title: Antiplasmodial and Cytotoxic Triterpenoids from the Bark of the Cameroonian Medicinal Plant Entandrophragma congoënse.
abstract: 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 Mosher's 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.
authors: †Department of Chemistry, Higher Teachers' Training College, University of Yaoundé I, P.O. Box 47, Yaoundé, Cameroon.|‡Institute of Environmental Research (INFU) of the Faculty of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, Otto-Hahn-Straße 6, D-44221 Dortmund, Germany.
authors: Gervais Mouthé
authors: GM
authors: Happi
authors: †Department of Chemistry, Higher Teachers' Training College, University of Yaoundé I, P.O. Box 47, Yaoundé, Cameroon.
authors: Simeon Fogue
authors: SF
authors: Kouam
authors: ‡Institute of Environmental Research (INFU) of the Faculty of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, Otto-Hahn-Straße 6, D-44221 Dortmund, Germany.
authors: Ferdinand Mouafo
authors: FM
authors: Talontsi
authors: ‡Institute of Environmental Research (INFU) of the Faculty of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, Otto-Hahn-Straße 6, D-44221 Dortmund, Germany.
authors: Marc
authors: M
authors: Lamshöft
authors: ‡Institute of Environmental Research (INFU) of the Faculty of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, Otto-Hahn-Straße 6, D-44221 Dortmund, Germany.
authors: Sebastian
authors: S
authors: Zühlke
authors: §Inorganic Chemistry, Department of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Straße 6, D-44221 Dortmund, Germany.
authors: Jonathan O
authors: JO
authors: Bauer
authors: §Inorganic Chemistry, Department of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Straße 6, D-44221 Dortmund, Germany.
authors: Carsten
authors: C
authors: Strohmann
authors: ‡Institute of Environmental Research (INFU) of the Faculty of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, Otto-Hahn-Straße 6, D-44221 Dortmund, Germany.
authors: Michael
authors: M
authors: Spiteller
mesh_terms: D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002163:Cameroon; D002738:Chloroquine / Q000494:pharmacology; D060467:Disease Resistance / Q000187:drug effects; D004912:Erythrocytes / Q000187:drug effects; D029582:Meliaceae / Q000737:chemistry*; D015394:Molecular Structure; D018482:Muscle, Skeletal / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D021261:Parasitic Sensitivity Tests; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D051381:Rats; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000962:Antimalarials; D014315:Triterpenes; C000600294:prototiamin C; D002738:Chloroquine