The first sorbicillinoid alkaloids, the antileukemic sorbicillactones A and B, from a sponge-derived Penicillium chrysogenum strain
| Autor: | Katja Maksimenka, Stefan Steffens, Sanja Perović-Ottstadt, Hideyuki Tsuruta, Jörg Mühlbacher, Rüdiger Stöhr, Jutta Wiese, Gerhard Lang, Olexandra Boreiko, Gerhard Bringmann, Tobias A. M. Gulder, Johannes F. Imhoff, Karsten Schaumann, Werner E.G. Müller |
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| Rok vydání: | 2005 |
| Předmět: |
Alanine
Circular dichroism Methionine Strain (chemistry) biology 010405 organic chemistry Stereochemistry Organic Chemistry 010402 general chemistry Mass spectrometry Penicillium chrysogenum biology.organism_classification 01 natural sciences Biochemistry 3. Good health 0104 chemical sciences chemistry.chemical_compound Sponge chemistry Drug Discovery Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Tetrahedron. 61:7252-7265 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2005.05.026 |
| Popis: | The saltwater culture of a Penicillium chrysogenum strain isolated from the Mediterranean sponge Ircinia fasciculata yielded three new sorbicillin-derived compounds (1-3), whose structures were elucidated mainly by 2D NMR and mass spectrometry. Among them, sorbicillactones A (1) and B (2) are the first sorbicillinoid natural products that contain nitrogen. Compound 1 is anti-HIV active and it exhibits a strong cytotoxic activity against L5178y leukemic cells, combined with a relatively low toxicity to cervical carcinoma HeLa S3 cells and pheochromocytoma PC 12 cells. The absolute configurations of I and 2 were elucidated by quantum chemical calculation of circular dichroism (CD) spectra. Another compound isolated, sorbivinetone (3), might be an artifact derived from sorbicillinol (4) by Diels-Alder reaction with ethyl vinyl ether. Furthermore, the known sorbicillinoid fungal metabolites oxosorbicillinol (5), sorbicillin (6), and bisvertinolone (7) were identified, as well as the alkaloids meleagrine and roquefortine C. The biosynthetic origin of sorbicillactone A (1) from acetate, alanine, and methionine was investigated by feeding experiments with C-13-labeled precursors |
| Databáze: | OpenAIRE |
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