Ferdinand Mouafo Talontsi

Antibacterial and antiplasmodial constituents of Beilschmiedia cryptocaryoides.

Four new beilschmiedic acid derivatives, cryptobeilic acids A-D (1-4), and tsangibeilin B (5) have been isolated from the bark of Beilschmiedia cryptocaryoides collected from Madagascar. Their structures were elucidated using detailed spectroscopic and spectrometric methods. Cryptobeilic acid A (1) and tsangibeilin B (5) structures were confirmed by single-crystal X-ray diffraction analysis. Compounds 1-5 displayed moderate antibacterial activity against Escherichia coli 6r3, Acinetobacter calcoaceticus DSM 586, and Pseudonamas stutzeri A1501, with the minimum inhibitory concentrations ranging from 10 to 50 μM, respectively. In addition, the compounds exhibited antiplasmodial activity against erythrocytic stages of chloroquine-resistant Plasmodium falciparum strain NF54 and weak cytotoxicity against L6 cell lines.

Penialidins A–C with strong antibacterial activities from Penicillium sp., an endophytic fungus harboring leaves of Garcinia nobilis

Three new polyketides named penialidins A-C (1-3), along with one known compound, citromycetin (4), were isolated from an endophytic fungus, Penicillium sp., harbored in the leaves of the Cameroonian medicinal plant Garcinia nobilis. Their structures were elucidated by means of spectroscopic and spectrometric methods (NMR and HRMS(n)). The antibacterial efficacies of the new compounds (1-3) were tested against the clinically-important risk group 2 (RG2) bacterial strains of Staphylococcus aureus and Escherichia coli. The ecologically imposing strains of E. coli (RG1), Bacillus subtilis and Acinetobacter sp. BD4 were also included in the assay. Compound 3 exhibited pronounced activity against the clinically-relevant S. aureus as well as against B. subtilis comparable to that of the reference standard (streptomycin). Compound 2 was also highly-active against S. aureus. By comparing the structures of the three new compounds (1-3), it was revealed that altering the substitutions at C-10 and C-2 can significantly increase the antibacterial activity of 1.

Tramadol—A True Natural Product?

We have independently investigated the source of tramadol, a synthetic analgesic largely used for treating moderate to severe pain in humans, recently found in the roots of the Cameroonian medicinal plant, Nauclea latifolia. We found tramadol and its three major mammalian metabolites (O-desmethyltramadol, N-desmethyltramadol, and 4-hydroxycyclohexyltramadol) in the roots of N. latifolia and five other plant species, and also in soil and local water bodies only in the Far North region of Cameroon. The off-label administration of tramadol to cattle in this region leads to cross-contamination of the soil and water through feces and urine containing parent tramadol as well as tramadol metabolites produced in the animals. These compounds can then be absorbed by the plant roots and also leached into the local water supplies. The presence of tramadol in roots is, thus, due to an anthropogenic contamination with the synthetic compound.

Antiplasmodial and cytotoxic dibenzofurans from Preussia sp. harboured in Enantia chlorantha Oliv.

Two unusual dibenzofurans, preussiafurans A-B (1-2), together with six known compounds have been isolated from the fungus Preussia sp. occurring in Enantia chlorantha Oliv. The structures were established on the basis of 1D and 2D NMR spectroscopy and MS analysis. Compounds 1-4 showed antiplasmodial activity against erythrocytic stages of chloroquine-resistant Plasmodium falciparum (NF54) and moderate cytotoxicity on L6 cell lines with IC50 values of 8.67 and 14.8 μM, respectively.

Minor secondary metabolites from the bark of Entandrophragma congoënse (Meliaceae).

Two new tirucallane-type triterpenoids were isolated from the bark of Entandrophragma congoënse (Meliaceae) along with five known compounds gladoral A, bipendensin, 4-hydroxymethyl-3,5-dimethyldihydrofuran-2(3H)-one, scopoletin and 5,7-dimethoxy-6-hydroxycoumarin. Their structures were elucidated by means of spectroscopic analyses including 1D and 2D-NMR spectroscopy, high resolution mass spectrometric data as well as the comparison of data with those reported in the literature. The tested compounds (1-4) displayed moderated antiplasmodial activity against erythrocytic stages of chloroquine-resistant Plasmodium falciparum strain NF54 and low cytotoxicity on L6 cell lines. All the isolated compounds are reported for the first time from the genus Entandrophragma.

Antiplasmodial and Cytotoxic Triterpenoids from the Bark of the Cameroonian Medicinal Plant Entandrophragma congoënse

Eight new triterpenoids, prototiamins A-G (1-6, 9) and seco-tiaminic acid A (10), were isolated along with four known compounds from the bark of Entandrophragma congoënse. Their structures were elucidated by means of HRMS and different NMR techniques and chemical transformations. Assignments of relative and absolute configurations for the new compounds were achieved using NOESY experiments and by chemical modification including the advanced Moshers method. Additionally, the structure and relative configuration of compound 3 were confirmed by single-crystal X-ray diffraction analysis. Compounds 1, 3, and 5 displayed significant in vitro antiplasmodial activity against the erythrocytic stages of chloroquine-sensitive Plasmodium falciparum strain NF54. Prototiamin C (3) was the most potent of the compounds isolated, with an IC50 value of 0.44 μM. All compounds tested showed low cytotoxicity for the L6 rat skeletal myoblast cell line.

Indolosesquiterpene alkaloids from the Cameroonian medicinal plant Polyalthia oliveri (Annonaceae).

The stem bark of Polyalthia oliveri was screened for its chemical constituents using liquid chromatography high resolution mass spectrometry resulting in the isolation of three indolosesquiterpene alkaloids named 8α-polyveolinone (1), N-acetyl-8α-polyveolinone (2) and N-acetyl-polyveoline (3), together with three known compounds, dehydro-O-methylisopiline (4), N-methylurabaine (5) and polycarpol (6). The structures of the compounds were elucidated by means of high resolution mass spectrometry and different NMR techniques and chemical transformations. Their absolute configurations were assigned by ab-initio calculation of CD and ORD data (for 2 and 3) and X-ray diffraction analysis (for 2). Compounds 2 and 3 exhibited moderate antiplasmodial activity against erythrocytic stages of chloroquine-sensitive Plasmodium falciparum NF54 strain and low cytotoxicity on rat skeletal myoblast (L6) cell line.

Isolation and characterization of six labdane diterpenes and one pregnane steroid of Turraeanthus africanus.

Six labdane diterpene derivatives, named turraeanins F-J (3-6, 8) and epi-turraeanin J (7), and a pregnane steroid derivative named turraeasterodionene (2), were isolated by preparative high performance liquid chromatography together with thirteen known compounds from the Cameroonian medicinal plant Turraeanthus africanus. Their structures were elucidated by means of nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry in conjunction with the published data for the analogs, as well as the fragmentation patterns of each compound. Most of the known compounds were obtained for the first time from this plant. The compounds (2-7) were tested for their antibacterial efficacies against both Gram-positive and Gram-negative bacteria, including some clinically-important Risk group 2 human pathogens. Compound 4 exhibited the most pronounced antibacterial effectiveness comparable to standard reference streptomycin, with more potency against Gram-positive than Gram-negative bacteria. By comparing compounds 3, 4 and 5, a tentative structure-activity relationship could be drawn; selected oxidations at C-16 and C-18 drastically reduced the antibacterial efficacy of the parent compound (4). These results revealed the potential of compound 4 as a suitable antibacterial lead compound that might be used for further development of other derivatives to increase the antimicrobial efficacy.

Sonhafouonic acid, a new cytotoxic and antifungal hopene-triterpenoid from Zehneria scabra camerunensis

A new hopene-type triterpenoid, namely sonhafouonic acid 1a was isolated from Zehneria scabra camerunensis, together with eight known compounds. The structure of 1a was established by extensive NMR and high resolution MS techniques and confirmed by single-crystal X-ray crystallographic analysis. Compound 1a exhibited inhibitory activity against mycelial growth of two peronosporomycete phytopathogens Pythium ultimum and Aphanomyces cochliodes and cytotoxicity towards brine shrimp larvae (Artemia salina) at 10 μg/mL.

Antimicrobial and cytotoxic constituents from native Cameroonian medicinal plant Hypericum riparium

Bioassay guided fractionation of Hypericum riparium leaves extract has resulted in the isolation and characterization of three new compounds namely chipericumin E (1), hyperenone C (3), and hyperixanthone (5), together with twenty known compounds. Their structures were elucidated based on comprehensive interpretation of spectroscopic and spectrometric data. Compounds 1-4, and 6-8 displayed moderate antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and cytotoxic effects on the human gastric cell line BGC-823 with IC50 values ranging from 6.54 to 18.50μM.