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We herein report on the first chemical assessment of Erythrococca anomala(Juss. ex Poir.) Prain (Euphorbiaceae), a genus that was – to the bestof our knowledge – not studied yet from a phytochemical perspective. Amolecular networking strategy was implemented to rapidly identify the knownspecialized metabolites from untargeted MS/MS analyses of E.anomala leaves ethanolic extract. This strategy allowed for theidentification of diverse C-glycosyl flavones and a cursory examinationof MS/MS spectra could extend the GNPS-provided annotation to pinpointthe structural novelty of further derivatives. The isolation of the sought-afterstructures could be streamlined based on MS-guidance and their structures,determined through extensive NMR analyses, displayed structural features in linewith MS²-based predictions. Anticipating sharp structural features at anearly stage of the dereplication process through a critical assessment of thetandem mass spectrometric landmarks was essential to embark on the isolation ofthe newly reported structures owing to the elevated number of flavonoidglycosides isomers thereof formerly known, which would have deterred us fromisolating them without the support of additional tandem mass spectrometricinformation. The isolation of the main components of the ethanolic extractcompleted the currently provided chemical report on E. anomala, alsoresulting in the description of a new phenylethanoid derivative (3) andof a new orcinol-based dimer (4). Anomaloflavone (1) exhibitsignificant activities with minimal inhibitory concentration values of25 µg/mL against Staphylococcus aureus andMycobacterium smegmatis while failing to exert an antibacterialactivity against Pseudomonas aeruginosa, while being devoid ofcytotoxicity against SiHa cells.

Anticipate, Target and Characterize: MS²-anticipated C-glycosylflavones from Erythrococca anomala