guaiane and cynaropicrin

The apolar organic extract obtained from aerial parts of Centaurea drabifolia Sibth. & Sm. subsp. detonsa (Bornm.) Wagenitz, growing wild in Turkey, was investigated for the first time for its secondary metabolite composition. Seven sesquiterpene lactones belonging to the guaiane class (1-7), including the new compound 4, along with a fatty acid lactone derivative (8), were isolated. The structures of these compounds were established by spectroscopic analysis, including 2D NMR spectroscopic techniques, with the stereostructure of the new guaiane 4 determined with the help of MTPA derivatization. Cytotoxic activities of compounds 1-7 were evaluated against two cancer cell lines, namely acute lymphoblastic leukemia (CCRF-CEM) and its multidrug-resistant subline CEM/ADR5000. Results showed that aguerin B (1) and cynaropicrin (2) showed a potent activity on both cell lines revealing interesting details about the structure-activity relationships in the class of acylated guaiane sesquiterpenes.

Topics: Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Centaurea; Drug Resistance, Neoplasm; Drug Screening Assays, Antitumor; Humans; Lactones; Leukemia; Molecular Structure; Plant Components, Aerial; Plant Extracts; Sesquiterpenes; Sesquiterpenes, Guaiane; Structure-Activity Relationship; Turkey