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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
Structure of ALTERNARIOL

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

HIDE SMILES / InChI

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.

Approval Year

PubMed

PubMed

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

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
by admin
on Fri Dec 15 18:20:26 GMT 2023
Edited
by admin
on Fri Dec 15 18:20:26 GMT 2023
Record UNII
KN9L4260JW
Record Status Validated (UNII)
Record Version
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Name Type Language
ALTERNARIOL
Common Name English
Code System Code Type Description
CAS
641-38-3
Created by admin on Fri Dec 15 18:20:26 GMT 2023 , Edited by admin on Fri Dec 15 18:20:26 GMT 2023
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WIKIPEDIA
ALTERNARIOL
Created by admin on Fri Dec 15 18:20:26 GMT 2023 , Edited by admin on Fri Dec 15 18:20:26 GMT 2023
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PUBCHEM
5359485
Created by admin on Fri Dec 15 18:20:26 GMT 2023 , Edited by admin on Fri Dec 15 18:20:26 GMT 2023
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FDA UNII
KN9L4260JW
Created by admin on Fri Dec 15 18:20:26 GMT 2023 , Edited by admin on Fri Dec 15 18:20:26 GMT 2023
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MESH
C005197
Created by admin on Fri Dec 15 18:20:26 GMT 2023 , Edited by admin on Fri Dec 15 18:20:26 GMT 2023
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CHEBI
64983
Created by admin on Fri Dec 15 18:20:26 GMT 2023 , Edited by admin on Fri Dec 15 18:20:26 GMT 2023
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EPA CompTox
DTXSID80214305
Created by admin on Fri Dec 15 18:20:26 GMT 2023 , Edited by admin on Fri Dec 15 18:20:26 GMT 2023
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