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=C2C(OC(=O)C3=C2C=C(O)C=C3O)=CC(O)=C1
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 |
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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 |
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PubMed
Title | Date | PubMed |
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Examination of Alternaria alternata mutagenicity and effects of nitrosylation using the Ames Salmonella test. | 2001 |
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Production of alternaria mycotoxins by Alternaria alternata isolated from weather-damaged wheat. | 2001 Apr |
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Production of alternariol and alternariol methyl ether by Alternaria alternata grown on fruits at various temperatures. | 2001 Apr |
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Survey of Brazilian tomato products for alternariol, alternariol monomethyl ether, tenuazonic acid and cyclopiazonic acid. | 2001 Jul |
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Analysis of agricultural commodities and foods for Alternaria mycotoxins. | 2001 Nov-Dec |
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6H-dibenzo[b,d]pyran-6-one derivatives from the cultured lichen mycobionts of Graphis spp. and their biosynthetic origin. | 2003 Jan |
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Liquid chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry of the Alternaria mycotoxins alternariol and alternariol monomethyl ether in fruit juices and beverages. | 2003 May 23 |
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Liquid chromatographic determination of Alternaria toxins in carrots. | 2004 Jan-Feb |
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Total synthesis of alternariol. | 2005 Apr 15 |
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Mycoflora and occurrence of alternariol and alternariol monomethyl ether in Brazilian sunflower from sowing to harvest. | 2005 Jul 13 |
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Mutagenicity of the mycotoxin alternariol in cultured mammalian cells. | 2006 Jul 14 |
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Analysis of alternariol and alternariol monomethyl ether on flavedo and albedo tissues of tangerines (Citrus reticulata) with symptoms of alternaria brown spot. | 2007 Jun 27 |
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Mycotoxin production by Alternaria strains isolated from Argentinean wheat. | 2007 Nov 1 |
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Alternaria toxins in wheat during the 2004 to 2005 Argentinean harvest. | 2008 Jun |
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Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. | 2008 Jun |
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Influence of alternariol (AOH) on regulator proteins of cap-dependent translation in porcine endometrial cells. | 2008 Nov 10 |
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Alternariol acts as a topoisomerase poison, preferentially affecting the IIalpha isoform. | 2009 Apr |
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The mycotoxins alternariol and alternariol methyl ether negatively affect progesterone synthesis in porcine granulosa cells in vitro. | 2009 Apr 25 |
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Development of a multi-mycotoxin liquid chromatography/tandem mass spectrometry method for sweet pepper analysis. | 2009 Jan |
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Cytotoxic metabolites produced by Alternaria no.28, an endophytic fungus isolated from Ginkgo biloba. | 2009 Nov |
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[Simultaneous determination of four Alternaria toxins in apple juice concentrate by ultra performance liquid chromatography-electrospray ionization tandem mass spectrometry]. | 2010 Dec |
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Light regulation of metabolic pathways in fungi. | 2010 Feb |
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Occurrence of mycotoxins in feed as analyzed by a multi-mycotoxin LC-MS/MS method. | 2010 Jan 13 |
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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 Jul 20 |
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Multi-mycotoxin analysis of maize silage by LC-MS/MS. | 2010 May |
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Analysis of multiple mycotoxins in cereals under ambient conditions using direct analysis in real time (DART) ionization coupled to high resolution mass spectrometry. | 2010 Oct 15 |
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Degradation of the Alternaria mycotoxins alternariol, alternariol monomethyl ether, and altenuene upon bread baking. | 2010 Sep 8 |
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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 Apr |
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Cell death induced by the Alternaria mycotoxin Alternariol. | 2012 Sep |
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An in vitro investigation of endocrine disrupting effects of the mycotoxin alternariol. | 2013 Aug 15 |
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Modulation of the cellular redox status by the Alternaria toxins alternariol and alternariol monomethyl ether. | 2013 Jan 10 |
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Autophagy and senescence, stress responses induced by the DNA-damaging mycotoxin alternariol. | 2014 Dec 4 |
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Oxidative DNA damage and disturbance of antioxidant capacity by alternariol in Caco-2 cells. | 2015 Jun 1 |
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The mycotoxin alternariol induces DNA damage and modify macrophage phenotype and inflammatory responses. | 2015 Nov 19 |
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Impact of Alternaria toxins on CYP1A1 expression in different human tumor cells and relevance for genotoxicity. | 2016 Jan 5 |
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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DTXSID80214305
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