|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.
|Source:||Chemical Research in Toxicology 28(8): 1519-21 (Journal)|
|Registered Authors:||Lorent, Kristin, Pack, Michael|
|PubMed:||26175131 Full text @ Chem. Res. Toxicol.|
Koo, K.A., Lorent, K., Gong, W., Windsor, P., Whittaker, S.J., Pack, M., Wells, R., Porter, J.R. (2015) Biliatresone, A Reactive Natural Toxin from Dysphania glomulifera and D. littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone. Chemical Research in Toxicology. 28(8):1519-21.
ABSTRACTWe 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.
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