Veronica: Acylated flavone glycosides as chemosystematic markers

HPLC/DAD and LC-MS of an extract of Veronica spicata (subgenus Pseudolysimachium, Plantaginaceae) revealed the presence of six 6-hydroxyluteolin glycosides acylated with phenolic acids, three of which are new compounds and which we called spicosides. A flavonoid survey of seven more species belonging to V. subgenus Pseudolysimachium and eight species of V. subgenus Pentasepalae showed that all the Pseudolysimachium species and four of the Pentasepalae species produced 6-hydroxyflavone glycosides, whereas the remaining four Pentasepalae species contained acetylated 8-hydroxyflavone glycosides instead. Spicosides appeared to be common in subgenus Pseudolysimachium (detected in five out of eight species), but we did not find them in subgenus Pentasepalae. Previously, acetylated 8-hydroxyflavone glycosides have been isolated from or detected in eight species of V. subgenus Pentasepalae (in 13 species altogether including the new results) and seven species of V. subgenus Pocilla. However, 6-hydroxyflavone glycosides occur in some other species of these subgenera. The results are discussed in an evolutionary context.