ZFIN ID: ZDB-PUB-150716-1
Biliatresone, A Reactive Natural Toxin from Dysphania glomulifera and D. littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone
Koo, K.A., Lorent, K., Gong, W., Windsor, P., Whittaker, S.J., Pack, M., Wells, R., Porter, J.R.
Date: 2015
Source: Chemical Research in Toxicology   28(8): 1519-21 (Journal)
Registered Authors: Lorent, Kristin, Pack, Michael
Keywords: none
MeSH Terms:
  • Animals
  • Benzodioxoles/chemistry*
  • Benzodioxoles/toxicity*
  • Biological Assay
  • Chenopodiaceae/chemistry*
  • Chromatography, High Pressure Liquid
  • Dose-Response Relationship, Drug
  • Embryo, Nonmammalian/drug effects
  • Lethal Dose 50
  • Molecular Structure
  • Plant Extracts/toxicity*
  • Propiophenones/chemistry*
  • Propiophenones/toxicity*
  • Toxins, Biological/chemistry*
  • Zebrafish/embryology
PubMed: 26175131 Full text @ Chem. Res. Toxicol.
We identified a reactive natural toxin, biliatresone, from Dysphania glomulifera and D. littoralis collected in Australia that produces extrahepatic biliary atresia in a zebrafish model. Three additional isoflavonoids, including the known isoflavone betavulgarin, were also isolated. Biliatresone is in the very rare 1,2-diaryl-2-propenone class of isoflavonoids. The α-methylene of the 1,2-diaryl-2-propenone of biliatresone spontaneously reacts via Michael addition in the formation of wa-ter and methanol adducts. The lethal dose of biliatresone in a zebrafish assay was 1 µg/mL, while the lethal dose of synthet-ic 1,2-diaryl-2-propen-1-one was 5 µg/mL, suggesting 1,2-diaryl-2-propenone as the toxic Michael acceptor.