Biliatresone, a Reactive Natural Toxin from Dysphania glomulifera and D. littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone.
Chem Res Toxicol
; 28(8): 1519-21, 2015 Aug 17.
Article
em En
| MEDLINE
| ID: mdl-26175131
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.
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Base de dados:
MEDLINE
Assunto principal:
Propiofenonas
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Toxinas Biológicas
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Extratos Vegetais
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Chenopodiaceae
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Benzodioxóis
Limite:
Animals
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article