Phenolic Compounds from Miconia myriantha Inhibiting Candida Aspartic Proteases

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-glucop...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2001-10, Vol.64 (10), p.1282-1285
Main Authors: LI, Xing-Cong, JACOB, Melissa R., PASCO, David S., ELSOHLY, Hala N., NIMROD, Alison C., WALKER, Larry A., CLARK, Alice M.
Format: Article
Language:English
Subjects:
Aspartic Acid Endopeptidases - antagonists & inhibitors
aspartic proteinase
Biological and medical sciences
Candida albicans
Candida albicans - drug effects
Candida albicans - enzymology
Candida albicans - metabolism
Chromatography, Thin Layer
Circular Dichroism
Ellagic Acid - chemistry
Ellagic Acid - pharmacology
Gallic Acid - chemistry
Gallic Acid - pharmacology
General pharmacology
Glucosides - chemistry
Glucosides - isolation & purification
Glucosides - pharmacology
Inhibitory Concentration 50
Magnetic Resonance Spectroscopy
Magnoliopsida - chemistry
Mass Spectrometry
Medical sciences
Miconia myriantha
Molecular Conformation
Molecular Structure
Pepsin A - antagonists & inhibitors
Peru
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Leaves - chemistry
Plants, Medicinal - chemistry
Protease Inhibitors - chemistry
Protease Inhibitors - isolation & purification
Protease Inhibitors - pharmacology
Spectrophotometry, Infrared
Spectroscopy, Fourier Transform Infrared
Structure-Activity Relationship
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Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np010172p