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BioViotica
Alternariol
85
CHF
CHF 85.00
In stock
BVT-0465-M0011 mgCHF 85.00
BVT-0465-M0055 mgCHF 275.00
| Product Details | |
|---|---|
| Synonyms | AOH; NSC 638263; 3,4',5-Trihydroxy-6'-methyldibenzo-α-pyrone |
| Product Type | Chemical |
| Properties | |
| Formula |
C14H10O5 |
| MW | 258.2 |
| CAS | 641-38-3 |
| RTECS | HP8757000 |
| Source/Host Chemicals | Isolated from Alternaria sp. |
| Purity Chemicals | ≥98% (HPLC) |
| Appearance | Light brown solid. |
| Solubility | Soluble in DMSO (20mg/ml) or DMF. Slightly soluble in acetone (1mg/ml). |
| Identity | Determined by 1H-NMR. |
| Declaration | Manufactured by BioViotica. |
| InChi Key | CEBXXEKPIIDJHL-UHFFFAOYSA-N |
| Smiles | OC1=CC(C2=C(C)C=C(O)C=C2O3)=C(C(O)=C1)C3=O |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | +4°C |
| Handling Advice | Keep cool and dry. |
| Use/Stability |
Stable for at least 1 year after receipt when stored at +4°C. After reconstitution protect from light at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Mycotoxin.
- Phytotoxin.
- Shows cytotoxic, teratogenic, mutagenic and genotoxic properties by DNA intercalation.
- Induces several types of DNA damage, including oxidative DNA damage, single-stranded DNA breaks (SSB) and double-strand, through AOH-induced ROS production and interaction with DNA topoisomerase.
- Inhibits the activity of topoisomerase IIα in mammalian cells.
- Induces cell growth arrest in G2/M phase.
- GSK-3β inhibitor (sub-μM IC50 values).
- Antiviral activity (herpes simplex).
- Hepatitis C NS3-4A protease inhibitor.
- Induces cytochrome P450 1A1 expression and apoptosis in mouse hepatoma cells.
Product References
- Studies in the biochemistry of micro-organisms. 90. Alternariol and alternariol monomethyl ether, metabolic products of Alternariatenuis: H. Raistrick, et al.; Biochem. J. 55, 421 (1953)
- Alternariol, a dibenzopyrone mycotoxin of Alternaria spp., is a new photosensitizing and DNA cross-linking agent: F. DiCosmo & N.A. Straus; Experientia 41, 1188 (1985)
- Evaluation of alternariol and alternariol methyl ether for mutagenic activity in Salmonella typhimurium: V.M. Davis & M.E. Stack; Appl. Environ. Microbiol. 60, 3901 (1994)
- Alternariol acts as a topoisomerase poison preferentially affecting the IIα isoform.: M. Fehr, et al.; Mol. Nutr. Food Res. 53, 441 (2009)
- Mechanism of Alternariol monomethyl ether-induced mitochondrial apoptosis in human colon carcinoma cells: F. Bensassi, et al.; Toxicology 290, 230 (2011)
- Heptaketides with antiviral activity from three endolichenic fungal strains Nigrospora sp., Alternaria sp. and Phialophora sp.: J.-W. He, et al.; Fitoterapia 83, 1087 (2012)
- Alternariol: D. Siegel, et al.; Acta Crystallogr. Sec. E Struct. Rep. Online 66, o1366 (2010)
- The Fungal Phytotoxin Alternariol 9-Methyl Ether and Some of Its Synthetic Analogues Inhibit the Photosynthetic Electron Transport Chain: A. Demuner, et al.; J. Nat. Prod. 76, 2234 (2013)
- Modulation of the cellular redox status by the Alternaria toxins alternariol and alternariol monomethyl ether: C. Tiessen, et al.; Toxicol. Lett. 216, 23 (2013)
- Mycotoxins from Alternaria: toxicological implications: C. Dall'Asta, et al.; Adv. Mol. Toxicol. 8, 107 (2014)
- Impact of Alternaria toxins on CYP1A1 expression in different human tumor cells and relevance for genotoxicity: G. Pahlke, et al.; Toxicol. Lett. 240, 93 (2016)
- Marine fungi as producers of benzocoumarins, a new class of inhibitors of glycogen-synthase-kinase 3β: J. Wiese, et al.; Mar. Drugs 2016, 14 (2016)
- Involvement of p38MAPK-ATF2 signaling pathway in alternariol induced DNA polymerase β expression: Z. Jimin, et al.; Oncol. Lett. 12, 675 (2016)
- Alternariol induce toxicity via cell death and mitochondrial damage on Caco-2 cells: C. Fernandez-Blanco, et al.; Food Chem. Toxicol. 88, 32 (2016)
- Mechanisms of Action and Toxicity of the Mycotoxin Alternariol: A Review: A. Solhaug, et al.; Basic Clin. Pharmacol. Toxicol. 119, 533 (2016)
- The Alternaria alternata Mycotoxin alternariol suppresses lipopolysaccharide-induced inflammation: S. Grover & C. B. Lawrence; Int. J. Mol. Sci. 2017, 18 (2017)
- Impact of phase I metabolism on uptake, oxidative stress and genotoxicity of the emerging mycotoxin alternariol and its monomethyl ether in esophageal cells: C. Tiessen, et al.; Arch. Toxicol. 91, 1213 (2017)
- Dual effectiveness of alternaria but not fusarium mycotoxins against human topoisomerase II and bacterial gyrase: K. Jarolim, et al.; Arch. Toxicol. 91, 2007 (2017)
- Genistein and delphinidin antagonize the genotoxic effects of the mycotoxin alternariol in human colon carcinoma cells: G. Aichinger, et al.; Mol. Nutr. Food Res. 2017, 61 (2017)
- Nonsteroidal mycotoxin alternariol is a full androgen agonist in the yeast reporter androgen bioassay: S. Stypula-Trebas, et al.; Environ. Toxicol. Pharmacol. 55, 208 (2017)
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