Two new tetracyclic polyketides with a spirocenter, simplicilones A (1) and B (2) were isolated from the broth-culture of the endophytic fungus Simplicilliumsubtropicum (SPC3) in the course of our screening for new bioactive secondary metabolites. This endophytoic fungus is naturally harboured in the fresh bark of the Cameroonian medicinal plant Duguetia staudtii (Engl. and Diels) Chatrou. The planar structures of the simplicilones were elucidated by MS and 1D as well as 2D NMR spectroscopic techniques. The relative configuration was assigned by NOESY experiments in conjunction with coupling constants; subsequently, the absolute configurations were assigned by the modified Mosher’s method. The compounds showed weak cytotoxic effects against the cell line KB3.1 (in vitro cytotoxicity (IC50) = 25 µg/mL for 1, 29 µg/mL for 2), but were inactive against the tested Gram-positive and Gram-negative bacteria as well as fungi.
Two xanthones, 2-(3-hydroxy-3,3-dimethyldihydroallyl)-dihydro-6-deoxyisojacareubin (1) and dihydro-6-deoxyjacareubin (2), and two 3⟶8 rotameric biflavonoids, (2R,3S)volkensiflavone-7-O--acetylglucopyranoside (3) and (2S,3S)-morelloflavone-7-O-acetylglucopyranoside (4), together with fifteen known compounds, were isolated from a dichloromethane/methanol (1/1, v/v) extract of the bark of the plant Allanblackia floribunda. The structures of the new compounds were elucidated by NMR spectroscopy and mass spectroscopic techniques and those of the known ones were deduced by comparison with data reported in the literature. The isolated biflavonoids were obtained as mixtures of conformers exhibiting duplicate NMR signals in solution at 25 °C and their respective absolute configurations were assigned using circular dichroism spectroscopy. Some of the isolated compounds were assessed for their antibacterial and antioxidant properties.
The phytochemical investigation of a previously unstudied species of the genus Indigofera, I. atriceps Hook.f. was undertaken and two new phenolic compounds, atricephenols A (1) and B(2) were isolated, along with nine known secondary metabolites viz., (-)-melilotocarpan D (3), genistein (4), melilotocarpan A (5), maackiain (6), p-hydroxybenzaldehyde (7), bornesitol (8), βsitosterol (9), sitosterol-3-O--D-glucopyranoside (10) and stigmasterol-3-O--Dglucopyranoside (11). Their structures were elucidated by extensive NMR spectroscopic analyses and HRESIMS, and by comparing their data with those reported in the literature.Compounds 1, 4, 7-11 were tested for their antibacterial efficacies and for their potential to inhibit the enzyme urease. Compounds 7 and 9 showed significant antibacterial activity against Salmonella typhi (ZOIs of 13 and 15 mm, respectively), while the best urease inhibition was measured for compound 9 with an IC 50 value of 18.6 µM, which is higher than that of the potent inhibitor, thiourea (IC 50 = 21.5 µM).
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