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A new dimeric naphtho-γ-pyrone, 2-hydroxydihydronigerone (1), along with five compounds, nigerone (2), pyrophen (3), kojic acid (4), 4-(hydroxymethyl)-5-hydroxy-2H-pyran-2-one (5), and p-hydroxyphenylacetic acid (6), was isolated from an endophytic fungus Aspergillus nigerAKRN associated with the roots of Entandrophragma congoënse. The structure of the new compound has been elucidated using spectroscopic data including 1D and 2D NMR as well as the high-resolution mass spectrometry. Compounds 1–5showed weak antimicrobial activity on five selected Gram-negative bacteria, namely Enterobacter aerogenes(CM64), Enterobacter cloacae(BM67), Klebsiella pneumonia(K2), and Escherichia coli(ATCC8739 and ATCC10536).

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 3were confirmed by single-crystal X-ray diffraction analysis. Compounds 1, 3, and 5displayed significant in vitro antiplasmodial activity against the erythrocytic stages of chloroquine-sensitive Plasmodium falciparumstrain NF54. Prototiamin C (3) was the most potent of the compounds isolated, with an IC50value of 0.44 μM. All compounds tested showed low cytotoxicity for the L6 rat skeletal myoblast cell line.

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