Secondary metabolites from two species of pulicaria and their cytotoxic activity

Abstract

Two new compounds, the sesquiterpene (1E,5E)-8 beta-acetoxy-4a-hydroxy-7 beta H-germacra-1(10),5-dien-14-oic acid (2), and a nor-sesquiterpene, (5E)-8 beta-acetoxy-4a-hydroxy-7 beta H-germacr-5-en-10-one (3), were isolated from Pulicaria canariensis ssp. lanata, along with ten known compounds, including the flavonoid 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (4). From Pulicaria burchardii, we isolated seven known compounds; the physical and spectroscopic data of the triterpenoid 3 beta-hydroxytaraxaster-20-en-30-al (1) are reported. The structures of compounds 13 were determined on the basis of HR-MS, and 1D- and 2D-NMR studies. The structure of 2 was corroborated by X-ray crystal diffraction. Cell viability experiments revealed that the semisynthetic flavonoid 4b was the most cytotoxic compound against human leukemia cells, and the cytotoxicity was caused by induction of apoptosis, as determined by microscopy of nuclear changes.