Herein, a chemophenetic significance, based on phenolic metabolite profiling of three Senecio (S. hercynicus, S. ovatus and S. rupestris) and two Jacobaea species (J. pancicii and J. maritima) coupled to morphometric data, is presented. A set of twelve morphometric characters were recorded from each plant species and used as predictor variables in a Linear Discriminant Analysis (LDA) model. From a total 75 observations (15 from each of the five species), the model correctly assumed their species' membership, except 2 observations. Among the studied species, S. hercynicus and S. ovatus presented the greatest morphological similarity. A phytochemical profiling of phenolic specialized metabolites by UHPLC-Orbitrap-HRMS revealed 46 hydroxybenzoic, hydroxycinnamic, acylquinic acids and their derivatives, 1 coumarin, and 21 flavonoids. Hierarchical and PCA clustering applied to the phytochemical data corroborated the similarity of S. hercynicus and S. ovatus, observed in the morphometric analysis. This study contributes to the phylogenetic relationships between the tribe Senecioneae taxa and highlights the chemophenetic similarity/dissmilarity of the studied species belonging to Senecio and Jacobaea genera.

Oleraceins are a class of indoline amide glycosides found in Portulaca oleracea L. (Portulacaceae), or purslane. These compounds are characterized with 5,6-dihydroxyindoline-2-carboxylic acid N-acylated with cinnamic acid derivatives, and many are glucosylated. Herein, hydromethanolic extracts of the aerial parts of purslane were subjected to UHPLC-Orbitrap-HRMS analysis, conducted in negative ionization mode. Diagnostic ion filtering (DIF), followed by diagnostic difference filtering (DDF), were utilized to automatically filter out MS data and select plausible oleracein structures. After an in-depth MS2 analysis, a total of 51 oleracein compounds were tentatively identified. Of them, 26 had structure matching one of already known oleraceins and the other 25 are new, undescribed in the literature structures, belonging to the oleracein class. Moreover, diagnostic fragment ions were selected, based on which clustering algorithms and visualizations were employed. As we demonstrate, clustering methods can provide valuable insights into the mass fragmentation elucidation of natural compounds in complex mixtures.