Iridoid patterns in Galium L. and some phylogenetic considerations.

From 19 species of Galium, members of 6 European sections of the genus, 24 compounds were isolated, namely 16 iridoid glucosides, 2 secoiridoid glucosides and 6 triterpene saponins (the later found only in G. rivale (Sibth. & Sm. Griseb.) The iridoid content was analyzed by thin layer chromatography - densitometry. An effort was made to clarify interspecies relationships, based on the obtained results and previous data. Generally, a nearly uniform iridoid pattern in the studied species was observed. Nevertheless, some distinctions gave reason the following chemical characters to be treated as taxonomic markers: iridoids, secogalioside (characteristic of G. mollugo group), iridoids V1 and V2 (G. humifusum Bieb. and G. verum L.), 6-acetylscandoside (G. incurvum group and G. verum) and the triterpene saponins, rivalioside A and rivalioside C (characteristic of G. rivale). The studied species regarding to the iridoids could be attributed to three lines of evolutionary differentiation. One line is leading to the differentiation of G. rivale. It contains specific triterpenoids as well as iridoid acids, which show parallel development of both glyceraldehyde 3-phosphate/pyruvate and mevalonate biosynthetic routes in this species. A second line includes G. mollugo and G. incurvum species groups and the species G. humifusum and G. verum. Variety of iridoid esters, hydroxy and carboxy derivatives of iridoids and secoiridoids characterised this line. Third line comprises the remaining studied species, members of different sections and species groups. They posses a nearly identical iridoid pattern, which suggests a convergent evolution regarding to the iridoids.