Polyoxygenated cyclohexene derivatives and flavonoids from the leaves of Uvaria pandensis

Three new oxygenated cyclohexene derivatives, pandensenol D - F (1–3), two new flavanoids, pandensone A and B (4–5), and seven known compounds (6–12) were isolated from the methanol extract of the leaves of Uvaria pandensis Verdc. (Annonaceae). The structures were characterized by NMR spectroscopic and mass spectrometric analyses. The isolated metabolites were evaluated for their antibacterial activity against the Gram-positive bacteria Bacillus subtilis and Staphylococcus epidermidis, the Gram-negative bacteria Enterococcus raffinosus, Escherichia coli, Paraburkholderia caledonica, Pectobacterium carotovorum and Pseudomonas putida, and for cytotoxicity against the MCF-7 human breast cancer cell line. Out of the tested compounds, pandensenol D (1) and (6′,7′-dihydro-8'α,9'β-dihydroxy)-3-farnesylindole (12) showed weak activity, whereas (8'α,9'β-dihydroxy)-3-farnesylindole (11) strong activity against B. subtilis. Four of the isolated compounds (1, 4, 11 and 12) showed moderate cytotoxicity against MCF-7 breast cancer cells (EC50 > 100 μM).