Abstract
Bergenin pentacetate (2), a peracetate derivative of biologically active lead compound Bergenin (1) isolated from Bergenia stracheyi was subjected to lipase catalyzed regioselective alcoholysis to obtain 3,4,10,11-tetracetate of Bergenin (3). The free hydroxyl group of 3 was derivatised using higher carboxylic acids to obtain acyl derivatives (4-7). These compounds synthesized via chemoenzymatic route were characterized using 1H NMR, 13C NMR and mass spectral data and evaluated for DPPH radical scavenging, antimicrobial and xanthine oxidase inhibitory activities. The studies revealed that biological activity of Bergenin can be optimized by selective modification of its structure.
Copyright © 2011 Elsevier Masson SAS. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / metabolism
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Anti-Bacterial Agents / pharmacology*
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Antioxidants / chemistry
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Antioxidants / metabolism
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Antioxidants / pharmacology*
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Bacteria / drug effects*
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Benzopyrans / chemistry
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Benzopyrans / metabolism
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Benzopyrans / pharmacology*
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Biocatalysis
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Biphenyl Compounds / metabolism
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Dose-Response Relationship, Drug
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / metabolism
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Enzyme Inhibitors / pharmacology*
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Free Radical Scavengers / metabolism
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Lipase / chemistry
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Lipase / metabolism*
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Microbial Sensitivity Tests
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Molecular Conformation
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Picrates / metabolism
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Saxifragaceae / chemistry
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Stereoisomerism
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Structure-Activity Relationship
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Xanthine Oxidase / antagonists & inhibitors
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Xanthine Oxidase / metabolism
Substances
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Anti-Bacterial Agents
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Antioxidants
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Benzopyrans
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Biphenyl Compounds
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Enzyme Inhibitors
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Free Radical Scavengers
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Picrates
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1,1-diphenyl-2-picrylhydrazyl
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Xanthine Oxidase
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Lipase
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bergenin