Dihydrophenanthrenes and other antifungal stilbenoids from Stemona cf. pierrei
| Autor: | Otmar Hofer, Thomas Pacher, Doris Engelmeier, Katharina Kostecki, Srunya Vajrodaya, Harald Greger |
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| Rok vydání: | 2004 |
| Předmět: |
Antifungal Agents
Stemona Stereochemistry Pinosylvin Germ tube Plant Science Horticulture Ring (chemistry) Biochemistry chemistry.chemical_compound Stilbenes Stemonaceae medicine Azepine Nuclear Magnetic Resonance Biomolecular Molecular Biology Molecular Structure biology Chemistry Alkaloid Fungi General Medicine Phenanthrenes biology.organism_classification medicine.drug_formulation_ingredient Cladosporium herbarum Biological Assay Chromatography Thin Layer |
| Zdroj: | Phytochemistry. 65:99-106 |
| ISSN: | 0031-9422 |
| DOI: | 10.1016/j.phytochem.2003.09.015 |
| Popis: | Three new dihydrophenanthrenes, stemanthrenes A-C, along with the new dihydrostilbene stilbostemin G were isolated and identified from the underground parts of Stemona cf. pierrei together with the known pinosylvin, 4'-methylpinosylvin, dihydropinosylvin, stilbostemins B, D, and E as well as the pyrrolo[1,2-a]azepine alkaloids protostemonine and stemonine. The structures of all new stilbenoids, elucidated by NMR analyses, showed a common substitution pattern for aromatic ring A and characteristic C-methylations for ring B. The trivial name racemosol, previously reported for S. collinsae, was renamed to stemanthrene D due to its priority for another compound. Bioautographic tests on TLC plates with Cladosporium herbarum displayed high antifungal activity for compounds with an unsubstituted aromatic ring A, e.g. pinosylvin, but only weak effects for the higher substituted stilbostemin G and stemanthrenes A-C. Similar results were obtained by germ tube inhibition of five microfungi using 2-fold serial broth dilutions determined by a microplate reader. Because of weak inhibition and chemical instability of stemanthrenes, no EC(50) and EC(90) values could be calculated. |
| Databáze: | OpenAIRE |
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