Antiplasmodial β-Triketone-Flavanone Hybrids from the Flowers of the Australian Tree Corymbia torelliana

J Nat Prod. 2018 Jul 27;81(7):1588-1597. doi: 10.1021/acs.jnatprod.8b00154. Epub 2018 Jul 3.

Abstract

The methanol extract of the flowers of the Australian eucalypt tree Corymbia torelliana yielded six new β-triketone-flavanone hybrids, torellianones A-F (1-6), the tetrahydroxycyclohexane torellianol A (7), and known β-triketones (4 S)-ficifolidione (8) and (4 R)-ficifolidione (9), and β-triketone-flavanones kunzeanone A (10) and kunzeanone B (11). Torellianones A and B, C and D, and E and F were each isolated as inseparable diastereomeric mixtures. Exchange correlations observed in a ROESY spectrum indicated that 5 and 6 also interconverted between stable conformers. The structures of 1-7 were elucidated from the analysis of 1D/2D NMR and MS data. Relative configurations of torellianones C-F and torrellianol A were determined from analysis of ROESY data. Compounds 1-10 were tested for antiplasmodial activity against a drug-sensitive (3D7) strain of Plasmodium falciparum, with 3-6 and 8-10 showing limited antiplasmodial activity, with IC50 values ranging from 3.2 to 16.6 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology
  • Flavanones / chemistry
  • Flavanones / isolation & purification*
  • Flavanones / pharmacology
  • Flowers / chemistry
  • HEK293 Cells
  • Humans
  • Ketones / chemistry
  • Ketones / isolation & purification*
  • Ketones / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Myrtaceae / chemistry*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Trees / chemistry

Substances

  • Antimalarials
  • Flavanones
  • Ketones
  • Plant Extracts