title: Biliatresone, a Reactive Natural Toxin from Dysphania glomulifera and D. littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone.
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.
authors.affiliation: †Department of Biological Sciences, University of the Sciences, Philadelphia, Pennsylvania 19104, United States.
authors.forename: Kyung A
authors.initials: KA
authors.lastname: Koo
authors.forename: Kristin
authors.initials: K
authors.lastname: Lorent
authors.forename: Weilong
authors.initials: W
authors.lastname: Gong
authors.affiliation: ⊥Faculty of Veterinary Science, University of Sydney, Sydney, New South Wales 2006, Australia.
authors.forename: Peter
authors.initials: P
authors.lastname: Windsor
authors.affiliation: #Hume Livestock and Pest Authority, Albury, New South Wales Australia.
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Whittaker
authors.forename: Michael
authors.initials: M
authors.lastname: Pack
authors.forename: Rebecca G
authors.initials: RG
authors.lastname: Wells
authors.affiliation: †Department of Biological Sciences, University of the Sciences, Philadelphia, Pennsylvania 19104, United States.
authors.forename: John R
authors.initials: JR
authors.lastname: Porter
mesh_terms: D000818:Animals; D052117:Benzodioxoles / Q000737:chemistry* / Q000633:toxicity*; D001681:Biological Assay; D019663:Chenopodiaceae / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004305:Dose-Response Relationship, Drug; D004625:Embryo, Nonmammalian / Q000187:drug effects; D007928:Lethal Dose 50; D015394:Molecular Structure; D010936:Plant Extracts / Q000633:toxicity*; D011427:Propiophenones / Q000737:chemistry* / Q000633:toxicity*; D014118:Toxins, Biological / Q000737:chemistry*; D015027:Zebrafish / Q000196:embryology
chemical_list: D052117:Benzodioxoles; D010936:Plant Extracts; D011427:Propiophenones; D014118:Toxins, Biological; C000608133:biliatresone