A B C
Z. Naturforsch. 2013, 68b, 924 – 930
doi:10.5560/ZNB.2013-3132
Steroids and Ceramide from the Stem Bark of Odyendyea gabonensis
Emmanuel Ngeufa Happi1, Simone Véronique Fannang2, Marie Fomani1, Suzye Mireille Moladje Donkwe1, Nkoungou Yomzak Carine Nicaise1, Jean Duplex Wansi1,3, and Norbert Sewald3
1 Department of Chemistry, University of Douala, Faculty of Science, 24157 Douala, Cameroon
2 Department of Pharmaceutical Science, University of Douala, Faculty of Medicine and Pharmaceutical Science, 2701 Douala, Cameroon
3 Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany
Reprint requests to E. N. Happi. Tel: +237-99-86-50-48. E-mail: ngeufa@yahoo.fr
Received May 10, 2013 / published online July 25, 2013
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 CH2Cl2 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 IC50 2.5 and 4.5 μm respectively.
Key words: Odyendyea gabonensis, Simaroubaceae, Steroids, Ceramide, Antimicrobial and Cytotoxicity Activities
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