Polyoxygenated cyclohexene derivatives and flavonoids from the leaves of Uvaria pandensis

Gasper Maeda; Pieter J Gilissen; Catarina Bourgard; Jelle van der Wal; Joan J E Munissi; Stephen S Nyandoro; Máté Erdélyi

doi:10.1016/j.fitote.2022.105170

Polyoxygenated cyclohexene derivatives and flavonoids from the leaves of Uvaria pandensis

Fitoterapia. 2022 Apr:158:105170. doi: 10.1016/j.fitote.2022.105170. Epub 2022 Mar 12.

Authors

Gasper Maeda¹, Pieter J Gilissen², Catarina Bourgard³, Jelle van der Wal³, Joan J E Munissi⁴, Stephen S Nyandoro⁵, Máté Erdélyi⁶

Affiliations

¹ Chemistry Department, College of Natural and Applied Sciences, University of Dar es Salaam, P.O. Box. 35061, Dar es Salaam, Tanzania; Department of Chemistry - BMC, Uppsala University, SE-751 23 Uppsala, Sweden.
² Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
³ Department of Chemistry and Molecular Biology, Center for Antibiotic Resistance Research (CARe), University of Gothenburg, SE-412 96 Gothenburg, Sweden.
⁴ Chemistry Department, College of Natural and Applied Sciences, University of Dar es Salaam, P.O. Box. 35061, Dar es Salaam, Tanzania.
⁵ Chemistry Department, College of Natural and Applied Sciences, University of Dar es Salaam, P.O. Box. 35061, Dar es Salaam, Tanzania. Electronic address: nyandoro@udsm.ac.tz.
⁶ Department of Chemistry - BMC, Uppsala University, SE-751 23 Uppsala, Sweden. Electronic address: mate.erdelyi@kemi.uu.se.

PMID: 35288209
DOI: 10.1016/j.fitote.2022.105170

Abstract

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).

Keywords: Annonaceae; Antibacterial activity; Cytotoxicity; Pandensenol; Pandensone; Uvaria pandensis.

MeSH terms

Anti-Bacterial Agents / pharmacology
Bacillus subtilis
Cyclohexenes
Flavonoids / analysis
Flavonoids / pharmacology
Humans
Molecular Structure
Plant Leaves / chemistry
Uvaria* / chemistry

Substances

Anti-Bacterial Agents
Cyclohexenes
Flavonoids
cyclohexene