Abstract
Five novel perhydrobenzannulated 5,5-spiroketal sesquiterpenes, namely, pleurospiroketals A-E (1-5), were isolated from the culture of the edible mushroom Pleurotus cornucopiae. Pleurospiroketals D (4) and E (5) were obtained as an isomeric mixture with a ratio of 5:4. Their structures were established by NMR, X-ray single-crystal diffraction, and CD data analysis. Pleurospiroketals A-E (1-5) are sesquiterpenoids with a unique benzannulated 5,5-spiroketal skeleton. Compounds 1-3 showed inhibitory activity against nitric oxide production in lipopolysaccharide-activated macrophages with IC(50) values of 6.8, 12.6, and 20.8 μM, respectively.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Crystallography, X-Ray
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Furans / chemistry
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Furans / isolation & purification*
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Furans / pharmacology
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HeLa Cells
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Humans
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Inhibitory Concentration 50
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Lipopolysaccharides / pharmacology
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Macrophages / drug effects
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Mice
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Molecular Conformation
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Molecular Structure
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Nitric Oxide / biosynthesis
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Nuclear Magnetic Resonance, Biomolecular
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Pleurotus / chemistry*
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Sesquiterpenes / chemistry
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Sesquiterpenes / isolation & purification*
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Sesquiterpenes / pharmacology
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Spiro Compounds / chemistry
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Spiro Compounds / isolation & purification*
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Spiro Compounds / pharmacology
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Stereoisomerism
Substances
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Furans
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Lipopolysaccharides
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Sesquiterpenes
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Spiro Compounds
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pleurospiroketal A
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spiroketal
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Nitric Oxide