Polyoxygenated cyclohexene derivatives and flavonoids from the leaves of Uvaria pandensis

• Published in: Fitoterapia Vol. 158; p. 105170
• Main Authors: Maeda, Gasper, Gilissen, Pieter J., Bourgard, Catarina, van der Wal, Jelle, Munissi, Joan J.E., Nyandoro, Stephen S., Erdélyi, Máté
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 01.04.2022; Elsevier Science Ltd
• Subjects: Annonaceae; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Bacillus subtilis; Bacteria; Breast cancer; Coliforms; Cyclohexene; Cyclohexenes; Cytotoxicity; E coli; Flavonoids; Flavonoids - analysis; Flavonoids - pharmacology; Gram-negative bacteria; Gram-positive bacteria; Humans; Metabolites; Molecular Structure; NMR; Nuclear magnetic resonance; Pandensenol; Pandensone; Plant Leaves - chemistry; Pseudomonas putida; Spectrometry; Toxicity; Uvaria - chemistry; Uvaria pandensis; Uvaria pandensis; Antibacterial activity; Cytotoxicity; Annonaceae; Pandensone; Pandensenol
• ISSN: 0367-326X; 1873-6971; 1873-6971
• DOI: 10.1016/j.fitote.2022.105170

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). [Display omitted]