New prenylated carbazole alkaloids from Zanthoxylum armatum

J Asian Nat Prod Res. 2014 Dec;16(12):1126-31. doi: 10.1080/10286020.2014.967228. Epub 2014 Oct 30.

Abstract

A phytochemical investigation on the ethyl acetate soluble fraction of Zanthoxylum armatum led in the isolation of two new prenylated alkaloids 2,6,7-trimethoxy-8-(3-methyl-2-butenyl)carbazole-3-carbaldehyde (1) and methyl-2,6,7-trimethoxy-8-(3-methyl-2-butenyl)carbazole-3-carboxylate (2), along with three known lignans cisamin (3), methyl pirpirtol (4), and fargesin (5) and one known alkaloid dictamine (6). Their structures were established on the basis of spectroscopic and crystallographic analysis and by comparison of the data with those in the literature. All the isolated compounds were screened for the DPPH free radical scavenging activity. Compounds 1, 2, and 6 showed profound activity while compounds 3-5 showed moderate activity.

Keywords: DPPH radical scavenging activity; Rutaceae; Zanthoxylum armatum; alkaloids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Benzodioxoles / isolation & purification
  • Biphenyl Compounds / pharmacology
  • Carbazoles / chemistry
  • Carbazoles / isolation & purification*
  • Carbazoles / pharmacology
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / isolation & purification*
  • Free Radical Scavengers / pharmacology
  • Lignans / isolation & purification
  • Molecular Structure
  • Pakistan
  • Picrates / pharmacology
  • Prenylation
  • Quinolines / chemistry
  • Quinolines / isolation & purification
  • Quinolines / pharmacology
  • Zanthoxylum / chemistry*

Substances

  • 2,6,7-trimethoxy-8-(3-methyl-2-butenyl)carbazole-3-carbaldehyde
  • Alkaloids
  • Benzodioxoles
  • Biphenyl Compounds
  • Carbazoles
  • Free Radical Scavengers
  • Lignans
  • Picrates
  • Quinolines
  • methyl-2,6,7-trimethoxy-8-(3-methyl-2-butenyl)carbazole-3-carboxylate
  • 1,1-diphenyl-2-picrylhydrazyl
  • fargesin
  • dictamnine