Nitrogen Oxide Inhibitory Trimeric and Dimeric Carbazole Alkaloids from Murraya tetramera

J Nat Prod. 2015 Oct 23;78(10):2432-9. doi: 10.1021/acs.jnatprod.5b00527. Epub 2015 Sep 1.

Abstract

Two new structurally unique trimeric carbazole alkaloids, murratrines A and B (1, 2), and 11 new carbazole dimers, murradines A-K (3-13), and four known analogues (14-17) were isolated from the leaves and stems of Murraya tetramera. The structures and relative configurations of 1-13 were elucidated on the basis of comprehensive 1D and 2D NMR spectroscopy, high-resolution mass spectrometry, and electronic circular dichroism (ECD) data analysis. Murratrines A and B (1, 2) both contain an unprecedented carbazole trimeric skeleton, and murradines A and D (3, 6) are the first natural C-1-C-3'-methyl-linked and C-6-C-3'-methyl-linked dimeric carbazole alkaloids, respectively. Compounds 4, 10, 14, 15, and 17 exhibited inhibition of nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells with IC50 values in the range of 11.2-19.3 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Animals
  • Carbazoles / chemistry
  • Carbazoles / isolation & purification*
  • Carbazoles / pharmacology*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Mice
  • Microglia / drug effects
  • Molecular Structure
  • Murraya / chemistry*
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plant Stems / chemistry

Substances

  • Alkaloids
  • Carbazoles
  • Drugs, Chinese Herbal
  • Lipopolysaccharides
  • murratrine A
  • Nitric Oxide