Phenolic compounds from Miconia myriantha inhibiting Candida aspartic proteases

J Nat Prod. 2001 Oct;64(10):1282-5. doi: 10.1021/np010172p.

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

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aspartic Acid Endopeptidases / antagonists & inhibitors
  • 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
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Magnoliopsida / chemistry*
  • Mass Spectrometry
  • Molecular Conformation
  • Molecular Structure
  • Pepsin A / antagonists & inhibitors
  • Peru
  • 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

Substances

  • Glucosides
  • Protease Inhibitors
  • mattucinol-7-O-(4' ',6' '-O-hexahydroxydiphenoyl)glucopyranoside
  • mattucinol-7-O-(4'',6''-di-O-galloyl)glucopyranoside
  • mattucinol-7-O-glucopyranoside
  • Ellagic Acid
  • Gallic Acid
  • Aspartic Acid Endopeptidases
  • Pepsin A