Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua
Autor: | RuAngelie Edrada-Ebel, Gerhard Bringmann, Gernot Brauers, Michael Wohlfarth, Udo Gräfe, Markus Heubes, Victor Wray, Albrecht Berg, Sudarsono Sudarsono, Karsten Schaumann, Jörg Mühlbacher, Peter Proksch |
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Rok vydání: | 2002 |
Předmět: |
Antifungal Agents
Stereochemistry Molecular Conformation Pharmaceutical Science Stereoisomerism Analytical Chemistry Stereocenter Lactones Drug Discovery Candida albicans Organic chemistry Animals Chromatography High Pressure Liquid Pharmacology chemistry.chemical_classification biology Bicyclic molecule Molecular Structure Chemistry Circular Dichroism Organic Chemistry Diastereomer Electron Spin Resonance Spectroscopy Penicillium Fungi imperfecti biology.organism_classification Porifera Sponge Complementary and alternative medicine Indonesia Molecular Medicine Lactone |
Zdroj: | Journal of natural products. 65(11) |
ISSN: | 0163-3864 |
Popis: | Fungal isolates of Penicillium cf. montanense were obtained from the marine sponge Xestospongia exiguacollected from the Bali Sea, Indonesia. Culture filtrates of the fungi yielded three novel decalactone metabolites, xestodecalactones A, B, and C (1, 2a, and 2b), consisting of 10-membered macrolides with a fused 1,3-dihydroxybenzene ring. Online HPLC-NMR, ESI-MS/MS, and -CD spectra were acquired, and the structures of the new compounds were established and confirmed on the basis of offline NMR spectroscopic ((1)H, (13)C, COSY, ROESY, (1)H-detected direct and long-range (13)C-(1)H correlations) and mass spectrometric (EIMS) data. Quantum chemical calculations of the CD spectra proved to be difficult because of the conformational flexibility of the xestodecalactones. These compounds, of which 2a and 2b, due to the additional stereocenter at C-9, are diastereomeric compounds, are structurally related to a number of biologically active metabolites found in terrestrial fungal strains. Compound 2a was found to be active against the yeast Candida albicans. |
Databáze: | OpenAIRE |
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