Structural investigation and elucidation of new communesins from a marine-derived Penicillium expansum Link by liquid chromatography/electrospray ionization mass spectrometry

Rapid Communications in Mass Spectrometry : RCM
Isabelle KerzaonOlivier Grovel

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.

References

Apr 1, 1977·Applied and Environmental Microbiology·A CieglerL K Jackson
Nov 1, 1996·International Journal of Food Microbiology·O FiltenborgU Thrane
Dec 26, 2001·The Journal of Organic Chemistry·A S RatnayakeT K Hemscheidt
Jan 5, 2002·Journal of Microbiological Methods·Anne LandreauJean François Verbist
Aug 29, 2003·Organic Letters·Seth L Crawley, Raymond L Funk
Mar 25, 2004·Natural Product Reports·Tim S Bugni, Chris M Ireland
Apr 2, 2004·Bioscience, Biotechnology, and Biochemistry·Hideo HayashiKohki Akiyama
Feb 26, 2005·Journal of Natural Products·Petur W DalsgaardCarsten Christophersen
Dec 6, 2005·Phytochemistry·Lucy J WigleyDavid A Perry
Nov 4, 2006·The Journal of Organic Chemistry·Jae Hong SeoSteven M Weinreb
Oct 25, 2007·Journal of the American Chemical Society·Jun YangYong Qin
Dec 11, 2007·Toxicon : Official Journal of the International Society on Toxinology·Isabelle KerzaonYves-François Pouchus

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Citations

Mar 26, 2010·The Journal of Organic Chemistry·Jae Hong SeoSteven M Weinreb
Feb 24, 2016·Marine Drugs·Rosario Nicoletti, Antonio Trincone
Jan 10, 2012·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Flaubert MbeunkuiMary Ann Lila
Nov 28, 2009·Toxicon : Official Journal of the International Society on Toxinology·Nicolas RuizYves François Pouchus
Feb 23, 2010·Angewandte Chemie·Peng LiuSteven M Weinreb
Jan 13, 2015·Angewandte Chemie·Hsiao-Ching LinYi Tang
Sep 8, 2012·Fungal Biology·Marieke VansteelandtOlivier Grovel
Dec 4, 2014·Journal of Chromatography. a·Jean-Luc WolfenderSamuel Bertrand
Apr 1, 2017·Critical Reviews in Food Science and Nutrition·Joanna TannousOlivier Puel
Oct 13, 2018·Organic & Biomolecular Chemistry·Chihiro TsukanoYoshiji Takemoto
Sep 17, 2020·International Journal of Molecular Sciences·Chrystian Zetina-SerranoOlivier Puel
Apr 27, 2010·Journal of Natural Products·Zhenyu LuWeiming Zhu

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