Title: Biliatresone, a Reactive Natural Toxin from Dysphania glomulifera and D. littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone.
Authors: Koo, Kyung A; Lorent, Kristin; Gong, Weilong; Windsor, Peter; Whittaker, Stephen J; Pack, Michael; Wells, Rebecca G; Porter, John R
Published In Chem Res Toxicol, (2015 Aug 17)
Abstract: 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 water and methanol adducts. The lethal dose of biliatresone in a zebrafish assay was 1 μg/mL, while the lethal dose of synthetic 1,2-diaryl-2-propen-1-one was 5 μg/mL, suggesting 1,2-diaryl-2-propenone as the toxic Michael acceptor.
PubMed ID:
26175131
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