Abstract
A protocol was established to produce bioactive compounds in a callus culture of Ageratina pichinchensis by using 1 mg L-1 NAA with 0.1 mg L-1 KIN. The phytochemical study of the EtOAc extract obtained from the callus biomass, allowed the isolation and characterization of eleven secondary metabolites, of which dihydrobenzofuran (5) and 3-epilupeol (7), showed important anti-inflammatory activity. Compound 5 inhibits in vitro the secretion of NO (IC50 = 36.96 ± 1.06 μM), IL-6 (IC50 = 73.71 ± 3.21 μM), and TNF-α (IC50 = 73.20 ± 5.99 μM) in RAW (Murine macrophage cells) 264.7 macrophages, as well as the activation of NF-κB (40% at 150 μM) in RAW-blue macrophages, while compound 7 has been described that inhibit the in vivo TPA-induced ear edema, and the in vitro production of NO, and the PLA2 enzyme activity. In addition, quantitative GC-MS analysis showed that the anti-inflammatory metabolites 5 and 7 were not detected in the wild plant. Overall, our results indicated that A. pichinchensis can be used as an alternative biotechnological resource for obtaining anti-inflammatory compounds. This is the first report of the anti-inflammatory activity of compound 5 and its production in a callus culture of A. pichinchensis.
Keywords:
3-epilupeol; Ageratina pichinchensis; anti-inflammatory; callus culture; dihydrobenzofuran.
MeSH terms
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Ageratina / chemistry*
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Animals
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Anti-Inflammatory Agents / isolation & purification
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Anti-Inflammatory Agents / pharmacology*
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Benzofurans / isolation & purification
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Benzofurans / pharmacology*
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Culture Techniques
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Ear
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Edema / chemically induced
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Edema / drug therapy*
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Edema / immunology
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Edema / pathology
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Ethanol / chemistry
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Interleukin-6 / antagonists & inhibitors
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Interleukin-6 / biosynthesis
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Kinetin / pharmacology
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Lipopolysaccharides / antagonists & inhibitors
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Lipopolysaccharides / pharmacology
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Male
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Mice
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NF-kappa B / antagonists & inhibitors
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NF-kappa B / metabolism
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Naphthaleneacetic Acids / pharmacology
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Nitric Oxide / antagonists & inhibitors
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Nitric Oxide / biosynthesis
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Pentacyclic Triterpenes / isolation & purification
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Pentacyclic Triterpenes / pharmacology*
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Phospholipases A2 / metabolism
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Plant Extracts / chemistry
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Plant Leaves / chemistry
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RAW 264.7 Cells
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Secondary Metabolism / drug effects
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Solvents / chemistry
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Tetradecanoylphorbol Acetate / administration & dosage
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Tumor Necrosis Factor-alpha / antagonists & inhibitors
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Tumor Necrosis Factor-alpha / biosynthesis
Substances
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Anti-Inflammatory Agents
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Benzofurans
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Interleukin-6
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Lipopolysaccharides
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NF-kappa B
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Naphthaleneacetic Acids
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Pentacyclic Triterpenes
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Plant Extracts
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Solvents
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Tumor Necrosis Factor-alpha
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interleukin-6, mouse
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Nitric Oxide
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1-naphthaleneacetic acid
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Ethanol
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Phospholipases A2
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Tetradecanoylphorbol Acetate
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Kinetin