Biliatresone

Biliatresone
Names
Preferred IUPAC name
1-(4,6-Dimethoxy-2H-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C18H16O6/c1-10(11-6-4-5-7-12(11)19)16(20)15-13(21-2)8-14-17(18(15)22-3)24-9-23-14/h4-8,19H,1,9H2,2-3H3
    Key: SIKIIXNKUAAGAM-UHFFFAOYSA-N
  • O=C(C(C1=C(O)C=CC=C1)=C)C2=C(OC)C3=C(OCO3)C=C2OC
Properties
C18H16O6
Molar mass 328.320 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biliatresone is an example of a very rare type of a naturally occurring isoflavonoid-related 1,2-diaryl-2-propenone found in Dysphania glomulifera and D. littoralis.[1][2][3] It has been found to cause extrahepatic biliary atresia in a zebrafish model. The enone moiety of biliatresone is particularly reactive, being enhanced by the methylenedioxy, methoxy and hydroxy groups,[4] and undergoes ready Michael addition of water and methanol.

  1. ^ Lorent, K.; et al. (May 2015). "Identification of a plant isoflavonoid that causes biliary atresia". Sci Transl Med. 7 (286): 286ra67. doi:10.1126/scitranslmed.aaa1652. PMC 4784984. PMID 25947162.
  2. ^ Koo, K.A.; et al. (Aug 2015). "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): 1519–1521. doi:10.1021/acs.chemrestox.5b00227. PMC 4755499. PMID 26175131.
  3. ^ Patman, G. (2015). "Biliary tract: Newly identified biliatresone causes biliary atresia". Nat Rev Gastroenterol Hepatol. 12 (7): 369. doi:10.1038/nrgastro.2015.91. PMID 26008130. S2CID 205488639.
  4. ^ Koo, K.A.; et al. (2016). "Reactivity of biliatresone, a natural biliary toxin, with glutathione, histamine, and amino acids". Chem. Res. Toxicol. 29 (2): 142–9. doi:10.1021/acs.chemrestox.5b00308. PMC 4757443. PMID 26713899.