Cruciasides C-G, monoterpenoid glycosides from Cruciata articulata

Cruciata articulata (L.) Ehrend. is a herbaceous species distributed in parts of Western Asia and the Mediterranean region. While research on other species in the Cruciata genus has revealed the presence of a range of flavonoids and terpenoids, few such studies have been conducted on C. articulata. Thus, in the current study, a phytochemical investigation of C. articulata was carried out. Molecular networking identified a large cluster of compounds sharing distinctive MS-MS fragmentation patterns that were targeted for isolation, leading to the isolation of five undescribed monoterpenoid glycosides, cruciasides C-G, along with two known monoterpenoid glycosides. The structures of these compounds were elucidated by using chemical and spectroscopic analyses, including 1D and 2D NMR, and MS-MS fragmentation. Structures for the ions observed in the MS-MS were proposed, and based on these fragmentation patterns, structures for several of the minor components observed in the molecular network were also proposed. All isolated compounds were tested for cytotoxic, anti-inflammatory, antimicrobial, and α-glucosidase inhibitory properties, but did not display any activity.