2. Academic Validation
  3. Oxygenated Cyclohexene Derivatives from the Stem and Root Barks of Uvaria pandensis

Oxygenated Cyclohexene Derivatives from the Stem and Root Barks of Uvaria pandensis

  • J Nat Prod. 2021 Dec 24;84(12):3080-3089. doi: 10.1021/acs.jnatprod.1c00811.
Gasper Maeda 1 2,  Pieter J Gilissen 3,  Anastasia Rudenko 4,  Jelle van der Wal 4,  Catarina Bourgard 4,  Arvind Kumar Gupta 5,  Per Sunnerhagen 4,  Joan J E Munissi 1,  Stephen S Nyandoro 1,  Máté Erdélyi 2
Affiliations

Affiliations

  • 1 Chemistry Department, College of Natural and Applied Sciences, University of Dar es Salaam, Dar es Salaam, Tanzania.
  • 2 Department of Chemistry-BMC, Uppsala University, SE-751 23 Uppsala, Sweden.
  • 3 Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
  • 4 Department of Chemistry and Molecular Biology, University of Gothenburg, and Centre for Antibiotic Resistance Research (CARe) at the University of Gothenburg, SE-405 30 Gothenburg, Sweden.
  • 5 Department of Chemistry-Ångström, Uppsala University, SE-751 20 Uppsala, Sweden.
PMID: 34802242 DOI: 10.1021/acs.jnatprod.1c00811
Abstract

Five new cyclohexene derivatives, dipandensin A and B (1 and 2) and pandensenols A-C (3-5), and 16 known secondary metabolites (6-21) were isolated from the methanol-soluble extracts of the stem and root barks of Uvaria pandensis. The structures were characterized by NMR spectroscopic and mass spectrometric analyses, and that of 6-methoxyzeylenol (6) was further confirmed by single-crystal X-ray crystallography, which also established its absolute configuration. The isolated metabolites were evaluated for Antibacterial activity against the Gram-positive bacteria Bacillus subtilis and Staphylococcus epidermidis and the Gram-negative bacteria Enterococcus raffinosus, Escherichia coli, Paraburkholderia caledonica, Pectobacterium carotovorum, and Pseudomonas putida, as well as for cytotoxicity against the MCF-7 human breast Cancer cell line. A mixture of uvaretin (20) and isouvaretin (21) exhibited significant Antibacterial activity against B. subtilis (EC50 8.7 μM) and S. epidermidis (IC50 7.9 μM). (8'α,9'β-Dihydroxy)-3-farnesylindole (12) showed strong inhibitory activity (EC50 9.8 μM) against B. subtilis, comparable to the clinical reference ampicillin (EC50 17.9 μM). None of the compounds showed relevant cytotoxicity against the MCF-7 human breast Cancer cell line.

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