Abstract
Guaiacol (2-methoxyphenol) and curcumin [1E,6E-1,7-di(4-hydroxy-3-methoxy-phenyl)-1,6-heptadiene-3,5-dione] were converted into their corresponding glucosides using glucose and an amyloglucosidase from Rhizopus. Guaiacol-alpha-D: -glucoside yields ranged from 3 to 52% with the highest at pH 7.0. Curcumin-bis-alpha-D: -glucoside yields ranged from 3 to 48% with the highest at pH 4.0 with 50% (w/w D: -glucose) of enzyme. The phenolic hydroxyl group of guaiacol and both phenolic hydroxyl groups of curcumin were glucosylated at the C1 carbon of alpha-D: -glucose indicating that the enzymatic reaction is stereospecific. Both guaiacol-alpha-D: -glucoside and curcumin-bis-alpha-D: -glucosides had antioxidant activities.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antioxidants / chemistry
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Antioxidants / metabolism
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Biphenyl Compounds / chemistry
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Biphenyl Compounds / metabolism
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Buffers
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Chromatography, High Pressure Liquid
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Curcumin / chemistry
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Glucan 1,4-alpha-Glucosidase / chemistry*
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Glucan 1,4-alpha-Glucosidase / metabolism
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Glucosides / chemical synthesis*
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Glucosides / chemistry
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Glucosides / metabolism
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Glycosylation
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Guaiacol / chemistry
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Hydrazines / chemistry
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Hydrazines / metabolism
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Hydrogen-Ion Concentration
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Kinetics
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Molecular Structure
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Picrates
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Rhizopus / enzymology*
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Spectrophotometry, Ultraviolet / methods
Substances
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Antioxidants
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Biphenyl Compounds
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Buffers
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Glucosides
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Hydrazines
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Picrates
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Guaiacol
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1,1-diphenyl-2-picrylhydrazyl
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Glucan 1,4-alpha-Glucosidase
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Curcumin