PUBLICATION
Biliatresone, A Reactive Natural Toxin from Dysphania glomulifera and D. littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone
- Authors
- Koo, K.A., Lorent, K., Gong, W., Windsor, P., Whittaker, S.J., Pack, M., Wells, R., Porter, J.R.
- ID
- ZDB-PUB-150716-1
- Date
- 2015
- Source
- Chemical Research in Toxicology 28(8): 1519-21 (Journal)
- Registered Authors
- Lorent, Kristin, Pack, Michael
- Keywords
- none
- 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
- PubMed
- 26175131 Full text @ Chem. Res. Toxicol.
Citation
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.
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 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.
Genes / Markers
Expression
Phenotype
Mutations / Transgenics
Human Disease / Model
Sequence Targeting Reagents
Fish
Orthology
Engineered Foreign Genes
Mapping