seco-iridoids from Calycophyllum spruceanum (Rubiaceae)

Phytochemistry. 2003 Sep;64(2):549-53. doi: 10.1016/s0031-9422(03)00153-5.

Abstract

Three seco-iridoids 7-methoxydiderroside, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochemistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosoma cruzi, with IC(50) values of 59.0, 90.2, 74,2 and 84.9 microg/mL, respectively and were compared to the standard gentian violet (IC(50) 7.5 microg/ml).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Glucosides / chemistry
  • Glucosides / isolation & purification
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Iridoid Glucosides
  • Iridoids / chemistry*
  • Iridoids / isolation & purification*
  • Iridoids / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Rubiaceae / chemistry*
  • Stereoisomerism
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / isolation & purification
  • Trypanocidal Agents / pharmacology
  • Trypanosoma cruzi / drug effects
  • Trypanosoma cruzi / genetics

Substances

  • Glucosides
  • Glycosides
  • Iridoid Glucosides
  • Iridoids
  • Trypanocidal Agents
  • secoxyloganin
  • loganin