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

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.

SUBMITTER: Maeda G

PROVIDER: S-EPMC8713284 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:The genus Gnidia, with species close to 152, is traditionally used to treat wide ranges of ailments in humans and animals. Gnidia involucrata is one of the species found in Ethiopia and traditionally used as a laxative, antirheumatic agent, insecticide, antibacterial agent, and antimalarial agent. In view of its traditional use, the root bark was sequentially extracted with n-hexane, EtOAc, and MeOH to afford 0.78%, 4%, and 6% crude extracts, respectively. The chromatographic separation of the EtOAc extract using silica gel column chromatography yielded three pure compounds: tetratriacontanyl caffeate (1), 12-O-dodeca-2,4-dienoylphorbol-13-acetate (2), and naringenin (3). This is the first report of the isolation of 1 and its kind from the genus and most probably from the Thymelaeaceae family. The structures of these compounds were characterized and identified by NMR and mass spectrometric analyses and comparison with literature data. The EtOAc extract and isolated compounds were assessed for their in vitro antibacterial and antioxidant activities. The EtOAc extract (1.5 mg/mL) showed significant inhibitory activity against S. aureus, E. coli, P. mirabilis, and K. pneumonia bacterial strains with the highest inhibition zone observed against S. aureus (23 mm), which is even greater than that of the reference drug ciprofloxacin (22 mm). However, the inhibition displayed on these bacterial strains for the three pure compounds was marginal with variable degrees of potency between the compounds. The better activity of the crude extract could be due to the synergistic interactions of several phytochemicals present in the extract, which cannot be the case when pure compounds are evaluated alone. The antioxidant activities of the extracts and isolated compounds were evaluated using DPPH and ferric thiocyanate methods. The EtOAc and MeOH extracts and compounds 1 and 2 were found to inhibit the DPPH radical by 70.7, 66.9, 85.8, and 52.8%, respectively. The EtOAc extract and compound 1 inhibited peroxidation of lipids by 84 and 86%, respectively. The radical scavenging displayed by compound 1 was significant compared with that displayed by ascorbic acid, indicating the strong antilipid peroxidation potential of the extract of root barks of G. involucrata. Therefore, the extracts of the root bark of G. involucrata can be used as a remedy in combating diseases caused by bacteria and free radicals provided that further comprehensive evaluation could be recommended for the conclusive decision on potential candidacy of this plant.

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

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