Abstract
A chemical study of the alga Cystoseira usneoides has led to the isolation of six new meroterpenoids, cystodiones A-F (1-6), together with six known related compounds (7-12). The structures of the new metabolites have been established by spectroscopic techniques. In antioxidant assays all of the tested meroterpenes, and in particular cystodiones A (1) and B (2), 6-cis-amentadione-1'-methyl ether (7), and amentadione-1'-methyl ether (8), exhibited strong radical-scavenging activity. In anti-inflammatory assays, usneoidone Z (11) and its corresponding 6E isomer (12) showed significant activity as inhibitors of the production of the proinflammatory cytokine TNF-α in LPS-stimulated THP-1 human macrophages.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Inflammatory Agents / chemistry
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Anti-Inflammatory Agents / isolation & purification*
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Anti-Inflammatory Agents / pharmacology
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Antioxidants / chemistry
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Antioxidants / isolation & purification*
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Antioxidants / pharmacology
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Cell Proliferation / drug effects
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Cytokines / metabolism
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Humans
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Lipopolysaccharides / pharmacology
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Macrophages / metabolism
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Molecular Structure
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Nitric Oxide / biosynthesis
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Nitric Oxide Synthase Type II / metabolism
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Nuclear Magnetic Resonance, Biomolecular
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Phaeophyceae / chemistry*
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Terpenes / chemistry
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Terpenes / isolation & purification*
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Terpenes / pharmacology*
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Tumor Necrosis Factor-alpha / biosynthesis
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Tumor Necrosis Factor-alpha / metabolism
Substances
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Anti-Inflammatory Agents
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Antioxidants
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Cytokines
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Lipopolysaccharides
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Terpenes
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Tumor Necrosis Factor-alpha
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Nitric Oxide
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Nitric Oxide Synthase Type II