Abstract
A chemical study on the anti-inflammatory components of the red alga Gracilaria verrucosa led to the isolation of new 11-deoxyprostaglandins ( 1- 4), a ceramide ( 5), and a C 16 keto fatty acid ( 6), along with known oxygenated fatty acids ( 7- 14). Their structures were elucidated on the basis of NMR and MS data. The absolute configurations of compounds 1- 5 were determined by Mosher's method. The anti-inflammatory activity of the isolated compounds ( 1- 14) was evaluated by determining their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 9 and 10 exhibited the most potent activity. In the evaluation of these two compounds and derivatized analogues ( 15- 40), the anti-inflammatory activity was enhanced in some synthetic analogues. These enone fatty acids were investigated as potential anti-inflammatory leads for the first time.
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, Non-Steroidal / chemistry
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Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
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Fatty Acids / chemical synthesis
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Fatty Acids / chemistry
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Fatty Acids / isolation & purification
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Fatty Acids / pharmacology
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Gracilaria / chemistry*
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Inflammation / chemically induced
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Inflammation / drug therapy
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Interleukin-6 / biosynthesis
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Korea
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Lipopolysaccharides / pharmacology
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Macrophages / metabolism*
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Mice
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Molecular Structure
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Nitric Oxide / analysis
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Nitric Oxide / biosynthesis
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Prostaglandins E / chemical synthesis
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Prostaglandins E / chemistry
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Prostaglandins E / isolation & purification*
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Prostaglandins E / pharmacology*
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Structure-Activity Relationship
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Tumor Necrosis Factor-alpha / biosynthesis
Substances
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Anti-Inflammatory Agents, Non-Steroidal
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Fatty Acids
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Interleukin-6
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Lipopolysaccharides
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Prostaglandins E
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Tumor Necrosis Factor-alpha
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Nitric Oxide