Anti-mycobacterial triterpenes from the Canadian medicinal plant Alnus incana

J Ethnopharmacol. 2015 May 13:165:148-51. doi: 10.1016/j.jep.2015.02.042. Epub 2015 Feb 25.

Abstract

Ethnopharmacological relevance: Alnus incana, commonly known as the gray or speckled alder, is a medicinal plant used by some Canadian First Nations to treat symptoms associated with tuberculosis. The aim of this study was to assess the anti-mycobacterial activity of an Alnus incana bark extract and to identify the active constituents of the extract.

Materials and methods: Methanolic extracts of the bark of A. incana were subjected to bioassay guided fractionation using Mycobacterium tuberculosis (H37Ra). The active constituents were identified by NMR and MS.

Results: Four pentacyclic lupane triterpenes were isolated and were identified as betulin, betulinic acid, betulone and lupenone. Betulin displayed a MIC of 12.5 μg/mL and an IC50 of 2.4 μg/mL against M. tuberculosis (H37Ra). Betulinic acid and betulone showed lower anti-mycobacterial activities with IC50 values of 84 and 57 μg/mL respectively. Lupenone was inactive against M. tuberculosis (H37Ra).

Conclusions: Betulin, betulinic acid and betulone were identified as the major anti-mycobacterial constituents in the bark of A. incana and the functionality at carbons 3 and 28 of the lupane skeleton would seem to be important in determining the anti-mycobacterial activity of the triterpenes. This work supports the ethnopharmacological use of A. incana by Canadian First Nations communities as a treatment for tuberculosis.

Keywords: Alnus incana; Antimycobacterial activity; Betulin; Betulinic acid; Betulone; Mycobacterium tuberculosis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alnus / chemistry*
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Betulinic Acid
  • HEK293 Cells / drug effects
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mycobacterium tuberculosis / drug effects*
  • Pentacyclic Triterpenes
  • Phytotherapy / methods
  • Plant Bark / chemistry*
  • Plant Extracts / isolation & purification*
  • Plant Extracts / pharmacology
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology

Substances

  • Anti-Bacterial Agents
  • Pentacyclic Triterpenes
  • Plant Extracts
  • Triterpenes
  • betulin
  • Betulinic Acid