Abstract
A series of tri-O-methylnorbergenin analogues 1-9 were synthesized and their antioxidant activities and inhibitory effects on tyrosinase were evaluated. Among tested analogues, compound 4 bearing cathechol moiety exhibited greater antioxidant activity and excellent inhibition on tyrosinase with IC50 value of 9.1 μM, comparable to that of corresponding positive controls. The inhibition mechanism analysis of compound 4 demonstrated that it was a mixed-type inhibitor on tyrosinase. These results suggest that these compounds may serve as a useful clue for further designing and development of novel potential tyrosinase inhibitors.
Keywords:
Antioxidant; Bergenin; Structure–activity relationship; Tri-O-methylnorbergenin analogues; Tyrosinase inhibitor.
Copyright © 2013 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antioxidants / chemical synthesis*
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Antioxidants / chemistry
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Antioxidants / metabolism
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Benzopyrans / chemical synthesis
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Benzopyrans / chemistry
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Benzopyrans / metabolism
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Benzopyrans / pharmacology
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Enzyme Activation / drug effects
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Enzyme Inhibitors / chemical synthesis*
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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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Hydroxybenzoates / chemical synthesis*
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Hydroxybenzoates / chemistry
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Hydroxybenzoates / metabolism
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Isocoumarins / chemical synthesis*
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Isocoumarins / chemistry
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Isocoumarins / metabolism
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Kinetics
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Monophenol Monooxygenase / antagonists & inhibitors*
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Monophenol Monooxygenase / metabolism*
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Protein Binding / drug effects
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Structure-Activity Relationship
Substances
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11-O-protocatechuoyl-tri-O-methylnorbergenin
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Antioxidants
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Benzopyrans
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Enzyme Inhibitors
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Hydroxybenzoates
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Isocoumarins
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norbergenin
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Monophenol Monooxygenase