Antiplasmodial alkaloids from the bark of Cryptocarya nigra (Lauraceae)

Molecules. 2013 Jul 8;18(7):8009-17. doi: 10.3390/molecules18078009.

Abstract

A dichloromethane extract of the stem bark of Cryptocarya nigra showed strong in vitro inhibition of Plasmodium falciparum growth, with an IC50 value of 2.82 μg/mL. The phytochemical study of this extract has led to the isolation and characterization of four known alkaloids: (+)-N-methylisococlaurine (1), atherosperminine (2), 2-hydroxyathersperminine (3), and noratherosperminine (4). Structural elucidation of all alkaloids was accomplished by means of high field 1D- and 2D-NMR, IR, UV and LCMS spectral data. The isolated extract constituents (+)-N-methylisococlaurine (1), atherosperminine (2) and 2-hydroxy-atherosperminine (3) showed strong antiplasmodial activity, with IC50 values of 5.40, 5.80 and 0.75 μM, respectively. In addition, (+)-N-methylisocolaurine (1) and atherosperminine (2) showed high antioxidant activity in a DPPH assay with IC50 values of 29.56 ug/mL and 54.53 ug/mL respectively. Compounds 1 and 2 also both showed high antioxidant activity in the FRAP assay, with percentages of 78.54 and 70.66 respectively and in the metal chelating assay, with IC50 values of 50.08 ug/mL and 42.87 ug/mL, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification
  • Antimalarials / pharmacology*
  • Cryptocarya / chemistry
  • Humans
  • Isoquinolines / chemistry
  • Isoquinolines / isolation & purification
  • Isoquinolines / pharmacology
  • Magnetic Resonance Spectroscopy
  • Malaria / drug therapy
  • Malaria / parasitology*
  • Molecular Structure
  • Phenanthrenes / chemistry
  • Phenanthrenes / isolation & purification
  • Phenanthrenes / pharmacology
  • Plant Bark / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plasmodium falciparum / drug effects*

Substances

  • 2-hydroxyatherosperminine
  • Alkaloids
  • Antimalarials
  • Isoquinolines
  • Phenanthrenes
  • Plant Extracts
  • atherospermine
  • coclaurine