Abstract
The synthesis and in vivo anti-inflammatory activity of a series of pseudopterosin analogues are presented. Synthetic tricyclic catechol aglycons with different substitution patterns were monofucosylated or -xylosylated. Anti-inflammatory activity was conserved over a wide range of structural modifications. The most active synthetic compound 33 reduced phorbol myristate acetate (PMA)-induced inflammation in the mouse ear by 72% at 50 μg/ear. This corresponds to 80% of the activity of natural pseudopterosin A.
Copyright © 2010 Elsevier Ltd. 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 / chemical synthesis*
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Anti-Inflammatory Agents / chemistry
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Anti-Inflammatory Agents / therapeutic use
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Catechols / chemistry
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Diterpenes / chemical synthesis
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Diterpenes / chemistry*
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Diterpenes / therapeutic use
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Galactosides / chemical synthesis*
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Galactosides / chemistry
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Galactosides / therapeutic use
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Glycosides / chemical synthesis
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Glycosides / chemistry*
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Glycosides / therapeutic use
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Inflammation / chemically induced
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Inflammation / drug therapy
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Mice
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Phenalenes / chemical synthesis*
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Phenalenes / chemistry
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Phenalenes / therapeutic use
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Structure-Activity Relationship
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Tetradecanoylphorbol Acetate / toxicity
Substances
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4-hydroxy-3,3-dimethyl-2,3,7,8,9,9a-hexahydro-1H-phenalen-5-yl 6-deoxygalactopyranoside
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Anti-Inflammatory Agents
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Catechols
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Diterpenes
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Galactosides
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Glycosides
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Phenalenes
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pseudopterosins
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catechol
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Tetradecanoylphorbol Acetate