Tissue-Specific Accumulation and Isomerization of Valuable Phenylethanoid Glycosides from Plantago and Forsythia Plants.

A comparative phytochemical study on the phenylethanoid glycoside (PhEG) composition of the underground organs of three Plantago species (P. lanceolata, P. major, and P. media) and that of the fruit wall and seed parts of Forsythia suspensa and F. europaea fruits was performed. The leaves of these Forsythia species and six cultivars of the hybrid F. × intermedia were also analyzed, demonstrating the tissue-specific accumulation and decomposition of PhEGs. Our analyses confirmed the significance of selected tissues as new and abundant sources of these valuable natural compounds. The optimized heat treatment of tissues containing high amounts of the PhEG plantamajoside (PM) or forsythoside A (FA), which was performed in distilled water, resulted in their characteristic isomerizations. In addition to PM and FA, high amounts of the isomerization products could also be isolated after heat treatment. The isomerization mechanisms were elucidated by molecular modeling, and the structures of PhEGs were identified by nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectrometry (HR-MS) techniques, also confirming the possibility of discriminating regioisomeric PhEGs by tandem MS. The PhEGs showed no cytostatic activity in non-human primate Vero E6 cells, supporting their safe use as natural medicines and allowing their antiviral potency to be tested.

Chemodiversity of Cirsium fruits: Antiproliferative lignans, neolignans and sesquineolignans as chemotaxonomic markers.

While analyzing the fruit composition of nine European Cirsium species representing three sections (i.e., Cephalonoplos, Chamaeleon and Eriolepis), four lignans, three neolignans and three sesquineolignans were determined and used as chemotaxonomic markers. Among them, desmethyl balanophonin and desmethyl picrasmalignan were determined for the first time in the plant kingdom, as the main metabolites of the Chamaeleon section. Prebalanophonin and prepicrasmalignan, identified so far exclusively in C. eriophorum, were also confirmed in C. boujartii and C. vulgare, highlighting the chemotaxonomic significance of these compounds in the Eriolepis section. The antiproliferative assay of the compounds isolated from their optimum sources, confirmed a dose-dependent inhibitory effect of the structures bearing the 4',7-epoxy moiety (balanophonin, picrasmalignan, desmethyl balanophonin, desmethyl picrasmalignan) against SW480 colon cancer cells, while those bearing the 4',7-dihydroxy motif (prebalanophonin, prepicrasmalignan) were inactive.