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-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.
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National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
Jacob
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Pasco
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ElSohly
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Nimrod
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Walker
L A
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Clark
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D016282:Aspartic Acid Endopeptidases / Q000037:antagonists & inhibitors; D002176:Candida albicans / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism; D002855:Chromatography, Thin Layer; D002942:Circular Dichroism; D004610:Ellagic Acid / Q000737:chemistry / Q000494:pharmacology; D005707:Gallic Acid / Q000737:chemistry / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D019684:Magnoliopsida / Q000737:chemistry*; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D010434:Pepsin A / Q000037:antagonists & inhibitors; D010568:Peru; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011480:Protease Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D013329:Structure-Activity Relationship
D005960:Glucosides; D011480:Protease Inhibitors; C439984:mattucinol-7-O-(4' ',6' '-O-hexahydroxydiphenoyl)glucopyranoside; C439985:mattucinol-7-O-(4'',6''-di-O-galloyl)glucopyranoside; C439986:mattucinol-7-O-glucopyranoside; D004610:Ellagic Acid; D005707:Gallic Acid; D016282:Aspartic Acid Endopeptidases; D010434:Pepsin A