Parvifloranines A and B, two 11-carbon alkaloids from Geijera parviflora

J Nat Prod. 2013 Jul 26;76(7):1384-7. doi: 10.1021/np400376r. Epub 2013 Jul 12.

Abstract

Two novel alkaloids (parvifloranines A and B), possessing an unusual 11-carbon skeleton linked with amino acids, were isolated from Geijera parviflora, an endemic Australian Rutaceae. Their structures were elucidated by extensive spectroscopic measurements including 2D NMR analyses. Parvifloranine A was found to be a mixture of two enantiomers, (S)-1 and (R)-1, in a ratio of 1:4, based on their separation using a chiral column. Parvifloranine B is also believed to be a mixture of enantiomers. Proposed biosynthetic pathways are discussed. Parvifloranine A inhibited the synthesis of nitric oxide in LPS-stimulated RAW 264.7 macrophages with an IC50 value of 23.4 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Australia
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism

Substances

  • Alkaloids
  • Lipopolysaccharides
  • parvifloranine A
  • parvifloranine B
  • Nitric Oxide