Abstract
Three sulfated phenolic compounds, juglanin B (11R)-O-sulfate (1), myricetin 3´-O-sulfate (2), and ampelopsin 3´-O-sulfate (3), were isolated from the leaves of Myrica rubra. Compound 1 was a new sulfated lignan, 2 was a new sulfated flavone, and 3 was a known sulfated flavone. The structures of the new compounds (1 and 2) were determined by acid hydrolysis and spectroscopic methods, including IR, FAB-MS, 1D and 2D NMR. The inhibitory activities of compounds 1-3 and their hydrolysates (1a-3a) against LPS-induced cytokine (TNF-α, IL-1β, and IL-6) production in macrophage RAW 264.7 cells were evaluated. The 2 new compounds (1 and 2) and their aglycones (1a and 2a) significantly reduced LPS-induced expression of iNOS and COX-2 proteins.
Keywords:
Diarylheptanoid; Flavonoid; Inflammation; Myrica rubra; RAW 264.7 cells; Sulfate.
© 2013. Published by Elsevier B.V. All rights reserved.
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 / isolation & purification
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Anti-Inflammatory Agents / pharmacology*
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Anti-Inflammatory Agents / therapeutic use
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Cyclooxygenase 2 / metabolism
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Cytokines / metabolism*
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Flavones / chemistry
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Flavones / isolation & purification
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Flavones / pharmacology*
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Flavones / therapeutic use
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Inflammation / chemically induced
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Inflammation / drug therapy
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Inflammation / metabolism*
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Inflammation Mediators / metabolism*
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Interleukins / metabolism
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Lignans / chemistry
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Lignans / isolation & purification
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Lignans / pharmacology*
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Lignans / therapeutic use
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Lipopolysaccharides
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Macrophages / drug effects
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Macrophages / metabolism
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Mice
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Molecular Structure
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Myrica / chemistry*
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Nitric Oxide Synthase Type II / metabolism
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Phytotherapy
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Plant Extracts / chemistry
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Plant Extracts / pharmacology*
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Plant Extracts / therapeutic use
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Plant Leaves / chemistry
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Sulfuric Acid Esters / chemistry
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Sulfuric Acid Esters / isolation & purification
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Sulfuric Acid Esters / pharmacology*
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Sulfuric Acid Esters / therapeutic use
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Tumor Necrosis Factor-alpha / metabolism
Substances
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Anti-Inflammatory Agents
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Cytokines
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Flavones
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Inflammation Mediators
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Interleukins
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Lignans
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Lipopolysaccharides
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Plant Extracts
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Sulfuric Acid Esters
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Tumor Necrosis Factor-alpha
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Nitric Oxide Synthase Type II
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Cyclooxygenase 2