New monoterpene glycosides and phenolic compounds from Distylium racemosum and their inhibitory activity against ribonuclease H

Bioorg Med Chem Lett. 2011 May 15;21(10):2840-4. doi: 10.1016/j.bmcl.2011.03.091. Epub 2011 Mar 30.

Abstract

Two new monoterpene glycosides, distyloside A-B (1-2), and a new megastigmane glucoside, iso-dihydrodendranthemoside A (3) were isolated from twigs and leaves of Distylium racemosum, along with five known phenolic compounds (4-8). The structures were established via spectroscopic techniques and chemical transformations, and the absolute stereochemistry of 3 was determined by Mosher's esterification. A homogeneous fluorescence resonance energy transfer (FRET) quenching assay was used to determine the inhibitory activity of isolates (1-8) on the ribonuclease H enzymes from HIV-1, 2, human, and Escherichia coli. Among them, 6″-O-galloylsalidroside (6) showed potent inhibitory effects with an IC(50) value of 3.5 μM on HIV-2, and 1.7 μM on human RNase H, respectively.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, N.I.H., Intramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enzyme Activation / drug effects*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Fluorescence Resonance Energy Transfer
  • Glycosides* / analysis
  • Glycosides* / pharmacology
  • HIV-1 / enzymology
  • HIV-2 / enzymology
  • Hamamelidaceae / chemistry*
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Monoterpenes* / analysis
  • Monoterpenes* / pharmacology
  • Phenols / analysis
  • Phenols / pharmacology
  • Plant Extracts / pharmacology*
  • Plant Leaves / chemistry
  • Plant Stems / chemistry*
  • Ribonuclease H / antagonists & inhibitors*

Substances

  • Enzyme Inhibitors
  • Glycosides
  • Monoterpenes
  • Phenols
  • Plant Extracts
  • Ribonuclease H