Steroids and Ceramide from the Stem Bark of Odyendyea gabonensis

Abstract

Two new steroids, 22E, 24R-stigmast-22-ene-3,6,11-trione (1) and 22E, 24R-3-acetylstigmasta-5,22-diene-7,11-dione (2), and one new ceramide, (2S,3S,4R,5R) N- (1,3,4,5-tetrahydroxyundecan-2-yl)tetradecanamide (7), together with eleven known compounds were isolated from the CH 2 Cl 2 extract of the stem bark of Odyendyea gabonensis. The structures of all compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral (EI and ESI) data, chemical reactions, and comparison with previously known analogs. Pure compounds were tested for their activity against the bacteria Bacillus subtilis, Staphylococcus aureus and Escherichia coli, the fungi Mucor miehei and Candida albicans, and the plant pathogen oomycetes Aphanomyces cochlioides, Pythium ultimum and Rhizoctonia solani using the paper disk agar diffusion assay. For active compounds, MICs were determined by the broth microdilution assay. Cytotoxic activity against the human lung adenocarcinoma cell line A 549 was evaluated by the MTT assay. All compounds delivered low to missing antimicrobial activities in the agar diffusion assay and MICs > 1 mg mL −1 . The alkaloids 10 and 11 displayed cytotoxic activity against the human lung adenocarcinoma cell line A549 with IC 50 2.5 and 4.5 µm respectively.