Flavonoids from two Turkish Centaurea species and their chemotaxonomic implications

Centaurea asutro-anatolica Hub.-Mor. and C. kizildaghensis Uzunh., E. Doğan & H. Duman, two indigenous perennial herbs from the Turkish flora, belong to the medicinally important genus Centaurea L. (fam: Asteraceae), which comprises ca. 600 species worldwide. While various Centaurea species are well-known for producing alkaloids, flavonoids, lignans and terpenoids, there is no report on any thorough phytochemical work on any of these two species available to date. In continuation of our phytochemical and bioactivity studies on the Turkish Centaurea species, four flavonoids apigenin (1), apigenin 7,4’-dimethyl ether (2), genkwanin (3) and quercetin (4) were isolated from the methanol extracts of the aerial parts of C. austro-anatolica and C. kizildaghensis, for the very first time. The structures of the flavonoids were elucidated conclusively by spectroscopic means, i.e., UV, MS and 1D and 2D NMR data analyses. The distribution of these flavonoids (1-4) within the genus Centaurea and their possible chemotaxonomic implications within the genus Centaurea or the family Asteraceae have been discussed.