| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 100mg | |||
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| Targets |
DNA (via intercalation); DNA topoisomerase; cytochrome P450 1A1 (CYP1A1). Alternariol exerts its genotoxic effects through DNA intercalation, inducing DNA damage. It interacts with DNA topoisomerase, leading to DNA strand breaks. The compound induces CYP1A1 expression. Its mycotoxicity is mediated through multiple mechanisms including oxidative stress and direct DNA damage.
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| ln Vitro |
Alternariol demonstrates cytotoxic activity in vitro against various cell lines. It induces apoptosis in mouse hepatoma cells at concentrations of 20 µM. The compound induces DNA damage, including oxidative damage and strand breaks. Its genotoxic and mutagenic properties have been characterized in various in vitro assays.
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| ln Vivo |
In vivo, Alternariol has been shown to be fetotoxic, teratogenic, and genotoxic in animal models. It is a contaminant in food and feed and has been associated with various health problems in humans and animals. The compound's toxicity has been studied in various animal models to assess its effects on development and organ function.
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| Enzyme Assay |
In vitro genotoxicity assays for Alternariol include the Ames test for mutagenicity, the comet assay for DNA damage, and the micronucleus test for chromosomal damage. Cells are treated with Alternariol at varying concentrations, and DNA damage is measured. ROS production may be assessed using fluorescent probes. Cytotoxicity is measured using MTT or other viability assays.
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| Cell Assay |
Cellular assays for Alternariol involve culturing various cell lines, including hepatoma cells, and treating them with Alternariol at varying concentrations. Apoptosis is measured using caspase activity assays or annexin V staining. DNA damage is assessed using the comet assay or γ-H2AX staining. CYP1A1 induction is measured by Western blotting or enzyme activity assays.
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| Animal Protocol |
In vivo animal studies for Alternariol have been conducted in rodents to assess its toxicological effects. The compound is typically administered orally. Fetotoxicity and teratogenicity are assessed in pregnant animals. Genotoxicity is assessed using the micronucleus test or comet assay in various tissues. Dosing regimens vary depending on the study.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Alternaria is metabolized in hepatic microsomes, preferentially at the aromatic ring position. The products of aromatic ring hydroxylation are catechols or hydroquinones, which may form reactive semiquinones and quinones, or undergo redox cycles. (A2981) Pharmacokinetic data for Alternariol are limited. The compound has a molecular weight of 258.23 and a molecular formula of C14H10O5. It is a fungal metabolite that can contaminate food and feed. Absorption, distribution, metabolism, and excretion parameters are not extensively documented. |
| Toxicity/Toxicokinetics |
Toxicity Summary
Alternaria is a cholinesterase, or acetylcholinesterase (AChE) inhibitor. Cholinesterase inhibitors (or "anticholinesterases") inhibit the activity of acetylcholinesterase. Because acetylcholinesterase plays a vital physiological role, chemicals that interfere with its activity are potent neurotoxins; even low doses can cause excessive salivation and lacrimation, followed by muscle spasms and ultimately death. Substances used in nerve gases and many pesticides have been shown to exert their effects by binding to serine residues at the active site of acetylcholinesterase, thus completely inhibiting the enzyme's activity. Acetylcholinesterase breaks down the neurotransmitter acetylcholine, which is released at the neuromuscular junction, causing muscle or organ relaxation. The mechanism of action of acetylcholinesterase inhibitors is to allow acetylcholine to accumulate and exert its sustained effect, ensuring the continuous transmission of nerve impulses and preventing muscle contraction from ceasing. The most common acetylcholinesterase inhibitors are phosphorus-containing compounds designed to bind to the enzyme's active site. Its structural requirements include a phosphorus atom with two lipophilic groups, a leaving group (such as a halogen or thiocyanate group), and a terminal oxygen atom. Alternariol is a toxic mycotoxin that is cytotoxic, genotoxic, fetotoxic, and teratogenic. It is a contaminant in food and feed and poses health risks to humans and animals. The compound is not used therapeutically and is studied primarily for its toxicological effects. |
| References | |
| Additional Infomation |
Alternariol is a benzo[c]chromene-6-one with a methyl group at position 1 and hydroxyl groups at positions 3, 7, and 9. It is the most important mycotoxin produced by Alternaria fungi, the most common fungal community globally infecting small grains. Alternariol has multiple functions, including as a metabolite, an EC 3.1.1.8 (cholinesterase) inhibitor, and a mycotoxin. It is a benzo[c]chromene one, belonging to the phenolic class of compounds. Alternariol has been reported in Alternaria, Sonneratia alba, and other organisms with relevant data. It is also found in mushrooms. Alternariol is present in the mycelium of Alternaria tenuis, the pathogen of Alternariol var. homophyton, and fruit spot disease in Carica papaya and Passiflora species. Alternaria is a toxic metabolite of Alternaria and a significant contaminant in grains and fruits. Alternaria belongs to the family of isocoumarins and their derivatives. These compounds are polycyclic aromatic hydrocarbons containing an isocoumarin group attached to their C1 carbon atom.
Alternariol is a mycotoxin produced by Alternaria molds, found as a contaminant in fruit and grain products. It is genotoxic and mutagenic, inducing DNA damage through intercalation and topoisomerase interaction. The compound is not a therapeutic agent and is studied for its toxicological properties. Its molecular formula is C14H10O5. |
| Molecular Formula |
C14H10O5
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|---|---|
| Molecular Weight |
258.2262
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| Exact Mass |
258.052
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| CAS # |
641-38-3
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| PubChem CID |
5359485
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| Appearance |
Off-white to light brown solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
586.9±39.0 °C at 760 mmHg
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| Melting Point |
350°C (rough estimate)
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| Flash Point |
232.3±20.6 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.731
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| LogP |
2.93
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
19
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| Complexity |
371
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
CEBXXEKPIIDJHL-UHFFFAOYSA-N
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| InChi Code |
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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| Chemical Name |
3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.8725 mL | 19.3626 mL | 38.7252 mL | |
| 5 mM | 0.7745 mL | 3.8725 mL | 7.7450 mL | |
| 10 mM | 0.3873 mL | 1.9363 mL | 3.8725 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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