LC-MS analysis of 13,28-epoxy-oleanane saponins in Maesa spp. extracts with antileishmanial activity

Phytochem Anal. 2009 Mar-Apr;20(2):159-67. doi: 10.1002/pca.1112.

Abstract

Introduction: Saponins are natural products that are well known for a wide range of biological activities. For saponins of Maesa balansae, selective antileishmanial activity has been described.

Objective: In view of their pharmacological interest, several Maesa species from the National Botanical Garden of Meise (Belgium) and wild-grown plants from Vietnam were screened for their antileishmanial potential and saponin content.

Methodology: Different parts of the plants (mainly leaves and twigs) were collected, dried and extracted. Plant extracts were evaluated by liquid chromatography/mass spectrometry (LC-MS) using electrospray ionisation in the negative ion mode and their saponin content was compared with those of Maesa balansae (maesabalides) and Maesa lanceolata (maesasaponins).

Results: Several Maesa species (M. ambigua, M. argentea, M. brevipaniculata, M. japonica and M. perlarius) showed potent antileishmanial activity (<0.1 microg/mL) and indeed contained known maesasaponins and maesabalides. However the leaves of M. argentea also revealed two new compounds. Two saponins with [M - H]- ions at m/z 1465 and 1477 were characterised. Their mass spectrometric fragmentation pattern revealed a structure that was the same or closely related to maesasaponin V.3 and VI.2, respectively, but had a glycan part with one additional hexose residue.

Conclusion: Several known as well as new saponins from Maesa species active against leishmaniasis were characterised using LC-MS.

MeSH terms

  • Animals
  • Antiprotozoal Agents / analysis*
  • Antiprotozoal Agents / pharmacology
  • Cell Line
  • Chromatography, Liquid / methods*
  • Leishmania / drug effects*
  • Primulaceae / chemistry*
  • Saponins / analysis*
  • Saponins / pharmacology
  • Species Specificity
  • Spectrometry, Mass, Electrospray Ionization / methods*

Substances

  • Antiprotozoal Agents
  • Saponins