title: Structural investigation and elucidation of new communesins from a marine-derived Penicillium expansum Link by liquid chromatography/electrospray ionization mass spectrometry.
abstract: Penicillium expansum is a ubiquitous species for which there are only few reports for chemical investigation in marine environments. Among the numerous secondary metabolites produced by this species, communesins represent a new class of cytotoxic and insecticidal indole alkaloids. In this study, we investigated a marine P. expansum strain exhibiting neuroactivity on a Diptera larvae bioassay. Bio-guided purification led to the isolation and the identification of communesin B as the main active compound by HRMS and 1H and 13C NMR. Liquid chromatography analyses with detection by electrospray ionization coupled with tandem mass spectrometry (LC/ESI-MS/MS) and high-resolution tandem mass spectrometry (LC/HRMS/MS) allowed the identification and characterization of four other known communesins (A, D, E and F) in the crude extract. A fragmentation model for dimethyl epoxide communesins was proposed after detailed interpretation of their MS/MS spectra. Further analyses of the extract using the modelled fragmentations led to the detection of seven new communesins found as minor compounds. Chemical structural elucidation of these new derivatives is discussed based on their fragmentation characteristics.
authors.affiliation: Université de Nantes, MMS-EA2160, Faculté de Pharmacie, F-44035 Nantes, France.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Kerzaon
authors.forename: Yves F
authors.initials: YF
authors.lastname: Pouchus
authors.forename: Fabrice
authors.initials: F
authors.lastname: Monteau
authors.forename: Bruno
authors.initials: B
authors.lastname: Le Bizec
authors.forename: Marie-Renée
authors.initials: MR
authors.lastname: Nourrisson
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Biard
authors.forename: Olivier
authors.initials: O
authors.lastname: Grovel
mesh_terms: D000818:Animals; D002853:Chromatography, Liquid / Q000379:methods*; D004175:Diptera / Q000187:drug effects; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000494:pharmacology; D009183:Mycotoxins / Q000737:chemistry* / Q000494:pharmacology; D010407:Penicillium / Q000737:chemistry*; D012623:Seawater / Q000382:microbiology*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D009183:Mycotoxins; C483283:communesin B