Abstract
Twelve metabolites were obtained from the culture media of Chaetomium nigricolor, including a new furan derivative, methyl succinyl Sumiki's acid (1), and two new atropisomers of the previously reported bis-naphtho-γ-pyrones, (aS)-asperpyrone A and (aS)-fonsecinone A (2 and 3). The structures were elucidated by spectroscopic, chemical, and chiroptical techniques. Compounds 2 and 3 inhibited nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 macrophages. Compound 2 was found to inhibit nuclear factor-kappa B and c-Jun N-terminal kinase activation, in turn suppressing pro-inflammatory mediators and cytokines including nitric oxide, prostaglandin E2, interleukin (IL)-1β, tumor necrosis factor-α, IL-6, and IL-12.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anti-Inflammatory Agents / chemistry*
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Anti-Inflammatory Agents / pharmacology*
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Cell Survival / drug effects
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Chaetomium / chemistry*
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Cytokines / antagonists & inhibitors
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Dinoprostone / biosynthesis
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Enzyme Activation
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Furans / isolation & purification
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Furans / pharmacology
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Inflammation Mediators / antagonists & inhibitors
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Isomerism
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JNK Mitogen-Activated Protein Kinases / metabolism
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Lipopolysaccharides / pharmacology
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Magnetic Resonance Spectroscopy
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Mice
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NF-kappa B / analysis
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Nitric Oxide / biosynthesis
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RAW 264.7 Cells
Substances
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Anti-Inflammatory Agents
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Cytokines
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Furans
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Inflammation Mediators
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Lipopolysaccharides
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NF-kappa B
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Nitric Oxide
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JNK Mitogen-Activated Protein Kinases
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Dinoprostone