Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H10O5 |
| Molecular Weight | 258.2262 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(O)=CC2=C1C3=C(C(=O)O2)C(O)=CC(O)=C3
InChI
InChIKey=CEBXXEKPIIDJHL-UHFFFAOYSA-N
InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3
| Molecular Formula | C14H10O5 |
| Molecular Weight | 258.2262 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Alternariol is the mycotoxin produced by Alternaria fungi. It occurs naturally in foodstuffs and is frequently found as contaminant in fruit and grain products. It forms reactive oxygen species and interacts with DNA topoisomerase, thereby generating both single- and double-strand DNA beaks. Alternariol demonstrated dual inhibition of acetylcholinesterase (AChE) and monoamine oxidase (MAO-A) enzymes extracted from whole and five different parts of male albino rat brains; namely: frontal cortex, basal ganglia, cerebellum, pons, medulla oblongata. In vitro studies have suggested that Alternariol may be linked to reduced immune response in case of infections and/or a disturbed balance of the adaptive immune system. Although the absorption appears to be relative low, it is nevertheless important to further clarify the mode of genotoxicity.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3899714 |
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Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18727009 |
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Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18727009 |
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Target ID: CHEMBL3396 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18727009 |
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Target ID: CHEMBL3199 |
1.8 mM [Ki] | ||
Target ID: CHEMBL3358 |
2.4 mM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Impact of Alternaria toxins on CYP1A1 expression in different human tumor cells and relevance for genotoxicity. | 2016-01-05 |
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| The mycotoxin alternariol induces DNA damage and modify macrophage phenotype and inflammatory responses. | 2015-11-19 |
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| Oxidative DNA damage and disturbance of antioxidant capacity by alternariol in Caco-2 cells. | 2015-06-01 |
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| Autophagy and senescence, stress responses induced by the DNA-damaging mycotoxin alternariol. | 2014-12-04 |
|
| An in vitro investigation of endocrine disrupting effects of the mycotoxin alternariol. | 2013-08-15 |
|
| Modulation of the cellular redox status by the Alternaria toxins alternariol and alternariol monomethyl ether. | 2013-01-10 |
|
| Cell death induced by the Alternaria mycotoxin Alternariol. | 2012-09 |
|
| Mouse hepatoma cell lines differing in aryl hydrocarbon receptor-mediated signaling have different activities for glucuronidation. | 2012-04 |
|
| The Alternaria mycotoxins alternariol and alternariol methyl ether induce cytochrome P450 1A1 and apoptosis in murine hepatoma cells dependent on the aryl hydrocarbon receptor. | 2012-04 |
|
| [Simultaneous determination of four Alternaria toxins in apple juice concentrate by ultra performance liquid chromatography-electrospray ionization tandem mass spectrometry]. | 2010-12 |
|
| Analysis of multiple mycotoxins in cereals under ambient conditions using direct analysis in real time (DART) ionization coupled to high resolution mass spectrometry. | 2010-10-15 |
|
| Production and migration of mycotoxins in sweet pepper analyzed by Multimycotoxin LC-MS/MS. | 2010-10-13 |
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| Degradation of the Alternaria mycotoxins alternariol, alternariol monomethyl ether, and altenuene upon bread baking. | 2010-09-08 |
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| Water activity and temperature effects on mycotoxin production by Alternaria alternata on a synthetic tomato medium. | 2010-09-01 |
|
| Self-reported chemicals exposure, beliefs about disease causation, and risk of breast cancer in the Cape Cod Breast Cancer and Environment Study: a case-control study. | 2010-07-20 |
|
| The transcription factor StuA regulates central carbon metabolism, mycotoxin production, and effector gene expression in the wheat pathogen Stagonospora nodorum. | 2010-07 |
|
| Alternariol. | 2010-05-15 |
|
| Multi-mycotoxin analysis of maize silage by LC-MS/MS. | 2010-05 |
|
| Impact of water activity and temperature on growth and alternariol and alternariol monomethyl ether production of Alternaria alternata isolated from soybean. | 2010-02 |
|
| Light regulation of metabolic pathways in fungi. | 2010-02 |
|
| Occurrence of mycotoxins in feed as analyzed by a multi-mycotoxin LC-MS/MS method. | 2010-01-13 |
|
| Effects of gamma radiation on the growth of Alternaria alternata and on the production of alternariol and alternariol monomethyl ether in sunflower seeds. | 2009-12 |
|
| Cytotoxic metabolites produced by Alternaria no.28, an endophytic fungus isolated from Ginkgo biloba. | 2009-11 |
|
| Stable isotope dilution assays of alternariol and alternariol monomethyl ether in beverages. | 2009-06-24 |
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| LC-MS/MS multi-analyte method for mycotoxin determination in food supplements. | 2009-06 |
|
| The mycotoxins alternariol and alternariol methyl ether negatively affect progesterone synthesis in porcine granulosa cells in vitro. | 2009-04-25 |
|
| Alternariol acts as a topoisomerase poison, preferentially affecting the IIalpha isoform. | 2009-04 |
|
| [Acute cytotoxicity of alternariol on NIH/3T3 cells]. | 2009-03 |
|
| Mycoflora and mycotoxin production in oilseed cakes during farm storage. | 2009-02-25 |
|
| An overview of conventional and emerging analytical methods for the determination of mycotoxins. | 2009-01 |
|
| Development of a multi-mycotoxin liquid chromatography/tandem mass spectrometry method for sweet pepper analysis. | 2009-01 |
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| New antitumour fungal metabolites from Alternaria porri. | 2009 |
|
| Influence of alternariol (AOH) on regulator proteins of cap-dependent translation in porcine endometrial cells. | 2008-11-10 |
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| Alternaria toxins in wheat during the 2004 to 2005 Argentinean harvest. | 2008-06 |
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| Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. | 2008-06 |
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| LC-MS/MS multi-method for mycotoxins after single extraction, with validation data for peanut, pistachio, wheat, maize, cornflakes, raisins and figs. | 2008-04 |
|
| Mycotoxin production by Alternaria strains isolated from Argentinean wheat. | 2007-11-01 |
|
| Analysis of alternariol and alternariol monomethyl ether on flavedo and albedo tissues of tangerines (Citrus reticulata) with symptoms of alternaria brown spot. | 2007-06-27 |
|
| [Putative mycotoxin-producing fungi isolated from alpataco (Prosopis flexuosa) fruits]. | 2007-03 |
|
| Novel oxidative in vitro metabolites of the mycotoxins alternariol and alternariol methyl ether. | 2007-03 |
|
| Real-time PCR quantification of the AM-toxin gene and HPLC qualification of toxigenic metabolites from Alternaria species from apples. | 2006-09-01 |
|
| Further examination of the effects of nitrosylation on Alternaria alternata mycotoxin mutagenicity in vitro. | 2006-07-14 |
|
| Mutagenicity of the mycotoxin alternariol in cultured mammalian cells. | 2006-07-14 |
|
| Survey of the mycobiota of Spanish malting barley and evaluation of the mycotoxin producing potential of species of Alternaria, Aspergillus and Fusarium. | 2006-04-25 |
|
| Estrogenic and clastogenic potential of the mycotoxin alternariol in cultured mammalian cells. | 2006-03 |
|
| Toxigenic fungi isolated from dried vine fruits in Argentina. | 2005-09-25 |
|
| Mycoflora and occurrence of alternariol and alternariol monomethyl ether in Brazilian sunflower from sowing to harvest. | 2005-07-13 |
|
| Total synthesis of alternariol. | 2005-04-15 |
|
| Toxigenic profile of Alternaria alternata and Alternaria radicina occurring on umbelliferous plants. | 2005-04 |
|
| Liquid chromatographic determination of Alternaria toxins in carrots. | 2004-04-16 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19408650
Logarithmic growth phase NIH/3T3 cells were treated at the dose of 10 uM/L and 50 uM/L altemariol. The inhibition rates of 10 uM/L and 50 uM/L altemariol were 19.88% and 32.47% respectively.
| Substance Class |
Chemical
Created
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admin
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Edited
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| Record UNII |
KN9L4260JW
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| Record Status |
Validated (UNII)
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| Record Version |
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ALTERNARIOL
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