana, CNRS Guyane, 275 Route de Montabo, 97334 Cayenne, France
*
Author to whom correspondence should be addressed.
Academic Editors: Orazio Taglialatela-Scafati and Bill J. Baker
Mar. Drugs 2021, 19(7), 378; https://doi.org/10.3390/md19070378
Received: 1 June 2021 / Revised: 25 June 2021 / Accepted: 26 June 2021 / Published: 29 June 2021
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. View Full-Text
Keywords: Penicillium restrictum; mussel-derived fungi; OSMAC; metabolome; pyran-2-one Penicillium restrictum; mussel-derived fungi; OSMAC; metabolome; pyran-2-one
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MDPI and ACS Style

Le, V.-T.; Bertrand, S.; Robiou du Pont, T.; Fleury, F.; Caroff, N.; Bourgeade-Delmas, S.; Gentil, E.; Logé, C.; Genta-Jouve, G.; Grovel, O. Untargeted Metabolomics Approach for the Discovery of Environment-Related Pyran-2-Ones Chemodiversity in a Marine-Sourced Penicillium restrictum. Mar. Drugs 2021, 19, 378. https://doi.org/10.3390/md19070378

AMA Style

Le V-T, Bertrand S, Robiou du Pont T, Fleury F, Caroff N, Bourgeade-Delmas S, Gentil E, Logé C, Genta-Jouve G, Grovel O. Untargeted Metabolomics Approach for the Discovery of Environment-Related Pyran-2-Ones Chemodiversity in a Marine-Sourced Penicillium restrictum. Marine Drugs. 2021; 19(7):378. https://doi.org/10.3390/md19070378

Chicago/Turabian Style

Le, Van-Tuyen, Samuel Bertrand, Thibaut Robiou du Pont, Fabrice Fleury, Nathalie Caroff, Sandra Bourgeade-Delmas, Emmanuel Gentil, Cedric Logé, Gregory Genta-Jouve, and Olivier Grovel. 2021. "Untargeted Metabolomics Approach for the Discovery of Environment-Related Pyran-2-Ones Chemodiversity in a Marine-Sourced Penicillium restrictum" Marine Drugs 19, no. 7: 378. https://doi.org/10.3390/md19070378

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