Alternariol
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| Category | Antibiotics |
| Catalog number | BBF-00664 |
| CAS | 641-38-3 |
| Molecular Weight | 258.23 |
| Molecular Formula | C14H10O5 |
| Purity | 97% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-00664 | 1 mg | $439 | In stock |
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Add to cartDescription
It is produced by the strain of Alternaria tenuis. The inhibition concentration of S. aureus and E. coli was 1:40000 and 1:20000, respectively.
Specification
| Synonyms | 3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one; 3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one; 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one; CCRIS 6734; AOH; KN9L4260JW; CHEBI:64983; NSC638263; 3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylic acid, gamma lactone; 3,7,9-Trihydroxy-1-methyl-6H-dibenzo(b,d)pyran-6-one; CHEMBL519982 |
| Storage | 2-8 °C |
| IUPAC Name | 3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one |
| Canonical SMILES | CC1=CC(=CC2=C1C3=C(C(=CC(=C3)O)O)C(=O)O2)O |
| InChI | 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 |
| InChI Key | CEBXXEKPIIDJHL-UHFFFAOYSA-N |
| Source | 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. |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 586.9 °C at 760 mmHg |
| Melting Point | 350 °C (dec.) |
| Density | 1.563 g/cm3 |
| Solubility | Soluble in Ethanol |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| 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. 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. |
| Toxicity | LDLo intraperitoneal in mouse: 100mg/kg |
Reference Reading
1. Interactions of Mycotoxin Alternariol with Cytochrome P450 Enzymes and OATP Transporters
Eszter Fliszár-Nyúl, Orsolya Ungvári, Ágnes Dombi, Csilla Özvegy-Laczka, Miklós Poór Metabolites. 2022 Dec 28;13(1):45. doi: 10.3390/metabo13010045.
Alternariol (AOH) is an emerging mycotoxin produced by Alternaria strains. The acute toxicity of the mycotoxin is low; however, chronic exposure to AOH may result in the development of endocrine disruptor and/or carcinogenic effects. The toxicokinetic properties of AOH have barely been characterized. Therefore, in this study, we aimed to investigate its interactions with CYP (1A2, 2C9, 2C19, 2D6, and 3A4) enzymes and OATP (1A2, 1B1, 1B3, and 2B1) transporters employing in vitro enzyme assays and OATP overexpressing cells, respectively. Our results demonstrated that AOH is a strong inhibitor of CYP1A2 (IC50 = 0.15 μM) and CYP2C9 (IC50 = 7.4 μM). Based on the AOH depletion assays in the presence of CYP enzymes, CYP1A2 is mainly involved, while CYP2C19 is moderately involved in the CYP-catalyzed biotransformation of the mycotoxin. AOH proved to be a strong inhibitor of each OATP transporter examined (IC50 = 1.9 to 5.4 μM). In addition, both direct and indirect assays suggest the involvement of OATP1B1 in the cellular uptake of the mycotoxin. These findings promote the deeper understanding of certain toxicokinetic interactions of AOH.
2. Testing Serum Albumins and Cyclodextrins as Potential Binders of the Mycotoxin Metabolites Alternariol-3-Sulfate, Alternariol-9-Monomethylether and Alternariol-9-Monomethylether-3-Sulfate
Beáta Lemli, Péter Vilmányi, Eszter Fliszár-Nyúl, Balázs Zoltán Zsidó, Csaba Hetényi, Lajos Szente, Miklós Poór Int J Mol Sci. 2022 Nov 18;23(22):14353. doi: 10.3390/ijms232214353.
Alternaria mycotoxins, including alternariol (AOH), alternariol-9-monomethylether (AME), and their masked/modified derivatives (e.g., sulfates or glycosides), are common food contaminants. Their acute toxicity is relatively low, while chronic exposure can lead to the development of adverse health effects. Masked/modified metabolites can probably release the more toxic parent mycotoxin due to their enzymatic hydrolysis in the intestines. Previously, we demonstrated the complex formation of AOH with serum albumins and cyclodextrins; these interactions were successfully applied for the extraction of AOH from aqueous matrices (including beverages). Therefore, in this study, the interactions of AME, alternariol-3-sulfate (AS), and alternariol-9-monomethylether-3-sulfate (AMS) were investigated with albumins (human, bovine, porcine, and rat) and with cyclodextrins (sulfobutylether-β-cyclodextrin, sugammadex, and cyclodextrin bead polymers). Our major results/conclusions are the following: (1) The stability of mycotoxin-albumin complexes showed only minor species dependent variations. (2) AS and AMS formed highly stable complexes with albumins in a wide pH range, while AME-albumin interactions preferred alkaline conditions. (3) AME formed more stable complexes with the cyclodextrins examined than AS and AMS. (4) Beta-cyclodextrin bead polymer proved to be highly suitable for the extraction of AME, AS, and AMS from aqueous solution. (5) Albumins and cyclodextrins are promising binders of the mycotoxins tested.
3. Alternariol monomethyl ether toxicity and genotoxicity in male Sprague-Dawley rats: 28-Day in vivo multi-endpoint assessment
Xinyao Tang, Yiyi Chen, Xia Zhu, Yeqiu Miao, Dongxia Wang, Jing Zhang, Ruirui Li, Lishi Zhang, Jinyao Chen Mutat Res Genet Toxicol Environ Mutagen. 2022 Jan;873:503435. doi: 10.1016/j.mrgentox.2021.503435. Epub 2021 Dec 2.
Alternariol monomethyl ether (AME), a typical Alternaria toxin, has often been detected in grains. We have measured the general toxicity and genotoxicity of AME with a 28-day multi-endpoint (Pig-a assay + in vivo micronucleus [MN] test + comet assay) platform. Male Sprague-Dawley rats were administered AME (1.84, 3.67, or 7.35 μg/kg body weight/day), N-Ethyl-N-nitrosourea (40 mg/kg body weight/day), or corn oil by gavage for 28 consecutive days. Another group (AME-high-dose + recovery) was maintained for a further 14 days after the end of the AME administration. Hematology and serum biochemistry results suggested that AME might compromise the immune system. The histopathology results indicated that AME can cause liver (inflammatory cell infiltration, steatosis, and edema), kidney (renal glomerular atrophy), and spleen (white pulp atrophy) damage. The genotoxicity results showed that AME can induce gene mutations, chromosome breakage, and DNA damage, but the effects were diminished after the recovery period. According to point-of-departure analysis (BMDL10), the risk to the population of exposure to AME cannot be ignored and further assessment is needed.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C14H10O5
Molecular Weight (Monoisotopic Mass): 258.0528 Da
Molecular Weight (Avergae Mass): 258.2262 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C14H10O5
Molecular Weight (Monoisotopic Mass): 258.0528 Da
Molecular Weight (Avergae Mass): 258.2262 Da
LC-MS/MS Spectrum - DI-ESI-qTof , Positive
Experimental Conditions
Instrument Type: DI-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Negative
Experimental Conditions
Ionization Mode: Negative
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C14H10O5
Molecular Weight (Monoisotopic Mass): 258.0528 Da
Molecular Weight (Avergae Mass): 258.2262 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C14H10O5
Molecular Weight (Monoisotopic Mass): 258.0528 Da
Molecular Weight (Avergae Mass): 258.2262 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
