Abstract
Honokiol, a biphenolic neolignan isolated from Magnolia officinalis, was reported to have a promising anti-inflammatory activity for the treatment of various diseases. There are many efforts on the synthesis and structure-activity relationship of honokiol derivatives. However, regioselective O-alkylation of honokiol remains a challenge and serves as a tool to provide not only some derivatives but also chemical probes for target identification and mode of action. In this study, we examined the reaction condition for regioselective O-alkylation, in which C2 and C4'-alkylated analogs of honokiol were synthesized and evaluated for inhibitory activity on nitric oxide production and cyclooxygenase-2 expression. Furthermore, we successfully synthesized a potential photoaffinity probe consisting of biotin and benzophenone based on a C4'-alkylated derivative.
Keywords:
Magnolia officinalis; O-alkylation; anti-inflammatory activity; honokiol; photoaffinity probe.
MeSH terms
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Alkylation
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Animals
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Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
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Anti-Inflammatory Agents, Non-Steroidal / chemistry
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
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Biphenyl Compounds / chemical synthesis
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Biphenyl Compounds / chemistry
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Biphenyl Compounds / pharmacology*
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Cyclooxygenase 2 / metabolism
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Cyclooxygenase 2 Inhibitors / chemical synthesis
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Cyclooxygenase 2 Inhibitors / chemistry
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Cyclooxygenase 2 Inhibitors / pharmacology*
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Humans
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Inflammation / drug therapy*
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Inflammation / metabolism
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Lignans / chemical synthesis
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Lignans / chemistry
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Lignans / pharmacology*
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Lipopolysaccharides / antagonists & inhibitors
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Lipopolysaccharides / pharmacology
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Mice
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Molecular Structure
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Nitric Oxide / antagonists & inhibitors
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Nitric Oxide / biosynthesis
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RAW 264.7 Cells
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Stereoisomerism
Substances
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Anti-Inflammatory Agents, Non-Steroidal
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Biphenyl Compounds
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Cyclooxygenase 2 Inhibitors
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Lignans
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Lipopolysaccharides
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honokiol
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Nitric Oxide
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Cyclooxygenase 2