In vitro acetylcholinesterase activity of peptide derivatives isolated from two species of Leguminosae

Pharm Biol. 2013 Jul;51(7):936-9. doi: 10.3109/13880209.2013.770536. Epub 2013 Apr 9.

Abstract

Context: Cratylia mollis Martius ex Benth. and Cenostigma macrophyllum Tul. (Leguminosae) are both endemic Brazilian plants and they are used by the natives as medicinal plants, and the leaves of C. mollis are also employed as forage for cattle during the dry season of region.

Objective: Isolation of the compounds responsible for the acetylcholinesterase (AChE) inhibition from the CHCl3 active extract.

Materials and methods: Two peptidic compounds were isolated by chromatographic techniques from the CHCl3 extract of the leaves of C. mollis and C. macrophyllum. They were identified by spectrometric data analysis (MS and NMR) and they were subjected to AChE inhibition employing Ellman's test.

Results: The peptides were identified as N-benzoylphenylalaninoyl-phenlyalaninolacetate (aurentiamide acetate) (1) and N-benzoylphenylalaninyl-N-benzoylphenylalaninate (2). Both peptides 1 and 2 exhibit AChE inhibition, with IC50 values equal to 111.34 µM and 137.6 µM, respectively.

Discussion and conclusion: Compound 1 (aurentiamide acetate) has rarely been isolated from the Leguminosae family, and N-benzoylphenylalaninyl-N-benzoylphenylalaninate (2) is a compound that has never previously been isolated from this family. Compound 1 is shown to be a potent inhibitor of AChE, with IC50 values similar to the physostigmine control (141.51 µM).

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / administration & dosage
  • Acetates / isolation & purification
  • Acetates / pharmacology
  • Acetylcholinesterase / drug effects*
  • Acetylcholinesterase / metabolism
  • Benzyl Compounds / administration & dosage
  • Benzyl Compounds / isolation & purification
  • Benzyl Compounds / pharmacology
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / pharmacology*
  • Dipeptides / administration & dosage
  • Dipeptides / isolation & purification
  • Dipeptides / pharmacology
  • Fabaceae / chemistry*
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Physostigmine / pharmacology
  • Plant Extracts / administration & dosage
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Leaves

Substances

  • Acetates
  • Benzyl Compounds
  • Cholinesterase Inhibitors
  • Dipeptides
  • N-benzoylphenylalaninyl-N-benzoylphenylalaninate
  • Plant Extracts
  • aurentiamide acetate
  • N-benzoylphenylalanylphenylalinol acetate
  • Physostigmine
  • Acetylcholinesterase