Biliatresone, a Reactive Natural Toxin from Dysphania glomulifera and D. littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone

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• 作者：Kyung A. Koo ; Kristin Lorent ; Weilong Gong ; Peter Windsor ; Stephen J. Whittaker ; Michael Pack ; Rebecca G. Wells ; John R. Porter
• 刊名：Chemical Research in Toxicology
• 出版年：2015
• 出版时间：August 17, 2015
• 年：2015
• 卷：28
• 期：8
• 页码：1519-1521
• 全文大小：221K
• ISSN：1520-5010

文摘

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 伪-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 渭g/mL, while the lethal dose of synthetic 1,2-diaryl-2-propen-1-one was 5 渭g/mL, suggesting 1,2-diaryl-2-propenone as the toxic Michael acceptor.