| Record Information |
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| Version | 2.0 |
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| Creation Date | 2010-05-03 20:06:17 UTC |
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| Update Date | 2014-12-24 20:26:27 UTC |
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| Accession Number | T3D3727 |
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| Identification |
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| Common Name | Alternariol |
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| Class | Small Molecule |
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| Description | Alternariol is found in mushrooms. Alternariol occurs in mycelium of Alternaria tenuis responsible for alternaria cone disorder in hops and fruit spot on papaya (Carica papaya) and Passiflora species.Alternariol is a toxic metabolite of Alternaria fungi. It is an important contaminant in cereals and fruits.
Alternariol belongs to the family of Isocoumarins and Derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. |
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| Compound Type | - Ester
- Food Toxin
- Fungal Toxin
- Metabolite
- Mycotoxin
- Natural Compound
- Organic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | 1-Methyl-3,7,9-trihydroxy-6H-Dibenzo(b,D)pyran-6-one | | 3,4',5-Trihydroxy-6'-methyldibenzo-a-pyrone | | 3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one | | 3,7,9-Trihydroxy-1-methyl-6H-dibenzo(b,D)pyran-6-one | | 3,7,9-Trihydroxy-1-methyl-6H-Dibenzo[b,D]pyran-6-one | | 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,D]pyran-6-one, 9CI | | Alternariol 3,4',5-Trihydroxy-6'-methyl-dibenzo[a]pyrone | | Alternariol from alternaria SP. | | AOH |
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| Chemical Formula | C14H10O5 |
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| Average Molecular Mass | 258.226 g/mol |
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| Monoisotopic Mass | 258.053 g/mol |
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| CAS Registry Number | 641-38-3 |
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| IUPAC Name | 3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one |
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| Traditional Name | alternariol |
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| SMILES | CC1=CC(O)=CC2=C1C1=C(C(=O)O2)C(O)=CC(O)=C1 |
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| InChI Identifier | 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 |
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| InChI Key | InChIKey=CEBXXEKPIIDJHL-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Coumarins and derivatives |
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| Sub Class | Not Available |
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| Direct Parent | Coumarins and derivatives |
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| Alternative Parents | |
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| Substituents | - Coumarin
- Isocoumarin
- Benzopyran
- 1-benzopyran
- 2-benzopyran
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Lactone
- Oxacycle
- Polyol
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | |
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| Chemical Roles | |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 350°C | | Boiling Point | Not Available | | Solubility | Not Available | | LogP | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0bu3-0190000000-ab90d95f25f23b1c1d4d | 2017-09-01 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-11b9-2202900000-492de99142b0a0d1994c | 2017-10-06 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-0a4i-0090000000-49a9dc87e5577f9cc6aa | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a4i-0290000000-913a843eb1fbe0ab9082 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a4i-0490000000-4c5e72338325be202711 | 2017-09-14 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-353041795899e746b989 | 2015-04-25 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0090000000-7411b04aa0ed4ee2981d | 2015-04-25 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-066u-1390000000-b231ee41769f3f5f967a | 2015-04-25 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-5c99e00473c8f7c5ab03 | 2021-09-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0090000000-5c99e00473c8f7c5ab03 | 2021-09-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05mo-1190000000-3f7f323bf357ac1a8f9d | 2021-09-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0090000000-95b8c497427d61e438f4 | 2015-04-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0090000000-51f692a816351a0b1b59 | 2015-04-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05mo-1290000000-46150e766500f30952d8 | 2015-04-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0090000000-adb7dbccff647a617461 | 2021-09-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0090000000-adb7dbccff647a617461 | 2021-09-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001u-0980000000-b815e685470eef6d7042 | 2021-09-24 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Oral, dermal, inhalation, and parenteral (contaminated drugs). (5) |
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| Mechanism of Toxicity | Alternariol is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. |
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| Metabolism | Alternariol is metabolized by microsomes in the liver, preferentially at aromatic positions. The products of aromatic hydroxylation are either catechols or hydroquinones, which may form reactive semiquinones and quinones or undergo redox cycling. (4) |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Alternariol is an altertoxin, which is a toxic metabolite of Alternaria fungi. It is an important contaminant in cereals, vegetables, and fruits, as well as in the ground, on wood or walls. (7, 1) |
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| Minimum Risk Level | Not Available |
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| Health Effects | Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides. |
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| Symptoms | Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result. |
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| Treatment | If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally. |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB30831 |
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| PubChem Compound ID | 5359485 |
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| ChEMBL ID | CHEMBL519982 |
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| ChemSpider ID | 4514301 |
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| KEGG ID | C16838 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 64983 |
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| BioCyc ID | Not Available |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | Not Available |
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| ACToR ID | Not Available |
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| Wikipedia Link | Alternariol |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | T3D3727.pdf |
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| General References | - Fehr M, Pahlke G, Fritz J, Christensen MO, Boege F, Altemoller M, Podlech J, Marko D: Alternariol acts as a topoisomerase poison, preferentially affecting the IIalpha isoform. Mol Nutr Food Res. 2009 Apr;53(4):441-51. doi: 10.1002/mnfr.200700379. [18727009 ]
- Brugger EM, Wagner J, Schumacher DM, Koch K, Podlech J, Metzler M, Lehmann L: Mutagenicity of the mycotoxin alternariol in cultured mammalian cells. Toxicol Lett. 2006 Jul 14;164(3):221-30. Epub 2006 Feb 7. [16464542 ]
- Lehmann L, Wagner J, Metzler M: Estrogenic and clastogenic potential of the mycotoxin alternariol in cultured mammalian cells. Food Chem Toxicol. 2006 Mar;44(3):398-408. Epub 2005 Sep 27. [16194592 ]
- Pfeiffer E, Schebb NH, Podlech J, Metzler M: Novel oxidative in vitro metabolites of the mycotoxins alternariol and alternariol methyl ether. Mol Nutr Food Res. 2007 Mar;51(3):307-16. [17340575 ]
- Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
- Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
- Wikipedia. Alternariol. Last Updated 12 April 2010. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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| Down-Regulated Genes | | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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