Abstract
Assay-guided fractionation of the ethanol extract of the twigs and leaves of Miconia myriantha yielded two new compounds, mattucinol-7-O-[4' ',6' '-O-(S)-hexahydroxydiphenoyl]-beta-D-glucopyranoside (1) and mattucinol-7-O-[4' ',6' '-di-O-galloyl]-beta-D-glucopyranoside (2), along with mattucinol-7-O-beta-D-glucopyranoside (3), ellagic acid (4), 3,3'-di-O-methyl ellagic acid-4-O-beta-D-xylopyranoside, and gallic acid. Complete (1)H and (13)C NMR assignments of compound 1, which possesses a hexahydroxydiphenoyl unit, were achieved using the HMBC technique optimized for small couplings to enhance the four-bond and two-bond H/C correlations. Compounds 1 and 4 showed inhibitory effects against Candida albicans secreted aspartic proteases, with IC(50) of 8.4 and 10.5 microM, respectively.
Publication types
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Aspartic Acid Endopeptidases / antagonists & inhibitors
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Candida albicans / drug effects
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Candida albicans / enzymology
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Candida albicans / metabolism
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Chromatography, Thin Layer
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Circular Dichroism
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Ellagic Acid / chemistry
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Ellagic Acid / pharmacology
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Gallic Acid / chemistry
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Gallic Acid / pharmacology
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Glucosides / chemistry
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Glucosides / isolation & purification*
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Glucosides / pharmacology
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Inhibitory Concentration 50
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Magnetic Resonance Spectroscopy
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Magnoliopsida / chemistry*
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Mass Spectrometry
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Molecular Conformation
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Molecular Structure
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Pepsin A / antagonists & inhibitors
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Peru
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Plant Leaves / chemistry
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Plants, Medicinal / chemistry*
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Protease Inhibitors / chemistry
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Protease Inhibitors / isolation & purification*
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Protease Inhibitors / pharmacology
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Spectrophotometry, Infrared
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Spectroscopy, Fourier Transform Infrared
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Structure-Activity Relationship
Substances
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Glucosides
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Protease Inhibitors
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mattucinol-7-O-(4' ',6' '-O-hexahydroxydiphenoyl)glucopyranoside
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mattucinol-7-O-(4'',6''-di-O-galloyl)glucopyranoside
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mattucinol-7-O-glucopyranoside
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Ellagic Acid
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Gallic Acid
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Aspartic Acid Endopeptidases
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Pepsin A