Veronica:: Iridoids and cornoside as chemosystematic markers

The iridoid glucoside, ajugol, and the phenylethanoid glucoside, cornoside, have been isolated from species of Veronica (Plantaginaceac) for the first time. The presence of these compounds has been screened in 18 plant accessions belonging to 15 species of Veronica (Plantaginaceae), by isolation or NMR spectroscopy of crude extracts. In addition, the distribution of iridoids in the genus has been reviewed, using mainly the published data of isolated compounds. Using the recent expansion and reclassification of the genus based on DNA-sequence results as the model, we find that the genus is rather homogeneous with regard to the distribution of iridoid glucosides, aucubin and/or catalpol as well as 6-O-esters of catalpol being universally present in 10 of the 12 subgenera for which data exist. Only the two subgenera Pocilla and Chamaedrys deviate from this pattern. Pocilla is heterogeneous; in this subgenus, species in subsect. Agrestes contain the standard iridoid garniture, while species in subsect. Biloba do not contain the 6-O-esters of catalpol, but ajugol instead. Veronica intercedens (subsect. Subracemosae) differs from the remainder of the subgenus in only containing 5-hydroxylated iridoids (melittoside and globularifolin) and is so far the only species within the genus in which such compounds have been detected. These chemical differences are clearly reflected in the DNA-based phylogram of the subgenus. Subg. Chamaedrys appears homogeneous in lacking iridoids or only containing these in small amounts, but instead half of the investigated species contained the phenylethanoid glucoside cornoside. The distribution of this compound in angiosperms is reviewed; cornoside often substitutes iridoid glucosides in plants where these are expected to be present. The chemical results of Veronica fit in very well with the phylogenetic implications of the DNA-sequence results. (c) 2005 Elsevier Ltd. All rights reserved.