Page last updated: 2024-10-15
biliatresone
Description
biliatresone: a cytotoxin isolated from Dysphania glomulifera and Dysphania littoralis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
biliatresone : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted at positions 5 by a 2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl group and at positions 4 and 6 by methoxy groups. A very rare type of isoflavonoid-related 1,2-diaryl-2-propenone found in Dysphania glomulifera (red crumbweed) and D. littoralis, the enone moiety is particularly reactive, undergoing ready Michael addition of water and methanol. Biliatresone has been found to cause extrahepatic biliary atresia (obliteration or discontinuity of the extrahepatic biliary system, resulting in obstruction to bile flow) in a zebrafish model. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|
| Dysphania | genus | [no description available] | Amaranthaceae | A family of flowering plants in the order Caryophyllales, with about 60 genera and more than 800 species of plants, with a few shrubs, trees, and vines. The leaves usually have nonindented edges.[MeSH] |
| Dysphania glomulifera | species | [no description available] | Amaranthaceae | A family of flowering plants in the order Caryophyllales, with about 60 genera and more than 800 species of plants, with a few shrubs, trees, and vines. The leaves usually have nonindented edges.[MeSH] |
Cross-References
Synonyms (12)
| Synonym |
|---|
| CHEBI:131631 |
| biliatresone |
| 1-(4,6-dimethoxy-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one |
| 2-[2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl]-1,3-dimethoxy-4,5-methylenedioxybenzene |
| 1801433-90-8 |
| 1-(4,6-dimethoxybenzo[d][1,3]dioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one |
| HY-119412 |
| CS-0068115 |
| MS-24915 |
| DTXSID901046375 |
| 1-(4,6-dimethoxy-2h-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one |
| AKOS040750800 |
Research Excerpts
Overview
Biliatresone is a very rare isoflavonoid with an α-methylene ketone between two phenyls, 1,2-diaryl-2-propenone. It causes extrahepatic biliary toxicity in zebrafish.
| Excerpt | Reference |
|---|
| "Biliatresone is a very rare isoflavonoid with an α-methylene ketone between two phenyls, 1,2-diaryl-2-propenone, along with methylenedioxy, dimethoxyl, and hydroxyl functional groups, that causes extrahepatic biliary toxicity in zebrafish." | ( Reactivity of Biliatresone, a Natural Biliary Toxin, with Glutathione, Histamine, and Amino Acids.
Koo, KA; Pack, M; Porter, JR; Waisbourd-Zinman, O; Wells, RG, 2016) |
| "Biliatresone is an electrophilic isoflavone isolated from Dysphania species plants that has been causatively linked to naturally occurring outbreaks of a biliary atresia (BA)-like disease in livestock. " | ( Glutathione antioxidant pathway activity and reserve determine toxicity and specificity of the biliary toxin biliatresone in zebrafish.
Blair, I; Gillespie, K; Koo, KA; Lorent, K; Marchione, DM; Pack, M; Porter, JR; Shin, D; So, J; Waisbourd-Zinman, O; Wells, RG; Wilkins, BJ; Zhao, X, 2016) |
Roles (2)
| Role | Description |
|---|
| toxin | Poisonous substance produced by a biological organism such as a microbe, animal or plant. |
| plant metabolite | Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Drug Classes (5)
| Class | Description |
|---|
| benzodioxoles | |
| enone | An alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position. |
| aromatic ketone | A ketone in which the carbonyl group is attached to an aromatic ring. |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| phenols | Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Research
Studies (9)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 0 (0.00) | 29.6817 |
| 2010's | 5 (55.56) | 24.3611 |
| 2020's | 4 (44.44) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (11.11%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 8 (88.89%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |